Refine Search
Sort by
$1,899,900
5 Beds 5 Baths
Lakefront Craftsman in one of Deep Creek Lake's finest communities. This 5-bed 5-bath home directly adjoins Deep Creek Lake with 100 ft of frontage and your very own boat slip. Clean, contemporary build with 3,788 finished sqft on 0.86 acres. Recently updated with new flooring, modern kitchen, bathroom vanities and rustic timber accents. Open main level with cathedral ceilings, hardwood floors, wood-burning fireplace, and a quartzite-topped kitchen with island and breakfast bar. Main-level primary suite plus two additional ensuite bedrooms. The walkout lower level adds a second living space with a gameroom, gas fireplace, and wet bar. The attached Indoor pool with a brand new liner sets this one apart. EV Charger included. Outdoor living includes a hot tub, fire pit, and a level yard at the water’s edge. Wraparound and screened decking to take in the lake views. An established rental, "Stilwater Serenity" makes an excellent private mountain/lake retreat or something that helps pay for itself when you're not using it. Call today for details!

200 Stilwater Dr, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$1,169,000
5 Beds 3 Baths
Enjoy approximately 5 ft water depth at your private pier on protected Whitemarsh Creek, off Rhode River—just a short boat ride to the Chesapeake Bay and all your favorite waterfront dining destinations! This property is built for both relaxation and entertaining, featuring a spacious TimberTech deck with stunning water views—perfect for hosting gatherings or enjoying peaceful evenings by the water. A 20,000 lb boat lift with remote makes boating effortless. Inside, you’ll find a flexible and inviting layout with: 2 bedrooms and 2 full baths on the main level, 3 additional bedrooms upstairs (one currently configured as an oversized walk-in closet—easily converted back), a very large owner’s suite with its own walk-in closet, a bright four-season room with a separate in-wall A/C unit and convenient dog door. The half-acre lot at the end of the street offers exceptional privacy, complemented by a flat, fenced yard—ideal for pets, play, and outdoor enjoyment. A charming paver walkway leads to the waterfront, enhancing the home’s outdoor appeal. Seller updates include: New Roof (2020), Two new high-efficiency heat pump systems, newer stainless steel appliances, including an induction stove, Updated flooring on main level, deck (2024), W&D (2021), sump pump, and recently cleaned vents. Opportunity knocks: The home offers a fantastic footprint for those looking to personalize and modernize. With great bones, waterfront location, and generous space, it’s the perfect canvas to create your dream home. ✨Wraparound porch. Private setting. Boater’s lifestyle. Endless potential.

3893 Cotter Dr, Edgewater

Listing courtesy of RE/MAX Leading Edge. Contact:

$189,000
Rare Easton Building Lot with Creek, Woods & Endless Possibilities Discover one of Easton's hidden gems! This beautiful, one-of-a-kind lot offers a private backyard sanctuary featuring a picturesque creek flowing through the property and peaceful wooded views. Nestled in a desirable family-friendly neighborhood, the lot is within walking distance of schools, ball fields, and community amenities. Whether you're planning to build your dream family home or a duplex investment property, this parcel is ready for development with essential utilities available, including broadband internet, public water, and public sewer. Opportunities like this are hard to find—enjoy the perfect blend of natural beauty, convenience, and development potential in a truly unique Easton location. Don't miss your chance to own this exceptional property!

Mecklenburg Ave, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$329,900
2 Beds 2 Baths
This stunning 2-bedroom, 2-bathroom condo offers the perfect blend of modern luxury and serene waterfront living. This charming home offers a modern and serene lifestyle, featuring recent updates that elevate its appeal. The bright and spacious living area flows seamlessly into a contemporary kitchen, equipped with stainless steel appliances and ample storage. Step outside to enjoy the community's private pool and picturesque picnic area right on the water, perfect for relaxing and socializing. Additional conveniences include an exterior storage closet and an in-unit laundry. Located in a prime area, this condo offers easy access to shopping, groceries, local movie theater, and, of course, the beautiful BEACH! Embrace the perfect blend of luxury, convenience, and waterfront living in this exceptional condo. **New Air Conditioning system installed 6/25**New Luxury vinyl plank flooring 3/26

