Luxury Homes in Chestertown, MD

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2 Listings

Price Reduced73Active

2 listings

Luxury Homes in Chestertown, MD

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2 Listings

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Luxury Homes in Chestertown, MD

2 Listings

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Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced73Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$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

29Active

$1,800,000

4 bd · 4 ba · 3,540 sqft

Little Harbor Way #1, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

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 12:34:08 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: 2026-10-01 12:34:08 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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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