Accessible homes for sale & real estate in Chestertown, MD

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NEW 22 HRS AGO

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (. 45 acres) and 300 S Mill (. 55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms wh

$1,195,000

2 beds1 bath806 sq ft

302 S Mill St, Chestertown, MD 21620

Downtown chestertown • 1960s brick home • Usable site

(410) 778-0330

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry ca

$649,000

4 beds3 baths2,864 sq ft

22400 Great Oak Landing Rd, Chestertown, MD 21620

Backs to woods • Large walk in pantry • Dual zone hvac

(410) 778-0330

COMING SOON

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a completer renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar plus seperate ding area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the h

$345,000

3 beds1.5 baths1,398 sq ft

217 Edmore Rd, Chestertown, MD 21620

Open floor plan • Complete renovation • Ss appliances

(410) 810-0010

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard.

$299,900

3 beds1 bath1,056 sq ft

124 Wilton Rd, Chestertown, MD 21620

Soft close cabinets • New lvp flooring • Custom countertops

(410) 810-0010

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a s

$750,000

3 beds2.5 baths2,176 sq ft

216 Birch Run Rd, Chestertown, MD 21620

Quiet cul-de-sac • Brick facade • Half acre lot

(410) 673-3344

Property at 8999 Orchard Dr, Chestertown, MD 21620, 5 beds, 3.5 baths

$824,900

5 beds3.5 baths4,353 sq ft

8999 Orchard Dr, Chestertown, MD 21620

(410) 778-0330

Property at 109 Parma Rd, Chestertown, MD 21620, 3 beds, 2 baths

$315,000

3 beds2 baths1,288 sq ft

109 Parma Rd, Chestertown, MD 21620

(410) 778-0330

Property at 117 N Water St Unit 3B, Chestertown, MD 21620, 1 bed, 1 bath

$295,000

1 bed1 bath— sq ft

117 N Water St Unit 3B, Chestertown, MD 21620

(410) 778-0330

Property at 115 Chester Arms Dr, Chestertown, MD 21620, 3 beds, 2 baths

$263,000

3 beds2 baths1,140 sq ft

115 Chester Arms Dr, Chestertown, MD 21620

(703) 378-8810

Property at 7828 Country Club Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths2,857 sq ft

7828 Country Club Ln, Chestertown, MD 21620

(410) 778-3779

Property at 129 Trafford Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$480,000

3 beds2.5 baths3,176 sq ft

129 Trafford Dr, Chestertown, MD 21620

(302) 422-2619

Property at 10540 Tonopah Rd, Chestertown, MD 21620, 3 beds, 2 baths

$279,000

3 beds2 baths1,404 sq ft

10540 Tonopah Rd, Chestertown, MD 21620

(410) 810-0010

Property at 21324 Persimmon Dr, Chestertown, MD 21620, 2 beds, 1 bath

$179,900

2 beds1 bath1,232 sq ft

21324 Persimmon Dr, Chestertown, MD 21620

(410) 822-6665

Property at 22470 Fairgale Farm Ln, Chestertown, MD 21620, 4 beds, 5 baths

$1,450,000

4 beds5 baths4,257 sq ft

22470 Fairgale Farm Ln, Chestertown, MD 21620

(410) 275-2118

Property at 213 Byford Dr, Chestertown, MD 21620, 4 beds, 2 baths

$372,000

4 beds2 baths1,277 sq ft

213 Byford Dr, Chestertown, MD 21620

(410) 810-0010

Property at 204 Double Creek Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths2,927 sq ft

204 Double Creek Rd, Chestertown, MD 21620

(410) 810-0010

Property at 103 Landing Ln, Chestertown, MD 21620, 2 beds, 2.5 baths

$499,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

Property at 201 N Lynchburg St, Chestertown, MD 21620, 1 bath

$750,000

— beds1 bath2,045 sq ft

201 N Lynchburg St, Chestertown, MD 21620

(302) 234-3800

Property at 106 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$799,900

3 beds3.5 baths2,092 sq ft

106 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 104 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$813,900

3 beds3.5 baths2,192 sq ft

104 Landing Ln, Chestertown, MD 21620

(410) 275-2118

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OPEN TODAY, 12PM TO 2PM

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in natur

$559,500

3 beds2 baths2,316 sq ft

12613 Walnut Valley Ct, Worton, MD 21678

Private acres • Fully remodeled • Vaulted great room

(410) 778-0330

OPEN TODAY, 10AM TO 12PM

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffe

$634,999

3 beds2.5 baths1,700 sq ft

21191 W Sharp St, Rock Hall, MD 21661

Coffered ceilings • Thick crown moldings • 7,850 sq ft lot

(410) 778-0330

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Welcome to this beautifully maintained `three-bedroom, two-bathroom home, built in 2021 and offering a like-new feeling. The thoughtfully designed interior features modern finishes throughout, including granite countertops, stainless steel appliances, tankless water heater, and the exterior features hardi-plank siding. Quality construction inside and out. This home is move-in ready and offers a perfect blend of modern comfort and small town living.

