5 Bedroom Homes in Chestertown, MD

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7 Listings

Map

7 Listings

56Active

7 listings

5 Bedroom Homes in Chestertown, MD

Show Map

7 Listings

Map

5 Bedroom Homes in Chestertown, MD

7 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

56Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$2,895,000

5 bd · 4 ba · 5,938 sqft

6324 Quaker Neck Rd, Chestertown, MD

John Boniface · Cross Street Realtors LLC

39Active

$675,000

5 bd · 3 ba · 2,838 sqft

212 Washington Ave, Chestertown, MD

Mary C Carlisle · Coldwell Banker Chesapeake Real Estate Company

Price Reduced45Active

$424,900

5 bd · 3 ba · 1,936 sqft

8630 Elm Rd, Chestertown, MD

Lawrence M. Lessin · Save 6, Incorporated

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced43Active

$825,000

5 bd · 4 ba · 2,639 sqft

7680 Country Club Ln, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

Price Reduced50Active

$339,000

5 bd · 3 ba · 3,371 sqft

6746 Quaker Neck Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

Price Reduced53Active

$509,000

5 bd · 4 ba · 3,816 sqft

103 Sutton Way, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

Price Reduced44Active

$1,245,500

5 bd · 5 ba · 3,243 sqft

105 High St, Chestertown, MD

Michael ONeill · Coldwell Banker Chesapeake Real Estate Company

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: 2026-10-03 04:09:30 UTC

Chestertown housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 16 sales · as of Sep 29, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $404,950
Homes for sale: 58
Median days on market: 14 days

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

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: 2026-10-03 04:09:30 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 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 16 sales · as of Sep 29, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $404,950
Homes for sale: 58
Median days on market: 14 days

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.

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Registered offenders on the map

Registered offenders on the map

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 Sep 27, 2026–Sep 29, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 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 Sep 27, 2026–Sep 29, 2026

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