Find Your Waterfront Oasis

Beautiful Waterways Abound...

The Chesapeake region is full of a variety of waterways to explore... kayaking, sailing, power sports, yachting and watching all the life that fills the areas. We live this life and know the areas and the unique characteristics of waterview and waterfront homes. Let us be your guide on this adventure!

there's no better way to ENJOY the water than to LIVE on the WATER

$685,000
3 Beds 3 Baths
117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit #1A, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,600,000
7 Beds 5 Baths
**Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit #1A, 1B, 2A, & 2B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$149,750
Discover 59.625± acres of diverse woodland in Worcester County, Maryland, offering a truly unique recreational and hunting opportunity. This impressive tract features a mixture of hardwoods and softwoods, highlighted by stands of stately cypress. As you walk the property, you’ll notice an array of cypress knees emerging from the forest floor, creating a distinctive landscape. The soils consist primarily of Puckum muck and Chicone mucky silt loam, giving the property a soft, organic bottom typical of high-quality wetland habitat. Despite the overall softness, the land includes transitions of firmer soils that naturally funnel wildlife and create ideal pinch points for whitetail deer to bed and travel. Numerous scrapes and rubs were seen throughout the property, indicating strong deer activity. The land has not been hunted in many years, making it an untouched and highly desirable habitat for both whitetails and other game. Turkeys are seen throughout the property during various times of the year, adding to the diverse wildlife appeal. The entire western boundary borders Dividing Creek, a beautiful waterway that enhances both scenery and habitat. During recent visits, abundant waterfowl were observed along the creek, including numerous puddle ducks such as black ducks and wood ducks, making this tract highly attractive for waterfowl enthusiasts. Access is convenient thanks to a newly established ingress/egress right-of-way from Fleming Mill Road, crossing the adjacent field and providing a direct approach to the property. In addition, a complete boundary survey was recently performed to clearly define acreage and property lines. This is a rare opportunity to own a one-of-a-kind recreational and hunting property in Worcester County—perfect for the sportsman, nature lover, or land investor. Don’t miss your chance to make this exceptional piece of Maryland’s Eastern Shore your own.

00 Fleming Mill Rd, Pocomoke City

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$539,900
2 Beds 1 Baths
When you enter this direct oceanfront 2-bedroom condominium you will immediately be taken back by the ocean views from the oversized picture windows. After taking in the stunning views you will start to note all of the upgrades made that give this condo a coastal cottage feel. Starting with the shiplap accent wall and moving to the large electric fireplace with stone hearth the gathering area is spacious and cozy all at the same time. Your friends and family will enjoy meals prepared in the fully remodeled kitchen featuring granite countertops, shaker style white cabinets to the ceiling, a tile backsplash, and stainless-steel appliances. Luxury Vinyl Plank flooring is installed throughout keeping all flooring cohesive leading from one room to the next. The primary bedroom also has primarily East exposure allowing occupants a fantastic view of the sunrise over the Atlantic Ocean each day through large operational windows. Slide the windows open at night to fall asleep to the sound of the waves crashing on the sand. This end unit condo has windows and sliders with North, East and Southern exposures providing the owner the opportunity to take advantage of cross breezes when the weather is pleasant. The bathroom is also remodeled and includes a beautiful, tiled shower with accent listello, matching river rock floor, and painters glass doors. The bathroom vanity has quartz counters that match the kitchen. This condo also features a stackable washer dryer providing all the convenience of home while visiting the beach. The condo fee includes cable and internet. Finally, the windjammer complex has a large private beach area as well as a designated area for grilling.

4503 Atlantic Ave Unit #200, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$315,000
1 Beds 2 Baths
JUST REDUCED! ADORABLE & WELL MAINTAINED WATERFRONT W/EASY ACCESS TO THE OPEN BAY! RESERVE STUDY HAS BEEN COMPLETED! 1 Bedroom + Loft Condo with DEEDED BOAT SLIP AT YOUR BACK DOOR! WINDOW & SLIDERS HAVE BEEN REPLACED, FLOORING & AIR CONDITIONERS! ! Experience coastal living at its finest in this charming 1-bedroom, 1.5-bath waterfront condo with a spacious loft that can easily serve as a second bedroom. Featuring a bright, open living area with soaring cathedral ceilings, this home offers an airy and inviting atmosphere filled with natural light.The primary bedroom includes access to a private deck, perfect for enjoying warm summer breezes.Step outside and you’ll find direct water access right off your back deck — ideal for fishing, crabbing, paddle boarding, or simply relaxing by the water. A deeded boat slip is included, making boating effortless and enhancing the true coastal lifestyle experience.Prefer the ocean? The beach is just a short walk away, giving you the best of both bay and beach living.Additional highlights include laminate flooring throughout, a large storage closet off the back deck for fishing gear and beach accessories, and the convenience of being sold fully furnished (with only a few exclusions) — making this a true turn-key opportunity. Whether you’re looking for a waterfront getaway, full-time residence, or investment property, this condo delivers location, lifestyle, and value in one beautiful package.

616 Salt Spray Rd Unit #7, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

$799,000
3 Beds 2 Baths
Experience elevated coastal living at High Point North 7A 🌊 — a rare 3-bedroom, 2-bath end-unit where sweeping bay and ocean views meet an unbeatable North Ocean City location ☀️🏖️. This oceanfront residence is bathed in natural sunlight thanks to its premier end-unit positioning. From the moment you enter the foyer, the stunning brick accent wall sets the tone for refined coastal elegance ✨. The open floor plan feels airy and inviting, with expansive windows framing breathtaking water views 🌅 The beautifully upgraded kitchen features stylish two-tone cabinetry, a breakfast bar, and a conveniently located washer and dryer — all seamlessly flowing into the dining area and oversized living room, creating the perfect space for entertaining 🍽️🥂. A thoughtfully designed wet bar/coffee station ☕🍸 offers effortless hosting for morning sunrises or evening cocktails. The spacious primary suite provides a private retreat with its own ensuite bath 🛁, while two additional bedrooms offer comfortable guest accommodations. One guest room is especially captivating — with bay views at the foot of the bed and ocean views to the side 🌊🌅. The fully enclosed oceanfront sunroom invites year-round relaxation — open the windows and let the sea breeze drift in 🌬️🌴 Complete with a built-in sound system 🎶 and electric entry lock 🔐, this home blends modern convenience with coastal sophistication. Residents enjoy an outdoor pool 🏊‍♀️, oceanfront sundeck 🌞, outdoor showers 🚿, and direct beach access 🏖️ — delivering true oceanfront living. This is North Ocean City at its finest — panoramic views, premier amenities, and a front-row seat to the Atlantic 🌊✨ Public tax records reflect 1,284 SF; however, a 2020 appraisal measured the unit at approximately 1,498 SF due to the enclosed front balcony and footprint modifications. Square footage is not guaranteed. Buyers are advised to verify to their satisfaction.

11400 Coastal Hwy Unit #7A, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$1,945,000
6 Beds 6 Baths
Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

228 Perry Cabin Dr Unit #228 / 226, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$469,990
3 Beds 2 Baths
** Waterfront Condo with Private Boat Slip in North Ocean City – Rare Canal-Front Opportunity ** Experience the best of coastal living in this beautifully maintained waterfront condo in North Ocean City, featuring 30 feet of canal frontage and a private boat slip that conveys with the sale. Located on the first floor for easy access and convenience, this spacious 3-bedroom, 2-bath residence offers the ideal blend of comfort, boating lifestyle, and investment potential. Lovingly cared for by the original long-term owners and never used as a rental, this move-in-ready property stands apart from many waterfront offerings in Ocean City. The open floor plan is designed for relaxed beach living, while the generous primary suite overlooks the canal, creating a peaceful waterfront retreat. Step outside to enjoy composite decking, wood railings, a vinyl bulkhead, and an electronic awning—thoughtful upgrades that enhance both enjoyment and durability. From your private slip, enjoy direct bay access for boating, fishing, paddle-boarding, crabbing, or evening sunset cruises. Just minutes from the beach, restaurants, shopping, golf, and entertainment, this prime North Ocean City location places everything you love about the Eastern Shore within easy reach. Offered furnished for a turnkey experience (excluding select personal items), this property also presents a unique opportunity for buyers seeking immediate income potential or long-term flexibility. The sellers are willing to lease the property back from the new owner on a long-term basis, creating an attractive option for investors seeking stable occupancy from day one. Waterfront condos with private boat slips, direct bay access, and this level of pride of ownership are becoming increasingly difficult to find. Don't miss the opportunity to own a premier canal-front property in one of Ocean City's most sought-after boating communities.

107 Newport Bay Dr Unit #A02, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777

$5,675,000
3 Beds 4 Baths
Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one. The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence. Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations. Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport. Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!

