5 Bedroom Homes in Chester, MD

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3 beds New construction With a pool

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5 Listings

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5 Bedroom Homes in Chester, MD

5 Listings

48Active
$400,000

5 listings

5 Bedroom Homes in Chester, MD

Show Map

5 Listings

Map

5 Bedroom Homes in Chester, MD

5 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

48Active
$400,000

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

5 bd · 4 ba · 3,250 sqft

1868 Roberta Dr, Chester, MD

Carley R. Cooper · Alex Cooper Auctioneers, Inc.

Price Reduced83Active

$525,000

5 bd · 4 ba · 3,552 sqft

326 Castle Marina Rd, Chester, MD

Virginia Elizabeth Dauses · Coldwell Banker Waterman Realty

Price Reduced49Active

$515,000

5 bd · 3 ba · 3,000 sqft

205 Anchor Ln, Chester, MD

Kathleen Higginbotham · Samson Properties

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

78Active

$2,840,000

5 bd · 4 ba · 1,704 sqft

300 Woods Point Rd, Chester, MD

Elinor W Warring · Tidewater Properties

Price Reduced44Active

$995,000

5 bd · 5 ba · 3,225 sqft

215 Kingfisher Ln, Chester, MD

Jennifer Anne Thomas · RE/MAX Executive

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: 2026-09-22 12:48:59 UTC

Chester housing market

August 2026

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 28, 2026

Median sale price: $567,500$359,000–$932,500 typical range
Price per sq. ft.: $290
Sales: 19
Paid in cash: 57.9%

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: 2026-09-22 12:48:59 UTC

Chester, MD community profile

Area: 22.5 sq. mi.

Source: HJN community data

Chester housing market

August 2026

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 28, 2026

Median sale price: $567,500$359,000–$932,500 typical range
Price per sq. ft.: $290
Sales: 19
Paid in cash: 57.9%

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 28, 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 28, 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