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109 Parma Rd, Chestertown
$325,000
3 Beds ⋅ 2 Baths
Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Coldwell Banker Realty.

601 Buckingham Dr, Stevensville
$465,000
3 Beds ⋅ 2 Baths
Welcome to 601 Buckingham Drive, where timeless character meets modern updates in the heart of Kent Island! Situated on a beautifully landscaped oversized corner lot, this charming home offers the perfect blend of comfort, convenience, and the sought-after Chesapeake Bay lifestyle. Step inside to discover stunning wood-beamed, vaulted ceilings that create an open, inviting feel throughout the living room and kitchen. A gorgeous original double-sided stone fireplace with a thick wood mantel serves as the centerpiece of the home, bringing warmth and character to both living spaces. Recent improvements provide peace of mind, including a **brand-new roof on both the home and detached rear building (2026)**, a new HVAC system, updated wood flooring in the TV room, new flooring in the sunroom, and a full suite of kitchen appliances replaced within the last four years. Outside, the mature landscaping and spacious corner lot provide exceptional curb appeal and plenty of room to relax, entertain, or garden. Location is everything, and this home truly delivers. Just one block away, enjoy a waterfront community park featuring a sandy beach, covered picnic pavilion, kayak launch, fishing pier, and breathtaking Chesapeake Bay sunsets. You'll also find another waterfront park just a few blocks away, along with Terrapin Nature Park, Matapeake Beach Park, Matapeake Dog Park, and the Kent Island Marina—all just minutes from your front door. Whether you're looking for a year-round residence, a weekend retreat, or a home that embraces the best of Eastern Shore living, 601 Buckingham Drive offers an incredible opportunity to enjoy the perfect combination of updated amenities, unique character, and unbeatable access to the water. There multiple parks in the neighborhood. Just at the end of the street a block away is the fishing pier and kayaks that are for Bay City residents. About five blocks away there's a larger waterfront park that has a children's playground and a lot of grass for picnics. Then there's the huge Terrapin Park with multiple long stretches of Bay, beaches, hiking trails, marshes and duck blinds etc. A huge nature preserve ready to call your own.

601 Buckingham Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

110 Boatswain Way Unit 3042, Chester
$699,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit 3042, Chester

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

Selling Office: Patterson-Schwartz-Middletown.

101 Edenderry Ave, Centreville
$495,000
5 Beds ⋅ 3 Baths
Welcome to 101 Edenderry Avenue, where space, comfort, and everyday functionality come together in one of Centreville's most desirable communities. Offering 5 true bedrooms, this home provides the flexibility today's buyers are searching for, whether you need space for a growing family, guests, a home office, or hobbies. The heart of the home is the spacious kitchen featuring abundant cabinetry, generous counter space, and a center island that opens seamlessly to the breakfast area and inviting family room, making it ideal for everyday living and entertaining alike. Natural light pours into the beautiful sunroom, creating the perfect spot to enjoy your morning coffee, unwind with a good book, or simply take in views of the private backyard. Formal living and dining rooms provide additional gathering spaces, while the thoughtfully designed floor plan offers room for everyone to spread out. Upstairs, you'll find five generously sized bedrooms, including a spacious owner's suite with a private bath and walk-in closet. Every bedroom offers comfortable living space, making this home a standout for buyers looking for true bedroom count without compromise. Step outside to enjoy the oversized backyard with plenty of room for entertaining, play, gardening, or creating your own outdoor retreat. Located in the sought-after North Brook community, you'll enjoy sidewalks, community amenities, nearby parks, schools, shopping, dining, and an easy commute to Annapolis, Easton, and the Bay Bridge. If you've been searching for a move-in ready home with 5 bedrooms, spacious living areas, and exceptional value in North Brook, this is an opportunity you won't want to miss.

101 Edenderry Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/MAX Executive.

12 Queen Anne Way Unit J, Chester
$379,900
1 Beds ⋅ 2 Baths
Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a wood-burning fireplace, skylights, and an abundance of natural light making it the perfect space for a home office, sitting area, guest space, or cozy retreat. Step outside and choose your view, from the garden-style front patio to the waterside patio out back or the upper-level balcony overlooking the water. With inviting indoor spaces, plenty of natural light, and multiple places to relax outdoors, this condo offers an easy, low maintenance, Eastern Shore lifestyle in a beautiful waterfront community.

