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5011 Bridgepointe Dr, Chester
$315,000
3 Beds ⋅ 3 Baths
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today! Home sold as-is.

5011 Bridgepointe Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact:

218 Upland Ln, Centreville
$925,000
5 Beds ⋅ 5 Baths
WOW! This one is an absolute 11 on a scale of 1–10! Thoughtfully updated with stylish, on-trend finishes throughout, this property is truly exceptional from top to bottom. From the moment you step onto the covered front porch and into the dramatic two-story foyer, you’ll feel the difference. A private dining room sits to one side while two spacious main-level offices on the other make balancing work and home life effortless. And YES—high-speed internet is available through Talkie Fiber! At the heart of the home is a bright and beautiful gourmet kitchen featuring stainless steel appliances, a full refrigerator and full freezer, center island seating, and the kind of layout that naturally becomes the gathering place for everyone. The adjoining living room is warm and inviting, anchored by a fireplace and framed by oversized windows that flood the space with natural light while overlooking the picturesque backyard. Upstairs, you’ll find a magazine-worthy laundry room along with three spacious bedrooms and two beautifully updated full baths. The primary suite was designed to feel like a true personal retreat—complete with vaulted ceilings, a private deck overlooking the grounds, and plenty of natural light. Start your mornings with coffee in the fresh air or unwind at the end of the day under the stars. The luxurious ensuite bath features a soaking tub, separate shower, double vanity, and soaring ceilings that make the space feel spa-like. And just when you think it can’t get any better… there’s approximately 1,800 additional square feet of finished living space in the lower level! Complete with a private movie theater with seating for eight, bedroom, full bath, family room, kitchenette, and private entrance, the lower level offers incredible flexibility for guests, multi-generational living, or an in-law suite. Situated on nearly 1.5 acres surrounded by mature trees, this property offers the peaceful privacy of your own backyard oasis. The in-ground pool with landscaping, fire pit, multiple lounging areas, and glowing string lights create the perfect setting for entertaining family and friends all summer long. And tucked beyond it all? A beach volleyball court and horseshoe pit that make this property feel like your own private resort. PLUS: (As if all that wasn't enough) There is a whole house Generac to ensure you never lose power AND a 46,000 Enphase Solar (owned--no lease takeover!!) that saves BIG on electric and also returns Solar Renewable Energy Credits (SREC). Brand New Roof, too! Sound too good to be true? It’s not… unless you wait too long. This GEM is guaranteed to turn heads the moment it hits the market—so be ready!

218 Upland Ln, Centreville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

109 2nd St, Chestertown
$125,000
**STARTING 9/5 & ENDING 9/12: For one week only, list price is reduced to $125,000 with all closing costs covered by seller!** Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton, and Middletown easy. Quotes are already available for septic installation, well installation, and clearing of the existing structure and brush.

109 2nd St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

114 Queens Colony High Rd, Stevensville
$689,900
4 Beds ⋅ 3 Baths
One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area.

114 Queens Colony High Rd, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

106 Encore Ct, Centreville
$569,000
3 Beds ⋅ 3 Baths
Set on a splendid site backing to open space and woods, this dramatic Gershwin model with a solarium extension and loft will delight you. As you walk through the living and dining room and on to the kitchen and family room, the floor-to-ceiling stone fireplace in the solarium will  draw your eye, with a half round window high on the wall above. Several transom windows add to the natural light flowing into the house. An office opposite the living/dining room could become an additional bedroom, with easy access to the hall bathroom, or a hobby room, music or reading room. Rich hardwood flooring through the formal  area and kitchen, with carpeting in other areas and bedrooms. The gourmet kitchen has granite countertops, cherry cabinets, an electric cooktop and double oven plus microwave, large refrigerator and dishwasher. Several appliances have been replaced. The en suite primary bedroom has two closets, and the bathroom has a soaking tub, double vanity and a large shower with a seat. The guest bedroom is located in a separate hallway with an adjacent bathroom. On the upper floor is a second family room, bathroom and spacious bedroom with a large closet. Over the garage is the sky basement generally used for storage, with attic access. The custom patio overlooks the woods, and a feeling of serenity descends as you enjoy the view and the birdsong. The Symphony Village community is well established, with mature trees throughout, and an impressive clubhouse with many amenities, including a concert hall for the many events organized by the various committees. The main gathering area is bright and welcoming, and is the location for semi-monthly social hours where you bring a dish to share and get to meet your neighbors. Several groups with varied interests meet in the clubhouse on a regular basis, and you might walk through the clubhouse and see folks learning to paint in the craft room, others playing pool, some playing mahjong in the concert hall, or committee meetings to keep things humming along. You can walk outside to the covered patio area and the pool beyond, where residents enjoy holiday picnics, quiet evening time, and fun with the kids during the day. The indoor pool is open every day from early morning until late at night, and you can show up for water aerobics every weekday morning at 9:00A.M. Currently there are Spanish classes offered, in addition to soul line dancing, and at any time you can learn how to play bridge or hand and foot, so there is plenty to keep everyone busy. However, there is no requirement to participate in any activities, and you can live a quiet life in Symphony Village enjoying retirement or still working. There are many areas to walk in around the neighborhood, and in the clubhouse grounds is a pergola to sit and  watch the world go by, a kids' playground, a picnic area, bocce, a putting green (and active league) and a trail leading to Dunkin' Donuts and the shopping center just minutes away.

