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$65,000
Residential Lot For Sale in the charming town of Barclay! This property offers a peaceful rural setting while remaining conveniently located just minutes from Route 301. The partly wooded property provides a blend of natural beauty and privacy, creating an ideal backdrop for your future home. A private well will be required for water service, and public sewer is available and ready for connection, offering added convenience for new construction. Connection fee information has been provided in the attached documents for prospective buyers. Current sewer service fee is $43.87 per month. Enjoy small-town living with easy access to major commuting routes and the surrounding Eastern Shore amenities. Buyer to verify all utility connections, fees, and building requirements with the appropriate authorities.

105 Barclay Cutoff Rd, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483

$997,000
5 Beds 4 Baths
WELCOME to the Eastern Shore -- This charming Nantucket style waterfront home offers unique privacy with the advantage of being in a wonderful water privilege community. Rare 1.5-acre lot offers a 5 bedroom, 3.5 bath renovated beauty that offers upgrades to include: true handsome hardwood floors, stunning renovated Coastal kitchen and baths, new windows, siding and doors. There are scenic wrap-around water views from almost every room. The water depth is low and small craft is advised in the creek.... which does exit into the bay.... The community boat ramp is directly across the street for easy boating. There are a couple of garage options available for this property: The garage option is " TO BE BUILT.... County has said OK to pool and garage addition, permit process has started...

101 Beachside Dr, Stevensville

Listing courtesy of Coastal Realty Maryland. Contact:

$700,000
3 Beds 3 Baths
Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$1,049,000
3 Beds 3 Baths
A Peaceful Waterfront Retreat Set along the quiet shores of Northwest Creek, this beautifully maintained single-story brick home offers sweeping 180-degree water views and a sense of calm from the moment you arrive. The back deck offers an escape to bird watch for eagles, osprey, blue heron, egrets and more during the day and stargaze at night. A gently winding walkway leads through lush, thoughtfully landscaped gardens filled with colorful blooms throughout the year. A Warm Welcome Step inside the foyer and the view immediately takes center stage. Straight ahead, past the living room is the sunlit three-season room. The sparkling water creates a stunning backdrop that draws you through the home. Living Areas & Kitchen The formal dining room and spacious living area feature warm wood floors, large windows, and plenty of natural light, all designed to showcase the peaceful waterfront setting. The kitchen is both functional and inviting, with upgraded appliances, Corian countertops, under-cabinet lighting, a tile backsplash, and generous cabinet space. Whether preparing meals or enjoying your morning coffee, the uninterrupted creek views make this space especially enjoyable. Private Bedroom Layout The split-bedroom floor plan provides privacy and comfort for both owners and guests. The primary suite is tucked away on the left side of the home and offers beautiful water views through oversized windows, along with rich wood flooring and a relaxing atmosphere. The spacious en-suite bath includes dual vanities, two walk-in closets, a walk-in shower, and a soaking tub. On the opposite side of the home, a separate hallway leads to two spacious guest bedrooms filled with natural light, a full guest bathroom with a shower, a convenient half bath and laundry room, and direct access to the oversized two-car garage. Additional Living Space Just beyond the kitchen, the home opens into a cozy den and library area. Built-in bookcases and a gas fireplace create the perfect setting for relaxing evenings, reading, or gathering with family and friends. The Three-Season Room French doors off the kitchen, Living room, or primary bed room lead into a large three-season room stretching across the back of the home. This room has both heat and a/c provided by a mini split. Surrounded by natural light and panoramic water views, this versatile space is ideal for morning coffee, casual dining, yoga, entertaining, or simply enjoying the peaceful scenery year-round. The roof was replaced in 2024 with 50 Year architectural shingles, and a transferrable warranty. Blending indoor comfort with the beauty of the outdoors, this waterfront home offers a quiet retreat designed for everyday living and relaxing. This home is close to many recreational amenities including parks, with bike trails, pickleball courts, fishing piers and a public golf course.

