Accessible homes for sale & real estate in Chester, MD

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FLOOR PLAN

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and features, including a new roof installed in 2026 with a transferable manufacturer’s warranty and a new kitchen completed in 2022 featuring GE Café appliances, including a professional 36” six-burner range with convection oven, an additional oven in the island, and an Advantiu

$819,900

3 beds2.5 baths2,479 sq ft

207 Thomas White Blvd, Chester, MD 21619

New kitchen • Ge cafe appliances • New roof

(443) 353-5281

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is

$897,750

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

Recent renovations • Raised garden beds • Premium lot

(410) 486-4504

NEW CONSTRUCTION

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Construction Complete, QUICK MOVE IN! Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style

$989,800

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

Waterfront home • Gourmet kitchen • Covered patio

(301) 945-9010

OPEN WED, 1PM TO 3PMVIDEO TOUR

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dini

$859,500

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

Expansive windows • Gas fireplace • Waterfront living

(410) 280-5600

VIDEO TOUR

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier

$5,400,000

7 beds8 baths10,667 sq ft

330 Serenity Ln, Chester, MD 21619

2.58 acre lot • 6 garage spots • Pool

(410) 280-5600

Property at 111 Marshgrass Way #41, Chester, MD 21619, 3 beds, 2.5 baths

$998,000

3 beds2.5 baths— sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

Property at 106 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,595 sq ft

106 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

Property at 114 Merganser Ct, Chester, MD 21619, 2 beds, 2 baths

$287,500

2 beds2 baths1,069 sq ft

114 Merganser Ct, Chester, MD 21619

(443) 988-0483

Property at 1000 Herons Nest Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$595,000

2 beds2.5 baths1,832 sq ft

1000 Herons Nest Way #43, Chester, MD 21619

(410) 224-2200

Property at 132 Wheelhouse Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$700,000

2 beds2.5 baths2,003 sq ft

132 Wheelhouse Way #11, Chester, MD 21619

(855) 450-0442

Property at 54F Queen Caroline Ct, Chester, MD 21619, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,440 sq ft

54F Queen Caroline Ct, Chester, MD 21619

(410) 643-2244

Property at 1000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$485,000

2 beds2.5 baths1,900 sq ft

1000 Herons Nest Way #22, Chester, MD 21619

(443) 274-1900

Property at 8-F Queen Victoria Way, Chester, MD 21619, 1 bed, 1 bath

$240,000

1 bed1 bath724 sq ft

8-F Queen Victoria Way, Chester, MD 21619

(410) 643-2244

Property at 111 Marshgrass Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$765,000

2 beds2.5 baths— sq ft

111 Marshgrass Way #43, Chester, MD 21619

(410) 263-8686

Property at 2000 Herons Nest Way #401, Chester, MD 21619, 3 beds, 2.5 baths

$700,000

3 beds2.5 baths2,602 sq ft

2000 Herons Nest Way #401, Chester, MD 21619

(855) 450-0442

Property at 4000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$515,000

2 beds2.5 baths1,900 sq ft

4000 Herons Nest Way #22, Chester, MD 21619

(410) 224-3200

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3D WALKTHROUGH

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Professional staging & photos coming soon! Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while t

$685,000

3 beds3 baths2,508 sq ft

259 Topside Dr #166, Stevensville, MD 21666

Custom backsplash • Gourmet kitchen • Cozy fireplace

(703) 378-8810

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
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

$375,000

3 beds1 bath1,300 sq ft

719 Old Love Point Rd, Stevensville, MD 21666

Spacious backyard • Community pool • Boat launch

(410) 224-2200

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Welcome to this like-new, impeccably maintained stone front end-unit townhome offering four finished levels of thoughtfully designed living space, 4/5 bedrooms, 4.5 bathrooms, and numerous custom upgrades throughout. Perfectly located just one mile from the Chesapeake Bay Bridge, this stunning home combines modern luxury with the convenience of Eastern Shore living. You are welcomed to the home by a partial wrap around porch, ideal for decorating and offers coverage for deliveries. Inside you will discover a beautifully updated interior with all four levels of stairs completely renovated with new flooring (2026), representing a $10,000 investment, luxury vinyl plank flooring, new carpet in

