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The buying timeline

Afford it

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How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

69 listings

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Compare selling options
Get an instant cash offer
Buy before you sell

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69 listings

Homes for Sale in Chester, MD

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24 of 69 Listings

Map

24 of 69 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

New48

Active

$429,000

3 bd · 2 ba · 1,200 sqft

1618 Chester Rd, Chester, MD

Warren S Hogan · Long & Foster Real Estate, Inc.

56Active

$915,000

4 bd · 4 ba · 3,424 sqft

202 Claiborne St, Chester, MD

Dee Dee R McCracken · Coldwell Banker Realty

26Active

$275,000

2 bd · 2 ba · 1,069 sqft

101 Bufflehead Ct, Chester, MD

Kevin McDermott · The KW Collective

41Active

$699,000

3 bd · 3 ba · 1,560 sqft

2703 Sherman Dr, Chester, MD

Tammy D Rosendale · Rosendale Realty

42Active

$545,000

3 bd · 3 ba · 2,100 sqft

100 Schooner Way, Chester, MD

Lauren Matera · LPT Realty, LLC

51Active

$749,990

3 bd · 3 ba · 2,602 sqft

830 Warbler Way #2824, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

Price Reduced20Active

$323,000

3 bd · 1 ba · 960 sqft

107 Lee Rd, Chester, MD

Verria Hairston · Open Door Brokerage, LLC

47Active

$789,990

2 bd · 3 ba · 1,900 sqft

830 Warbler Way #2843, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

53Active

$599,900

3 bd · 4 ba · 2,100 sqft

208 Widgeon Way, Chester, MD

Carol L Tinnin · RE/MAX Leading Edge

54Active

$1,350,000

4 bd · 3 ba · 3,680 sqft

1509 Calvert Rd, Chester, MD

Jimmy J White Jr. · Long & Foster Real Estate, Inc.

1Active

$300,000

3 bd · 2 ba · 1,160 sqft

205 Dominion Ln, Chester, MD

Jonathan C Nicholls · EXP Realty, LLC

16Active

$40,000

0 bd · 0 ba · 830 sqft

8-E Piney Narrows Rd, Chester, MD

Kaitlyn Cole Collins · Benson & Mangold, LLC

50Active

$769,900

2 bd · 3 ba · 2,014 sqft

168 Redstart Dr, Chester, MD

Carol L Tinnin · RE/MAX Leading Edge

37Active

$744,900

2 bd · 3 ba · 1,900 sqft

111 Marshgrass Way #43, Chester, MD

Jimmy J White Jr. · Long & Foster Real Estate, Inc.

44Active

$599,000

5 bd · 3 ba · 1,852 sqft

231 Dominion Rd, Chester, MD

Dane P Ways · Long & Foster Real Estate, Inc.

62Active

$412,000

3 bd · 2 ba · 1,337 sqft

117 Wright Rd, Chester, MD

Diane Superczynski · Douglas Realty LLC

66Active

$799,000

3 bd · 3 ba · 2,575 sqft

223 Evelyne St, Chester, MD

Tara Trout · Samson Properties

39Active

$549,950

2 bd · 3 ba · 2,000 sqft

630 Warbler Way #12, Chester, MD

Ralph S. Kennedy · RE/MAX Executive

39Active

$499,000

2 bd · 3 ba · 1,680 sqft

7-B Queen Victoria Way #B, Chester, MD

Christina Sousa · RE/MAX Allegiance

25Active

$999,990

3 bd · 3 ba · 2,772 sqft

114 Kinglet Ct, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

27Active

$899,990

3 bd · 3 ba · 2,772 sqft

247 Redstart Dr, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

25Active

$969,990

2 bd · 3 ba · 2,010 sqft

118 Kinglet Ct, Chester, MD

David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

48Active

$1,199,900

5 bd · 3 ba · 3,000 sqft

162 Kirwans Landing Ln, Chester, MD

Jessica DuLaney · Next Step Realty

Price Reduced45Active

$630,000

5 bd · 3 ba · 2,818 sqft

1616 Postal Rd, Chester, MD

Carol Eaton · Coldwell Banker Realty

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: 2026-10-16 22:22:27 UTC

Chester housing market

September 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 22, 2026

Median sale price: $400,000$280,000–$716,500 typical range
Price per sq. ft.: $277
Sales: 16
Paid in cash: 56.3%

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

Median list price: $554,500

Chester, MD community profile

Area: 22.5 sq. mi.

Source: HJN community data

Nearby areas

ZIP codes

21223 (320)
21224 (285)
21230 (267)
21217 (218)
21213 (200)
21216 (155)
21122 (134)
21401 (133)

Cities

Baltimore (2,274)
Annapolis (312)
Glen Burnie (153)
Pasadena (134)
Easton (126)
Stevensville (93)
Chestertown (64)
Edgewater (61)

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: 2026-10-16 22:22:27 UTC

Chester, MD community profile

Area: 22.5 sq. mi.

Source: HJN community data

Chester housing market

September 2026 · This period is still settling

Selling at 99.0% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 22, 2026

Median sale price: $400,000$280,000–$716,500 typical range
Price per sq. ft.: $277
Sales: 16
Paid in cash: 56.3%

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

Median list price: $554,500

Homes for sale

Median days on market

22 days

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

Year-over-year: -23.4%

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.

Chester, MD Homes for Sale | Realty.com

Nearby areas

ZIP codes

21223 (320)
21224 (285)
21230 (267)
21217 (218)
21213 (200)
21216 (155)
21122 (134)
21401 (133)

Cities

Baltimore (2,274)
Annapolis (312)
Glen Burnie (153)
Pasadena (134)
Easton (126)
Stevensville (93)
Chestertown (64)
Edgewater (61)