12 Queen Anne Way Unit J, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: RE/MAX Leading Edge.

92 Long Creek Dr, Stevensville
$1,900,000
5 Beds ⋅ 5 Baths
Welcome to 92 Long Creek Drive, an extraordinary Kent Island waterfront estate where luxury living meets exceptional investment potential. Perfectly positioned on more than 2.5 private acres with approximately 250 feet of shoreline, this remarkable property offers the opportunity to enjoy a waterfront retreat while benefiting from an established, successful short-term vacation rental with proven income history. Profit and loss statements are available upon request, and the home is available fully furnished for a truly turnkey experience. Spanning nearly 4,000 square feet across four finished levels, the home features five bedrooms, four full baths, multiple living and entertaining spaces, and sweeping water views from nearly every room. The beautifully renovated kitchen is the heart of the home, offering white cabinetry, granite countertops, a commercial-grade refrigerator, custom pantry, shiplap accents, generous dining space, and stunning waterfront vistas. The primary suite is a peaceful retreat with panoramic water views and a luxurious bath featuring a soaking tub and tiled shower. Multiple living areas—including a lower-level recreation room with a full bar and full bath—provide abundant space for entertaining family and guests. Outside, every detail has been designed to embrace the Chesapeake Bay lifestyle. Enjoy the in-ground pool, outdoor kitchen and pavilion, expansive waterside deck and patio, beautifully landscaped grounds, and a private pier with boat lift and new electric service for enjoying boating, fishing, crabbing, paddleboarding, and kayaking. The property also includes an attached garage and a heated detached three-car garage, providing exceptional storage for vehicles, boats, water toys, and recreational equipment. Whether you're searching for a full-time waterfront residence, an unforgettable family retreat, or an investment property with an established rental history, 92 Long Creek Drive delivers an exceptional lifestyle just minutes from the Bay Bridge, Annapolis, and the rest of Maryland's Eastern Shore.

92 Long Creek Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

209 3rd St, Crumpton
$337,500
3 Beds ⋅ 2 Baths
Motivated Seller!!! Loan is assumable for a qualified veteran. Opportunity to own a beautiful rancher on 0.46 ac in the town of Crumpton. This home was built in 2021. It has been maintained, and kept meticulously. It compares nicely to new construction. The front porch welcomes you to a well-designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. This home offers plenty of room for all of your outdoor activities. It's two blocks to the boat ramp (Chester River). Easy commute to Route 301, Chestertown, Middletown, and the Bay Bridge. This is a one of a kind listing. Don't wait. Schedule your showings today!

209 3rd St, Crumpton

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

34 Queen Anne Way, Chester
$490,000
2 Beds ⋅ 3 Baths
WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and doors), new white cabinetry, beautiful quartz countertops with beveled white backsplash, updated bathroom vanities, flooring and modern lighting fixtures. The light-filled open floor plan is designed to highlight the panoramic Chester River views. The spacious family room off the kitchen features an oversized sliding glass door leading to a private balcony with beautiful eastern water views—perfect for morning coffee or relaxing evenings overlooking the river. Upstairs, the primary bedroom suite offers elevated water views and a private full bath. A second large bedroom and additional full bath complete the upper level, with washer and dryer conveniently located between the bedrooms. Residents of Queen’s Landing enjoy exceptional waterfront amenities including a private marina, swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and pickleball courts, and scenic waterfront walking paths. Ideally located just minutes from shopping, dining, entertainment, the Cross Island Trail, and the Chesapeake Bay Bridge, this home is perfect as a full-time residence or weekend waterfront retreat on Maryland’s Eastern Shore. Schedule your private tour today!

34 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

Selling Office: Coldwell Banker Realty.

204 Double Creek Rd, Chestertown
$525,000
3 Beds ⋅ 3 Baths
Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or additional side entrance provides a practical everyday entry. The first-floor primary suite offers comfortable main-level living and includes cathedral ceilings, a private door leading to a roomy composite back deck, and an attached bathroom with marble heated flooring and a walk-in shower, along with a spacious walk-in closet. Upstairs, the home offers two bedrooms with a loft area in between , providing flexible additional living space. Custom inlay flooring is featured in the formal dining room, living room, foyer, primary suite and first-floor extra room, tastefully alternating wood types and adding subtle character. Overall, this home offers quality construction, thoughtful design, and a layout that works well for everyday living. Still more details and touches to be seen when you come to visit. This home truly is move in ready.