1 Shipwright Harbor, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$739,900
2 Beds 3 Baths
HUGE PRICE CHANGE!!! Seller is motivated! Incredible Coastal Living for you in Ocean City, Maryland! Deeded Boat Slip #2 is available for separate purchase of $140k. It will house up to a 40 foot Vessel. -- Taxes and Condo fees are separate for slip. There is a Boat Slip available for additional cost- has electric and water. Step into your dream getaway with this completely updated coastal-style condominium, perfectly designed for relaxation and enjoyment. This stunning improved two-bedroom, two-and-a-half-bath unit offers a blend of modern elegance and beach-side charm, making it the ideal retreat for anyone looking to embrace the vibrant Ocean City lifestyle. The Interior Highlights include: Fully renovated kitchen. Enjoy cooking in your state-of-the-art kitchen featuring stainless steel appliances, gorgeous quartz countertops, and abundant cabinetry that provides ample storage. Enjoy the spacious layout.... the open floor plan is enhanced by new luxury vinyl plank flooring that effortlessly combines style and durability, making it perfect for beach living. Many finishing touches that are thoughtful design elements adding a touch of sophistication and comfort. There is additional storage space in the garage underneath of the unit and a storage closet that stays locked as well for anything that you may need to place there for safekeeping. Harbour Island is home to the 53 yr old. World’s Largest Billfishing Tournament!" This could be right out your back door for 1 week in August each year!! So exciting and a huge event for Ocean City! **Outdoor and Community Amenities:** - **Boat Slip **: available too!! Size is 12 x 38, could hold a possibly a 40 ft vessel. Imagine the convenience of easily parking your boat right here, or even renting it out for additional income for WMO. If you need some extra room for guests, they could sleep peacefully right on your boat!! - **Harbour Island Community**: Take advantage of the outdoor pools, or the Reel Inn Restaurant which is perfect for summer relaxation or entertaining friends and family. **Location, Location, Location:** - **Proximity to the Beach**: A short stroll takes you up to the beach, where you can soak up the sun, enjoy the waves, and create lasting summer memories. Explore a variety of nearby restaurants and shops, catering to all tastes and preferences. Whether you’re a fishing enthusiast or simply love the beach atmosphere, this location has it all! This beautifully renovated condominium is not just a home; it’s a lifestyle waiting for you to embrace. Don’t miss the chance to own this piece of paradise in Ocean City—schedule your viewing today and experience coastal living at its finest! Here you will have a front row seat to the largest White Marlin Tournament on the East Coast!!

401 S 14th St Unit #4, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$1,190,000
3 Beds 3 Baths
Discover this mid-town gem on Ocean City's beachfront—an intimate four unit building offering privacy, space, and unbeatable views. This beautifully furnished 3 bedroom, 3 bath condominium delivers 1,880 sq. ft. of coastal comfort. It features an elevator keyed exclusively to your private lobby and entrance door, providing easy access and security. The well-designed layout includes an open living, dining and kitchen with a separate wet bar and beverage cooler, perfect for family gatherings or entertainment. With ample living space, and thoughtful features, this home presents an ideal opportunity to experience the charm and ambiance of beach living. Each unit has two assigned parking spaces and there are two more for guests of the owners. From the moment you enter the building, the experience feels exclusive. You can walk up the west side stairs or ride the private keyed elevator to your lobby and front door. Inside, the layout is bright, open, and designed for easy beach living. A guest bedroom is to the left of the hallway with a custom closet featuring California Style built ins for effortless organization. Across the hall, the sunny south guest bedroom offers a double slider to the west facing balcony, where you can soak up year round sun and warm winter light. This bedroom has an ensuite bath. Continue down the hall, to the left is a large coat closet. To the right is a dedicated laundry area with full size Whirlpool side by side washer and dryer, plus open shelving above. Then this beach home opens up into a dramatic living, dining, and kitchen space with 10' ceilings and plenty of room to entertain. The wet bar—with a built in wine cooler, sink, and generous cabinetry—sets the tone for gatherings, while the expansive kitchen offers KraftMaid cabinetry, Corian counters, a glass cooktop , built in oven, and thoughtful storage upgrades like pull out shelves and a lazy Susan in the lower corner. The living area features a natural gas fireplace, built in shelving, and the included LG TV has "accessible" surround sound speakers in place. From here, step into the spacious main bedroom, complete with access to the oceanfront balcony and abundant natural light. The ensuite bath includes a jetted tub, separate walk in shower, double sinks, a seated vanity area, and a large linen and clothes closets. There is a lockable storage closet with shelves for owners who may want to rent. This can be your private retreat by the sea. The building is undergoing its routine exterior refresh—caulking, coating, and painting—part of a proactive maintenance schedule completed every 5–6 years by the owners and management team. Another special feature of this building is the rooftop deck -- for sunning, relaxing and enjoying sunrises, sunsets and fireworks throughout town, especially popular Seacrets Bar and Restaurant on the bay side. If you’re looking for a beachfront home that combines privacy, space, elegance and stunning views with the ease of condo living, this one delivers it all. The unit was freshly painted unit May, 2026. Seller is providing a 1 year American Home Warranty to buyers at closing. Appliances ages: water heater -- 2013, refrigerator -- 2023, HVAC -- 2024, water conditioner under sink -- 2017, washer and dryer -- 2015, Disposal -- 2021

5105 Atlantic Ave Unit #101, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$7,500,000
5 Beds 7 Baths
This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection dancing across the water and spilling into a home designed to embrace the view at every turn. This extraordinary residence is both a private retreat and an entertainer’s dream, with expansive balconies and roof decks on every level, making indoor/outdoor living a breeze. Inside, soaring ceilings and walls of glass frame the ever-changing views like a living masterpiece, while the grand chef’s kitchen, stone-floored sunroom, and elegant dining spaces invite gatherings large and small. The primary suite is an entire level of indulgence, complete with soaring ceilings, a fireplace, spa-like bath, wet bar, expansive dressing room, laundry, and its own private balcony for starlit evenings. Additional ensuite bedrooms and a guest suite with kitchenette ensure comfort for family and friends, while the lower level—with wine cellar, kitchenette, and direct access to the pool—extends the living space to the outdoors. With a sandy beach and two private piers, one tucked into Crouches Cove and the other stretching into the Severn river, this estate offers not just a home but a lifestyle of breathtaking vistas on the water, boating adventures at your doorstep, and the unmatched beauty of Annapolis waterfront living. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis, convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly special property with EPIC water views, resort like amenities and a great private setting, this is the property you have been waiting for. Welcome Home!

125 S Winchester Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$390,000
4 Beds 3 Baths
Wake up to wide, unobstructed water views in this spacious end-unit waterfront condo located in the heart of Crisfield. With 4 bedrooms and 3 full baths, this beautifully designed residence offers the ideal blend of comfort, functionality, and coastal lifestyle. The bright, open main level features expansive windows that capture natural light and showcase stunning water views. A main-floor bedroom and full bathroom provide flexibility for guests, multi-generational living, or those seeking convenient first-floor access. Step onto the screened deck overlooking the water, perfect for morning coffee, evening sunsets, or entertaining with a view. Upstairs, the generous primary suite includes a private full bath and its own balcony with panoramic water views. Two additional bedrooms and another full bathroom complete the upper level, offering ample space for family, guests, or a home office. Outdoor enthusiasts will appreciate the attached garage and the included deep-water boat slip, ideal for boating, fishing, and exploring the Chesapeake Bay. Community amenities include a pool, private piers, sandy shoreline access, and beautifully maintained waterfront grounds. Accessibility features include a main-level bedroom and full bath, wide interior spaces, and attached garage access, offering convenience and flexibility for a variety of living needs. Located in the waterfront town of Crisfield, known as the Crab Capital of the World, residents enjoy local seafood restaurants, marinas, seasonal festivals, and waterfront events throughout the year. Nearby attractions include Janes Island State Park with miles of kayaking trails and wildlife observation. Ocean City beaches are approximately one hour away, and the property offers accessible commuter routes to Salisbury, Washington, DC, and Baltimore, making it suitable for a primary residence, second home, or investment opportunity. Whether you are looking for full-time waterfront living, a weekend retreat, or a boat-ready getaway, this rare end-unit condo delivers space, views, and lifestyle in one exceptional package.