110 Carville Ct, Stevensville

Listing courtesy of Compass. Contact: (301) 298-1001

$269,900
2 Beds 2 Baths
Sellers offering to pay capital contribution fee with acceptable offer. 55 and over community, this newly updated home features an inviting open floor plan, highlighted by luxurious vinyl plank and ceramic tile flooring, along with cozy carpeting in the primary bedroom. The galley kitchen, complete with upgraded countertops and built-ins, flows seamlessly into the dining and living areas, making it ideal for entertaining or quiet evenings at home. Enjoy the warmth of the gas fireplace, or step outside to your porch overlooking the beautifully maintained common areas. The property includes an attached garage with a paved driveway, ensuring easy access and ample parking. Residents benefit from a well-managed association that covers custodial services, exterior maintenance, and snow removal, allowing you to focus on enjoying life. The community offers lovely common grounds and a party room for gatherings. Located near local parks and excellent public services, this neighborhood fosters a vibrant lifestyle. With nearby towns like Chestertown and Centreville for shopping and restaurants and recreational facilities, you'll find everything you need just a short distance away. Experience the comfort of home in a community that values connection and convenience. Recent updates include; Finished 2nd floor with drywall, electric, lights & ceiling fans, paint and carpet. Installed new LVP flooring through most of 1st floor, installed foam insulation, new sump pump and dehumidifier in crawl space. Installed brand new REEM HVAC system. New washer/dryer. New water softener and reverse osmosis water filter. Completely new kitchen with cabinets, sink, quartz counter tops, disposal, gas stove/oven and under cabinet lighting. New insulated garage door with new opener and key pad entry. New ceiling fan in guest bedroom. New carpet in primary bedroom, new LVP flooring in primary bathroom, new light fixtures in primary bedroom and closets. Come see the 55+ community; The Pond at Church Hill. The community encircles a large, grassy, common area with a shaded pond at one end. This is an interior unit with 2 bedrooms/2 baths and newly finished 2nd floor that could be bedrooms, craft, or recreation room. Lots of possibilities.. The area also features 2 established community theatres!

116 The Pond Way Unit #3C, Church Hill

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$362,500
2 Beds 3 Baths
Welcome to 1302 Marion Quimby Dr. Nestled in the serene Thompson Creek community, this charming townhouse with a new HVAC and hot water heater offers a perfect blend of comfort and modern living. With 1,161 square feet of thoughtfully designed space, this home features two spacious bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking tranquility and convenience. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The contemporary design is enhanced by plush brand new carpeting and elegant ceramic tile flooring, creating a warm and welcoming atmosphere. The living room is anchored by a cozy fireplace, complete with glass doors and a stylish mantel, perfect for those chilly evenings spent at home. The kitchen is a culinary delight, featuring ample table space for casual dining and modern appliances, including a dishwasher, microwave, and electric oven/range. Whether you're preparing a gourmet meal or enjoying a quick breakfast, this kitchen is designed to meet your needs. Retreat to the primary suite, which boasts an en-suite bathroom for added privacy and convenience. Thoughtful window treatments throughout the home allow for natural light while maintaining a sense of intimacy. Step outside to enjoy the beautiful exterior features, including a charming balcony and deck over-looking Thompson Creek and gorgeous water views and sunsets, perfect for sipping your morning coffee or unwinding after a long day. The community amenities are a true highlight, offering access to a refreshing outdoor pool, tennis courts, and scenic jog/walk paths that wind through beautifully landscaped grounds. The property is situated on the banks of Thompson Creek, providing stunning views of the water, lush pastures, and surrounding trees. Imagine relaxing on your deck while listening to the gentle sounds of the creek, creating a peaceful oasis right at your doorstep. With unassigned off-street parking and a well-maintained community that includes exterior building maintenance, management, and trash services, this home offers both convenience and peace of mind. Experience the perfect blend of comfort, community, and natural beauty in this delightful townhouse. Whether you're looking for a weekend getaway or a permanent residence, this property is sure to meet your needs and exceed your expectations.