204 Double Creek Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

306 Old Line Dr, Centreville
$680,000
3 Beds ⋅ 3 Baths
Spacious Claiborne Fields Home with Beautiful Views & Convenient Centreville Location! Welcome home to this spacious and beautifully situated 3-bedroom, 3-bath, large bonus room over garage home in the established and highly sought-after community of Claiborne Fields. With a 2-car garage and plenty of room both inside and out, this home offers the space and setting you've been looking for. The property sits on a beautiful lot with expansive views of open fields, mature trees, and a peaceful pond. The outdoor spaces are truly a highlight, with a wonderful sunroom and patio with a permanent umbrella—perfect for morning coffee, afternoon relaxation, or gathering with family and friends while enjoying the scenery. Inside, the generous floor plan offers comfortable living spaces, original hardwood floors, and plenty of room for everyday living and entertaining. The home has been thoughtfully maintained and features numerous updates and improvements, including a newer roof, newer heat pumps and furnace, Anderson 400 Series windows, granite countertops, Rinnai tankless hot water, water treatment system, and an encapsulated crawl space. Enjoy the best of both worlds—a peaceful neighborhood setting with beautiful open views, while being just minutes from downtown Centreville. Shopping, restaurants, parks, schools, and local amenities are all conveniently close by. A wonderful opportunity to enjoy space, privacy, beautiful surroundings. Come see why this one is special!

306 Old Line Dr, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: Compass.

247 Breeding Blvd, Stevensville
$685,000
6 Beds ⋅ 5 Baths
**KENT ISLAND LIVING, THOUGHTFULLY DESIGNED FOR EVERYDAY LIFE!** OPEN DAILY BY APPT - Or stop by one of our OPEN HOUSES! With OVER $50,000 worth of upgrades when built - This beautiful Ellendale home offers the space you need, the flexibility you want, and an unbeatable Kent Island location just minutes from the Chesapeake Bay Bridge. While this is one of the community's larger homes, the thoughtfully designed floor plan keeps the main living areas comfortably centered on the main and upper levels, with the finished English basement providing additional space when you need it. The main level is where everyday life happens, with a beautiful gourmet kitchen featuring granite countertops, stainless steel appliances, an oversized island, and a butler's pantry with cabinetry and a beverage refrigerator. The kitchen opens to the family room and casual dining area, with sliding doors leading to the deck and fenced backyard. A private office and formal dining room add even more functionality without taking away from the open feel of the main living space. Upstairs, you'll find four bedrooms, including an expansive primary suite with dual walk-in closets and a spacious en-suite bath, plus a second primary bedroom/Jr. suite and two additional bedrooms connected by a Jack and Jill bath. The finished English basement adds an entirely separate level of flexibility with two additional bedrooms, both with walk-in closets, a full bath, a second family room, and a recreation/game room. Use it for guests, extended family, hobbies, entertaining, or simply have the extra space available when you need it. With nearly 4,300 square feet, a two-car garage, and six bedrooms total, this home offers plenty of room without requiring every square foot to be part of your everyday routine. And the location is hard to beat. Ellendale is close to Kent Island's schools, shopping, waterfront restaurants, marinas, parks, resorts, and water access, while the Chesapeake Bay Bridge is just minutes away for an easy commute off the island. Community amenities include a pool, tot lot, walking trails, and creek access for kayaking and other water activities. **Come see how this spacious home can give you room to live, room to host, and room to grow, all in the heart of Kent Island.**

247 Breeding Blvd, Stevensville

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

Selling Office: Unrepresented.

