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3 beds New construction With a pool

Waterfront Homes in Chestertown, MD

9 listings

Waterfront Homes in Chestertown, MD

Waterfront Homes in Chestertown, MD

9 Listings

Waterfront Homes in Chestertown, MD

9 Listings

18Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$295,000

1 bd · 1 ba · 0 sqft

117 N Water St #3B, Chestertown, MD

Michael ONeill · Coldwell Banker Chesapeake Real Estate Company

$885,000

5 bd · 4 ba · 2,639 sqft

7680 Country Club Ln, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

Price Reduced50Active

$1,375,000

4 bd · 5 ba · 4,257 sqft

22470 Fairgale Farm Ln, Chestertown, MD

Ashton M Kelley · Gunther-McClary Real Estate

Price Reduced73Active

$1,500,000

7 bd · 5 ba · 5,400 sqft

117 Water St N #1a, 1B, 2a, & 2B, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$200,000

1 bd · 1 ba · 700 sqft

117 Water St N #1B, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$375,000

2 bd · 1 ba · 787 sqft

117 Water St N #2a, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$350,000

1 bd · 1 ba · 850 sqft

117 Water St N #2B, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$685,000

3 bd · 3 ba · 3,000 sqft

117 Water St N #1a, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$1,459,000

3 bd · 3 ba · 2,231 sqft

Little Harbor Way #1, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

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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.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

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: 2026-09-15 19:52:55 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 that sold · County records, as of Aug 28, 2026

Median sale price: $321,000$192,500–$573,750 typical range
Price per sq. ft.: $181
Sales: 16
Paid in cash: 25.0%

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

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 3.6%

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.