$605,000

4 beds4.5 baths2,850 sq ft

222 Jessica Lyn Ave Unit G5, Stevensville, MD 21666

Quartz countertops • Private balcony • Gourmet kitchen

(410) 647-8000

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the p

$749,900

3 beds2 baths— sq ft

130 Oyster Cove Dr #130, Grasonville, MD 21638

Community pool • Gated entrance • 3rd floor penthouse

(410) 643-5005

NEW CONSTRUCTION

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flo

$819,990

2 beds2.5 baths1,900 sq ft

102 Boatswain Way #2932, Chester, MD 21619

Quartz countertops • Pendant lighting • Electric fireplace

(410) 208-3500

NEW CONSTRUCTION

ABOUT THIS HOME
Accessible Home for sale in Chester, MD:
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flo

$919,990

2 beds2.5 baths1,900 sq ft

102 Boatswain Way #2943, Chester, MD 21619

Quartz countertops • Pendant lighting • Electric fireplace

(410) 208-3500

Property at 102 Sophie Ln, Stevensville, MD 21666, 3 beds, 2.5 baths

$459,900

3 beds2.5 baths1,880 sq ft

102 Sophie Ln, Stevensville, MD 21666

(410) 255-3690

Property at 102 Boatswain Way #2911, Chester, MD 21619, 2 beds, 2.5 baths

$619,990

2 beds2.5 baths2,003 sq ft

102 Boatswain Way #2911, Chester, MD 21619

(410) 208-3500

Property at 222 Moorings Cir #126, Stevensville, MD 21666, 3 beds, 3 baths

$600,000

3 beds3 baths2,074 sq ft

222 Moorings Cir #126, Stevensville, MD 21666

(443) 574-1600

Property at 102 Boatswain Way #2933, Chester, MD 21619, 2 beds, 2.5 baths

$819,990

2 beds2.5 baths1,900 sq ft

102 Boatswain Way #2933, Chester, MD 21619

(410) 208-3500

Property at 110 Boatswain Way #3042, Chester, MD 21619, 2 beds, 2.5 baths

$739,990

2 beds2.5 baths1,900 sq ft

110 Boatswain Way #3042, Chester, MD 21619

(410) 208-3500

Property at 111 Ryan Dorsey Ln, Stevensville, MD 21666, 3 beds, 2.5 baths

$424,989

3 beds2.5 baths1,900 sq ft

111 Ryan Dorsey Ln, Stevensville, MD 21666

(443) 249-7653

Property at 121 Eareckson Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths2,141 sq ft

121 Eareckson Ln, Stevensville, MD 21666

(410) 643-2244

Property at 105 Bobbit Ct, Stevensville, MD 21666, 3 beds, 2 baths

$389,000

3 beds2 baths1,134 sq ft

105 Bobbit Ct, Stevensville, MD 21666

(410) 224-8200

Property at 1301 Marion Quimby Dr, Stevensville, MD 21666, 3 beds, 3 baths

$379,900

3 beds3 baths1,789 sq ft

1301 Marion Quimby Dr, Stevensville, MD 21666

(410) 827-4663

Property at 931 Petinot Pl, Stevensville, MD 21666, 4 beds, 2 baths

$509,995

4 beds2 baths2,000 sq ft

931 Petinot Pl, Stevensville, MD 21666

(443) 249-7653

Property at 845 Moorings Cir #138, Stevensville, MD 21666, 2 beds, 2 baths

$569,900

2 beds2 baths2,088 sq ft

845 Moorings Cir #138, Stevensville, MD 21666

(410) 224-2200

Property at 107 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

107 Petrie Way, Stevensville, MD 21666

(410) 280-5600

Property at 350 Narrows Pointe Dr, Grasonville, MD 21638, 3 beds, 3.5 baths

$1,215,000

3 beds3.5 baths2,742 sq ft

350 Narrows Pointe Dr, Grasonville, MD 21638

(410) 295-6579

Property at 109 Bayview, Grasonville, MD 21638, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,044 sq ft

109 Bayview, Grasonville, MD 21638

(410) 224-2200

Accessible Homes for Sale in Chester

There are currently 16 accessible homes for sale in Chester at a median listing price of $574K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 77 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 15 homes have been sold in Chester. In addition to houses in Chester, there were also 17 condos, 21 townhouses, and 0 multi-family units for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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