Cheap homes for sale & real estate in Chestertown, MD

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OPEN OCT 31, 10AM TO 12PM

ABOUT THIS HOME
Cheap Home for sale in Chestertown, MD:
Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. * * A brand-new well and septic system have just been installed * * , providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space cente

$365,000

3 beds2.5 baths2,294 sq ft

24607 Chestertown Rd, Chestertown, MD 21620

Working fireplace • 0.653-acre lot • Formal dining room

(410) 778-0330

READY TO BUILD

ABOUT THIS HOME
Cheap Home for sale in Chestertown, MD:
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
Cheap Home for sale in Chestertown, MD:
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

FOR SALE BY OWNER

ABOUT THIS HOME
Cheap Home for sale in Chestertown, MD:
Good House LLC is offering a vacant parcel in Kent County, Maryland, identified as parcel 03-016048, full tax account 1503016048, in the Clarissa Rd area. Approximately 16,500 sq ft / 0.379 acre, Lots 428-429, deed reference Liber 1268 / Folio 155. All sizes are approximate and are not a survey. Kent County Planning& apos; s August 29, 2026 written reply confirmed CAR zoning for this parcel. The County identified public-road frontage, but did not confirm an approved entrance, legal access or buildability. County Environmental Health reported in August 2026 that no existing well, septic, percolation-test or land-evaluation records were found. Wet-season testing and a successful land eval

$9,900

— beds— baths— sq ft

Clarissa Rd, Chestertown, MD 21620

Listed 6 days

FOR SALE BY OWNER

ABOUT THIS HOME
Cheap Home for sale in Chestertown, MD:
Good House LLC is offering a vacant parcel in Kent County, Maryland, identified as parcel 06-006027, full tax account 1506006027, in the Buck Neck Landing Rd (Melitota area) area. Approximately 2.00 acres, deed reference Liber 1249 / Folio 85; map 27, grid 3C, parcel 58. All sizes are approximate and are not a survey. Kent County Planning& apos; s August 29, 2026 written reply confirmed Village zoning for this parcel. The County did not confirm road frontage or an approved entrance for this parcel. An existing County Roads inquiry remains unanswered in the latest local record; neither legal nor physical access is represented as confirmed. County Environmental Health reported in August 2

$24,900

— beds— baths— sq ft

Buck Neck Rd, Chestertown, MD 21620

Listed 6 days

Property at Schooner Rd, Chestertown, MD 21620

$9,900

— beds— baths— sq ft

Schooner Rd, Chestertown, MD 21620

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

$369,990

3 beds2 baths2,158 sq ft

Rosecliff | Finished Basement Plan, Chestertown, MD 21620

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 21338 Virginia Ave, Chestertown, MD 21620, 2 beds, 2 baths

$400,000

2 beds2 baths1,000 sq ft

21338 Virginia Ave, Chestertown, MD 21620

(410) 810-0010

Property at 8820 Cumberland St, Chestertown, MD 21620, 3 beds, 2 baths

$312,500

3 beds2 baths1,080 sq ft

8820 Cumberland St, Chestertown, MD 21620

(410) 391-6900

Property at 22974 Bay Shore Rd, Chestertown, MD 21620, 2 beds, 2 baths

$315,000

2 beds2 baths1,440 sq ft

22974 Bay Shore Rd, Chestertown, MD 21620

(410) 822-6665

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

$439,990

2 beds2 baths2,346 sq ft

Alberti Ranch | Finished Basement Plan, Chestertown, MD 21620

Listing provided by Zillow

Property at 8732 Elm Rd, Chestertown, MD 21620, 3 beds, 2 baths

$289,000

3 beds2 baths1,056 sq ft

8732 Elm Rd, Chestertown, MD 21620

(410) 778-0330

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 23208 Buck Neck Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$319,900

3 beds2.5 baths1,650 sq ft

23208 Buck Neck Rd, Chestertown, MD 21620

(855) 450-0442

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 24775 Langford Rd, Chestertown, MD 21620, 3 beds, 1 bath

$305,000

3 beds1 bath1,008 sq ft

24775 Langford Rd, Chestertown, MD 21620

(410) 398-9200

Property at 7415 Wilkins Ln, Chestertown, MD 21620, 3 beds, 1 bath

$222,000

3 beds1 bath936 sq ft

7415 Wilkins Ln, Chestertown, MD 21620

(410) 810-0010

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 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 8630 Elm Rd, Chestertown, MD 21620, 5 beds, 2.5 baths

$399,900

5 beds2.5 baths1,936 sq ft

8630 Elm Rd, Chestertown, MD 21620

(301) 355-6104

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 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 124 Wilton Rd, Chestertown, MD 21620, 3 beds, 1 bath

$294,900

3 beds1 bath1,056 sq ft

124 Wilton Rd, Chestertown, MD 21620

(410) 810-0010

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

$269,000

3 beds2 baths1,404 sq ft

10540 Tonopah Rd, Chestertown, MD 21620

(410) 810-0010

Property at 10781 Fermoy Rd, Chestertown, MD 21620, 4 beds, 2.5 baths

$429,500

4 beds2.5 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

(855) 450-0442

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 6746 Quaker Neck Rd, Chestertown, MD 21620, 5 beds, 2.5 baths

$339,000

5 beds2.5 baths3,371 sq ft

6746 Quaker Neck Rd, Chestertown, MD 21620

(410) 810-0010

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 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 23043 Bay Shore Spur, Chestertown, MD 21620, 4 beds, 3 baths

$385,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

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 222 Dutchess Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,096 sq ft

222 Dutchess Rd, Chestertown, MD 21620

(410) 275-2118

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

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Cheap Homes for Sale in Chestertown

There are currently 75 cheap homes for sale in Chestertown at a median listing price of $420K. 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 110 days. This map is refreshed with the newest listings in Chestertown every 15 minutes.

In the past month, 11 homes have been sold in Chestertown. In addition to houses in Chestertown, there were also 3 condos, 17 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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