303 Creeks End Ln, Stevensville
$649,900
4 Beds ⋅ 3 Baths
Experience the Chesapeake Bay lifestyle at 303 Creeks End Lane in Cox Creek Landing, a sought-after waterfront-access community in Stevensville on Kent Island, Maryland. This four-bedroom, two-and-a-half-bath home offers community water access—an exceptional combination for boating and waterfront-lifestyle enthusiasts. A welcoming front porch introduces a thoughtfully designed interior that balances comfort, function and flexibility. The main level features a spacious first-floor primary bedroom with a private full bath, plus a conveniently located powder room for guests. A separate home office with elegant glass doors provides dedicated space for remote work, studying or a quiet retreat. At the heart of the home is an open-concept kitchen and family room highlighted by vaulted ceilings that create a bright, airy atmosphere. The adjoining sun-filled morning room overlooks the landscaped backyard and offers an inviting setting for casual dining, morning coffee or everyday relaxation. Outside, a brick patio surrounded by lush, mature landscaping creates a private outdoor oasis for entertaining, dining or unwinding. A side-load two-car garage provides generous parking and storage while enhancing the home’s curb appeal. The upper level includes three additional generously sized bedrooms and a full bathroom, giving the home a total of four bedrooms with flexible options for guests, hobbies or additional workspace. Located in Cox Creek Landing, this Kent Island property combines boating access, comfortable indoor and outdoor living, and proximity to Stevensville shopping, restaurants and everyday conveniences. With a main-level primary suite, home office, vaulted family room, two-car garage, community pier access, boat-slip easement and boat lift, 303 Creeks End Lane presents a rare opportunity to own a well-appointed home in one of Kent Island’s desirable water-access communities.

303 Creeks End Ln, Stevensville

Listing courtesy of Paul Wesley Real Estate. Contact:

Selling Office: HomeSmart.

1810 Love Point Rd, Stevensville
$2,775,000
5 Beds ⋅ 5 Baths
This exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding. Complete with a Two car garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living and scenic beauty

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: Coldwell Banker Realty.

47-F Queen Anne Way, Chester
$555,000
2 Beds ⋅ 3 Baths
Set directly along the Chester River in desirable Queen’s Landing, this waterfront home puts the water at the center of everyday living, with incredible views from the main level, sunroom, patio, and both upstairs bedrooms. The shoreline feels remarkably close, creating a peaceful backdrop that can be enjoyed from nearly every principal living space. Renovations and upgrades throughout complement the setting, including wide-plank luxury vinyl plank flooring and an open-concept floor plan designed to keep the water in view. The remodeled kitchen, completed in 2022, features soft-close white cabinetry, quartz countertops, stainless steel appliances, a pantry, and a stainless steel sink and faucet positioned to overlook the entire main level and the Chester River beyond. Open to the living and dining combination, the kitchen creates an easy flow for everyday living and entertaining. A fireplace, added in 2025, brings a cozy focal point to the spacious gathering area while the water remains part of the view. Further along, a finished sunroom, unique to this home, extends the living space toward the water, with oversized sliding glass doors opening directly to the patio. Added in 2023, the patio provides an inviting place to sit outdoors and take in the ever-changing river scenery. Upstairs, both bedrooms enjoy water views, with the waterfront primary bedroom offering windows that act as artwork overlooking the serene Chester River. The remodeled primary bath features a convenient barn door, new shower with floor-to-ceiling tile, frameless glass door, and luxury vinyl plank flooring. The generous second bedroom also has an en-suite bath with luxury vinyl plank flooring. Additional improvements include a new front door, whole-house paint and electrical upgrades, second-floor carpet, a 2025 HVAC system, and first-floor luxury vinyl plank flooring added in 2026. The Queen’s Landing community offers a true waterfront lifestyle with a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. A kayak launch is conveniently located at the end of the street, while a deeded 25-foot boat slip is also available for purchase, adding even more opportunity to enjoy life on the Chester River. With water views woven throughout the home and direct access to the community’s waterfront amenities, this is a special opportunity to embrace the Chesapeake lifestyle from the comfort of home.

47-F Queen Anne Way, Chester

Listing courtesy of Northrop Realty. Contact:

Selling Office: Compass.