109-D Waters Edge Unit #109D, Crisfield

Listing courtesy of Samson Properties. Contact: 4433437660

$2,950,000
7 Beds 8 Baths
Waterfront Estate | Headwaters of the Shingle Landing River | Positioned on over two private waterfront acres at the headwaters of the Shingle Landing River, this exceptional custom residence by White Creek Homes, Inc. embodies refined coastal living at its finest. Encompassing over 7,000 square feet, the home offers 6 bedrooms, 5 full baths, and 1 half bath, thoughtfully designed to balance architectural presence with everyday comfort. A sweeping approach framed by professional landscaping and curated hardscapes sets a distinguished tone. Beyond, your private dock invites effortless days on the water—boating to nearby waterfront restaurants, fishing at sunrise, or enjoying peaceful afternoons kayaking along the river. Inside, the architectural flow is intentional and elegant. The foyer introduces gracious formal and informal living spaces, including a formal dining room, a refined living room with fireplace, and a separate sitting room anchored by its own fireplace. Expansive windows frame serene water views throughout. The main-level primary suite is a private sanctuary featuring panoramic river vistas, a spa-inspired bath with soaking tub and glass-enclosed tiled shower, a dedicated dressing room, and generous walk-in closets—offering a five-star retreat experience at home. The kitchen reflects both craftsmanship and performance, appointed with Sub-Zero and Wolf appliances, custom cabinetry, and seamless connectivity to a sunlit breakfast room overlooking the water. An adjacent fireside gathering space creates an inviting setting for relaxed mornings and intimate evenings. The second level is thoughtfully configured for both privacy and functionality, offering two en suite bedrooms, two additional bedrooms connected by a Jack-and-Jill bath, and a fifth bedroom serviced by a full bath located just off the private fitness studio. A dedicated laundry room enhances convenience on this level. The third floor provides an additional family retreat with access to a private rear deck overlooking the waterway—an elevated vantage point for quiet reflection or relaxed entertaining. Outdoor living is equally compelling, with expansive hardscapes, integrated gas grill, and fire feature creating a resort-style terrace designed for refined gatherings. A detached garage with unfinished bonus space above offers flexibility for guest quarters, studio, or executive workspace. Ideally located, the property offers convenient access to the charm and fine dining of Berlin, the beaches and boardwalk of Ocean City, and the coastal lifestyle of Fenwick Island. Regional and private air travel is easily accommodated via Salisbury Regional Airport, making this estate as accessible as it is private. This is not simply a home—it is a private waterfront estate curated for those who value craftsmanship, discretion, and an uncompromising coastal lifestyle.

10542 Egret Ct, Bishopville

Listing courtesy of Keller Williams Realty. Contact: steve@srarealty.com

$2,500,000
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$524,900
2 Beds 2 Baths
Perched high on the 20th floor of the iconic Golden Sands Condominium, this direct oceanfront two-bedroom condo delivers breathtaking, floor-to-ceiling views of the Atlantic Ocean from the moment you step inside. The spacious primary suite offers sweeping ocean views and direct balcony access, creating a true retreat above the shoreline. Fall asleep each night to the rhythm of the waves and wake each morning to a spectacular sunrise over the ocean, all without leaving the comfort of your bed! The second bedroom captures beautiful views of Assawoman Bay, offering a peaceful contrast of sunrise and sunset vistas. A thoughtfully designed Jack-and-Jill layout provides each bedroom with its own private half bath, connected by a shared tub and shower, perfect for guests, family, or rental flexibility. Recent updates include a new HVAC (2024), hot water heater (2023), and carpet replacement (2023). The open-concept living area is designed for effortless coastal living, whether you're relaxing after a day at the beach, preparing meals, or entertaining with the ocean as your backdrop. Golden Sands is known for its exceptional resort-style amenities, including an expansive outdoor pool, sun-drenched pool deck, Tiki Bar beachside snack shack, top-floor indoor pool and fitness center with panoramic ocean and bay views, sauna, game room, sport courts, and on-site shops and dining. Whether you're searching for a weekend getaway, a high-demand investment property, or your own year-round oceanfront escape, this 20th floor residence offers the elevation, views, and amenities that make Golden Sands one of Ocean City's most sought-after oceanfront buildings.

10900 Coastal Hwy Unit #2012, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$2,500,000
5 Beds 1 Baths
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$580,000
4 Beds 2 Baths
Introducing 13374 Cove Landing Rd.—a canal-front opportunity in the desirable Bayview Estates community, offering private dock access and exceptional coastal potential. While this home carries a Bishopville, MD address, it is located within Bayview Estates and accessed through the Delaware side of the community, offering the convenience of coastal Maryland and Delaware living. Nestled on nearly a half-acre corner lot, this waterfront retreat provides tranquil canal-front living with a private dock. Due to seasonal tides, the dock is best suited for launching smaller craft or short-term tie-ups, while the nearby community boat ramp provides convenient access for larger vessels. From here, enjoy boating through Grey’s Creek to Assawoman Bay and waterfront dining destinations, with Ocean City’s inlet approximately 25 minutes away by water. By land, you are just six miles from both Ocean City and Fenwick Island beaches and minutes from Bayside Golf Resort, shopping, and dining. Inside, the welcoming floor plan features a bright breakfast room entry, a spacious eat-in kitchen with abundant cabinetry and prep space, and a sun-filled living room connected by a wide pass-through ideal for entertaining. The main level includes a primary bedroom with hall bath access and an additional guest bedroom. Upstairs, two additional bedrooms with charming dormer details provide flexible living space, along with a large bonus room spanning the length of the garage—perfect for a family room, game room, or home gym—opening to a Juliet balcony overlooking the canal and yard. An oversized two-car garage offers exceptional storage for vehicles, tools, and coastal gear. Being sold as-is, this property presents an excellent opportunity to create your dream waterfront retreat in an unbeatable coastal location, and for added peace of mind the seller is also offering a home warranty.

13374 Cove Landing Rd, Bishopville

Listing courtesy of Northrop Realty. Contact: (302) 539-2900

$310,000
2 Beds 2 Baths
Your perfect beach escape is finally here. Welcome to Windward Landing South, Unit 204—a second-floor, 2-bedroom, 2-bath condo that checks every box for the coastal lifestyle. Tucked away on the bayside yet just a short distance to the beach, this condo offers the best of both worlds. The bright, open living room flows effortlessly onto a spacious balcony overlooking the canal—an ideal spot to start your mornings or wind down after a day spent at the beach or relaxing by the outdoor pool. Designed for easy entertaining, the open kitchen features a breakfast bar and connects seamlessly to the dining area, offering plenty of space to gather with family and friends. Both bedrooms are spacious, with the primary suite featuring balcony access and an upgraded ensuite bath for added comfort. Boaters, this one’s for you—boat slips are available for just $100 per year (as available), making it easy to enjoy endless days on the water. Each unit also includes its own private storage/utility closet conveniently located just across the hall. The location is hard to beat, with quick access to Ocean City favorites like the Greene Turtle, Gold Coast Mall, Starbucks, Tail Chasers, and so many other local favorites. Whether you’re going out for dinner, grabbing coffee, or heading to the beach, everything you love is right nearby. If you’re dreaming of your own slice of beach life, this condo delivers it all. Come see why Windward Landing South 204 feels like vacation the moment you walk in.

170 Captains Quarters Rd Unit #204, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$549,900
2 Beds 3 Baths
Wow—this stunning 2BR/2.5BA waterfront condo with a deeded boat slip #31 in Harbour Club is truly one of a kind. Completely remodeled between 2022 and 2025, this home showcases modern coastal luxury throughout and is one of the largest floor plans in Harbour Club. Deeded Boat Slip #31 conveys with the sale. The condo is being sold furnished, beautifully designed in neutral tones and ready for immediate enjoyment. The chef in your family will be thrilled with the gourmet kitchen featuring sleek, stylish cabinetry, quartz countertops, and high-end appliances—an entertainer’s dream. The dining area flows seamlessly off the kitchen, creating the perfect space for family meals and gatherings with friends. The spacious family room overlooks the water and features a glass slider that opens to a stunning composite deck. Enjoy a cold summer drink while taking in breathtaking views of the Ocean City skyline, boats cruising the canal, and unforgettable sunsets. The waterfront primary suite is a true retreat, complete with a glass slider leading to the deck and serene water views. The luxurious primary bath offers a rain shower, upgraded mirrors and lighting, and custom built-ins. The second bedroom is generously sized and features an upgraded en-suite bath. A convenient half bath for guests and a dedicated laundry room complete the layout. Additional upgrades include Luxury Vinyl Plank flooring throughout, custom tile in the bathrooms, HVAC replaced June 2025. This is without question one of the most stunning, jaw-dropping waterfront condos on the market—a rare opportunity to own coastal luxury at its finest. Enjoy resort-style amenities including tennis courts, a fitness center, clubhouse, sauna, indoor heated pool, lap pool, family pool, and a kiddie pool. The location is unbeatable—just minutes from the beach, restaurants, shops, grocery stores, and mini golf. Come see this stunning condo today and experience the very best of coastal living!