1302 Marion Quimby Dr, Stevensville

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

$499,987
4 Beds 3 Baths
25K PRICE IMPROVEMENT....Welcome to 116 Meadow Brook Way, a spacious and beautifully maintained home located in the sought-after North Brook community of Centreville. Step inside to find an inviting open floor plan featuring updated LVP flooring, custom trim work, and freshly updated living spaces. The main level offers a formal LR and DR areas, home office, along with a dramatic two-story family room highlighted by a cozy gas fireplace. The spacious kitchen boasts abundant cabinetry, brand new granite tops, a center island, and flows seamlessly into the bright sunroom bump out, creating the perfect setting for everyday living and entertaining. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite featuring dual walk-in closets and a luxurious spa like bath with double vanities, a soaking tub, and separate shower. The additional bedrooms offer plenty of space for family and guests. This basement is one of kind with fully finished rec room and the remainder of the basement partially finished walls and exposed beams perfect for his man cave, kid hangout, or family enjoyment. Additional space for future buildout including a 3 piece rough in and ample storage and future expansion. Most exterior basement walls professionally foam insulated for extra energy savings in addition to the solar energy savings! Outside, enjoy a white vinyl fully fenced backyard with patio and plenty of room for outdoor gatherings, pets, and play.

116 Meadow Brook Way, Centreville

Listing courtesy of RE/MAX Leading Edge. Contact:

$629,900
2 Beds 2 Baths
Enjoy added savings with $2,000 toward the buyer's closing costs, plus the seller will pay the HOA fees for the remainder of 2026 with an acceptable offer. Welcome to easy, elevated living in the sought after 55+ community of Bay Bridge Cove. This beautifully maintained Oxford model end-unit villa offers peaceful pond and fountain views in a tranquil setting. The open floor plan features an expansive kitchen with granite countertops, stainless steel appliances, white cabinetry, and an abundant workspace, all flowing seamlessly into the spacious living area with a cozy gas fireplace. A desirable 4-foot bump-out enhances the living space, providing additional room for entertaining, relaxing, and enjoying the home's open feel. Off of the living room is a bright and inviting sunroom offering versatile space that can be tailored to your needs. Luxury vinyl plank flooring extends throughout the main living areas, while the bedrooms offer the comfort of carpet. Just beyond the sunroom, the enclosed screened porch with privacy sun shades creates the perfect spot to enjoy your morning coffee or unwind while taking in the water views. This villa offers two bedrooms and two full bathrooms, including a spacious primary suite with a tray ceiling, generous closet space, and a private bath. The second bedroom provides flexible space for guests, hobbies, or a home office and is conveniently located near the full hall bathroom. Residents of Bay Bridge Cove enjoy an exceptional lifestyle with amenities that include a clubhouse, outdoor pool, fitness center, tennis courts, bocce ball courts, dog park, and a full calendar of community activities and events. Lawn care, snow removal, and community management are included for truly low-maintenance living. Conveniently located near shopping, dining, Route 50, and the Chesapeake Bay Bridge, this home offers the perfect combination of comfort, convenience, and active adult living.

521 Moorings Cir Unit #245, Stevensville

Listing courtesy of RE/MAX Advantage Realty. Contact:

$395,000
4 Beds 3 Baths
Kent Island Living at Its Best – Location, Lifestyle & Unlimited Potential! Rare opportunities like this are becoming harder to find in Stevensville. Nestled within a highly sought-after waterfront community, this spacious 4-bedroom, 2.5-bath home offers the perfect combination of location, lifestyle, and value. Situated directly across from the school and just a short stroll to the community recreation fields, this home provides everyday convenience that families will appreciate. The detached garage offers additional storage, workspace, or room for all your outdoor and recreational gear. Inside, you'll find generous living spaces and a layout designed for comfortable living. While some cosmetic updates could enhance the home's appeal, this is the perfect opportunity for buyers to add their own style and create a home that reflects their personal taste. Rather than paying a premium for someone else's renovations, you'll have the chance to customize the finishes you love while building equity in an established neighborhood where location truly matters. The real showstopper is the incredible community lifestyle. Residents enjoy exclusive access to a private beach, community pool, boat launch, and clubhouse, providing endless opportunities for boating, fishing, swimming, social gatherings, and enjoying the Chesapeake Bay. Imagine spending your weekends on the water, relaxing by the beach, or gathering with neighbors at community events, all just minutes from your front door. Whether you're looking for a primary residence, a place to grow, or an investment in one of Kent Island's most desirable communities, this home delivers exceptional value and endless potential. Homes with this combination of space, amenities, convenience, and opportunity are increasingly rare. Bring your vision, add your personal touch, and discover why so many people are choosing to call Stevensville and Kent Island home. Don't miss this chance to create something truly special while enjoying the waterfront lifestyle you've always wanted.

606 Old Love Point Rd, Stevensville

Listing courtesy of Thyme Real Estate Co LLC. Contact: 3026900245

$549,999
3 Beds 2 Baths
Resting on 1+ acres of partially wooded property, this beautiful Cape Cod is awaiting it's next owner. As you arrive at this home, you'll feel the peace and quiet atmosphere that surrounds you. Park on the oversized driveway and walk along the rustic brick sidewalk to the front door. As you enter the home you'll find the living and dining area, kitchen and family room with propane fireplace, bedroom and full bath. Passing through the family room, you'll enter the rear oversized three season room that leads to the heated pool and hot tub, patio and pergola for your relaxation. Recent updates to this home include two new mini splits air/heat units 2025 & 2026, new roof 2022, new doors (front, side and 18' garage door) 2025, new Anderson windows (main house and garage) 2025, fresh paint 2025, new carpet 2026, new dishwasher 2024 also added was a Rinnai Tankless Water Heater. The oversized garage also has a studio/storage area with stair above.

814 Wrights Neck Rd, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$495,000
4 Beds 4 Baths
Welcome to this Ellendale Community end unit townhome! Turn-Key 4-Bedroom, 3.5 Bath Home . Eastern Shore Lifestyle & Easy Commuting. This home offers a bright, open layout designed for effortless everyday living and entertaining. With high-end upgrades and fresh paint, you can move right in and start enjoying the relaxed Eastern Shore lifestyle. Interior Features & Upgrades Bedrooms/Baths: 4 spacious bedrooms and 3.5 pristine bathrooms. Open Layout: Seamless flow between the living areas—perfect for hosting friends and family. Premium Upgrades. Outdoor Living Spacious Deck. The main level transitions directly to a large outdoor deck, ideal for grilling, relaxing, and entertaining. Commuter’s Dream: Located just 2 minutes from the Bay Bridge, offering a quick, stress-free commute while preserving that coveted Eastern Shore tranquility. Resort-Style Neighborhood. Situated just steps from the community clubhouse, park, and swimming pool. Community Amenities Enjoy a true lifestyle community featuring: Walking trails & a tot lot. Swimming pool & clubhouse, Kayak ramp & fishing pier. Contact us today to schedule your private tour.

226 Liam Thomas Ln Unit #D6, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102240600

$459,000
4 Beds 2 Baths
Don’t miss the opportunity to own this charming 4-bedroom home featuring 2 recently renovated baths, a flexible office/den, and a BRAND NEW ROOF! The spacious kitchen with peninsula seating flows seamlessly into the dining area, creating the perfect gathering space for family and friends. The expansive family room is filled with natural light thanks to vaulted ceilings, skylights, and oversized windows that create an open and airy feel throughout. A screened-in porch adds even more living space to enjoy year-round, while the large deck, accessible from both the main living area and the primary suite, offers the perfect setting for morning coffee, evening entertaining, or simply relaxing at the end of the day. Located in the desirable Kent Island Estates community, this home offers the Eastern Shore lifestyle you’ve been searching for, complete with access to multiple beaches, a playground, and the Southern Kent Island Trail. Come experience all this home has to offer!

