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3 Bedroom Homes in Chestertown, MD

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10 of 34 Listings

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10 of 34 Listings

Price Reduced92Active

3 Bedroom Homes in Chestertown, MD — Page 2

34 listings

3 Bedroom Homes in Chestertown, MD

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10 of 34 Listings

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3 Bedroom Homes in Chestertown, MD

10 of 34 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced92Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$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

26Active

$786,900

3 bd · 3 ba · 1,964 sqft

#35 Landing Ln, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

24Active

$765,900

3 bd · 3 ba · 1,964 sqft

#37 Landing Ln, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

26Active

$753,500

3 bd · 3 ba · 1,964 sqft

#36 Landing Ln, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

23Active

$839,500

3 bd · 3 ba · 1,964 sqft

102 Little Harbor Way, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

24Active

$813,900

3 bd · 4 ba · 2,192 sqft

104 Landing Ln, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

24Active

$799,900

3 bd · 4 ba · 2,092 sqft

106 Landing Ln, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

23Active

$849,900

3 bd · 3 ba · 1,980 sqft

104 Little Harbor Way, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

25Active

$320,000

3 bd · 2 ba · 1,096 sqft

222 Dutchess Rd, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

1 2

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: 2026-10-01 12:37:23 UTC

Chestertown housing market

September 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 18 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $360,000$252,500–$627,500 typical range
Price per sq. ft.: $214
Sales: 31
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $404,950
Homes for sale: 58
Median days on market: 19 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 33.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,728 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

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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: 2026-10-01 12:37:23 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

September 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 18 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $360,000$252,500–$627,500 typical range
Price per sq. ft.: $214
Sales: 31
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $404,950
Homes for sale: 58
Median days on market: 19 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 33.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,728 sq. ft.