$435,000

3 beds2 baths1,568 sq ft

414 Church St, Sudlersville, MD 21668

Hardi-plank siding • Granite countertops • 0.47 acre lot

(410) 543-4545

COMING SOON

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
COMING SOON! This exceptional 4-bedroom, 2.5-bath custom home offers a level of thoughtful design, upgrades, and attention to detail that truly sets it apart. Located on a desirable cul-de-sac and backing to woods and community open space, this home combines an impressive interior with privacy and outstanding outdoor living. From the moment you arrive, the custom character is evident in the beautiful curb appeal, stone-faced foundation, welcoming front porch, and handsome wood accents. Inside, the showpiece kitchen is designed for both everyday living and entertaining, featuring high-end appliances, upgraded finishes, and a huge center island offering abundant prep space, seating, and a nat

$699,500

4 beds2.5 baths2,378 sq ft

478 Eagle Manor Dr, Church Hill, MD 21623

High-end appliances • Community open space • Backs to woods

(443) 988-0114

FLOOR PLAN

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend r

$419,000

3 beds2 baths1,056 sq ft

405 Rings End Rd, Millington, MD 21651

Quiet cul-de-sac • Newer roof • Wooded acres

(217) 285-9000

ABOUT THIS HOME
Accessible Home for sale in Chestertown, MD:
Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage

$515,000

7 beds5 baths3,836 sq ft

11960 Flour Mill St, Kennedyville, MD 21645

Mother-in-law suite • Efficiency kitchen • Walk-in closet

(410) 778-0330

Property at 611 Clark Corners Rd, Centreville, MD 21617, 4 beds, 2.5 baths

$549,987

4 beds2.5 baths2,596 sq ft

611 Clark Corners Rd, Centreville, MD 21617

(443) 249-7653

Property at 20714 Wilkins Ave, Rock Hall, MD 21661, 3 beds, 2.5 baths

$599,900

3 beds2.5 baths1,920 sq ft

20714 Wilkins Ave, Rock Hall, MD 21661

(410) 639-4003

Property at 143 Thicket Ct, Centreville, MD 21617, 5 beds, 3.5 baths

$915,000

5 beds3.5 baths4,342 sq ft

143 Thicket Ct, Centreville, MD 21617

(410) 263-8686

Property at 114 Edenderry Ave, Centreville, MD 21617, 3 beds, 2 baths

$484,500

3 beds2 baths1,974 sq ft

114 Edenderry Ave, Centreville, MD 21617

(443) 988-0483

Property at 24050 Macs Ln, Worton, MD 21678, 3 beds, 3 baths

$935,000

3 beds3 baths2,102 sq ft

24050 Macs Ln, Worton, MD 21678

(410) 778-0330

Property at 21232 Rock Hall Ave, Rock Hall, MD 21661, 2 beds, 2 baths

$330,000

2 beds2 baths1,200 sq ft

21232 Rock Hall Ave, Rock Hall, MD 21661

(410) 442-4455

Property at 6202 Rock Hall Rd, Rock Hall, MD 21661, 2 beds, 1.5 baths

$425,000

2 beds1.5 baths2,368 sq ft

6202 Rock Hall Rd, Rock Hall, MD 21661

(410) 778-0330

Property at 24274 Waterview Dr, Worton, MD 21678, 4 beds, 3.5 baths

$765,000

4 beds3.5 baths3,006 sq ft

24274 Waterview Dr, Worton, MD 21678

(410) 778-0330

Property at 11106 Plum Dr, Worton, MD 21678, 3 beds, 1 bath

$267,500

3 beds1 bath1,008 sq ft

11106 Plum Dr, Worton, MD 21678

(410) 810-0010

Property at 21123 Striper Run, Rock Hall, MD 21661, 3 beds, 2.5 baths

$389,900

3 beds2.5 baths2,040 sq ft

21123 Striper Run, Rock Hall, MD 21661

(443) 249-7653

Property at Price Station Rd, Centreville, MD 21617, 4 beds, 2 baths

$649,500

4 beds2 baths2,000 sq ft

Price Station Rd, Centreville, MD 21617

(443) 988-0114

Property at 12712 and 12714 Still Pond Rd, Still Pond, MD 21667, 6 beds, 5 baths

$549,000

6 beds5 baths4,305 sq ft

12712 and 12714 Still Pond Rd, Still Pond, MD 21667

(410) 778-0330

Property at 337 Roe Ingleside Rd, Centreville, MD 21617, 4 beds, 2.5 baths

$589,500

4 beds2.5 baths3,216 sq ft

337 Roe Ingleside Rd, Centreville, MD 21617

(301) 970-2447

Property at 112 Lently Farm Ln, Centreville, MD 21617, 4 beds, 2.5 baths

$524,900

4 beds2.5 baths2,004 sq ft

112 Lently Farm Ln, Centreville, MD 21617

(301) 352-4065

Accessible Homes for Sale in Chestertown

There are currently 20 accessible homes for sale in Chestertown at a median listing price of $378K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestertown stay on the market for 117 days. This map is refreshed with the newest listings in Chestertown every 15 minutes.

In the past month, 5 homes have been sold in Chestertown. In addition to houses in Chestertown, there was also 1 condo, 16 townhouses, and 1 multi-family unit for sale in Chestertown last month. Find your dream home in Chestertown 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 Chestertown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestertown. Our Chestertown real estate stats and trends will give you more information about home buying and selling trends in Chestertown. If you're looking to sell your home in the Chestertown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestertown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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