318 Wicomico Rd, Stevensville

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

$599,900
3 Beds 4 Baths
Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186

$4,995,000
5 Beds 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

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

$1,200,000
4 Beds 3 Baths
Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

202 Royston Shores Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$455,000
4 Beds 2 Baths
Lovely historic home in the heart of downtown Centreville. Walking distance to all the town has to offer. This home boasts so many wonderful features, from the private but yet easy to maintain backyard to the tranquil enclosed porch perfect for all 4 seasons. During the holidays enjoy watching the Centreville Holiday Parade right from the comfort of your front porch, everyone will want an invite to enjoy that! The main level is made just right for easy flow from room to room or close them off and enjoy comfort in the back of house with the flow from kitchen to porch for entertaining. The 2nd floor has 3 bedrooms and a fabulous full bath with your choice, soak the day away in your clawfoot tub or a quick easy shower in the separate enclosed shower. There is a separate HVAC that services this floor and the 3rd floor. The 3rd floor is perfect for teens or a hobby room, with a sleeping cove and plenty of room to spread out this will soon be a favorite room to escape to! Plus, there's additional storage on the 3rd floor. Seller added 3 mini splits to the 1st floor in 2025, as well as leaf lifters to the gutters that come with a lifetime warranty. The trim and shutters have been freshly painted as well. Check this beauty out today!

126 S Commerce St, Centreville

Listing courtesy of Rosendale Realty. Contact: 4107580333

$640,000
4 Beds 3 Baths
Beautifully maintained home tucked away in a small enclave of just 46 homes, conveniently located just off Route 50 in Chester. This spacious property offers a 2-car garage complete with a utility tub and whole-house water softener system. Major updates provide peace of mind, including a newer roof and HVAC system. The encapsulated crawlspace features a dehumidifier and sump pump for added efficiency and protection. Step outside and enjoy your private backyard retreat featuring a deck, patio area, fire pit, hot tub, sunshade awning, storage shed, and fully fenced yard—perfect for entertaining or relaxing. Inside, the kitchen is designed for gathering with abundant cabinet and counter space, a custom island, granite countertops, and an open, functional layout. The main level features LVP flooring, an updated powder room, spacious living room with a cozy wood-burning stove, dining area, and dedicated office/flex space. Upstairs you’ll find four generously sized bedrooms and an updated hall bath. The oversized primary suite offers a beautifully updated bathroom featuring a separate soaking tub and stand-up shower, walk-in closet, and a unique niche room located between the bedroom and closet. This versatile bonus space offers endless possibilities—nursery, sewing room, reading nook, fitness area, office, or private retreat. Need even more space? On the upper level ,A possible fifth bedroom with closet, fresh paint, and new carpet provides flexibility as a bedroom, media room, playroom, home gym, or bonus space. Convenient Eastern Shore living with quick access to Route 50, shopping, dining, and commuting routes. Located in an intimate community of just 46 homes, this property combines space, flexibility, and thoughtful updates both inside and out.