170 Captains Quarters Rd Unit #201, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$8,995,000
6 Beds 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$274,600
1 Baths
Wake up to breathtaking sunrises and unwind with sweeping sunset views in this beautifully updated oceanfront penthouse studio, perfectly positioned with coveted southern exposure. Offering expansive panoramic vistas of both the ocean and bay, this light-filled retreat captures the essence of coastal living. Inside, the space has been thoughtfully refreshed with new Coretec flooring and fresh, modern paint, creating a clean and inviting atmosphere that complements the natural beauty just beyond your windows. The open layout maximizes both comfort and functionality, making it ideal as a serene getaway, investment property, or year-round residence. This unit is being sold fully furnished and is truly turn key for immediate enjoyment from day one. Simply arrive and start your oceanfront escape! Whether you're enjoying your morning coffee while watching the waves roll in or taking in the tranquil bay views at dusk, this studio delivers an unmatched coastal experience. Don’t miss this rare opportunity to own a slice of paradise with dual water views and stylish recent upgrades. Professional photos coming soon.

10300 Coastal Hwy Unit #1802, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$1,778,000
4 Beds 3 Baths
Location, Location, Location! Direct Oceanfront Penthouse Living- This is truly a rare opportunity—the first time this spectacular penthouse unit has ever been offered for resale! Located on the 8th-floor southeast corner, this 4-bedroom, 3-bath condo delivers breathtaking, unobstructed ocean views that stretch for miles. Enjoy one of the largest balconies in Ocean City, with approximately 60 linear feet of covered and uncovered space—perfect for soaking up the sun, relaxing in the shade, or taking in both stunning sunrises over the Atlantic and sunsets over the bay. Situated in the highly desirable Calypso Condominium, a beachfront building in mid-town Ocean City, this property is known for its spacious private balconies, outdoor pool, and unbeatable central location near restaurants, shopping, and local attractions. With direct beach access and convenient proximity to Route 90, getting around town is effortless. Inside, you’ll find a beautifully designed kitchen featuring granite countertops, ample cabinetry, and generous counter space, flowing seamlessly into the dining area where you can enjoy incredible views down the beach. The oversized family room offers the perfect space for entertaining family and friends and opens directly onto the expansive balcony, where you can enjoy both covered seating for cool summer breezes and an uncovered area ideal for sunbathing. The primary bedroom is oceanfront with private balcony access and a spacious en-suite bath, while a second oceanfront bedroom also offers balcony access, allowing guests to enjoy the same stunning views. Two additional bedrooms and bathrooms provide plenty of room for family and visitors. The building features a large outdoor swimming pool perfect for relaxing after a day at the beach, along with elevator access for convenience and both a deeded parking space and an additional space, ensuring plenty of parking for you and your guests. You also have an assigned storage locker on the ground flood for your beach gear. This property would make a wonderful second home or vacation rental it is well-suited for family vacations thanks to its layout, amenities, and prime location. If you’ve been waiting for the ultimate Ocean City penthouse with unmatched views, space, and comfort-this is it!

6201 Atlantic Ave Unit #806, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$565,000
3 Beds 3 Baths
WOW, you are absolutely going to fall in Love with this adorable cottage that is just steps from a trail that will lead you to a secluded beach along the shoreline of the Chesapeake Bay. Located on a quiet street in the amenity rich community of Chesapeake Ranch Estates. This community offers so much: -> Airport -> Campgrounds -> Clubhouse -> 2 Amazing Beaches on the Chesapeake -> Community Gardens -> Horseshoe Pit -> Lake Lariat + Beach -> Walking Trails and more! This well designed cottage was built in 2014, and offers a light filled primary suite on the waterside of the main level along with an open floorpan where the kitchen, dining and family rooms flow seamlessly together. The 2nd level is well appointed with two nicely sized guest bedrooms that are divided by a Jack & Jill full bath. The views of the Chesapeake can be enjoyed from most rooms within the house, as well as the rear deck, or the bayside fire pit area a perfect spot for watching the boats and ships pass while enjoying quality time with friends and family. Let the sounds of the Chesapeake sooth your heart, mind and soul in a home that offers just what you need without all the complications.

