21690, MD homes for sale & real estate

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OPEN OCT 31, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
21690, MD Homes for Sale
Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on . 53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating c

$495,000

3 beds2.5 baths1,656 sq ft

10 Cedar Chase Ct, Chestertown, MD 21620

Waterviews • Upper-level deck • Historic district

(410) 778-3779

3D WALKTHROUGH

ABOUT THIS HOME
21690, MD Homes for Sale
Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drai

$679,900

3 beds3.5 baths3,228 sq ft

8986 Orchard Dr, Chestertown, MD 21620

Screened-in porch • 1.84 acre lot • 2 garage spots

(410) 822-6665

READY TO BUILD

ABOUT THIS HOME
21690, MD Homes for Sale
Welcome to Radcliffe Meadows Single-Family Homes, a new community of spacious single-family homes in Chestertown designed for the way you live today. Nestled in a charming small-town setting just minutes from downtown Chestertown, shopping, dining, and everyday conveniences, Radcliffe Meadows offers the space you want, the flexibility you need, and a location that makes it easy to enjoy the best of Maryland's Eastern Shore. The Allegheny single-family home allow today's families to easily spend time together or spread out. The convenient family entry off the 2-car garage controls clutter. The inviting family room opens to the dining area and gourmet kitchen, so entertaining is easy. Extend

$419,990

4 beds3.5 baths2,397 sq ft

Allegheny | Finished Basement Plan, Chestertown, MD 21620

Covered porch • Walk-in closet • Finish the basement

Listing provided by Zillow

READY TO BUILD

ABOUT THIS HOME
21690, MD Homes for Sale
Welcome to Radcliffe Meadows Single-Family Homes, a new community of spacious single-family homes in Chestertown designed for the way you live today. Nestled in a charming small-town setting just minutes from downtown Chestertown, shopping, dining, and everyday conveniences, Radcliffe Meadows offers the space you want, the flexibility you need, and a location that makes it easy to enjoy the best of Maryland's Eastern Shore. The Columbia single-family home is just as inviting as it is functional. Discover a magnificently spacious floor plan with custom flex areas. The welcoming family room effortlessly flows into the gourmet kitchen and dining area, so you never miss a moment. Add a covered

$449,990

4 beds2.5 baths3,133 sq ft

Columbia | Finished Basement Plan, Chestertown, MD 21620

Covered porch • Walk-in closet • Gourmet kitchen

Listing provided by Zillow

READY TO BUILD

ABOUT THIS HOME
21690, MD Homes for Sale
Welcome to Radcliffe Meadows Villas, a new community of low-maintenance villa homes in Chestertown designed for everyday ease. Set in a peaceful location just minutes from downtown, shopping, dining, and local attractions, Radcliffe Meadows Villas offers the convenience you need in a setting that makes it easy to enjoy the best of Maryland's Eastern Shore. The Rosecliff townhome villa radiates elegance by blending sophistication and low-maintenance living. The first floor features soaring 9 ft. ceilings, a gourmet kitchen with 42" cabinets, ample counter space, and a pantry for extra storage. In the main living area, the great room opens into the dining room and kitchen, ideal for gath

$369,990

3 beds2 baths2,158 sq ft

Rosecliff | Finished Basement Plan, Chestertown, MD 21620

Ample counter space • Extra storage • Gourmet kitchen

Listing provided by Zillow

Property at 234 N Kent St, Chestertown, MD 21620, 5 beds, 2 baths

$325,000

5 beds2 baths1,802 sq ft

234 N Kent St, Chestertown, MD 21620

(410) 673-3344

Property at 212 Washington Ave, Chestertown, MD 21620, 5 beds, 3 baths

$675,000

5 beds3 baths2,838 sq ft

212 Washington Ave, Chestertown, MD 21620

(410) 778-0330

Property at 105 N Water St #3, Chestertown, MD 21620, 2 beds, 2 baths

$459,000

2 beds2 baths1,098 sq ft

105 N Water St #3, Chestertown, MD 21620

(410) 778-0330

Property at 326 Talbolt Blvd, Chestertown, MD 21620, 3 beds, 3 baths

$549,990

3 beds3 baths3,301 sq ft

326 Talbolt Blvd, Chestertown, MD 21620

Listing provided by Zillow

Property at Alberti Ranch | Finished Basement Plan, Chestertown, MD 21620, 3 beds, 2 baths

$439,990

3 beds2 baths2,346 sq ft

Alberti Ranch | Finished Basement Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at 104 Lincoln Dr, Chestertown, MD 21620, 3 beds, 1 bath

$275,000

3 beds1 bath960 sq ft

104 Lincoln Dr, Chestertown, MD 21620

(443) 274-1900

Property at 103 Metcalf Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$259,900

3 beds2.5 baths1,280 sq ft

103 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at Bramante Ranch | Finished Basement Plan, Chestertown, MD 21620, 3 beds, 2 baths