324 Loblolly Way, Grasonville

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

$339,900
3 Beds 1 Baths
Welcome home to this charming 3-bedroom, 1-bath rancher nestled in the heart of Centreville! This cozy home offers an inviting open-concept living and dining area, an eat-in kitchen with updated appliances, and comfortable carpeted bedrooms. Enjoy relaxing on the perfect front porch or entertaining in the spacious, private backyard, complete with a new vinyl privacy fence. Additional updates include a new HVAC system installed in 2022, providing peace of mind for years to come. Conveniently located near schools, shopping, restaurants, and everyday amenities, this home combines comfort, convenience, and charm. Don't miss your opportunity to make this adorable rancher your new home! Interior pictures will be available on 6/4/26

458 Railroad Ave, Centreville

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

$575,000
5 Beds 3 Baths
Welcome to 126 E Brook Drive in North Brook. If you've been searching for a home that offers space, style, and flexibility, this stunning North Brook property delivers it all. From the moment you step inside, you'll be impressed by the beautifully updated high-end kitchen, thoughtfully designed with quality finishes, abundant cabinetry, and plenty of workspace for cooking, entertaining, and everyday living. The kitchen flows seamlessly into the main living areas, creating the open and inviting floor plan today's buyers are looking for. One of the home's most desirable features is the main-level bedroom, offering incredible flexibility for guests, multi-generational living, a private home office, or anyone seeking first-floor convenience. With five true bedrooms, everyone has room to spread out and enjoy their own private space. The generously sized bedrooms provide comfort and functionality, while the spacious layout offers the flexibility modern families need. The full basement, over 1,600 sq ft, presents endless possibilities, whether you're looking for additional living space, a recreation room, home gym, workshop, or simply exceptional storage. Step outside to enjoy the large deck, perfect for summer barbecues, morning coffee, or relaxing evenings overlooking the backyard. Located in the highly sought-after North Brook community, this home combines generous living space, thoughtful updates, and a prime Centreville location close to schools, parks, shopping, dining, and major commuter routes. Five true bedrooms. A main-level bedroom. A stunning kitchen. A full basement. And room for everyone. In today’s market, this alone is luxury in North Brook.

126 E Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$1,900,000
3 Beds 2 Baths
Steeped in history and surrounded by the timeless beauty of Maryland’s Eastern Shore, 1130 Old Love Point Road presents a once-in-a-generation opportunity to own an extraordinary family farm in the heart of Kent Island. Spanning approximately 36.73 acres, this remarkable property blends agricultural heritage, historic character, and exceptional future potential in one of the Shore’s most storied locations. At the center of the property sits an historic Victorian farmhouse dating to circa 1896, recognized by the Maryland Historical Trust as a historically contributing structure representative of the classic 19th-century Delmarva farmhouse. The home and grounds reflect generations of stewardship and offers tremendous opportunity for its next generation renovation, rehabilitation and future development. Old Love Point Road itself carries a rich and fascinating history. Before the Chesapeake Bay Bridge connected Maryland to the Eastern Shore, Love Point served as one of the principal gateways to the Shore. Ferries, steamships, and rail lines once brought travelers from Baltimore and Annapolis to Kent Island, where they continued eastward across Maryland and Delaware. Love Point became known as a romantic waterfront destination and transportation hub, welcoming visitors arriving by ferry and the historic Queen Anne’s Railroad. The property’s location captures the spirit of that history while offering exceptional convenience to today’s modern traveler. Situated just minutes from Route 50 and the Chesapeake Bay Bridge, the farm offers easy access to Annapolis, Washington D.C., Baltimore, and the Delaware beaches while maintaining the peaceful charm of Eastern Shore living. Currently farmed and designated as prime farmland, the property is ideally suited for a gentleman’s farm, equestrian estate, vineyard, winery, agritourism venue, or luxury country retreat. The Development Analysis Report identifies a winery as one of the site’s most favorable and viable uses, noting that agritourism operations such as vineyards and wineries are specifically encouraged within Queen Anne’s County’s future agricultural economy plans. In addition to its agricultural and lifestyle appeal, the property also offers substantial long-term development potential. Located within the County’s Suburban Estate zoning district and designated growth area, the site may support future residential subdivision opportunities, including large-lot estate development, clustered single-family communities, multifamily concepts, or additional residential lots under current moratorium guidelines. Whether envisioned as a private family compound, vineyard and winery destination, legacy investment, or future development opportunity, 1130 Old Love Point Road represents a rare chance to own a meaningful piece of Maryland’s Eastern Shore history — where the past, present, and future converge along one of Kent Island’s most iconic roads.

