Chester, MD Real Estate & Homes For Sale

41 homes

  • 1308 Saint Marys Rd, Chester, MD 21619
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    NEWOPEN SAT, 12-2PM0.77 ACRES
    $749,900
    2bd
    2ba
    1,971 sqft (on 0.77 acres)
    1308 Saint Marys Rd,
    Chester, MD 21619
    Berkshire Hathaway HomeServices PenFed Realty
  • 209 Evelyne St, Chester, MD 21619
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    NEW - 20 HRS AGO
    $859,000
    3bd
    3ba
    2,771 sqft
    209 Evelyne St,
    Chester, MD 21619
    Redfin Corp
  • 23 Queen Victoria Way #23D, Chester, MD 21619
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    OPEN SUN, 12-2PM
    $595,000
    3bd
    3ba
    1,680 sqft
    23 Queen Victoria Way #23D,
    Chester, MD 21619
    RE/MAX Executive
  • 308 Blenny Ln, Chester, MD 21619
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    NEWCOMING SOON 4/26
    $389,900
    3bd
    4ba
    1,899 sqft
    308 Blenny Ln,
    Chester, MD 21619
    RE/MAX Executive
  • 225 Thomas White Blvd, Chester, MD 21619
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    OPEN SUN, 11-1PM
    $659,999
    3bd
    2ba
    2,140 sqft
    225 Thomas White Blvd,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 206 Blenny Ln, Chester, MD 21619
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    $385,000
    3bd
    4ba
    1,899 sqft
    206 Blenny Ln,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 248 Evelyne St, Chester, MD 21619
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    OPEN SUN, 11-1PM
    $925,000
    4bd
    5ba
    4,470 sqft
    248 Evelyne St,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 37 Queen Anne Way, Chester, MD 21619
    $377,500
    2bd
    3ba
    1,440 sqft
    37 Queen Anne Way,
    Chester, MD 21619
    Realty Navigator
  • 1757 Harbor Dr, Chester, MD 21619
    NEW CONSTRUCTION0.55 ACRES
    $887,690
    4bd
    4ba
    1757 Harbor Dr,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 112 Bentons Pleasure Rd, Chester, MD 21619
    1.84 ACRES
    $775,000
    4bd
    3ba
    2,532 sqft (on 1.84 acres)
    112 Bentons Pleasure Rd,
    Chester, MD 21619
    Benson & Mangold, LLC
  • 202 Merganser Ct, Chester, MD 21619
    $295,000
    2bd
    2ba
    1,073 sqft
    202 Merganser Ct,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 104 John Gibson Dr, Chester, MD 21619
    FORECLOSURE
    3bd
    3ba
    2,464 sqft
    104 John Gibson Dr,
    Chester, MD 21619
    EXIT First Realty
  • 203 Skipper Ln, Chester, MD 21619
    0.52 ACRES
    $764,989
    5bd
    5ba
    3,900 sqft (on 0.52 acres)
    203 Skipper Ln,
    Chester, MD 21619
    Coldwell Banker Realty
  • 102 Ringneck Ct, Chester, MD 21619
    $369,999
    3bd
    3ba
    1,747 sqft
    102 Ringneck Ct,
    Chester, MD 21619
    RE/MAX Executive
  • 1112 Hopkins Rd, Chester, MD 21619
    NEW CONSTRUCTION0.53 ACRES
    $669,800
    4bd
    3ba
    2,600 sqft (on 0.53 acres)
    1112 Hopkins Rd,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 53E Queen Caroline Ct, Chester, MD 21619
    $329,000
    2bd
    3ba
    1,280 sqft
    53E Queen Caroline Ct,
    Chester, MD 21619
    Realty Navigator
  • 224 Switchgrass Way #1831, Chester, MD 21619
    NEW CONSTRUCTION
    $1,115,000
    3bd
    3ba
    2,600 sqft
    224 Switchgrass Way #1831,
    Chester, MD 21619
    KOVO Realty
  • 224 Switchgrass Way #1833, Chester, MD 21619
    NEW CONSTRUCTION
    $902,900
    2bd
    3ba
    1,900 sqft
    224 Switchgrass Way #1833,
    Chester, MD 21619
    KOVO Realty
  • 224 Switchgrass Way #1834, Chester, MD 21619
    NEW CONSTRUCTION
    $1,095,000
    3bd
    3ba
    2,600 sqft
    224 Switchgrass Way #1834,
    Chester, MD 21619
    KOVO Realty
  • 224 Switchgrass Way #1842, Chester, MD 21619
    NEW CONSTRUCTION
    $1,004,000
    2bd
    3ba
    1,900 sqft
    224 Switchgrass Way #1842,
    Chester, MD 21619
    KOVO Realty
  • 3000 Herons Nest Way #34, Chester, MD 21619
    OPEN SAT, 12-4PM
    $689,800
    3bd
    3ba
    2,600 sqft
    3000 Herons Nest Way #34,
    Chester, MD 21619
    RE/MAX Executive
  • 2802 Cox Neck Rd, Chester, MD 21619
    1.28 ACRES
    $954,000
    4bd
    4ba
    3,692 sqft (on 1.28 acres)
    2802 Cox Neck Rd,
    Chester, MD 21619
    Coldwell Banker Realty
  • 306 Drake Tail Pl, Chester, MD 21619
    $334,900
    3bd
    3ba
    1,440 sqft
    306 Drake Tail Pl,
    Chester, MD 21619
    Compass
  • 129 Wheelhouse Way #2021, Chester, MD 21619
    NEW CONSTRUCTION
    $899,900
    3bd
    3ba
    2,601 sqft
    129 Wheelhouse Way #2021,
    Chester, MD 21619
    KOVO Realty
  • 1007 Dominion Rd, Chester, MD 21619
    0.51 ACRES
    $424,987
    1007 Dominion Rd,
    Chester, MD 21619
    Coldwell Banker Realty
  • 203 Riverside Dr, Chester, MD 21619
    $225,000
    203 Riverside Dr,
    Chester, MD 21619
    RE/MAX Executive
  • 1518 Saint Marys Rd, Chester, MD 21619
    NEWOPEN SAT, 2-4PM0.46 ACRES
    $829,000
    3bd
    2ba
    2,000 sqft (on 0.46 acres)
    1518 Saint Marys Rd,
    Chester, MD 21619
    RE/MAX Executive
  • 166 Warbler Way #33, Chester, MD 21619
    NEW CONSTRUCTION
    $649,900
    2bd
    3ba
    1,900 sqft
    166 Warbler Way #33,
    Chester, MD 21619
    KOVO Realty
  • 111 Bluebell Ct, Chester, MD 21619
    $575,900
    2bd
    2ba
    1,693 sqft
    111 Bluebell Ct,
    Chester, MD 21619
    Douglas Realty, LLC
  • 121 Gunners Rest Ln, Chester, MD 21619
    16.28 ACRES
    $1,100,000
    3bd
    3ba
    2,686 sqft (on 16.28 acres)
    121 Gunners Rest Ln,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 45 Queen Neva Ct, Chester, MD 21619
    $349,000
    2bd
    3ba
    1,312 sqft
    45 Queen Neva Ct,
    Chester, MD 21619
    Coldwell Banker Realty
  • 4000 Herons Nest Way #31, Chester, MD 21619
    $649,900
    3bd
    3ba
    2,602 sqft
    4000 Herons Nest Way #31,
    Chester, MD 21619
    Realty Navigator
  • 1409 Queen Anne Dr, Chester, MD 21619
    0.34 ACRES
    $635,000
    4bd
    3ba
    2,800 sqft (on 0.34 acres)
    1409 Queen Anne Dr,
    Chester, MD 21619
    Chesapeake Real Estate Associates, LLC
  • 1000 Herons Nest Way #22, Chester, MD 21619
    $539,900
    2bd
    3ba
    1,900 sqft
    1000 Herons Nest Way #22,
    Chester, MD 21619
    Keller Williams Select Realtors
  • Lot 6 Norman Ct, Chester, MD 21619
    NEW CONSTRUCTION0.64 ACRES
    $674,900
    4bd
    3ba
    Lot 6 Norman Ct,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • Parks Rd, Chester, MD 21619
    0.68 ACRES
    $300,000
    Parks Rd,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • Lot 52 Woods Rd, Chester, MD 21619
    NEW CONSTRUCTION0.94 ACRES
    $699,900
    4bd
    3ba
    Lot 52 Woods Rd,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • Lot 53 Woods Rd, Chester, MD 21619
    NEW CONSTRUCTION0.94 ACRES
    $629,900
    4bd
    3ba
    Lot 53 Woods Rd,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • Lot 9 Harbor Dr, Chester, MD 21619
    NEW CONSTRUCTION0.55 ACRES
    $699,900
    4bd
    4ba
    2,350 sqft (on 0.55 acres)
    Lot 9 Harbor Dr,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • Lot 8 Harbor Dr, Chester, MD 21619
    NEW CONSTRUCTION0.55 ACRES
    $594,900
    4bd
    3ba
    1,553 sqft (on 0.55 acres)
    Lot 8 Harbor Dr,
    Chester, MD 21619
    Keller Williams Flagship of Maryland

