Homes Under $1M in Chestertown, MD

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24 of 52 Listings

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24 of 52 Listings

23Active

52 listings

Homes Under $1M in Chestertown, MD

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24 of 52 Listings

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Homes Under $1M in Chestertown, MD

24 of 52 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

23Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$312,500

3 bd · 2 ba · 1,080 sqft

8820 Cumberland St, Chestertown, MD

Frederick Golding · RE/MAX Advantage Realty

22Active

$329,900

2 bd · 2 ba · 1,440 sqft

22974 Bay Shore Rd, Chestertown, MD

Mae Nordhoff · Benson & Mangold, LLC

51Active

$489,000

2 bd · 2 ba · 1,098 sqft

105 N Water St #3, Chestertown, MD

Lisa P Raffetto · Coldwell Banker Chesapeake Real Estate Company

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

24Active

$289,000

3 bd · 2 ba · 1,056 sqft

8732 Elm Rd, Chestertown, MD

Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company

16Active

$259,900

3 bd · 3 ba · 1,280 sqft

103 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

23Active

$229,000

3 bd · 1 ba · 936 sqft

7415 Wilkins Ln, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

Price Reduced30Active

$285,000

3 bd · 1 ba · 960 sqft

104 Lincoln Dr, Chestertown, MD

Crystal M Smith · RE/MAX Executive

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 Reduced36Active

$335,000

3 bd · 2 ba · 1,398 sqft

217 Edmore Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

35Active

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced45Active

$370,000

4 bd · 3 ba · 2,504 sqft

123 Trafford Dr, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

Price Reduced48Active

$499,900

3 bd · 3 ba · 2,076 sqft

1003 Twin Ct, Chestertown, MD

Jody Baker · Cross Street Realtors LLC

Price Reduced34Active

$259,000

3 bd · 2 ba · 1,140 sqft

115 Chester Arms Dr, Chestertown, MD

Jarnell Preston Foster · Samson Properties

Price Reduced37Active

$399,000

2 bd · 2 ba · 1,904 sqft

7982 Radcliffe Rd, Chestertown, MD

Abigail H Usilton · Doug Ashley Realtors, LLC

23Active

$299,900

3 bd · 1 ba · 1,056 sqft

124 Wilton Rd, Chestertown, MD

Elizabeth Middleton Green · Doug Ashley Realtors, LLC

Price Reduced35Active

$359,000

2 bd · 2 ba · 1,036 sqft

101 S College Ave, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

Price Reduced45Active

$424,900

5 bd · 3 ba · 1,936 sqft

8630 Elm Rd, Chestertown, MD

Lawrence M. Lessin · Save 6, Incorporated

Price Reduced21Active

$269,000

3 bd · 2 ba · 1,404 sqft

10540 Tonopah Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

15Active

$480,000

3 bd · 3 ba · 3,176 sqft

129 Trafford Dr, Chestertown, MD

Teresa A Queen · Elevated Real Estate Solutions

Price Reduced25Active

$349,900

4 bd · 2 ba · 1,476 sqft

1010 Twin Ct, Chestertown, MD

Jason Dey · Kevin Dey Realty

10Active

$259,900

3 bd · 2 ba · 1,280 sqft

115 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

34Active

$325,000

4 bd · 2 ba · 2,198 sqft

200 Manor Ave, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

52Active

$750,000

3 bd · 3 ba · 2,176 sqft

216 Birch Run Rd, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

Price Reduced43Active

$825,000

5 bd · 4 ba · 2,639 sqft

7680 Country Club Ln, Chestertown, MD

John J Burke · 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: 2026-10-03 22:16:04 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 22:16:04 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

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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 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