154 Encore Ct, Centreville
$549,000
3 Beds ⋅ 2 Baths
Welcome to this gorgeous home in Symphony Village at Centreville, an amenity-rich 55+ community offering an exceptional lifestyle just outside historic downtown Centreville. Situated on the largest and most premium lot in the neighborhood, this property enjoys a peaceful, private setting bordered by mature woods and a tranquil stream. The open concept home features a chef’s kitchen is the heart of the home, with beautiful Calcutta quartz counters, subway tile backsplash, stainless steel appliances including a gas range, abundant cabinetry, two pantries and recessed lighting. The kitchen opens seamlessly to the spacious family room, where a vaulted ceiling, gas fireplace, and French doors to the 20 x 25 deck create a warm and welcoming gathering space. A separate living room sits on the opposite side of the kitchen and flows into the dining area, offering plenty of room for both casual and formal entertaining. The spacious primary suite is a true retreat, highlighted by beautiful hickory wood floors, a lighted tray ceiling, sitting area with an arched window overlooking the woods, and two walk-in closets. The luxurious ensuite bathroom features separate vanities, a private water closet, and a glass-enclosed step-in shower. Designed for easy single-level living with a walkout basement, the home offers three bedrooms and two full bathrooms, while crown molding throughout adds an elegant finishing touch. Thoughtful updates include 2025 quartz countertops and a tankless water heater, 2024 heat pump and new stairs from the deck to the yard, 2023 roof, 2021 primary bathroom renovation, and 2020 appliances. The beautifully landscaped front and rear yards, mature trees, and covered front porch create an inviting first impression, while the backyard provides a serene retreat surrounded by nature.Enjoy the outdoors from the deck overlooking the wooded backdrop and stream, with convenient stairs leading directly to the yard. Symphony Village offers an impressive array of amenities and activities designed for active 55+ living. Ideally located just outside downtown Centreville, you'll have easy access to the Chester River, local dining and shopping, and Routes 301 and 50, making trips to the Delaware and Maryland beaches convenient in one direction and Baltimore and Washington, D.C. in the other. A rare opportunity to own the most desirable lot in Symphony Village and enjoy beautiful surroundings, exceptional updates, and an outstanding location. The fully outfitted laundry room offers custom shelving for exceptional organization and convenience. With its thoughtful layout, abundant natural light, wooded views, and generous gathering spaces, this home is perfectly suited for both relaxed living and entertaining family and friends.

154 Encore Ct, Centreville

Listing courtesy of Compass. Contact:

Selling Office: Long & Foster Real Estate, Inc..

4300 Main, Grasonville
$435,000
3 Beds ⋅ 2 Baths
Location, Location, Location! This GVC zoned property offers multiple possibilities to both investors and businesses located across from Grasonville Post Office. Perfect for anyone looking to expand their business in a growing area or investor looking for a great multiuse rental property. This corner property features 1000 sf storefront with additional warehouse, loading dock and storage containers, remolded 2nd floor 2 bedroom/ 1 full bath with deck and sunroom. Recent renovations include new roof and skylights, siding, new upper level and warehouse windows, new kitchen, new bath with tiled floor/shower bath and walls and flooring throughout 2nd floor apartment. Rare find with possible owner financing to qualifying Buyers.

4300 Main, Grasonville

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Sampson Properties.

902 Moorings Cir Unit 10, Stevensville
$565,000
2 Beds ⋅ 2 Baths
Experience the relaxed coastal lifestyle you've been dreaming of at 902 Moorings Circle in the highly sought-after 55+ community of Bay Bridge Cove! This beautifully maintained Oxford Model villa offers the perfect blend of comfort, convenience, and resort-style amenities on Maryland's Eastern Shore. Designed for easy, one-level living, this 2-bedroom, 2-bath home features a bright, open floor plan filled with natural light. The spacious kitchen boasts granite countertops, modern appliances, and abundant cabinetry, flowing seamlessly into the living room with a cozy gas fireplace. A separate formal dining room provides the perfect setting for holiday gatherings and entertaining. The private primary suite offers a tray ceiling, generous walk-in shower with low entry, dual vanities, and a linen closet. A second bedroom provides flexible space for guests, a home office, or hobbies. New carpet has been installed in both bedrooms for the next owner. Enjoy your morning coffee or evening glass of wine from the screened porch, host summer crab feasts, or fire up the grill on the adjoining paver patio. A spacious crawlspace provides exceptional storage, while the attached two-car garage adds everyday convenience. Bay Bridge Cove offers more than a home—it's a lifestyle. Residents enjoy a beautifully appointed clubhouse with a fitness center, yoga studio, game room, gathering spaces, and an outdoor pool. Walking trails, scenic ponds, and a full calendar of clubs and social events make it easy to stay active and connected. Located on Kent Island just minutes from the Chesapeake Bay Bridge, you'll enjoy quick access to Annapolis, Baltimore, Washington, D.C., Ocean City, and Delaware beaches while coming home to the peaceful charm of the Eastern Shore. Whether you're boating, fishing, dining on the waterfront, or simply enjoying the slower pace of life, this home offers the perfect place to embrace your next chapter.