12468 El Dorado Ln, Lusby

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

$235,000
3 Beds 2 Baths
* * * WATERFRONT * * * Updated 3-4BR/2BA American Foursquare with private dock and little pond-front beach. Updates galore - vinyl replacement windows, gorgeous + durable luxury vinyl plank flooring throughout, architectural-shingle roof, kitchen, baths, fixtures, + more! Charming front porch leads into the welcoming foyer. Spacious living room. Bright + cheery kitchen - granite counters, dining area, breakfast bar + nook. 1st floor BR w/ full, en-suite bath - could also function as a study or guest room. Upstairs, 3 additional bedrooms, 2nd full bath. Unfinished basement completes the home's interior. Enjoy autumn mornings on the large deck overlooking your expansive pondfront yard. Great location - minutes to locals' favorite shopping, dining, + plenty of community events in Downtown Salisbury. Conveniently located to public parks, golf, beloved Salisbury Zoo. Sizes, taxes approximate

1002 W Main St, Salisbury

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$2,349,000
3 Beds 4 Baths
Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like a getaway and every detail is designed for ease. This completely renovated property offers the perfect balance of charm, comfort, and low-maintenance living, making it an ideal full-time residence or lock-and-go retreat. New owner’s thoughtfully completed the whole house renovation in the last year, with additional second floor Restoration Hardware full bath, creating beautiful 2nd upper level bedroom suite, updated kitchen and appliances, new first floor flooring, custom designed kitchen pantry and primary bedroom closet by Chesapeake Closets, raised lower level ceiling to 10’, fresh paint inside and out, all decks and staircase to water polyurethaned, significant landscaping and hardscaping of entire property with expanded driveway to 3-4 cars, new Ring security system and Leaf Gutter system, and more! Previous owner recent improvements in last 1 to 2 years include, new second floor dormer, covered balcony, windows and flooring, new primary bedroom full bath and lower level full bath with Restoration Hardware, new 1st floor gas fireplace and mantel, new roof, new pressure treated stairs to water, new deep water 50’ floating dock with water and power. The home is move-in ready and designed to maximize both lifestyle and convenience. Inside, tall ceilings and walls of windows invite natural light to pour in while framing the surrounding landscape and wide, open water views. The open floor plan creates an easy flow between the gourmet kitchen, dining area, and living room with fireplace, all seamlessly extending to the waterside covered porch, an inviting space for al fresco dining, morning breezes, or unwinding after a day on the water. Upstairs, two ensuite bedrooms provide private retreats, including a serene primary suite with its own balcony overlooking the water, perfect for capturing sunsets and summer breezes. The lower level offers additional flexibility with a family room, guest bedroom, and full bath, ensuring plenty of space for visiting family and friends. Outdoors, the boating lifestyle takes center stage. The recently built deep-water floating dock with a 50-foot slip, complemented by a dedicated mooring ball defensive, creates an exceptional setup for effortless days on the water with quick access to the Severn River, Annapolis Harbor, and the Chesapeake Bay beyond. Epping Forest enhances the experience with a vibrant, amenity-rich setting, offering a clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, and scenic walking trails, along with a full calendar of social events and clubs. All just minutes from downtown Annapolis and convenient commuter routes, this is a rare opportunity to enjoy a truly turnkey waterfront lifestyle in one of the area’s most cherished communities. Epping Forest is a Special Tax District ($2,934.96/yr.) with binding Rules & Regulations. Welcome Home!

327 Riverview Trl, Annapolis

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

$525,000
3 Beds 4 Baths
Save up to $320/month with a Lender Paid 1 Point Buy Down with accepted offer by 6/30/26 - Ask Lender for details! Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $540,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

$389,000
1 Beds 2 Baths
Make the most of waterfront living in this charming two-story, one-bedroom, 1.5-bath condo, beautifully updated and offering its own private deep-water boat slip with quick access to the open bay. The home features an open living-and-dining layout with a complete floor replacement (¾-inch plywood and ½-inch OSB) topped with luxury vinyl flooring. The living space opens directly to your private deck overlooking the water, creating the perfect setting for relaxing or entertaining. The updated kitchen includes stainless steel appliances, granite/quartz countertops, and a convenient breakfast bar. Upstairs, the primary suite has been fully renovated, featuring new drywall, recessed lighting, and a spa-like bath with a tile-enclosed shower, double vanity, and heated floors. No detail has been overlooked. Additional highlights include an encapsulated crawl space with a dehumidifier and thoughtful upgrades throughout, making this a true turn-key property. Located in the well-maintained Old Port Cove community, residents enjoy a community pool, large overflow parking area, and a welcoming pet-friendly environment. Just a short walk to the beach, boardwalk, and local dining and shopping, this condo offers everything needed to embrace the coastal lifestyle. Don’t miss this rare opportunity to own a fully renovated waterfront home with a private boat slip.

