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The buying timeline

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62 listings

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62 listings

Homes for Sale in Chestertown, MD

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14 of 62 Listings

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14 of 62 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced13Active

$750,000

0 bd · 2 ba · 2,045 sqft

201 N Lynchburg St, Chestertown, MD

John W. Ford · RE/MAX Associates-Hockessin

26Active

$786,900

3 bd · 3 ba · 1,964 sqft

#35 Landing Ln, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

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

22Active

$1,099,900

4 bd · 4 ba · 2,784 sqft

#25 Landing Ln, Chestertown, MD

Julia Hilfiker · 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

Price Reduced53Active

$509,000

5 bd · 4 ba · 3,816 sqft

103 Sutton Way, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

25Active

$320,000

3 bd · 2 ba · 1,096 sqft

222 Dutchess Rd, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

29Active

$1,800,000

4 bd · 4 ba · 3,540 sqft

Little Harbor Way #1, Chestertown, MD

Julia Hilfiker · Gunther-McClary Real Estate

Price Reduced27Active

$385,000

4 bd · 3 ba · 2,630 sqft

23043 Bay Shore Spur, Chestertown, MD

Robin Fithian · Rock Hall Properties Real Estate

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

1 2 3

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 22, 2026

Median sale price: $355,320$245,000–$615,000 typical range
Price per sq. ft.: $219
Sales: 21
Paid in cash: 47.6%

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

Median list price: $404,950

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

By price

Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K
Homes Under $1M

By bedrooms

3 Bedroom Homes

By type

Single-Family Homes

Nearby areas

ZIP codes

21220 (140)
21001 (96)
21078 (96)
21221 (93)
21014 (91)
21015 (83)
21666 (83)
21619 (74)

Cities

Bel Air (174)
Baltimore (139)
Annapolis (123)
Aberdeen (97)
Havre de Grace (96)
Middle River (94)
Stevensville (83)
Chester (74)

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

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 22, 2026

Median sale price: $355,320$245,000–$615,000 typical range
Price per sq. ft.: $219
Sales: 21
Paid in cash: 47.6%

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

Median list price: $404,950

Homes for sale

Median days on market

19 days

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

Year-over-year: 31.6%

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 Homes for Sale — Page 3 | Realty.com

Nearby areas

ZIP codes

21220 (140)
21001 (96)
21078 (96)
21221 (93)
21014 (91)
21015 (83)
21666 (83)
21619 (74)

Cities

Bel Air (174)
Baltimore (139)
Annapolis (123)
Aberdeen (97)
Havre de Grace (96)
Middle River (94)
Stevensville (83)
Chester (74)