New Construction Homes in Chestertown, MD

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3 beds New construction With a pool

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12 Listings

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New Construction Homes in Chestertown, MD

12 Listings

35Active

12 listings

New Construction Homes in Chestertown, MD

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12 Listings

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New Construction Homes in Chestertown, MD

12 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

35Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

10Active

$259,900

3 bd · 2 ba · 1,280 sqft

115 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

10Active

$264,900

3 bd · 2 ba · 0 sqft

121 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

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

25Active

$1,459,000

3 bd · 3 ba · 2,231 sqft

Little Harbor Way #1, 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: 2026-09-08 16:20:00 UTC

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.

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: 2026-09-08 16:20:00 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.

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

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

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

Chestertown, MD community profile

Explore Chestertown homes

Your local brokerage

Listing data & MLS disclosures

Chestertown, MD community profile

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

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

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