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5 Bedroom Homes in Chester, MD
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3 bedsNew constructionWith a pool

5 Bedroom Homes in Chester, MD

5 Bedroom Homes in Chester, MD

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7 Listings
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5 Bedroom Homes in Chester, MD

7 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 1868 Roberta Dr — photo48Active

    $400,000

    5 bd · 4 ba · 3,250 sqft

    1868 Roberta Dr, Chester, MD

    Carley R. Cooper · Alex Cooper Auctioneers, Inc.

  2. 2513 Cecil Dr — photoPrice Reduced60Active

    $1,290,000

    5 bd · 2 ba · 2,700 sqft

    2513 Cecil Dr, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  3. 111 Flycatcher Way — photo25Active

    $1,200,000

    5 bd · 5 ba · 3,225 sqft

    111 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  4. 205 Anchor Ln — photoPrice Reduced48Active

    $525,000

    5 bd · 3 ba · 3,000 sqft

    205 Anchor Ln, Chester, MD

    Kathleen Higginbotham · Samson Properties

  5. 2702 Sherman Dr — photo65Active

    $989,000

    5 bd · 4 ba · 2,752 sqft

    2702 Sherman Dr, Chester, MD

    Justin Kennedy · Samson Properties

  6. 233 Kingfisher Ln — photoPrice Reduced84Active

    $999,000

    5 bd · 5 ba · 3,225 sqft

    233 Kingfisher Ln, Chester, MD

    Tara Trout · Samson Properties

  7. 215 Kingfisher Ln — photoPrice Reduced44Active

    $995,000

    5 bd · 5 ba · 3,225 sqft

    215 Kingfisher Ln, Chester, MD

    Jennifer Anne Thomas · RE/MAX Executive

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    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    August 2026 · This period is still settling

    Chester 12-month median sale price trend

    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.