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Chester, MD Homes for Sale | Realty.com
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Homes for Sale in Chester, MD

Homes for Sale in Chester, MD

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24 of 74 Listings
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Homes for Sale in Chester, MD

24 of 74 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 2703 Sherman Dr — photo32Active

    $699,000

    3 bd · 3 ba · 1,560 sqft

    2703 Sherman Dr, Chester, MD

    Tammy D Rosendale · Rosendale Realty

  2. 107 Lee Rd — photo20Active

    $330,000

    3 bd · 1 ba · 960 sqft

    107 Lee Rd, Chester, MD

    Verria Hairston · Open Door Brokerage, LLC

  3. 830 Warbler Way #2824 — photo51Active

    $749,990

    3 bd · 3 ba · 2,602 sqft

    830 Warbler Way #2824, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  4. 830 Warbler Way #2843 — photo47Active

    $789,990

    2 bd · 3 ba · 1,900 sqft

    830 Warbler Way #2843, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  5. 208 Widgeon Way — photo53Active

    $599,900

    3 bd · 4 ba · 2,100 sqft

    208 Widgeon Way, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  6. 1509 Calvert Rd — photo51Active

    $1,350,000

    4 bd · 3 ba · 3,680 sqft

    1509 Calvert Rd, Chester, MD

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

  7. 8-E Piney Narrows Rd — photo16Active

    $40,000

    0 bd · 0 ba · 830 sqft

    8-E Piney Narrows Rd, Chester, MD

    Kaitlyn Cole Collins · Benson & Mangold, LLC

  8. 168 Redstart Dr — photo50Active

    $769,900

    2 bd · 3 ba · 2,014 sqft

    168 Redstart Dr, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  9. 111 Marshgrass Way #43 — photo40Active

    $744,900

    2 bd · 3 ba · 1,900 sqft

    111 Marshgrass Way #43, Chester, MD

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

  10. 231 Dominion Rd — photo44Active

    $599,000

    5 bd · 3 ba · 1,852 sqft

    231 Dominion Rd, Chester, MD

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

  11. 117 Wright Rd — photo62Active

    $412,000

    3 bd · 2 ba · 1,337 sqft

    117 Wright Rd, Chester, MD

    Diane Superczynski · Douglas Realty LLC

  12. 223 Evelyne St — photo66Active

    $799,000

    3 bd · 3 ba · 2,575 sqft

    223 Evelyne St, Chester, MD

    Tara Trout · Samson Properties

  13. 630 Warbler Way #12 — photo39Active

    $549,950

    2 bd · 3 ba · 2,000 sqft

    630 Warbler Way #12, Chester, MD

    Ralph S. Kennedy · RE/MAX Executive

  14. 7-B Queen Victoria Way #B — photo39Active

    $499,000

    2 bd · 3 ba · 1,680 sqft

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

    Christina Sousa · RE/MAX Allegiance

  15. 114 Kinglet Ct — photo25Active

    $999,990

    3 bd · 3 ba · 2,772 sqft

    114 Kinglet Ct, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  16. 247 Redstart Dr — photo27Active

    $899,990

    3 bd · 3 ba · 2,772 sqft

    247 Redstart Dr, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  17. 118 Kinglet Ct — photo25Active

    $969,990

    2 bd · 3 ba · 2,010 sqft

    118 Kinglet Ct, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  18. 162 Kirwans Landing Ln — photo34Active

    $1,199,900

    5 bd · 3 ba · 3,000 sqft

    162 Kirwans Landing Ln, Chester, MD

    Jessica DuLaney · Next Step Realty

  19. 1351 Calvert Rd — photo49Active

    $645,000

    6 bd · 3 ba · 2,700 sqft

    1351 Calvert Rd, Chester, MD

    Julie G Katcef · Engel & Volkers Annapolis

  20. 1616 Postal Rd — photo45Active

    $635,000

    5 bd · 3 ba · 2,818 sqft

    1616 Postal Rd, Chester, MD

    Carol Eaton · Coldwell Banker Realty

  21. 510 Auckland Way — photo31Active

    $410,000

    3 bd · 3 ba · 1,899 sqft

    510 Auckland Way, Chester, MD

    Dawn Haskins Smith · Engel & Volkers Annapolis

  22. 15-E Queen Anne Way #E — photo51Active

    $539,000

    2 bd · 3 ba · 1,680 sqft

    15-E Queen Anne Way #E, Chester, MD

    Jason French · Benson & Mangold, LLC

  23. 320 Bayberry Dr — photo90Active

    $859,900

    3 bd · 2 ba · 2,331 sqft

    320 Bayberry Dr, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  24. 1012 Auckland Way — photo35Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

12…4
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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.

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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: 2026-10-09 17:28:03 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Nearby areas

    ZIP codes

    • 21223 (302)
    • 21224 (287)
    • 21230 (256)
    • 21217 (214)
    • 21213 (176)
    • 21216 (160)
    • 21122 (140)
    • 21403 (127)

    Cities

    • Baltimore (2,161)
    • Annapolis (304)
    • Glen Burnie (148)
    • Pasadena (140)
    • Easton (123)
    • Stevensville (86)
    • Chestertown (62)
    • Edgewater (62)

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    September 2026 · This period is still settling

    Chester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 15 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $400,000$284,250–$656,750 typical range
    Price per sq. ft.
    $278
    Sales
    14
    Paid in cash
    57.1%

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

    Median list price
    $554,500
    Homes for sale
    46
    Median days on market
    21 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.