3 Bedroom Homes in Chestertown, MD

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3 beds New construction With a pool

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24 of 32 Listings

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3 Bedroom Homes in Chestertown, MD

24 of 32 Listings

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32 listings

3 Bedroom Homes in Chestertown, MD

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24 of 32 Listings

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3 Bedroom Homes in Chestertown, MD

24 of 32 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

New23

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Active

$229,000

3 bd · 1 ba · 936 sqft

7415 Wilkins Ln, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

32Active

$304,000

3 bd · 2 ba · 1,232 sqft

7464 Shortall St, Chestertown, MD

Samantha A Grimes · Chesapeake Real Estate Associates, LLC

35Active

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

43Active

$524,900

3 bd · 3 ba · 2,076 sqft

1003 Twin Ct, Chestertown, MD

Jody Baker · Cross Street Realtors LLC

26Active

$299,900

3 bd · 1 ba · 1,056 sqft

124 Wilton Rd, Chestertown, MD

Elizabeth Middleton Green · Doug Ashley Realtors, LLC

21Active

$279,000

3 bd · 2 ba · 1,404 sqft

10540 Tonopah Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

55Active

$315,000

3 bd · 2 ba · 1,288 sqft

109 Parma Rd, Chestertown, MD

Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company

15Active

$480,000

3 bd · 3 ba · 3,176 sqft

129 Trafford Dr, Chestertown, MD

Teresa A Queen · Elevated Real Estate Solutions

10Active

$259,900

3 bd · 2 ba · 1,280 sqft

115 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

52Active

$750,000

3 bd · 3 ba · 2,176 sqft

216 Birch Run Rd, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

Price Reduced9Active

$145,000

3 bd · 2 ba · 1,192 sqft

409 Calvert St, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

Price Reduced20Active

$324,000

3 bd · 2 ba · 1,216 sqft

9126 Fairlee Rd, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

34Active

$325,000

3 bd · 1 ba · 1,000 sqft

896 Washington Ave, Chestertown, MD

Peter D Heller · Coldwell Banker Chesapeake Real Estate Company

68Active

$799,000

3 bd · 3 ba · 2,857 sqft

7828 Country Club Ln, Chestertown, MD

Sarah E. King · Cross Street Realtors LLC

10Active

$264,900

3 bd · 2 ba · 0 sqft

121 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced27Active

$239,900

3 bd · 2 ba · 1,280 sqft

104 Conley Dr, Chestertown, MD

Heather Kooser · Cummings & Co. Realtors

Price Reduced26Active

$275,000

3 bd · 3 ba · 1,900 sqft

104 Acorn Dr, Chestertown, MD

Sarah E. King · Cross Street Realtors LLC

Price Reduced29Active

$275,000

3 bd · 1 ba · 1,248 sqft

956 Washington Ave, Chestertown, MD

Grace M Crockett · Doug Ashley Realtors, LLC

Price Reduced10Active

$315,000

3 bd · 2 ba · 1,232 sqft

8706 Elm Rd, Chestertown, MD

Andrew Hanson Meikle · Doug Ashley Realtors, LLC

31Active

$898,000

3 bd · 4 ba · 2,172 sqft

226 S Water St, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

Price Reduced92Active

$829,000

3 bd · 4 ba · 2,472 sqft

106 Queen St S, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

46Active

$685,000

3 bd · 3 ba · 3,000 sqft

117 Water St N #1a, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

Price Reduced38Active

$545,000

3 bd · 3 ba · 2,927 sqft

204 Double Creek Rd, Chestertown, MD

Grace M Crockett · Doug Ashley Realtors, LLC

26Active

$786,900

3 bd · 3 ba · 1,964 sqft

#35 Landing Ln, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-03 23:56:09 UTC

Chestertown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Median list price: $478,000
Homes for sale: 59
Median days on market: 17 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,735 sq. ft.

Chestertown, MD community profile

Population: 5,632
Median income: $48,766
Housing units: 2,458
People per sq. mi.: 42.6
Area: 132.2 sq. mi.

Source: HJN community data

Explore Chestertown homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-03 23:56:09 UTC

Chestertown, MD community profile

Population: 5,632
Median income: $48,766
Housing units: 2,458
People per sq. mi.: 42.6
Area: 132.2 sq. mi.

Source: HJN community data

Chestertown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Median list price: $478,000
Homes for sale: 59
Median days on market: 17 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,735 sq. ft.

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Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Chestertown, MD community profile

Explore Chestertown homes

Your local brokerage

Listing data & MLS disclosures

Chestertown, MD community profile

Chestertown housing market

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026