2 Bedroom Homes in Chester, MD

Save search

3 beds New construction With a pool

Hide Map

20 Listings

Map

2 Bedroom Homes in Chester, MD

20 Listings

New22

20 listings

2 Bedroom Homes in Chester, MD

Hide Map

20 Listings

Map

2 Bedroom Homes in Chester, MD

20 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

New22

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Active

$669,990

2 bd · 2 ba · 1,690 sqft

641 Warbler Way, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

47Active

$719,990

2 bd · 3 ba · 1,900 sqft

736 Warbler Way #2733, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced26Active

$789,990

2 bd · 3 ba · 2,010 sqft

536 Warbler Way, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced47Active

$819,990

2 bd · 3 ba · 1,900 sqft

102 Boatswain Way #2932, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced47Active

$919,990

2 bd · 3 ba · 1,900 sqft

102 Boatswain Way #2943, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced56Active

$619,990

2 bd · 3 ba · 2,003 sqft

102 Boatswain Way #2911, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced47Active

$819,990

2 bd · 3 ba · 1,900 sqft

102 Boatswain Way #2933, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced47Active

$719,990

2 bd · 3 ba · 1,900 sqft

110 Boatswain Way #3042, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced84Active

$697,900

2 bd · 2 ba · 2,118 sqft

121 Merlin Dr, Chester, MD

Yael E Beckman · Coldwell Banker Realty

Price Reduced23Active

$525,000

2 bd · 3 ba · 2,003 sqft

230 Switchgrass Way #12, Chester, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced50Active

$595,000

2 bd · 3 ba · 1,832 sqft

1000 Herons Nest Way #43, Chester, MD

Dee Dee R McCracken · Coldwell Banker Realty

Price Reduced29Active

$699,000

2 bd · 3 ba · 2,003 sqft

132 Wheelhouse Way #11, Chester, MD

Matthew Thomas Arnold · Real Broker, LLC

40Active

$349,500

2 bd · 3 ba · 1,312 sqft

45-G Queen Neva Ct, Chester, MD

John V Freeman · Coldwell Banker Realty

Price Reduced27Active

$287,500

2 bd · 2 ba · 1,069 sqft

114 Merganser Ct, Chester, MD

Beverly A Sloane · Benson & Mangold, LLC

Price Reduced56Active

$485,000

2 bd · 3 ba · 1,900 sqft

1000 Herons Nest Way #22, Chester, MD

Ralph S. Kennedy · RE/MAX Executive

56Active

$765,000

2 bd · 3 ba · 0 sqft

111 Marshgrass Way #43, Chester, MD

John V Freeman · Coldwell Banker Realty

Price Reduced52Active

$515,000

2 bd · 3 ba · 1,586 sqft

34-E Queen Anne Way, Chester, MD

Lona Sue Todd · Taylor Properties

Price Reduced70Active

$499,000

2 bd · 3 ba · 1,900 sqft

4000 Herons Nest Way #22, Chester, MD

Carol L Tinnin · RE/MAX Leading Edge

Price Reduced66Active

$479,000

2 bd · 3 ba · 2,003 sqft

3000 Herons Nest Way #11, Chester, MD

John V Freeman · Coldwell Banker Realty

2Active

$19,500

2 bd · 1 ba · 764 sqft

1405 Little Creek Rd, Chester, MD

Dustin Parker · The Parker Group

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: 2026-09-02 19:02:30 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

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: 2026-09-02 19:02:30 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.

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

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

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