902 Moorings Cir Unit 10, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: Compass.

114 Merganser Ct, Chester
$280,000
2 Beds ⋅ 2 Baths
"Why rent when you can own?" or are you looking for a weekend home? This condo is has so many options at an affordable price. Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Also, owning the upper level gives you the security if you are a lock and leave weekender. 2nd floor condos feature vaulted ceilings that are unavailable on the main level. Soaring vaulted ceilings, open floor, beautiful hardwood floors, gourmet Kitchen offers all brand new appliances including refrigerator, dishwasher, stove with glass top, microwave and garbage disposal. The beautiful living area features a gas fireplace for those chilly days coming soon and the dining area is perfect for entertaining and flows from the kitchen, dining to the balcony. This condo also includes a new efficient hot water heater and stackable full size washer and dryer. Owner has meticulously maintained this home. The spacious primary suite offers a peaceful retreat with a generous bedroom, walk-in closet and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. Another full bath is located near the second bedroom. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. Bayside is a friendly pet community with many paths for dog walking. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

114 Merganser Ct, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

719 Old Love Point Rd, Stevensville
$370,000
3 Beds ⋅ 1 Baths
Charming 3-Bedroom Rancher on a Spacious Double Lot Welcome home to this charming 3-bedroom, 1-bath rancher offering comfortable one-level living with plenty of space to make your own. Situated on a desirable double lot, this property features a spacious backyard with lots of room to play, relax, garden, or entertain family and friends. Inside, you’ll find beautiful hardwood floors throughout, a separate dining room, and a nice-sized kitchen with plenty of potential. A bonus space provides an opportunity to create whatever suits your needs—whether it’s a home office, hobby room, playroom, or additional living space. Seller has replaced the roof gutters and down spouts in addition the seller encapsulated the crawl space. Located in a wonderful community with an array of amenities, including a community pool, beach, boat launch, and more. A community marina is also available for a separate fee, making this an ideal location for those who enjoy spending time on the water. Conveniently located with an easy commute to the Bay Bridge, shopping, dining, and other everyday conveniences. This is a wonderful opportunity to own a home with a great yard, desirable community amenities, and plenty of potential—all at a reasonable price. Don’t miss your chance to make this home your own!

719 Old Love Point Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

114 Sonata Way, Centreville
$504,900
3 Beds ⋅ 2 Baths
Welcome to 114 Sonata Way in the beautiful community of Symphony Village at Centreville, the completed 55+ Active Adult Community in Queen Anne's County MD. This beautiful 3 bedroom, 2 full bath, Shubert model home has everything you want in one level living. Resting on a premium lot backing to the community clubhouse, pavilion, pickleball/tennis courts, putting green and pools, you won't have to go far to enjoy all the amenities Symphony Village has to offer. When you enter the home, you'll notice the beautiful hardwood flooring leading you past the front office/3rd bedroom, 2nd bedroom and full bath. To the right you'll find the laundry room, entrance to the garage and finished sky basement with heat and cooling vents for yearly comfort. Moving through, the dining room is to your left and a quiet, sitting room is located on the right. Directly in front of you you'll find the bright and open family room, kitchen, and breakfast nook all with views of the fireplace on the feature wall and the beautifully landscaped common areas of the community. But you haven't seen the best of this home until you tour the large master suite, master bath and his and her walk-in closets. We surely don't want you to miss the rear screened paver patio on the rear of the home where you'll enjoy plenty of relaxation.

114 Sonata Way, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Long & Foster Real Estate, Inc..

123 Flycatcher Way, Chester
$950,000
3 Beds ⋅ 3 Baths
The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, elegant pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive finish. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 and the loft for added comfort. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat designed for everyday ease. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

123 Flycatcher Way, Chester

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

Selling Office: Real Broker, LLC.