201 S Heron Dr Unit #26B28, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$899,900
3 Beds 2 Baths
New Price— $899,900 | Quay 507 | Direct Oceanfront: Wake up to the Atlantic every single morning. This fully renovated, turnkey-furnished 3-bedroom, 2-bath residence at The Quay is the oceanfront reset button you've been waiting for — move-in ready, beautifully styled, and priced to sell. Every inch of Unit 507 has been reimagined for effortless coastal living. The open-concept kitchen anchors the home with a large center island — the kind built for morning coffee, wine nights, and everyone gathering in one place — plus a dedicated solid-surface beverage station that turns entertaining into an afterthought instead of a chore. Designer furnishings throughout by Donaway Furniture mean you can close on this home and start living the beach life the same week — no shopping, no waiting, no stress. Ocean views stretch across the living space and primary suite, framing sunrise after sunrise over the Atlantic. Two full baths and three genuinely spacious bedrooms give this layout rare flexibility for full-time living, a second home, or a high-performing rental. Why buyers love The Quay: - Indoor heated pool for year-round swimming - Oceanside outdoor pool steps from the sand - Onsite security for true peace of mind - Direct oceanfront building on Coastal Highway — beach access without crossing a street. Fully furnished. Fully renovated. Fully ready. Oceanfront inventory this turnkey rarely sits long at this price point — schedule your private showing before Quay 507 is gone.

10700 Coastal Hwy Unit #507, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$549,000
2 Beds 2 Baths
Front-Row to the Atlantic – 10th Floor Oceanfront Living at The Atlantis Welcome to The Atlantis Condominiums in Ocean City, Maryland, where oceanfront living becomes an everyday experience. This beautifully maintained two-bedroom, two-bath direct oceanfront residence is perched on the 10th floor, offering the perfect vantage point, high enough for sweeping, unobstructed Atlantic views, yet close enough to feel connected to the rhythm and energy of the beach below. From the moment you enter, the open-concept layout draws your eye straight to the horizon. Natural light fills the spacious living and dining areas, while the ocean becomes the backdrop to nearly every space. Designed for both relaxation and entertaining, the seamless flow creates an inviting coastal retreat that feels as effortless as it is refined. Then there’s the balcony, and it truly delivers. Spacious and open, it serves as your private front-row seat to nature’s daily masterpiece. Begin your mornings with coffee and the sound of waves rolling onto the shore. Breathe in the salt air as seabreezes drift by. Watch the sky ignite at sunrise and unwind in the evening with cocktails accompanied by the soothing orchestra of the Atlantic. It’s more than outdoor space, it’s an immersive sensory experience. The updated kitchen continues the coastal narrative with crisp white cabinetry, gleaming granite countertops, a large-format sea-foam blue/green glass tile backsplash, and stainless steel appliances. It’s as functional as it is beautiful, perfectly positioned for both casual meals and hosting gatherings by the sea. The primary suite is a serene retreat, highlighted by a large picture window that frames breathtaking ocean vistas, a view you’ll wake up to every morning. Two additional bedrooms provide comfortable accommodations for family and guests, while two full baths, abundant closet space, and an in-unit washer and dryer add everyday convenience. Tasteful coastal finishes and furnishings, included in the sale, make this a truly move-in-ready opportunity. Life at The Atlantis offers resort-style amenities designed to elevate every stay. Residents enjoy an oceanfront Olympic-sized pool, direct beach access, three high-speed elevators, year-round security, on-site management, a newly updated lobby, a convenient snack shack, and even a designated dog-walking area. It’s a secure, well-managed building known as one of Ocean City’s most desirable oceanfront addresses. Whether you’re searching for a vacation escape, a full-time residence, or a strong investment property, this 10th-floor oceanfront condo delivers location, lifestyle, and views that never grow old. Furnished and lovingly maintained, it’s ready to welcome you to your own slice of Atlantic paradise.

10300 Coastal Hwy Unit #1006, Ocean City

Listing courtesy of Northrop Realty. Contact: (302) 703-1144

$529,990
3 Beds 3 Baths
Enjoy your favorite beverage on the gracious, expansive deck overlooking the Stoney Creek. This versatile waterfront property provides comfortable living for multigenerational family, living in and renting out the in-law suite or even Airbnb. Experience the epitome of luxury living in this stunning raised ranch nestled in the serene Pine Haven community. This property seamlessly blends modern elegance with timeless charm. The exquisite brick exterior invites you into a world of comfort and sophistication. With almost 3,000 finished square feet of thoughtfully designed space, this home boasts a finished basement with full kitchen, bath and bedroom/den, perfect for in-law suite or income generating rental. The one bed plus den basement suite can easily rent for over $1,500/month in this area. The inviting fireplace, adorned with glass doors and a sleek screen, creates a cozy ambiance for gatherings or quiet evenings at home. Enjoy the convenience of laundry facilities on both the main floor and in the basement, enhancing your everyday living experience. Step outside to discover your own private oasis, featuring 50 feet of creek frontage. The gentle sounds of the flowing water create a tranquil backdrop, ideal for unwinding after a long day, watching ducks and turtle on a tranquil day. The lush surroundings and picturesque views of the Stoney Creek enhance the property's allure, offering a unique connection to nature right at your doorstep. Imagine summer cookout or morning tea in the massive 22' x 20' deck overlooking the Stoney Creek. There is also a large shed with electrical. The backyard is truly entertainers paradise! Located in a prime area, this home provides easy access to the beauty of the outdoors while maintaining proximity to local amenities. Pine Haven residents can enjoy access to a beach, boat ramp, and dock on Stoney Creek with a voluntary HOA fee of only $40/year! Embrace a lifestyle of exclusivity and comfort in this remarkable residence, where every detail has been curated for your enjoyment. Don't miss the opportunity to make this luxurious retreat your own. Updated kitchen, bathrooms, newer high efficiency central air with oil furnace backup

7686 Briar Ln, Pasadena

Listing courtesy of Libra Realty, LLC. Contact:

$550,000
14-Acre Commercial Property with Redevelopment Potential | Western Maryland Discover a rare opportunity to reimagine this 14-acre commercial property in the scenic mountains of Western Maryland, just outside city limits and minutes from I-68, Downtown Cumberland, UPMC–Western Maryland, and Allegany College. Formerly operated as a zoo and community center with a pool, the property offers a unique canvas for creative commercial, recreational, or redevelopment uses. Existing improvements—including the main buildings, barn, and a small apartment complex—will require full redevelopment, allowing a buyer to design a project tailored to their vision. Utilities & Infrastructure Highlights: Two working wells on the property One well services three nearby homes, the apartment units, and a mobile home A second well services various outbuildings and a bathroom on the lower portion of the property County sewer is available throughout the property One bathroom currently utilizes a septic tank but can easily be connected to the county sewer Additional Features: Expansive acreage with flexibility for a variety of commercial uses Seller may consider partial financing for qualified buyers Scenic, accessible location with strong redevelopment potential Virtual tour available, including aerial views of the property This is a chance to transform a site with history, character, and scale into something entirely new. Schedule a tour and explore the possibilities.

10105 Cottage Inn Ln Ne, Cumberland

Listing courtesy of RG Realty, Inc.. Contact:

$2,500,000
4 Beds 4 Baths
Welcome to this charming Cape Cod waterfront home in the heart of Linstead on the Severn, where classic coastal character meets bright, open living. Thoughtfully renovated in 2016, the home showcases custom finishes and inviting spaces designed to flow seamlessly from room to room, all framed by peaceful water views that define relaxed waterfront living. The main level welcomes you with a cozy seating area and fireplace, leading into an open living and dining space featuring vaulted ceilings, beautiful hardwood floors, and walls of windows that capture sweeping views of Yantz Creek. The chef’s kitchen is both stunning and functional, offering custom cabinetry, a striking backsplash, quartz countertops with a large island, a La Cornue gas range, and a sun-filled breakfast nook. Upstairs, you’ll find three bedrooms and two full bathrooms, including a luxurious primary suite with a marble double vanity, soaking tub, glass-enclosed shower, and walk-in closet. A fourth bedroom or office on the main level, with an adjacent full bath, provides flexible living options. The finished lower level adds a recreation room with a third fireplace, full bath, and laundry room, plus access to the two-car garage with EV charging. Step outside from this level to the covered walk-out patio for effortless indoor-outdoor living. Waterfront features include a private pier with approximately 5' MLW, a 20,000-lb boat lift, and jet ski lift, and boathouse with rooftop deck ideal for entertaining and boating enthusiasts. Enjoy Linstead’s sought-after community amenities, including private beaches, pier, pavilion, playground, and year-round events, all within the Severna Park school district and convenient to major commuter routes. This is a rare opportunity to experience waterfront living at its finest—schedule your private tour today!