2817 Tern Dr Unit #28D4, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$1,349,000
Discover a rare opportunity to own 180 feet of prime Deep Creek Lake frontage along the highly sought-after Marsh Hill Road, just steps from the year-round recreation of Wisp Resort. This unique lakefront property offers incredible flexibility, whether you're looking to build a private estate or develop multiple homes,. The parcel can be utilized as three separate 60-foot building lots, each with its own single-slip Type A dock permit—perfect for individual vacation homes or resale. Alternatively, combine into two 90-foot lots with unrestricted Type A dock permits for larger lakefront retreats, or retain the full 180 feet for an expansive dream home with panoramic water views and ample space for outdoor living. Adding to its value, the property also includes a quarter-acre lot directly across Marsh Hill Road, ideal for constructing a guest house, carriage home, or additional garage space. With a mostly level approach to the water, utility access at the street, and unmatched proximity to skiing, golf, marinas, and restaurants, this offering combines convenience, natural beauty, and development potential. Whether you're a builder, investor, or dream-home buyer, this is a once-in-a-generation chance to secure premier shoreline on Deep Creek Lake within close proximity to Wisp Resort. Don’t miss out—properties of this caliber are rarely available. Parcels are also available for sale separately.

Marsh Hill Rd, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

$1,295,000
5 Beds 3 Baths
Welcome home! The sunrises are amazing and the sunsets are inspirational in this five bedroom, architect-designed, two-level colonial that sits nestled in privacy along Lyons Creek and the Patuxent River amid 5.8 acres of woodlands and waterfront. Includes a private pier/dock with a boat lift as well as community boat dock. Massive kitchen and living room with multiple attached porches and patios are perfect for entertaining. Three of the Five bedrooms (including the large downstairs owners’ suite & 2 west-facing bedrooms upstairs), have open views of Lyons Creek and the Patuxent River. Check out the upper and lower verandahs perfect for contemplative morning coffee times or evening reading with a glass of award wining wine. House is much larger and still has second areas that could be turned into additional living space. The upstairs bedrooms each come with walk-in closets, private entries to the covered verandah, and a jack-and-jill bathroom. The third upstairs bedroom is east-facing and spacious with an extra large walk-in closet, and an even larger adjacent unfinished attic space that has many potential uses. The downstairs guest bedroom is east-facing and adjacent to a large, well-lit rec room with wood-burning stove and private entry. It also has direct access to a full-size bathroom with a jacuzzi tub. This guest bedroom can alternatively be used as a downstairs private office. The modern kitchen is well-equipped with spacious granite countertops, a 6-burner Viking gas stovetop, Wolf multi-function full-size oven, built-in CAFÉ Advantium microwave & convection oven, Kenmore dishwasher, abundant oak cabinetry and floors throughout, built-in kitchen desk, and a large refrigerator that blends seamlessly with the wooden cabinetry. The house is designed with gatherings in mind, and the open-plan, eat-in-kitchen, and adjacent living area share an awesome 2-sided fireplace (originally woodburning, converted to gas). The downstairs owners’ suite includes a large bedroom, two walk-in closets, and an adjacent bathroom suite with heated stone tile floors, a soaking tub with waterfront views, a stone tile shower, individual his and her sinks, and a privacy closet with toilet and a separate sink. An additional ‘hobby room’ provides a 2nd refrigerator and additional cabinets and countertop spaces, as well as a built-in ironing board, for crafting and storage. This room adjoins the spacious laundry room next door which has additional storage cabinets. Beyond the laundry room, there is an additional climate-controlled storage room for cleaning and maintenance supplies. For vehicles and additional storage, there is a detached 3-car garage with an open upstairs loft space. The garage includes an attached fully-enclosed garden shed on one side, and an attached carport on the other. The Patuxent Palisades neighborhood is a highly desirable community. The neighborhood amenities include a shared park with pond, paved walking trail, play equipment, and tables and chairs for picnicking; a boat dock on the Patuxent River; and seasonal community activities. Experience and view the wonder of nature with bird-watching, boating, kayaking, canoeing, paddleboarding, water-skiing, hiking, camping, and fishing available right in your backyard. This easy to maintain 5.8 acre lot offers plenty of room for exploring. The Chesapeake Bay is less than 15 miles to the east, and Washington DC is only 30 miles to the northwest. For the everyday necessities, Dunkirk Town Center, with three grocery stores and all the other services, is just minutes away . Schools are close by as well. Check out the community park. Community has a gated private dock access for larger boats. Call your Realtor and come see this unique and delightful property.