126 Meadowcroft Dr, Centreville
$530,000
5 Beds ⋅ 3 Baths
Welcome to 126 Meadowcroft Drive — a beautifully updated 5‑bedroom, 2.5‑bath home tucked in one of Centreville’s most desirable neighborhoods. With a brand‑new roof within the last few years and newer dual‑zoned HVAC units, this spacious home offers modern comfort, low maintenance, and peace of mind from day one. Step inside to find fresh updates throughout, including stylish finishes, gas fireplace and a bright, inviting layout perfect for both everyday living and entertaining. The main level features generous living spaces, an updated kitchen, and a flexible floor plan suited for today’s lifestyle. Upstairs, five well‑sized bedrooms provide ample room for family and guests. The primary suite offers its own private bathroom with a tile shower and soaking tub, while an additional full bath ensures convenience for all. Outside, enjoy a quiet setting with space to relax on the back patio complete with a firepit—ideal for anyone seeking both comfort and room to unwind in a well‑established community. Move‑in ready and thoughtfully updated, 126 Meadowcroft Drive delivers ease of ownership and timeless small‑town charm. Don’t miss this opportunity!

126 Meadowcroft Dr, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Redfin Corp.

7328 Kent Point Rd, Stevensville
$8,000,000
8 Beds ⋅ 10 Baths
Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

7328 Kent Point Rd, Stevensville

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

Selling Office: TTR Sotheby's International Realty.

702 Dixon Dr, Stevensville
$514,900
3 Beds ⋅ 4 Baths
Tucked away in the peaceful Cloverfields community, this beautifully updated Cape Cod with sunroom and second floor addition blends classic charm with modern comfort. Nearly every inch of the home has been renovated, including a full interior remodel, brand-new kitchen and bathrooms, two added full baths (for a total of four!), new flooring, lighting, paint, windows, roof, skylights, HVAC systems, exterior doors, and more. There’s even a new second laundry room, front porch, paved driveway extension, encapsulated crawlspace, privacy landscaping, and custom closet system. The property also includes two storage sheds, one with electricity — perfect for a workshop, hobby space, or she-shed. Inside, the open floor plan creates an inviting space that’s great for both everyday living and entertaining. The family room feels warm and welcoming with recessed lighting and a cozy electric fireplace. The kitchen is designed for both style and function with custom storage, granite countertops, ample table space, a pantry, and ENERGY STAR appliances. The home offers three spacious bedrooms, including a relaxing primary suite with a spa-like bathroom. Extras like wainscoting, skylights, and main level bedroom add even more comfort and character throughout the home. Outside, the level 0.34-acre lot offers plenty of room to enjoy the outdoors, whether you’re relaxing on the large deck and patio or hosting friends and family. And the location is hard to beat — just four blocks from the Chester River with access to amazing Cloverfields amenities including a community pool, beach, basketball courts, boat ramp, boat slips, playgrounds, and scenic trails. This home offers the perfect mix of modern updates, outdoor living, and laid-back community charm — truly a place you’ll love coming home to.

702 Dixon Dr, Stevensville

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

Selling Office: Taylor Properties.

712 Bay Dr, Stevensville
$1,750,000
4 Beds ⋅ 3 Baths
712 Bay Drive isn't simply a waterfront home—it's a turnkey Chesapeake lifestyle, beautifully executed from shore to door. Just two years young, this exceptional waterfront residence combines thoughtful design, elevated finishes and impressive waterfront infrastructure with sweeping views of the Bay. The open-concept main level was designed around the view, with a dramatic wall of windows overlooking the water and a propane fireplace anchoring the living space. The kitchen delivers both beauty and function with an extra-long island, quartz countertops, high-end appliances, crisp white cabinetry, statement hood and walk-in pantry. The main-level primary suite offers a private retreat with a walk-in closet and beautifully finished bath featuring a spacious walk-in shower and shiplap detailing. Upstairs, you'll find three additional bedrooms, a bonus room and abundant walk-in storage, plus a floored, temperature-controlled attic. And then there's the waterfront. A vaulted covered side porch creates another incredible place to take in the views, complete with a hot tub that conveys, while the home's piling construction creates an expansive “Below Deck” entertaining area at ground level—perfect for waterfront gatherings, crab feasts and relaxed summer evenings. The waterfront infrastructure is equally impressive, with a newer bulkhead and pier, 12,500-lb boat lift, electric and water at the pier directly on the Chesapeake Bay. Thoughtful systems include a whole-house water filtration system, tankless water heater, two-year-old roof and HVAC, plus electric HVAC with propane backup for efficiency and peace of mind. Newer construction. Exceptional waterfront infrastructure. Thoughtfully engineered. Turnkey. And a front-row seat to life on the Bay.

712 Bay Dr, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: TTR Sotheby's International Realty.

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