143 Boone Trl, Severna Park

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171

$1,099,900
3 Beds 3 Baths
PRICE IMPROVEMENT! Experience an exceptional waterfront lifestyle in this newly constructed custom home, thoughtfully designed with luxury, comfort, and breathtaking water views in mind. Situated on over 2 private acres with approximately 340 feet of waterfront, this one-of-a-kind residence offers a rare opportunity to own a truly distinctive property in Southern Maryland. Inside, you’ll find high-end finishes, an open-concept floor plan, a gourmet chef’s kitchen, an elevator serving multiple levels, two gas fireplaces, spacious balconies, skylights, dual-zone HVAC, and two laundry areas for ultimate convenience. Wake up to spectacular sunrises, enjoy boating, fishing, kayaking, or simply relax while taking in the peaceful waterfront setting from your own backyard. Unlike older waterfront homes, this newly built residence offers the peace of mind that comes with modern construction, energy efficiency, and premium craftsmanship. The adjacent 3.36-acre waterfront lot is also available for purchase, creating an extraordinary opportunity for additional privacy, a future guest home (subject to approvals), or a multi-generational waterfront estate. Conveniently located within driving distance of Washington, DC, Northern Virginia, and Annapolis, this home is ideal as a primary residence, luxury weekend retreat, or vacation getaway. Significant price improvement. Schedule your private tour today and discover one of Southern Maryland’s most exceptional waterfront opportunities.

16242 Thomas Rd, Piney Point

Listing courtesy of Realty ONE Group Capital. Contact: (202) 932-5100

$1,975,000
5 Beds 3 Baths
Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

14183 Roberts Dr, Golts

Listing courtesy of Gunther-McClary Real Estate. Contact:

$2,100,000
5 Beds 4 Baths
SELLERS WILL BUY YOUR RATE DOWN 2% IF YOU CAN SETTLE WITIN 60 DAYS, CONSTRUCTION IS 90% COMPLETE. Stunning New Waterfront Construction in Bowleys Quarters... Welcome to 1105 Chester Road, an exceptional brand-new construction offering 4,000 sq. ft. of luxury living space in the sought-after waterfront community of Bowleys Quarters. Designed with a perfect blend of modern style and timeless craftsmanship, this home showcases 5 spacious bedrooms, 4 full bathrooms, and a half bathroom making it ideal for both everyday living and entertaining. The exterior boasts board-and-batten siding in Carbon, accented with black windows, doors, and trim, and complemented by natural wood porch posts and a stone veneer façade. A two-story addition expands the living space, while a stamped concrete patio with outdoor kitchen and fireplace provides the ultimate setting for gatherings. Step outside to your private waterfront retreat featuring a bulkhead shoreline and a 100-foot gray pier with pilings, perfect for boating, fishing, and enjoying wide water views. With a boat slip included, you can launch directly from your property and explore the Chesapeake Bay. Inside, you’ll find expansive open-concept living areas, high ceilings, and an abundance of natural light. The gourmet kitchen is designed for both style and function, while the generous bedrooms and spa-like bathrooms offer comfort and privacy for family and guests alike. This is a rare opportunity to own a brand-new waterfront estate in one of Maryland’s most desirable boating communities. Main image is a rendering, drawings are available upon request.

1105 Chester Rd, Baltimore

Listing courtesy of RE/MAX Components. Contact: 4105613017

$2,495,000
5 Beds 4 Baths
Price improvement. Welcome home to this stunning waterfront property in Cove Creek Club on Kent Island. Cove Creek is a Golfer's Paradise! This remarkable five bedroom, four bathroom home offers an unparalleled blend of privacy, elegance, and panoramic coastal beauty all located on your very own private peninsula. With an impressive 566 feet of protected shoreline where Tanner’s Creek converges with Cove Creek, opening directly to the Eastern Bay, this southern-facing residence offers breathtaking water views from nearly every room. Upon entering, you’re greeted by a dramatic two-story foyer with soaring vaulted and coffered ceilings that set an immediate tone of refinement, drawing the eye straight through to the large backyard and shimmering water views beyond. The thoughtfully designed main level features high ceilings throughout and a serene primary suite with views of the pool and waterfront. The primary retreat offers a custom walk-in closet with built-ins, tray ceiling, and a spa-inspired bath with dual vanities, private water closet, soaking tub, expansive walk-in shower, and plantation shutters for added privacy. Upstairs, enjoy a recreation room with wide angle water views and balcony perfect for enjoying sunsets while playing a game of pool or darts. Four additional bedrooms can be found here as well, two on either side of the home sharing jack-and-jill style bathrooms with private closets. Designed for effortless entertaining and elevated everyday living, the open-concept living and dining spaces flow seamlessly from the beautifully updated kitchen. Here, refined finishes include soft-close cabinetry, granite countertops, a marble backsplash, center island, walk-in pantry, stainless-steel appliances, gas cooktop, wine refrigerator, and warming drawer. The kitchen opens to an inviting living room with sliding doors to access the outdoor living area. Outside you’ll find extensive hardscaping with a built-in grill, granite countertops, and a granite dining table seating eight, perfect for hosting refined waterfront gatherings. The resort-style backyard is a private sanctuary, featuring a sparkling pool and a private pier equipped with three boat lifts—ideal for boating, paddle boarding, crabbing, or simply enjoying sunsets accompanied by visits from blue herons and bald eagles. Professionally designed landscaping offers year-round color with mature plantings all complemented by a lush, level lawn maintained by a multi-zone irrigation system. Additional highlights include a spacious three-car garage with room for vehicles, golf carts, and storage, along with premium finishes throughout that reflect timeless craftsmanship and meticulous attention to detail. As a resident of Cove Creek, enjoy access to an exceptional array of private amenities including a USGA-rated golf course, deep-water marina, private beach, clubhouse, fitness center, tennis, pickleball, and bocce courts, boat ramp and storage yard, as well as miles of scenic walking and biking trails - all located on Kent Island, just minutes from the Chesapeake Bay Bridge and Route 50.

137 Tanners Point Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$8,950,000
24 Beds 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971

$5,350,000
4 Beds 6 Baths
Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence by award-winning firm - Pacquin Design Build, presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture sweeping river views, abundant natural light, and a seamless connection between indoor and outdoor living. The proposed floor plan balances timeless elegance with everyday comfort, featuring open yet well-defined living spaces that flow effortlessly toward the waterfront. A chef’s kitchen anchors the main level, opening to inviting gathering areas and expansive terraces overlooking the river. Walls of glass frame the ever-changing water views, while a main-level bedroom suite offers flexibility for guests or convenient single-level living. The upper level is designed as a private retreat, highlighted by a serene primary suite with elevated river views and additional bedrooms thoughtfully arranged for family and guests. Outdoors, the concept plan showcases a resort-inspired setting with a waterfront pool, generous patios, and sweeping lawn leading to approximately 389 feet of rip-rap shoreline. Boating, paddleboarding, and relaxed days by the water are central to the lifestyle this property affords. The lot is fully usable, offers ample mean low water depth, has an approved perc, and does not require flood insurance, making it an ideal canvas for a custom estate, family compound, or legacy retreat. Lot can be purchased separately for $2,250,000 (MDTA2012470) Set within the natural beauty and refined charm of Talbot County, and just moments from the Chesapeake Bay, this extraordinary offering combines privacy, scale, and location. A rare chance to bring a bespoke coastal vision to life on one of the Eastern Shore’s most desirable riverfront parcels—perfect as a year-round residence or second-home sanctuary. Located in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

Morgans Point Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$7,500,000
6 Beds 8 Baths
Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

7508 Cooper Point Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$2,000,000
4 Beds 2 Baths
Some properties come along once in a generation. This is one of them. Tucked within the coveted Holland Point community of North Beach, Maryland, this rare and expansive waterfront compound offers something the Chesapeake Bay area simply does not produce anymore — significant water frontage, a grandfathered private dock that is the longest in North Beach, and the kind of breathing room and flexibility that coastal dreamers spend a lifetime searching for. From sunrise to sunset, the views across the bay are nothing short of extraordinary. Whether you’re casting a line off the dock, pulling in with your boat after a day on the water, or simply sitting on the porch watching the last light melt into the Chesapeake, this property delivers the full Bay experience in a way few others can. The main waterfront residence has been thoughtfully updated where it counts — featuring a refreshed kitchen, dining area, and bath — and opens into a generously scaled living area designed for effortless entertaining. Multiple bedrooms, each with its own in-room sink, offer a charming nod to a bygone era of gracious hosting, while a spacious family room positioned closest to the water keeps you connected to the views at every turn. Step outside to a lovely enclosed wraparound patio that flows naturally to the oversized dock — the perfect perch for avid boaters and sunset watchers alike. What truly sets this compound apart is what’s included beyond the main house. A second improved waterfront property, directly adjacent, comes with the sale — featuring a substantial garage base suitable for boats and vehicles, and an upper level that opens into a bright, airy great room with a full bath and flexible space ideal for guests, a studio, or a private home office. Completely self-contained, it functions as its own retreat while remaining part of your larger compound. Together, these two properties create something genuinely rare on the Chesapeake — a compound with room to spread out, house your toys, welcome your people, and savor coastal living exactly on your own terms. Whether your vision is multigenerational living, a boater’s paradise, a creative haven, or simply an extraordinary primary or vacation retreat, this Holland Point compound has the bones, the footprint, and the waterfront to make it all possible. Opportunities like this do not come twice.