Chester, MD Real Estate Trends

Learn about the Chester, MD housing market through trends and averages.

Affordability of Living in Chester, MD

The median home value is $478,077
MonthMedian home value
March 2023$459k
April 2023$461k
May 2023$463k
June 2023$467k
July 2023$469k
August 2023$472k
September 2023$475k
October 2023$477k
November 2023$477k
December 2023$477k
January 2024$477k
February 2024$478k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Chester, MD, by Home Size

Currently, there are 7 new listings and 41 homes for sale in Chester.
Home SizeHome Value*
2 bedrooms (14 homes)$373,266
3 bedrooms (16 homes)$443,995
4 bedrooms (12 homes)$610,807
*Home value over the past month

What Locals Say about Chester

  • Dlmaheux
    "I’ve been here 20 years and don’t even lock my doors the majority of the time. Super safe. Wonderful sense of community all around "
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  • Peggy Young
    "Board meetings, water aerobics, pickle ball, tennis, a gym, kayaking, paddle boarding. Mah jongg, bingo, games day, social committee,walking club "
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  • Peggy.young
    "Lots of spaces to walk dogs, lots of people who love dogs. Great way to meet neighbors. Just about everyone on the shore has a dog. Also a number of good kennels for when you travel. "
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  • Wilson
    "Not very many families, but within a great school district. Good community for people who don’t really have children. "
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