12124 Palisades Dr, Dunkirk

Listing courtesy of Tyler Duncan Realty Partners, Inc.. Contact:

$329,900
1 Beds 1 Baths
Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks, and boating convenience—all just steps away. This property is not only the perfect getaway, but also a proven Vacation Rental Income Producing Condo —Recognized as one of the top-performing rental units in the SilverTree building, averaging $30,000 per year in Vacation Rental Income. Whether you're looking for a low-maintenance lake retreat or a high-performing income-producing property, this unit delivers the best of both worlds in one of Deep Creek’s most desirable lakefront communities. Call today to schedule a private showing.

565 Glendale Rd Unit #125, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$645,000
4 Beds 3 Baths
Motivated Seller-Make your waterfront dream a reality! Welcome to this stunning 4-bedroom, 3-bath brick home on Rumsey Island, offering breathtaking water views and exceptional indoor-outdoor living. Designed with an open-concept layout on both the main level and fully finished lower level, this home is perfect for relaxing and entertaining. The beautifully crafted sunroom features cathedral ceilings and panoramic views of the water, filling the space with natural light and serenity. Step outside to enjoy 112 feet of prime waterfront, complete with a private 35-foot dock equipped with electric and water—ideal for boating enthusiasts. Multiple outdoor spaces, including two decks, a patio, and a charming gazebo, provide the perfect setting for gatherings or quiet moments by the water. The finished lower level adds incredible versatility with a cozy fireplace, wet bar, additional bedroom, full bath, and walk-out access to the backyard and waterfront. This pet-friendly home also includes thoughtful features like multiple doggie doors and a fenced area in back. Additional highlights include stainless steel appliances, built-in lighting throughout, fruit trees, a new bulkhead, tankless water heater, and new fencing for added privacy. With endless amenities and a setting that feels like a private retreat, this is a rare opportunity to own your own piece of waterfront paradise.

112 Shell Cove Ct, Joppa

Listing courtesy of Weichert, Realtors - Diana Realty. Contact: (410) 893-1200

$449,900
3 Beds 2 Baths
This condominium in the upscale Harbour Lights community offers what is possibly the most premium waterfront location in Somerset County! Top floor, corner unit has spectacular unobstructed nearly 360 degree panoramic views of the Tangier Sound, Annamessex River, Crisfield City Dock and beyond to the Bay! Witness "life on the bay" with the passage of both recreational and commercial boat traffic passing before your eyes! Wraparound deck provides views and screened porch space to the west(for our truly spectacular sunsets) , north and east! Kitchen has all upgraded black stainless appliances, granite countertops, tile flooring. Dining area and living room have wood flooring. Laundry has upgraded appliances. Primary suite has direct access to the screened porch and a large primary bath with jetted tub and shower, and walk in closet. Two additional bedrooms have a hall bath conveniently located nearby. The well maintained pool is a bonus, and there are boat slips available in the Harbour Lights marina. A short drive will take you to Janes Island State Park, renowned for waterfront camping facilities and a natural protected environment. Enjoy nature kayaking and bird watching in a peaceful surrounding. Nearby is the Crisfield Airport for aviators. Family friendly Crisfield has festivals and activities all summer long. If you want to visit Smith or Tangier Islands, the ferry boats are located just at the City Dock, or take your own boat 12 miles to experience island life. Harbour Lights has security access to both the lobby and the pool area. All furnishings can be purchased at a reasonable cost.