852 Bay Front Ave, North Beach

Listing courtesy of Compass. Contact: (703) 229-8935

$399,999
2 Beds 2 Baths
Experience waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining guests, or simply enjoying spectacular sunset views over the water. Boating enthusiasts will love the private dock with electric power providing direct access to the Chester River for boating, kayaking, fishing, swimming, and paddleboarding. Your private escape just steps from home. The river truly becomes an extension of your backyard. Inside, the light-filled two-bedroom layout offers comfortable and easy living, making it perfect as a primary residence, weekend getaway, or waterfront investment property. Additional highlights include: • New roof • Public water and sewer • No HOA – enjoy privacy and flexibility • Quiet, scenic waterfront setting Located just minutes from Middletown, Delaware, you'll have convenient access to shopping, restaurants, and medical facilities while still enjoying the tranquility of riverfront living. This is a rare opportunity to own an inviting Chester River waterfront property where stunning views, boating access, and peaceful surroundings come together to create a truly special home.

32135 River Rd, Millington

Listing courtesy of Coldwell Banker Realty. Contact: timothy.dominick@cbmove.com

$2,249,000
8 Beds 9 Baths
Welcome to a rare waterfront masterpiece on a premier point lot in Ocean Pines. Located at 26 W Mallard Drive on a quiet cul-de-sac, this exceptional direct bayfront coastal-style home offers breathtaking, unobstructed views of the Isle of Wight Bay and the Ocean City skyline. Built in 1983 and impeccably maintained, the residence spans just over 5,000 sq. ft. with 8 bedrooms and 8.5 baths, ideal for large gatherings or multi-generational living. Designed to maximize waterfront living, the home features multiple balconies and expansive decks, an outdoor summer kitchen, hot tub, private pier with boat lift, and generous outdoor entertaining spaces perfect for hosting unforgettable bayfront gatherings. Inside, an elevator servicing up to the third level adds convenience and accessibility. The chef’s kitchen is outfitted with 42” cabinetry, granite countertops, stainless steel appliances, multiple ovens, and a GE induction cooktop, complemented by an abundance of storage and prep space. Additional highlights include six refrigerators, a dedicated laundry room, 200-amp whole-house generator, storm shutters, four storage sheds, and an encapsulated crawlspace with dehumidifier and sump pump. Situated within amenity-rich Ocean Pines, residents enjoy access to parks and recreation, aquatics, championship golf, marina, beach club, and more. This extraordinary bayfront property combines space, luxury, and lifestyle—an unparalleled opportunity on Maryland’s Eastern Shore.

26 West Mallard, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$2,250,000
Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to its generous scale and direct river access with 389 feet of rip-rap shoreline. Perfect for your custom estate, family compound, or legacy retreat, this sanctuary marries natural splendor with the refined charm of Talbot County's coastal haven. Spanning 4.18 acres, a fully usable lot provides versatile space to build your future home with breathtaking river vistas. Boasting direct frontage on the Tred Avon River with ample mean low water depth In a market where waterfront estates command premiums, this rare 4+ acre offering represents an unparalleled canvas for your vision. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

Morgans Point Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$599,990
3 Beds 5 Baths
TO BE BUILT WATERFRONT STRAUSS! Welcome to One Westport! Baltimore’s newest waterfront townhome community featuring modern 3- and 4-story garage townhomes with private rooftop decks and scenic views of the Patapsco River and city skyline. Just steps from the MTA Light Rail, One Westport offers easy access to stadiums, dining, entertainment, and cultural hotspots. Convenience, views, and vibrant city living...all in one place. The largest floorplan at Westport, the Strauss offers the space and customizing details of single-family living with the convenience of a townhome, plus incredible waterfront views! A 2-car garage and finished recreation room is included on the lower level, offering an optional first floor bedroom, plus an included 4th floor with rooftop deck and sweeping waterfront and city views is the perfect spot for entertaining! On the main living level, an enormous Kitchen with island opens onto a bright and airy Living Room, perfect for entertaining. A window-lined Morning Room off the Kitchen provides room for dining and is accented with an optional hutch. Up a flight of stairs designed to be elegant and functional, the upper level boasts three bedrooms, two baths, and a 2nd floor laundry. No need to worry about storage space – generous closets abound in all bedrooms. The primary bedroom is a private retreat accented with a tray ceiling and featuring an enormous walk-in closet. The primary bath boasts a soaking tub and separate shower with seat. Let us show you the value of new construction and forget the costly repairs and maintenance of an older home. We stand by our homes, so included is a new home warranty, giving you the peace of mind that you deserve. Other homesites are available. End of Group homesites will be subject to a premium. All photos are representative only. Ask about closing assistance available with use of seller's preferred mortgage. The community is located at the intersection of Waterview Ave & Kloman Street in Baltimore MD 21230

Kloman St & Waterview Ave Unit #WATERFRONT STRAUSS, Baltimore

Listing courtesy of NVR, INC.. Contact: 4108787465

$3,100,000
4 Beds 4 Baths
Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$1,679,000
4 Beds 4 Baths
Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

24390 Oakwood Park Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$1,459,000
3 Beds 3 Baths
**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,950,000
5 Beds 5 Baths
Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

21485 Island Club Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$3,999,900
4 Beds 7 Baths
Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

27473 Westpoint Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,489,000
4 Beds 5 Baths
MOTIVATED SELLERS WITH A BIG PRICE IMPROVEMENT! DON'T MISS THIS BEAUTIFUL HOME ON THE POTOMAC RIVER! Discover ultimate waterfront living at 11260 Keokee Court in Swan Point, MD. Welcome to your dream home on the Potomac River, nestled in the sought-after resort-style community of Swan Point! This stunning waterfront property features over 5,000 square feet of lavish living space, highlighted by it's Luxurious primary suite boosting a stone fireplace, separate sitting area , walk-in closet, and an ensuite bathroom with dual sinks, a large walk in shower, and separate jacuzzi tub to relax and wash the day away. Enjoy the large private balcony overlooking the Potomac river to take in the sun or unwind in the evening after a long day. The guest suite is perfect for accommodating visitors or an au pair, complete with its own walk-in closet, a living area, and a full bathroom. This thoughtfully designed layout includes two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring comfort and privacy for family and friends. The gourmet kitchen is a culinary enthusiast's dream, equipped with high-end Subzero appliances, a generous island, and ample table space for casual dining. A large screened porch off the kitchen invites you to enjoy serene river views while entertaining or relaxing. For elegant gatherings, the formal dining room provides an inviting space for special occasions, while the office/den, with it's cozy fireplace, offers a tranquil workspace. The expansive family room dazzles with a stone fireplace and floor-to-ceiling windows that frame breathtaking views of the Potomac River. Just of the family room you can unwind in the bar/game room that seamlessly transitions to an outdoor oasis. The extensively hardscaped patio with built-in fire pit area and beautifully landscaped yard are perfect for taking in the stars, while the putting green area satisfies the golf enthusiasts. This spacious backyard is ideal for both play and relaxation. Enjoy peaceful mornings by the water, exciting boating adventures, and delightful gatherings in your outdoor haven. The property also includes a private 1,000-foot pier with lighting, water access, and a boat lift, providing easy access to all the recreational opportunities the Potomac River has to offer. As a resident of Swan Point, you'll enjoy a variety of community amenities, including an Olympic-size pool overlooking the water, walking and biking trails, tennis and racquetball courts, a marina, and a sandy picnic area by the Potomac River. The beautiful 18-hole golf course features a putting green and driving range. The Country Club's Restaurant and Bar offers a wonderful dining experience for those evenings when you don’t feel like cooking, along with engaging events such as wine tastings, painting parties, murder mystery dinners, Sunday brunches, and a Summer Concert Series on the veranda. Note*** Just a 25 min drive to Dahlgren Naval Base and an hours drive to Joint Base Andrews and Patuxent River Naval Base. Other exciting conveniences to note, we are a quick 10 minute drive to Cobb Island where there are 4 waterfront restaurants, night life, the Cobb Island Market (offering groceries, fresh produce and a butcher on site) and a Dollar General. Also, Walmart and Target both deliver to the neighborhood! This property isn’t just a home; it’s a lifestyle. Don’t miss your chance to own this exceptional waterfront property!