106 Encore Ct, Centreville

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

109 Birch Rd, Stevensville
$419,900
3 Beds ⋅ 2 Baths
*BACK ON THE MARKET WITH A MAJOR PRICE IMPROVEMENT! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity! Seller will consider leasing the property to qualified tenants for $3000 per month plus $3000 security deposit.

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

1 Bunker, Grasonville
$699,000
4 Beds ⋅ 3 Baths
Highly motived sellers enjoyed Prospect Bay and want you to as well--they just reduced again making it super attractive. Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

4000 Herons Nest Way Unit 22, Chester
$489,000
2 Beds ⋅ 3 Baths
REDUCED! Four Seasons @ Kent Island - 55+ Community - Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 24,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit 22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

3000 Herons Nest Way Unit 11, Chester
$439,500
2 Beds ⋅ 3 Baths
Luxury Coastal Living | $55K in Owner Upgrades | Move-In Ready! Recently improved price! No construction delays, no waiting, and exceptional upgrades already included. Water and sewer are included in the monthly COA fee. Discover this beautifully upgraded, 2,003 sq. ft. first-floor condo on Kent Island. This meticulously maintained home shows like a model and is ready for immediate occupancy! Step inside to a bright, open-concept floor plan featuring luxury vinyl plank flooring throughout, crown molding, recessed lighting, and a cozy fireplace. The gourmet kitchen impresses with quartz countertops, an oversized island, and sleek Wi-Fi-enabled appliances—perfect for entertaining! Enjoy peaceful green-space views and seasonal water glimpses from your private patio, accessible from both the living room and spacious owner’s suite. The luxurious primary bath features dual vanities and a frameless glass shower. A generous guest suite with private bath and a versatile bonus room with frosted glass doors provide plenty of space for guests, a home office, or hobbies. Additional highlights include interior access to a private one-car garage, secure storage, and a prime location just steps from the waterfront and walking trails. Experience resort-style living with indoor and outdoor pools, pickleball and tennis courts, firepits, a dog park, kayak and paddleboard launch, and direct access to the Cross Island Trail.

3000 Herons Nest Way Unit 11, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

222 Dutchess Rd, Chestertown
$298,000
3 Beds ⋅ 2 Baths
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

915 Sportsman Neck Rd, Queenstown
$375,000
Two peaceful acres nestled in Hickory Ridge Community at the very end of Sportsman Neck Rd. Perc approved. Backs to woods/ravine. Water views of the Wye River! Level and clear with mature trees. Very rare opportunity to own a property in a well established quiet community close to the water. Close to Rt 50 for easy access to the Bay Bridge or Easton. Appointment required.

915 Sportsman Neck Rd, Queenstown

Listing courtesy of Kevin Dey Realty. Contact:

Sparks Corner Sparks Corner Sparks Mill At Route 213 Road, Centreville
$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $836.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Corner Sparks Corner Sparks Mill At Route 213 Road, Centreville

Listing courtesy of Tidewater Properties. Contact:

Sparks Mill Corner - E&W Sparks Mill Corner - E&W Sparks Mill At Route 213 Road, Centreville
$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $837.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Mill Corner - E&W Sparks Mill Corner - E&W Sparks Mill At Route 213 Road, Centreville

Listing courtesy of Tidewater Properties. Contact:

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