1130 Old Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 746-2090

$500,000
4 Beds 3 Baths
Beautiful Home with Finished Waterproofed Basement & Chesapeake Bay Water Access! Don't miss this exceptional home featuring a professionally waterproofed basement with a transferable warranty. The lower level offers a spacious recreation/living room, full bath, bedroom, and abundant storage space—perfect for guests, extended family, or a home office. You are first greeted by a cozy front porch overlooking the spacious corner lot. The main level boasts an open-concept floor plan with luxury vinyl plank flooring throughout, custom-built shelving, and a welcoming living room highlighted by a fireplace with a wood stove insert. The spacious kitchen is designed for both everyday living and entertaining, featuring granite countertops, white cabinetry, a center island, and a dining area. Step outside to enjoy the large backyard complete with a deck, patio, and oversized storage shed. An oversized garage provides ample space for vehicles, hobbies, tools, or workshop projects. Located in a desirable community offering a playground and water privileges on the Chesapeake Bay, you'll enjoy easy access to the beach and breathtaking sunset views. This home combines comfort, space, and a fantastic lifestyle opportunity. Schedule your showing today—this one won't last long!

101 Birch Road, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$499,000
4 Beds 3 Baths
Welcome to 336 Timber Lane—a beautifully maintained Colonial offering the space, comfort, and lifestyle today's buyers are looking for, all in a convenient Grasonville location just minutes from Kent Island and the Bay Bridge. With over 2,100 square feet, this move-in ready home features 4 bedrooms, 2.5 baths, hardwood flooring, a cozy fireplace, and a spacious, flowing floor plan designed for everyday living and effortless entertaining. The bright kitchen overlooks the family room, creating the perfect gathering place for holidays, game nights, or simply spending time together. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet and private en-suite bath, while three additional bedrooms provide flexibility for family, guests, a home office, or fitness space. Step outside and enjoy a generous backyard with plenty of room for entertaining, gardening, play, or simply relaxing after a day on the water. One of Grasonville's best-kept secrets is the lifestyle. You'll enjoy quick access to marinas, waterfront restaurants, boating, fishing, shopping, and Route 50—all while experiencing less congestion than many neighboring communities. Best of all, this home offers an incredible opportunity to enjoy the Eastern Shore lifestyle while getting more home for your investment than many comparable properties on Kent Island. Whether you're commuting, raising a family, or looking for a place to enjoy everything the Chesapeake Bay has to offer, 336 Timber Lane delivers the perfect blend of space, value, and location.

336 Timber Ln, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

$344,900
2 Beds 3 Baths
Motivated seller! Experience relaxed waterfront living in this beautifully updated townhome condominium overlooking scenic Thompson Creek, where stunning water views, community amenities, and an exceptional coastal lifestyle come together. Thoughtfully renovated and move-in ready, this waterfront retreat blends modern upgrades with inviting indoor and outdoor spaces designed for both everyday comfort and, entertaining.The main level welcomes you with an updated kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Just beyond, the sunken living room creates a warm and inviting atmosphere highlighted by a beautiful brick gas fireplace (ready for propane hookup if desired and easily convertible back to wood-burning), a custom wet bar, and seamless access to the spacious waterfront deck, perfect for enjoying peaceful sunsets over the creek. Recent improvements totaling approximately $20,000 include luxury vinyl plank flooring, new carpet upstairs, fresh interior paint throughout, and new blinds, giving the home a refreshed, modern feel. Upstairs, you'll find two generously sized bedrooms, ample closet space, and 2.5 baths, including a spacious primary suite with a well-appointed ensuite bath. A private balcony off the primary bedroom provides tranquil water views, breathtaking sunsets, and peaceful views of the community walking paths. Outdoor living is truly at the heart of this property. Enjoy boating, fishing, kayaking, swimming, and waterfront recreation just moments from your door. Residents have access to a community pool, clubhouse, tennis courts, scenic walking and jogging paths, nearby marinas, and multiple boat launch options, including Thompson Creek Landing within walking distance and convenient access to Kent Island. Situated along the banks of Thompson Creek, this home offers picturesque views of the water, mature trees, and surrounding natural beauty, creating a peaceful setting perfect for relaxing, entertaining, or simply enjoying the waterfront lifestyle. Additional conveniences include unassigned off-street parking and a well-maintained community offering exterior building maintenance, professional management, and trash service, providing low-maintenance living and added peace of mind. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this home offers the perfect blend of comfort, recreation, and coastal charm in an unbeatable waterfront setting.