11260 Keokee Ct, Issue

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$799,000
Discover an unparalleled opportunity to own a stunning 1.69-acre parcel of land nestled along the serene banks of Hickory Landing Creek. This exclusive waterfront property boasts an impressive 400 feet of pristine water frontage, offering breathtaking panoramic views that will captivate your senses and inspire your imagination. Imagine waking up to the gentle sounds of nature, with the shimmering waters just steps away. This idyllic location is a haven for water enthusiasts, providing private access for fishing, boating, kayaking, and swimming. Whether you seek tranquil afternoons on the water or exhilarating adventures, this property caters to your every desire. The lush landscape surrounding the creek creates a picturesque backdrop, perfect for crafting your dream retreat or luxurious residence. With riparian rights, you have the freedom to enhance your waterfront experience, including the potential for a private dock site, allowing for seamless access to your favorite water activities. Embrace the exclusive lifestyle that comes with this remarkable property, where every day feels like a vacation. The combination of natural beauty, water access, and the potential for luxurious development makes this land a rare gem in today's market. Don't miss your chance to create a legacy in this enchanting setting, where luxury meets nature in perfect harmony. Potential for 2 building sites with creek views. Original cabin still on property but not habitable. Previous septic system exits but cannot be used again and must be reperced for new system. Deep water and previously there was a pier on the shore. Truley one of the nicest lots on the water.

45410 Clarks Mill Rd, Hollywood

Listing courtesy of United Real Estate Premier. Contact: 3017875000

$575,000
3 Beds 2 Baths
With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

20160 Garrett Hwy Unit #F501-701, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$749,900
3 Beds 3 Baths
What an opportunity to own a condo located in a Bayfront building, featuring not only Bay views, but also Ocean and City views. Enter this 3 bedroom 3 bathroom condo and you will immediately notice that both guest rooms have their own attached bathrooms allowing guests privacy and convenience. Continue down the entrance hallway taking in the ceramic tile floors that lead you to a large kitchen with stainless steel appliances, ceramic tile backsplash, and granite countertops. You will be astounded by the views from this end-unit condominium with 3 sliding glass door in the great room. The floors in the dining room and living room are maintenance free luxury vinyl plank and this area also features a gas fireplace for warming up on chilly nights. Step outside and take in all of the natural beauty Ocean City has to offer from the oversized wrap around balcony just off of the great room. The luxury vinyl plank flooring continues into the primary bedroom that has it's own sliding glass door and bay views. The primary bedroom also has a walk in closet and oversized bathroom with jetted bathtub and walk in shower. The Bella Vista complex features a secure lobby, bay view glass elevator, indoor and outdoor pools, and an abundance of parking. The close proximity to miniature golf and popular restaurants ensures you will always have entertainment! The complex is professionally managed by a local management company providing that regular maintenance to the building is completed. Take a look at this condo that has everything you are looking for in a second home or investment property.

4601 Coastal Hwy Unit #501, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$499,900
2 Beds 2 Baths
Enjoy waterfront living with this cottage style home offering breathtaking views of the Patuxent River and St. Thomas Creek. The open main-level floor plan of this 2BR 2FB home captures water views from most areas of the home, as does the rear of the fully finished walkout-level basement. The spacious walk-up attic could potentially offer future expansion into a third floor, perhaps maybe with dormers, to further expand living space with even more stunning panoramic views. Enjoy the outdoors from the large rear deck or take advantage of direct water access with a private pier, jet ski ramp, boat lift, pier-side storage shed, and small beach area at the water’s edge. The pier provides easy access to navigable waters, perfect for boating, fishing, and exploring the Patuxent River, the Solomons Island area and the many Chesapeake waterways. A detached screened patio with a wood burning stove invites outdoor dining or peaceful relaxation with picturesque water views. Set in a peaceful, private country setting, this property invites you to entertain or just simply relax and unwind while enjoying unforgettable sunrises and sunsets over the water, all from the comfort of your own backyard. Don't miss this rare opportunity to enjoy your own piece of waterfront paradise. The horse shoe style driveway with parking area offers plenty of off street parking. The home is being sold in as-is condition. Current septic system has failed and seller is in current contact with the St. Marys County Health Department determining what septic options will be available for buyer installation upon purchase. The cost of the system replacement could potentially be offset through the The Maryland Bay Restoration Fund. Interested purchasers may want to contact the St. Mary’s County Health Department’s Clear Water Program, which administers the Bay Restoration Fund (BRF) in St. Mary’s County, for further information.

43979 Drum Cliff Rd, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$6,499,900
8 Beds 9 Baths
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$850,000
3 Beds 4 Baths
Coastal Living at Its Best in Island Cove Imagine waking up to the gentle shimmer of the water and the scent of salty ocean air. This beautiful three-year-young condo in Island Cove captures the essence of coastal living, offering serene water views, modern finishes, the perfect blend of comfort and convenience, and is being sold fully furnished for a turnkey experience. Situated between the ocean and the bay, this contemporary retreat features three levels of outdoor living, each with its own balcony to take in the ocean breezes and stunning views. Step outside your front door, hop on your boat, and set off for your next adventure, whether it’s boating, fishing, or simply cruising the bay. Inside, you’ll find light-filled spaces styled in soothing coastal tones. The entry level features a private bedroom with a sliding barn door leading to an attached bath, plus direct access to the two-car garage. The main living level is open and airy, designed for easy entertaining and relaxed everyday living. The kitchen boasts white quartz countertops, sleek tile backsplash, stainless steel appliances, and an island with seating that’s perfect for gathering with friends and family. Flowing seamlessly from the kitchen are the dining area and spacious living room, which opens to a balcony where you can unwind and enjoy the view. Durable LVP flooring runs throughout this level, adding both beauty and practicality. Upstairs, you’ll find two spacious bedrooms, each with its own private en suite bath. The primary suite is a true retreat, featuring a vaulted ceiling, private balcony, and a spa-inspired bathroom with a dual vanity and a glass-enclosed tiled shower with a rain shower head. Whether you’re looking for a full-time residence, vacation home, or investment property, this Island Cove condo offers a low-maintenance, high-style lifestyle just moments from the sand, surf, shopping, and dining.

212 25th St, Ocean City

Listing courtesy of Northrop Realty. Contact: (302) 539-2900

$3,400,000
7 Beds 7 Baths
Welcome to this one of a kind house design built by John Heagy, a masterpiece, in highly sought-after Long Beach Estates — a true coastal craftsman estate that defines luxury and timeless design. Boasting 7 bedrooms and 7 baths, this home offers over 2.47 acres of beautifully landscaped grounds with expansive waterfront views. Two first-floor primary suites provide convenience and comfort, while a chef’s gourmet kitchen with a butler’s pantry makes entertaining effortless. Enjoy movie nights in your six-person theater room, or step out from any main-level room onto multiple covered flagstone patios—the perfect spots to take in the tranquil scenery. The second floor features five additional bedrooms, each with its own bath, and a covered porch with a stunning mahogany ceiling. This home was built to last, built for entertaining, and built to impress. Bring all your toys — there’s room for everything with an attached 3-car garage and a breezeway leading to a matching 35x60 toy garage with one 10ft garage door and another 14ft door, perfect for your boat, RV, or car collection. The property is less a golf cart ride away from a luxury yacht basin, plenty of entertainment, and social gatherings, private beach and pool, with other yacht owners...the perfect spot to keep your own yacht!! This is not just a home — it’s a lifestyle, a statement, and a legendary purchase.

1206 Chesapeake Ave, Middle River

Listing courtesy of RE/MAX Advantage Realty. Contact:

$999,000
4 Beds 4 Baths
Boat Slip included with Purchase for Limited Time !! Absolutely Stunning Villa MOVE IN READY in Ocean City! This MOVE IN READY Villa showcases an open concept perfect for entertaining! LVT through the main living areas set the tone for the tastefully designed space. Let's get cooking! Stainless Steel Appliances, White Kitchen Cabinetry with Soft Close, Quartz Countertops, Recessed Lighting, and an Electric Stove make cooking and cleanup a breeze! With so many amazing places to enjoy your meal, Morning Breakfast/ Brunch in the Dining Area or Kitchen Island, Relax with Morning Coffee on the Deck overlooking the Beautiful Bay Views. Time to unwind and Snuggle up for a movie by the Fireplace after a long day soaking in the sun. Primary Suite Boasting Walk in Closet, En - Suite with Soaking Tub, double vanity and access your private Deck. This sprawling Villa Showcases 3 Other Bedrooms and 3 Full Baths. Not that you should ever need to leave this amazing Space but if Sunshine is what you are looking for... Take in All Ocean City has to Offer with just a short Walk to all the Major Attractions. Headed back from the beach and don't want to bring the sand inside? Rinse off in the Outdoor Shower. Covered Parking to keep your car cooler on those hot summer days! Take Advantage of dock access to our Private Boat Slips with Electric & Water available with purchase for a limited time! Welcome Home to Son Ray Villas! ** Furnished Unit Options Available. Interior Photos Virtually Staged.