$464,990

3 beds2 baths2,642 sq ft

Bramante Ranch | Finished Basement Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at Caroline | Finished Basement Plan, Chestertown, MD 21620, 3 beds, 2.5 baths

$399,990

3 beds2.5 baths2,603 sq ft

Caroline | Finished Basement Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at Anderson | Finished Basment Plan, Chestertown, MD 21620, 3 beds, 2.5 baths

$484,990

3 beds2.5 baths3,176 sq ft

Anderson | Finished Basment Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at 216 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$730,000

3 beds2.5 baths2,176 sq ft

216 Birch Run Rd, Chestertown, MD 21620

(410) 673-3344

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

$259,000

3 beds2 baths1,140 sq ft

115 Chester Arms Dr, Chestertown, MD 21620

(703) 378-8810

Property at Bramante 2-Story | Finished Basement Plan, Chestertown, MD 21620, 3 beds, 3 baths

$499,990

3 beds3 baths3,301 sq ft

Bramante 2-Story | Finished Basement Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at 233 Duke of Kent St, Chestertown, MD 21620, 3 beds, 2 baths

$420,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

Property at 123 Trafford Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$370,000

4 beds2.5 baths2,504 sq ft

123 Trafford Dr, Chestertown, MD 21620

(443) 215-4663

Property at 101 S College Ave, Chestertown, MD 21620, 2 beds, 1.5 baths

$359,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

Property at 106 Queen St S, Chestertown, MD 21620, 3 beds, 3.5 baths

$829,000

3 beds3.5 baths2,472 sq ft

106 Queen St S, Chestertown, MD 21620

(443) 215-4663

Property at 300 and 302 S Mill St, Chestertown, MD 21620, 2 beds, 1 bath

$1,195,000

2 beds1 bath806 sq ft

300 and 302 S Mill St, Chestertown, MD 21620

(410) 778-0330

Property at 104 Conley Dr, Chestertown, MD 21620, 3 beds, 1.5 baths

$239,900

3 beds1.5 baths1,280 sq ft

104 Conley Dr, Chestertown, MD 21620

(410) 823-0033

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 117 Water St N Unit 1A, Chestertown, MD 21620, 3 beds, 3 baths

$685,000

3 beds3 baths3,000 sq ft

117 Water St N Unit 1A, Chestertown, MD 21620

(410) 673-3344

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

$200,000

1 bed1 bath700 sq ft

117 Water St N Unit 1B, Chestertown, MD 21620

(410) 673-3344

Property at 104 Acorn Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$275,000

3 beds2.5 baths1,900 sq ft

104 Acorn Dr, Chestertown, MD 21620

(410) 778-3779

Property at 956 Washington Ave, Chestertown, MD 21620, 3 beds, 1 bath

$275,000

3 beds1 bath1,248 sq ft

956 Washington Ave, Chestertown, MD 21620

(410) 810-0010

Property at 115 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,280 sq ft

115 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at 103 Sutton Way, Chestertown, MD 21620, 5 beds, 3.5 baths

$509,000

5 beds3.5 baths3,816 sq ft

103 Sutton Way, Chestertown, MD 21620

(410) 673-3344

Property at 330 Talbot Blvd Unit YG7FHY, Chestertown, MD 21620, 3 beds, 3.5 baths

$489,990

3 beds3.5 baths2,603 sq ft

330 Talbot Blvd Unit YG7FHY, Chestertown, MD 21620

Listing provided by Zillow

Property at 896 Washington Ave, Chestertown, MD 21620, 3 beds, 1 bath

$325,000

3 beds1 bath1,000 sq ft

896 Washington Ave, Chestertown, MD 21620

(410) 778-0330

Property at 117 Water St N Unit 2A, Chestertown, MD 21620, 2 beds, 1 bath

$375,000

2 beds1 bath787 sq ft

117 Water St N Unit 2A, Chestertown, MD 21620

(410) 673-3344

Property at 121 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths— sq ft

121 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at 117 Water St N Unit 2B, Chestertown, MD 21620, 1 bed, 1 bath

$350,000

1 bed1 bath850 sq ft

117 Water St N Unit 2B, Chestertown, MD 21620

(410) 673-3344

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 105 High St, Chestertown, MD 21620, 5 beds, 4.5 baths

$1,195,000

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

(410) 778-0330

Property at 234 N College Ave, Chestertown, MD 21620, 2 beds, 1 bath

$79,000

2 beds1 bath1,296 sq ft

234 N College Ave, Chestertown, MD 21620

(410) 823-0033

Property at 106 Harlan Loop, Chestertown, MD 21620, 4 beds, 2.5 baths

$425,000

4 beds2.5 baths3,165 sq ft

106 Harlan Loop, Chestertown, MD 21620

(866) 987-3937

Property at 226 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$898,000

3 beds3.5 baths2,172 sq ft

226 S Water St, Chestertown, MD 21620

(410) 275-2118

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