103 Williams St Unit #617, Crisfield

Listing courtesy of Wilson Realty. Contact: (410) 968-1882

$2,295,000
4 Beds 4 Baths
Set on a 2.38 acre peninsula with 1,100 feet of waterfrontage, 1301 Broadview Drive is a thoughtfully crafted waterfront retreat defined by exceptional materials, timeless detail, and water views from every room. The exterior pairs stone and cedar shingles with copper lanterns and bluestone hardscaping for a classic Eastern Shore look, while inside, custom millwork, mahogany accents, brass floor registers, and a refined mix of designer fixtures and finishes create a warm and elevated feel throughout. The main level is designed for both everyday living and effortless entertaining, centered around an open gourmet kitchen with Shaw fireclay sinks, Waterworks fixtures, marble counters and backsplash, a mahogany island, and a fully integrated appliance suite. A beautifully finished butler’s pantry, breakfast area with custom bench seating, and great room with custom built ins and a gas fireplace with marble surround add both style and function. A dining room, library or office with built ins, powder room, mudroom, and laundry room complete the main level, while the covered deck provides the perfect place to take in the sunset. Upstairs, the private spaces are equally inviting, highlighted by a serene primary suite with a large walk-in closet, private deck, and a spacious marble bath with soaking tub and custom shower. Additional bedrooms offer custom closets, designer lighting, and beautifully finished baths, while a gym and rear upper deck add to the home’s comfort and flexibility. Outside, sweeping views stretch across the Chesapeake Bay, Little Choptank River, and Fishing Creek, with a waterside pool (as-Is) , pier with lift, boat ramp, and detached storage garage completing this exceptional property. Modern conveniences including Nest climate control, security cameras, fiber wiring in most rooms, and smartphone-controlled dimmers add ease to a home where craftsmanship, comfort, and waterfront living come together beautifully.

1301 Broadview Dr, Cambridge

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

$98,500
Welcome to a rare opportunity to own 137 acres of pristine waterfront property on Smith Island, Maryland. This secluded piece of paradise offers a unique combination of marshlands, high ground, sandy beaches, and roughly 1.36 miles of waterfront footage, making it a premier destination for outdoor enthusiasts, waterfowl hunters, and nature lovers alike. Surrounded by the Chesapeake Bay’s rich estuarine environment, this property provides exceptional hunting opportunities, with an abundance of scoters, long-tailed ducks, bluebills, mallards, black ducks, buffleheads, and geese frequently seen throughout the area. Whether you’re setting up blinds along the marsh or exploring the creeks and open waters, this is a true sportsman’s retreat. Beyond hunting, the property is a fisherman’s dream, offering excellent opportunities for striped bass, trout, red drum, white perch, and various other species of fish in the surrounding waters. Along the sandy beaches, you’ll find mussels and oysters in abundance, making for a unique and rewarding experience as you gather fresh shellfish straight from the shoreline. The land itself is both wild and scenic, featuring untouched marshlands ideal for birdwatching and conservation, along with high-ground areas that could serve as a secluded retreat or campsite. The newly constructed stone barrier walls, part of the Rhodes Point Navigation Improvement Project, provide additional protection against erosion while enhancing access to the property and preserving its valuable shoreline. The island is reachable by private boat or the Smith Island Ferry from Crisfield, where you’ll find a charming, tight-knit island community known for its famous Smith Island Cake, fresh seafood, and rich maritime heritage. The island is deeply connected to the crabbing and oyster industries, with local watermen harvesting some of the finest blue crabs and oysters in the Chesapeake Bay. Visitors can experience the daily rhythms of this traditional way of life, whether by chatting with local watermen, enjoying fresh seafood at a waterfront eatery, or even taking part in crabbing excursions. The Smith Island Cultural Center is also a great way to immerse yourself in the island's history and tradition. For those looking to extend their stay, Smith Island offers cozy rental homes and bed-and-breakfasts, many of which provide modern comforts while preserving the island’s historic charm. Whether you’re seeking a peaceful getaway or an immersive outdoor experience, Smith Island provides the perfect backdrop for unparalleled recreation, hunting, and waterfront living. Contact Land Specialist Casey Kennedy today to schedule your showing of this beautiful, rare and unique Smith Island offering.