1505 Saint Louis Ave Unit #301, Ocean City

Listing courtesy of The Pinnacle Real Estate Co.. Contact:

$5,000,000
3 Beds 4 Baths
Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$1,275,000
3 Beds 4 Baths
REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AND a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. The result was a wider Dining Room adding more natural light, wider decks, and more WATERVIEWS! Inside you'll find an open floor plan that's perfect for entertaining! It has hardwood floors, a dramatic floor to ceiling stone fireplace, a gourmet kitchen with high end newer stainless steel appliances & finishes, granite countertops, and ensuite bathrooms in all the bedrooms! Enjoy Beautiful Water Views from nearly every room thanks to thoughtfully designed architectural windows. Two covered decks with remote controlled screens invite you to relax and take in the breathtaking views over the Chester River. You also have a 2 car attached garage! Located in an exclusive gated community on a private peninsula, this home backs up to the renowned Safe Harbor Marina that offers a pool, fitness center, and over 600 slips, making it a boaters dream! Narrows Pointe is just around the corner from many great ( docking) restaurants, tiki bars, coffee and dessert spots! Golf enthusiasts will love being just 5 minutes from Queenstown Golf Links, close to other courses too! Outlet shopping is nearby for convenience. Only 20 minutes from Annapolis and Easton, 45 minutes from BWI Airport, 55 minutes from Washington, DC & Baltimore, and 1 1/2 hours away from Ocean City ! Whether you're looking for a year-round residence or a weekend retreat, this home offers the ultimate Chesapeake Bay lifestyle !

346 Narrows Pointe Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$2,549,000
2 Beds 3 Baths
Welcome to the Four Seasons Private Residences in the heart of Harbor East, where luxury, location, and lifestyle converge. From the 23rd floor, this gorgeous 2-bedroom, 2.5-bathroom residence offers spectacular views of the Inner Harbor and marina and the Baltimore city skyline through floor-to-ceiling windows. This refined residence features rich walnut herringbone flooring, a gas fireplace, and high-end finishes throughout. The gourmet kitchen is outfitted with elegant cabinetry, a gas cooktop, wall oven, huge island with breakfast bar, and elegant quartz countertops. The adjacent dining area and wet bar with sink and wine fridge are ideal for entertaining or for a quiet night at home. The primary suite includes a custom walk-in closet and a luxurious marble bathroom with double sinks, a large soaking tub, and separate shower. A second bedroom, also nicely sized, offers comfort and privacy for guests or family. Enjoy your morning coffee or evening wine on the private balcony, and enjoy the shimmering waterfront and Baltimore skyline. As a resident, you’ll have exclusive access to the private 28th-floor amenity level featuring an indoor saltwater infinity pool, sauna, outdoor deck, fitness center, meeting rooms, and lounging areas — plus a dog-walking area for your furry family members. You’ll also enjoy full access to all hotel amenities, including the outdoor pool and valet services. This property comes with one dedicated parking space in the garage with easy resident access. The Four Seasons features four on-site restaurants, and many amazing dining options just a short walk away in Harbor East and Fells Point. Shopping, parks, harbor activities, museums, and miles scenic waterfront walkways are all close enough to enjoy every day. Experience luxury living at the Four Seasons, it’s more than a residence, it’s a lifestyle.

300 International Dr Unit #2301, Baltimore

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435

$260,000
1 Baths
****Owner occupied but easy to show.**** Take advantage of this prime, Direct Oceanfront opportunity showcasing breathtaking views in the highly sought-after North Ocean City! This southern exposure, end-unit property is complete with an updated bathroom and kitchen, new luxury vinyl plank flooring, beautiful granite countertops, a glass tile backsplash, stainless steel appliances, a portable cooktop, Ninja Air Fryer and a high-end Advantium microwave/conventional oven for your effortless culinary endeavors. The Murphy bed and sofa comfortably accommodate up to four, while a custom-built closet provides ample storage. Enjoy the spacious balcony that offers panoramic views of the dunes and the ocean. Keep an eye out for the saltwater foxes that travel the dunes, adding a touch of coastal wildlife charm to your surroundings. This condo features brand new hurricane shutters, an on-demand hot water heater, central A/C, two new ceiling fans, and a sizable storage room beneath the building for all your beach essentials. Being sold furnished with minor exclusions. The building is further highlighted by an elevator, swimming pool, an outdoor shower to rinse off the sand after a fabulous beach day, and a 24/7 on-site resident manager. Enjoy the rarity of low condo fees and taxes. Additionally, there's a convenient on-site laundry room. Ideally located within walking distance of Northside Park, Starbucks, Tailchasers Restaurant, Grotto Pizza, and so much more! As a delightful bonus, savor unobstructed views of fireworks from the bay side of the building. This is a unique opportunity to experience coastal living at its finest. Don’t wait, book your showing appointment today! Cash preferred or BOC funding exclusively at 50% down or less pending buyer qualification.

12305 Wight St Unit #310, Ocean City

Listing courtesy of Northrop Realty. Contact: (302) 539-0800

$799,900
2 Beds 3 Baths
Bayfront Luxury in Prestigious Harbour Island – Home of the White Marlin Open Step into coastal sophistication with this rare southern-facing end-unit townhouse in the exclusive gated community of Harbour Island, host of the world-famous White Marlin Open. Perfectly positioned on the bay front with sweeping views of Assateague Island, the marina, and open water, this 2 bedroom, 2.5 bath residence seamlessly blends luxury living with effortless style. Impeccably maintained and thoughtfully upgraded, this home has been decorated with designer furnishings and curated finishes, and also offers proven investment potential as a high-end seasonal rental, grossing $40,000–$50,000 annually. Inside, natural light pours across freshly painted interiors and new upstairs flooring. A wood-burning fireplace anchors the living space, complemented by Pottery Barn lighting, custom window treatments; Plantation Shutters, and Vertiglide sliders by Designing Windows. The gourmet feel is elevated with four spacious balconies offering private outdoor retreats—each with breathtaking water views and premium Telescope outdoor furniture included. Recent enhancements include a completely remodeled powder room (2020), new mini-split and heat pump systems both upstairs and down (2020), custom closet installations throughout, new shower door sliders, and a newer stackable washer/dryer. Comfort and convenience are built in at every turn, including a professionally installed EV charger in the garage. Whether entertaining or unwinding, this residence offers an unmatched lifestyle: four balconies for dining or relaxing against a backdrop of boats in the marina, sunsets over the bay, and panoramic views stretching to Assateague. Offered fully furnished with high-end pieces, this turnkey home allows you to enjoy the best of Harbour Island immediately—where world-class fishing, the excitement of the White Marlin Open, and the vibrance of Ocean City are all at your doorstep. Boat slips available for purchase. Call us today for an exclusive showing!

401 14th St Unit #1, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$415,000
6 Beds 3 Baths
Beautiful Waterfront Retreat on Tangier Sound Welcome to the island life! This unique waterfront home offers a rare opportunity to own a property with 180 feet of bulkhead on the navigable Tangier Sound. Imagine spending your days crabbing and fishing right from your own backyard, and your mornings with a cup of coffee watching breathtaking sunrises. The evenings are just as magical, with romantic sunsets that are perfect for a quiet glass of wine. The home's main floor features an open floor plan with a combination living room and kitchen, complete with new granite countertops. The upstairs loft is a versatile space with two large rooms, both offering incredible water views of the Tangier Sound. From here, you can watch crab and oyster boats sail by from the nearby marina. The property also includes a separate laundry room and a double-car garage with high-bay doors, perfect for storing extra-large items. A public boat ramp is less than five minutes away, so you can easily launch your boat, jet skis, kayaks, and canoes. This is your chance to enjoy your very own waterfront island property! More Details This home has three bedrooms and two full bathrooms. There are three additional guest rooms, perfect for visitors. The owner has more renovations planned and is willing to work with the buyer to choose some of the final updates. Don't let this incredible opportunity pass you by!

10515 Cassandra Dr, Deal Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4105463211

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