1102 Marion Quimby Dr, Stevensville

Listing courtesy of Redfin Corp. Contact: 3016586186

$425,500
3 Beds 4 Baths
Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades. Welcome to Bayside living at its finest. This meticulously maintained home sits in one of Chester's most desirable waterfront communities, offering nearby water access for morning walks along the Chester River, resort-style outdoor pool for summer enjoyment, and professionally maintained grounds. Minutes from Route 50/301 for easy commuting, yet peacefully situated in a serene riverside setting close to shopping, dining, and recreational activities. The owners have transformed this residence with quality upgrades throughout. Real hardwood flooring spans the entire main and upper levels with no carpet anywhere in the home. The entry welcomes you with elegant slate tile while abundant natural light floods every room, creating bright and inviting spaces perfect for both daily living and entertaining. The completely renovated chef-inspired kitchen features top-tier stainless steel appliances including Thermador induction cooktop, GE Monogram wall oven, and Bosch dishwasher. Granite countertops, updated cabinetry, and recessed lighting complete this stunning space. The open-concept design connects seamlessly to the spacious living area, making entertaining effortless and family gatherings comfortable. Your main level living room centers around a cozy gas fireplace surrounded by built-in bookshelves, creating the perfect gathering spot year-round. Step outside to your private deck with retractable awning where you can enjoy winter water views of the Chester River. This outdoor space provides an ideal extension of your living area for morning coffee, evening relaxation, or weekend entertaining. The upper level primary suite serves as your personal retreat with a spacious walk-in closet and luxurious ensuite bathroom featuring a jetted soaking tub and separate shower. Your own private outdoor deck off the primary suite provides a serene escape for morning coffee or quiet evening moments. The second bedroom on this level includes its own attached full bathroom, offering privacy and comfort for family or guests. The versatile top-floor loft space features abundant natural light, two generous walk-in closets, and another full bathroom. Use this flexible area as a guest suite, home office, creative studio, or third bedroom based on your lifestyle needs. The possibilities are endless with this unique third-level retreat. Modern systems ensure comfort and efficiency throughout. The recently updated HVAC system provides year-round climate control while reducing energy costs. High-efficiency washer and dryer convey with the home for added value. The attached one-car garage offers protected parking and additional storage space, while the end-unit positioning provides enhanced privacy with no neighbors on one side. This home is completely turnkey and move-in ready. The combination of hardwood floors, premium Thermador and GE Monogram appliances, modern HVAC system, and updated finishes throughout means you can move in immediately and start enjoying your new lifestyle without any projects or renovations required. Low-maintenance living at its best. Your monthly Condo fee includes lawn maintenance, snow removal, community pool access, and recreation facilities, allowing you to spend your time enjoying the waterfront lifestyle rather than maintaining property. This is the perfect balance of Chester River community living with modern convenience and resort-style amenities. The value proposition is compelling. This home's aggressive positioning combined with over $50,000 in premium upgrades creates an exceptional opportunity for discerning buyers. The motivated seller situation, extensive recent improvements, prime end-unit location

807 Auckland Way, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442