Smith Island, Ewell

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

$1,250,000
5 Beds 4 Baths
🔥 Eastern Shore Waterfront Estate 🔥 Welcome to a true sportsman’s paradise tucked along the shores of the Chesapeake Bay—where space, privacy, and waterfront living come together in a BIG way. Built in 1988 and spanning nearly 5,000+/- square feet, this one checks boxes most properties can’t even reach… 🏡 5 Bedrooms | 3.5 Baths | 4,933+/- Sq Ft Step inside and you’ll find: • A massive eat-in country kitchen (with heated floors 👀) • Formal dining for hosting the big nights • TWO oversized family rooms for spreading out • Space for everyone… and then some But here’s where it gets wild 👇 🎯 Next-Level Extras: • Huge workshop + multiple garage spaces • Dedicated entertainment hall with FULL kitchen, bar & pool table • Built for hosting, holidays, and unforgettable weekends 🌅 Waterfront Lifestyle: • Private pier on Brooks Creek • TWO boat lifts + electric lift • Westerly sunset views over the Bay (the kind people chase 🌅) • Expansive deck for relaxing or entertaining • Private pond adding to the already unreal setting ⚙️ Major Upgrades: • Geothermal system (efficient + smart) • New roof (Oct 2024) • Expanded shop addition This isn’t just a home… it’s a compound. A retreat. A place people don’t want to leave once they get here. 💬 If you’ve been waiting for something special on the Eastern Shore… this is it.

5253 Ragged Point Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800

$656,000
3 Beds 3 Baths
Enjoy the charm of coastal-inspired Eastern Shore living with award-winning Bay to Beach Builders, known for their Amish craftsmanship and exceptional attention to detail. The Surfside includes 3 bedrooms and 2.5 baths, featuring a thoughtfully designed two-story layout with open-concept living areas and inviting porch spaces that capture the relaxed feel of coastal living. The main level offers a welcoming kitchen, dining area, and great room ideal for everyday living and entertaining, while the second floor provides a private owner’s suite and additional bedrooms for family or guests. Located in Cape Isle of Wight in West Ocean City, this corner waterfront homesite offers direct access to the open bay and the Ocean City inlet, making it an excellent location for enjoying boating and waterfront living. The additional adjacent lot is also available for purchase, providing even more opportunity in this desirable coastal community. Choose the Surfside as shown or explore a variety of models and custom options to create the perfect home for this exceptional setting that fits your lifestyle and vision. Concept home pending final approvals. This brand-new home can be yours !!CALL TODAY FOR DETAILS!!

Lot #1 Exeter Rd, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$850,000
3 Beds 3 Baths
A rare opportunity to own a true waterfront compound in the highly desirable Wilson Point community. Tucked away on a quiet dead-end street, 1122 Beech Drive offers the perfect blend of privacy, lifestyle, and income potential. The main residence features 2 bedrooms, 2.5 baths, and a versatile first-floor office that can easily function as a third bedroom. Interior highlights include rich hardwood flooring, ceramic tile, a wood-burning fireplace, and a basement providing additional living or storage space. Designed for both relaxation and entertaining, the outdoor setting captures the essence of Chesapeake living—complete with a long private pier, expansive flat waterfront lot, Trex deck, and a covered screened porch. A detached crab shack adds charm and functionality, ideal for summer gatherings and waterfront enjoyment. The sale also includes two additional cottages (1124 & 1126 Beech Drive), each offering 2 bedrooms and 1 full bath. One unit is currently occupied by a long-term tenant, while the other is vacant and ready for immediate rental, guest use, or personal enjoyment—providing built-in flexibility and income potential. A large driveway accommodates multiple vehicles with ease, complemented by a detached garage and carport for additional storage or workspace. Whether you’re seeking a private waterfront retreat, a multi-generational property, or an income-producing investment, this exceptional offering delivers a rare combination of lifestyle and opportunity in one of Middle River’s most sought-after waterfront communities.

1122 Beech Dr, Baltimore

Listing courtesy of Platinum Realty Group. Contact:

$4,158,000
9 Beds 8 Baths
Nestled within the prestigious Wolf Farm community, this exquisite residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This property is one of few on Kent Island that has unobstructed views of Annapolis, Baltimore and the Chesapeake Bay Bridge. Guests are welcomed with a gated circular drive adorn with stone pillars, lush flower beds and a professionally manicured lawn. The neoclassical architectural style mimics that of Thomas Jeffersons home Monticello. Spanning an impressive 10,152 square feet, the kitchen has been meticulously renovated in 2026, ensuring convenience of use while gazing at the Bay. Step inside to discover an open floor plan that invites natural light to dance across the stunning marble and luxury vinyl plank flooring. The eat-in kitchen and separate formal dining room provide ample space for entertaining, while the pantry ensures that all your culinary needs are met. The primary suite is a true sanctuary, boasting a bay-front view, a lavish primary bath, and expansive walk-in closets. Each of the nine bedrooms is designed with comfort in mind, offering generous space and thoughtful details. With eight full bathrooms, morning routines are a breeze, ensuring privacy and convenience for all. The heart of the home is complemented by three elegant fireplaces, creating cozy nooks for relaxation. Recessed lighting and upgraded countertops throughout add a touch of sophistication, while the wet/dry bar and custom wine cellar elevate your entertaining experience. Step outside to your personal oasis, where a stunning in-ground pool awaits, surrounded by multiple terraces and balconies that overlook the serene Chesapeake Bay. With 500 feet of waterfrontage, this property offers unparalleled access to the water, complete with a private composite dock that accommodates multiple slips for your boating adventures. Whether you enjoy power boating or kayaking, the navigable waters provide endless opportunities for exploration. Additional features include a full daylight basement with outside access, perfect for guests or recreational activities, and an attached side-entry garage with ample driveway space for up to 15 vehicles. This home is not just a residence; it's a lifestyle. Experience the tranquility of waterfront living combined with the luxury of modern amenities, all within the embrace of a warm and inviting atmosphere. Embrace the exclusive lifestyle that awaits you in this remarkable property.

319 Blue Bay Rd, Stevensville

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

$7,900,000
8 Beds 6 Baths
"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

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

$1,999,900
3 Beds 4 Baths
Experience the beauty of waterfront living at 245 Long Point Road on sought-after Little Round Bay. Perfectly positioned across from St. Helena Island, this exceptional home offers breathtaking water views and seamless indoor-outdoor living. Designed to maximize its spectacular setting, the open-concept floor plan features a dramatic family room with soaring cathedral ceilings, a cozy gas fireplace, and walls of windows that frame the waterfront. The gourmet kitchen offers generous workspace, high quality appliances, and an inviting layout ideal for entertaining. Overlooking the main living area, the loft provides the perfect space for a home office, library, or study. The spacious primary suite is a private retreat featuring two walk-in closets and a dedicated vanity room. Two additional bedrooms and 3½ baths provide comfortable accommodations for family and guests, while the finished lower level offers flexible space for a theater, recreation room, home gym, or additional entertaining area. Step outside to enjoy a Trex composite waterside patio with stairs leading to your private pier with deep water access to park multiple boats. Boating enthusiasts will appreciate the boat lift, two jet ski lifts, and water and electric service at the dock. Crowning the boat lift is an extraordinary second floor party deck above the boat lift—an incredibly rare waterfront feature that can no longer be replicated under today's regulations—creating an unmatched setting for enjoying and entertaining while taking in panoramic views of Little Round Bay. A versatile waterfront shed with electricity offers endless possibilities as a workshop, storage area, or charming waterfront bar. Now offered at $1,999,900, this exceptional property presents an incredible opportunity to own in one of Anne Arundel County's most desirable waterfront locations. Being sold As Is, the home has been priced to reflect the opportunity for a new owner to update and personalize the interiors while preserving the property's outstanding waterfront amenities and irreplaceable setting. Whether you envision tasteful cosmetic updates or a more comprehensive renovation, this home provides the perfect canvas to create a custom waterfront retreat tailored to your own style. Opportunities to purchase a property with this combination of location, views, private pier with stairs to access boat lift, rare party deck, and endless potential are increasingly rare. Perfectly positioned just off the Severn River, this exceptional property offers the rare opportunity to create a waterfront retreat uniquely your own, where boating, kayaking, unforgettable sunsets, and effortless waterfront entertaining become part of everyday life. (3 pictures AI - digitally altered to show possibilities - noted on the picture)

245 Long Point Rd, Crownsville

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

$840,000
Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat. With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and abundant wildlife all around, creating a peaceful and scenic setting. For outdoor enthusiasts, this property offers deep water access suitable for larger boats, with easy access to Breton Bay and the lower Potomac River. Boating, fishing, and crabbing are all easily accessible. Located in the desirable Leonardtown area, the property is just minutes from Breton Bay Golf & Country Club and a short drive to Leonardtown Wharf and Town Square for dining, shopping, and local amenities. The property is currently under agricultural assessment and enrolled in the Forest Management Program, providing reduced property taxes. Access to local builders and preliminary pricing information is available to assist with planning and development. A unique opportunity to own a sizable waterfront parcel offering privacy, usable land, and water access.

Ferny Hills Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169