Chester, MD Real Estate & Homes For Sale

38 homes

  • 203 Skipper Ln, Chester, MD 21619
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    0.52 ACRES
    $764,989
    5bd
    5ba
    3,900 sqft (on 0.52 acres)
    203 Skipper Ln,
    Chester, MD 21619
    Coldwell Banker Realty
  • 103 Old Point Rd, Chester, MD 21619
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    5.34 ACRES
    $549,900
    3bd
    2ba
    1,456 sqft (on 5.34 acres)
    103 Old Point Rd,
    Chester, MD 21619
    Taylor Properties
  • 248 Evelyne St, Chester, MD 21619
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    NEWCOMING SOON 4/9
    $925,000
    4bd
    4ba
    3,870 sqft
    248 Evelyne St,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 102 Ringneck Ct, Chester, MD 21619
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    OPEN SAT, 12-2PM
    $379,999
    3bd
    3ba
    1,747 sqft
    102 Ringneck Ct,
    Chester, MD 21619
    RE/MAX Executive
  • 545 Cross Creek Ct, Chester, MD 21619
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    COMING SOON 4/5
    Berkshire Hathaway Homeservice Homesale Realty
  • 202 Merganser Ct, Chester, MD 21619
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    COMING SOON 3/31
    $303,000
    2bd
    2ba
    1,073 sqft
    202 Merganser Ct,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 230 Cross Creek Ct, Chester, MD 21619
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    0.43 ACRES
    $574,900
    4bd
    3ba
    2,332 sqft (on 0.43 acres)
    230 Cross Creek Ct,
    Chester, MD 21619
    Benson & Mangold, LLC
  • 1112 Hopkins Rd, Chester, MD 21619
    NEW CONSTRUCTION0.53 ACRES
    $629,900
    4bd
    3ba
    2,600 sqft (on 0.53 acres)
    1112 Hopkins Rd,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • 112 Bentons Pleasure Rd, Chester, MD 21619
    COMING SOON 4/31.84 ACRES
    $749,900
    4bd
    3ba
    2,532 sqft (on 1.84 acres)
    112 Bentons Pleasure Rd,
    Chester, MD 21619
    Benson & Mangold, LLC
  • 53E Queen Caroline Ct, Chester, MD 21619
    Realty Navigator
  • 224 Switchgrass Way #1831, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 224 Switchgrass Way #1833, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 224 Switchgrass Way #1834, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 224 Switchgrass Way #1842, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 3000 Herons Nest Way  #34, Chester, MD 21619
    RE/MAX Executive
  • 2802 Cox Neck Rd, Chester, MD 21619
    OPEN SAT, 1-3PM1.28 ACRES
    $984,000
    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
    $349,900
    3bd
    3ba
    1,440 sqft
    306 Drake Tail Pl,
    Chester, MD 21619
    Compass
  • 224 Switchgrass Way #1821, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 129 Wheelhouse Way #2021, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 1007 Dominion Rd, Chester, MD 21619
    0.51 ACRES
    Coldwell Banker Realty
  • 203 Riverside Dr, Chester, MD 21619
    RE/MAX Executive
  • 166 Warbler Way  #33, Chester, MD 21619
    NEW CONSTRUCTION
    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
    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
    Keller Williams Select Realtors
  • Lot 6 Norman Ct, Chester, MD 21619
    NEW CONSTRUCTION0.64 ACRES
    Keller Williams Flagship of Maryland
  • 119 Cavalier Ct, Chester, MD 21619
    $819,900
    3bd
    4ba
    3,200 sqft
    119 Cavalier Ct,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 1221 Cox Neck Rd, Chester, MD 21619
    $534,900
    4bd
    3ba
    1,482 sqft
    1221 Cox Neck Rd,
    Chester, MD 21619
    Jorge A. Zea
  • 106 Blenny Ln, Chester, MD 21619
    OPEN SAT, 11-1PM
    $383,900
    3bd
    4ba
    1,899 sqft
    106 Blenny Ln,
    Chester, MD 21619
    Coldwell Banker Realty
  • Parks Rd, Chester, MD 21619
    0.68 ACRES
    Long & Foster Real Estate, Inc.
  • Lot 52 Woods Rd, Chester, MD 21619
    NEW CONSTRUCTION0.94 ACRES
    Keller Williams Flagship of Maryland
  • Lot 53 Woods Rd, Chester, MD 21619
    NEW CONSTRUCTION0.94 ACRES
    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
    $584,900
    4bd
    3ba
    1,553 sqft (on 0.55 acres)
    Lot 8 Harbor Dr,
    Chester, MD 21619
    Keller Williams Flagship of Maryland
  • Parcel 378 Bentons Pleasure Rd   #8, Chester, MD 21619
    0.78 ACRES
    Coldwell Banker Waterman Realty

