4 Bedroom Homes in Chester, MD

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3 beds New construction With a pool

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11 Listings

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4 Bedroom Homes in Chester, MD

11 Listings

46Active

11 listings

4 Bedroom Homes in Chester, MD

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11 Listings

Map

4 Bedroom Homes in Chester, MD

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

46Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$569,900

4 bd · 3 ba · 2,332 sqft

233 Cross Creek Ct, Chester, MD

Christopher B Nagel · Rory S. Coakley Realty, Inc.

39Active

$825,000

4 bd · 3 ba · 3,291 sqft

313 Thomas White Blvd, Chester, MD

Carol Snyder · Monument Sotheby's International Realty

123Active

$747,900

4 bd · 3 ba · 3,142 sqft

209 Harrier Way, Chester, MD

Violeta I Aguirre · Long & Foster Real Estate, Inc.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

53Active

$868,000

4 bd · 3 ba · 3,168 sqft

113 Bentons Pleasure Rd, Chester, MD

Temple H Peirce Jr. · Cummings & Co. Realtors

Price Reduced25Active

$779,990

4 bd · 3 ba · 2,791 sqft

715 Warbler Way, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

63Active

$749,000

4 bd · 4 ba · 2,185 sqft

134 Richard Ingle Way, Chester, MD

Barbara A McCaffrey · Redfin Corp

Price Reduced63Active

$724,999

4 bd · 3 ba · 3,151 sqft

233 Peregrine Dr, Chester, MD

Michelle W Abplanalp · Rosendale Realty

Price Reduced35Active

$825,000

4 bd · 4 ba · 3,312 sqft

232 Evelyne St, Chester, MD

Courtney Chipouras · TTR Sotheby's International Realty

Price Reduced78Active

$1,195,000

4 bd · 5 ba · 4,413 sqft

2855 Cox Neck Rd, Chester, MD

Tricia Z Wilson · Wilson Realty & Staging LLC

Price Reduced32Active

$374,900

4 bd · 4 ba · 1,899 sqft

208 Blenny Ln, Chester, MD

Pamela B Ackermann · RE/MAX Executive

64Active

$1,294,800

4 bd · 4 ba · 0 sqft

1757 Harbor Dr, Chester, MD

George 112,540 Bailey · Keller Williams Flagship

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: 2026-09-04 14:44:54 UTC

Chester housing market

August 2026 · This period is still settling

Selling at 99.4% of asking price

Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026

Homes that sold · County records, as of Aug 14, 2026

Median sale price: $567,500$387,500–$843,750 typical range
Price per sq. ft.: $317
Sales: 11
Paid in cash: 54.6%

Homes on the market · MLS, as of Aug 26, 2026–Aug 31, 2026

Median list price: $564,450
Homes for sale: 46
Median days on market: 17 days

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

Year-over-year: -8.8%

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

Median home size: 1,728 sq. ft.

Chester, MD community profile

Area: 22.5 sq. mi.

Source: HJN community data

Explore Chester 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: 2026-09-04 14:44:54 UTC

Chester, MD community profile

Area: 22.5 sq. mi.

Source: HJN community data

Chester housing market

August 2026 · This period is still settling

Selling at 99.4% of asking price

Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026

Homes that sold · County records, as of Aug 14, 2026

Median sale price: $567,500$387,500–$843,750 typical range
Price per sq. ft.: $317
Sales: 11
Paid in cash: 54.6%

Homes on the market · MLS, as of Aug 26, 2026–Aug 31, 2026

Median list price: $564,450
Homes for sale: 46
Median days on market: 17 days

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

Year-over-year: -8.8%

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

Median home size: 1,728 sq. ft.

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Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chester housing market

Homes that sold · County records, as of Aug 14, 2026

Homes on the market · MLS, as of Aug 26, 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

Chester, MD community profile

Explore Chester homes

Your local brokerage

Listing data & MLS disclosures

Chester, MD community profile

Chester housing market

Homes that sold · County records, as of Aug 14, 2026

Homes on the market · MLS, as of Aug 26, 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