Homes Near Chester, MD

We found 30 more homes matching your filters just outside Chester

  • Kerr Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family, Chester, MD 21619
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    NEW CONSTRUCTION
  • 920 Monroe Manor Rd, Stevensville, MD 21666
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    COMING SOON 4/50.34 ACRES
    $550,000
    4bd
    2ba
    1,848 sqft (on 0.34 acres)
    920 Monroe Manor Rd,
    Stevensville, MD 21666
    Northrop Realty
  • 5 Manor Ct, Stevensville, MD 21666
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    COMING SOON 4/50.39 ACRES
    $525,000
    4bd
    3ba
    3,144 sqft (on 0.39 acres)
    5 Manor Ct,
    Stevensville, MD 21666
    Keller Williams Flagship of Maryland
  • 404 Main St, Stevensville, MD 21666
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    COMING SOON 4/120.29 ACRES
    $489,900
    3bd
    2ba
    1,340 sqft (on 0.29 acres)
    404 Main St,
    Stevensville, MD 21666
    Clark & Co Realty, LLC
  • Thompson Creek Rd, Stevensville, MD 21666
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    29.52 ACRES
    The Land Group
  • Munich Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family, Chester, MD 21619
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    NEW CONSTRUCTION
  • 124 Warbler Way, Chester, MD 21619
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    NEW CONSTRUCTION
    $674,900
    2bd
    2ba
    1,996 sqft
    124 Warbler Way,
    Chester, MD 21619
    KOVO Realty
  • 119 Peregrine Dr, Chester, MD 21619
    NEW CONSTRUCTION
    $654,900
    2bd
    2ba
    1,996 sqft
    119 Peregrine Dr,
    Chester, MD 21619
    KOVO Realty
  • 105 Warbler Way, Chester, MD 21619
    NEW CONSTRUCTION
    $669,900
    2bd
    2ba
    1,996 sqft
    105 Warbler Way,
    Chester, MD 21619
    KOVO Realty
  • 352 Topside Dr #229, Stevensville, MD 21666
    Keller Williams Flagship of Maryland
  • 109 Bayview, Grasonville, MD 21638
    $475,000
    3bd
    4ba
    2,044 sqft
    109 Bayview,
    Grasonville, MD 21638
    RE/MAX Leading Edge
  • 213 Creeks End Ln, Stevensville, MD 21666
    Coldwell Banker Waterman Realty
  • 224 Switchgrass Way #1843, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 158 Sailcloth Way, Chester, MD 21619
    $899,900
    3bd
    4ba
    3,494 sqft
    158 Sailcloth Way,
    Chester, MD 21619
    Long & Foster Real Estate, Inc.
  • 3801 Main St, Grasonville, MD 21638
    0.26 ACRES
    $425,000
    2bd
    1ba
    1,176 sqft (on 0.26 acres)
    3801 Main St,
    Grasonville, MD 21638
    Long & Foster Real Estate, Inc.
  • 129 Wheelhouse Way #2011, Chester, MD 21619
    NEW CONSTRUCTION
    KOVO Realty
  • 315 Allison Jane Dr #G-20, Stevensville, MD 21666
    NEW CONSTRUCTION
    Long & Foster Real Estate, Inc.
  • 325 Larch Pl, Stevensville, MD 21666
    0.69 ACRES
    $674,900
    4bd
    3ba
    2,232 sqft (on 0.69 acres)
    325 Larch Pl,
    Stevensville, MD 21666
    Douglas Realty, LLC
  • 157 Sailcloth Way, Chester, MD 21619
    $615,000
    3bd
    3ba
    2,223 sqft
    157 Sailcloth Way,
    Chester, MD 21619
    RE/MAX One
  • 201 Jessica Lyn Ave, Stevensville, MD 21666
    NEW CONSTRUCTION
    Keller Williams Flagship of Maryland
  • Bridgeview Ln, Stevensville, MD 21666
    16.09 ACRES
    Benson & Mangold, LLC
5 More Homes
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We found 5 more homes that match your search in other listings.

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 5 new listings and 38 homes for sale in Chester.
Home SizeHome Value*
2 bedrooms (11 homes)$373,266
3 bedrooms (15 homes)$443,995
4 bedrooms (11 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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  • Colinjgallagher525
    "Tucked away million dollar homes with great down-to-earth people living in them. It’s a warm community and bay living at its finest. "
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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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  • Trulia User
    "Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
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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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  • Taylor T.
    "Lots of dogs everyone walks them all hours of the night and their is little stops with bags to pick up Feeses "
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  • kara
    "I've lived here for three years and the neighbors are very friendly mostly. They look out for each other..."
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  • Robert M Heyn
    "Its always so pleasant here in Chester. Its like Everyone says HI and knows one another. The school systems are great and Chester is central located to all surrounding areas of shopping, dining, water, Annapolis and Easton. Some of tue most beautiful views in the MD pertaining to water and nature."
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  • J0J0s4X4
    "They are required to clean up after them. The HOA used to pay a pooper scooper company which provided pooper containers, scoops, and bags after used to be deposited in the container. The Board decided that the dog owners should pick up the cost of picking up after their dogs and quit paying the $26,000 per year for the company."
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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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  • J0J0s4X4
    "it is a child friendly development and very safe. also, most homeowners have video security systems."
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  • Peggy y.
    "Chester is a real community, where you know just about everyone. I live in a condo, so life is as easy as it gets. There are lots of walking trails, and you are always a stone’s throw from the Chesapeake Bay or the Chester River."
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