5,231

Chester, MD Homes

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    • /28

      Not Listed For Sale

      110 Hopkins Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 2024
      110 Hopkins Rd, Chester, MD 21619

      Last Sold Summary

      • 123 Days On Market

      Last Listing Agent George Bailey Keller Williams Flagship

  • /12

    $886,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • /60

    $339,900

    Sold Jan 14, 2026

    30 C Queen Mary Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1999

    Last Sold Summary

    • $236/SF
    • 81 Days On Market

    Last Listing Agent Dori Savani Douglas Realty, LLC

    30 C Queen Mary Ct, Chester, MD 21619
    • /55

      Not Listed For Sale

      218 Switchgrass Way Unit 1732, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2025
      218 Switchgrass Way Unit 1732, Chester, MD 21619

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /38

    $974,990

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    323 Kingfisher Ln, Chester, MD 21619

    Efficient kitchen with gray cabinetry, quartz countertops, & matte black finishes.Open concept living areas featuring a vaulted ceiling, stained beams, & cozy fireplace.Lavish primary suite & plus bath with generous walk-in closet.Private Extra Suite perfect for overnight guests.Formal home office provides a quiet area for studying or reading.Versatile screened patio for

    K. Hovnanian Homes Builder
    323 Kingfisher Ln, Chester, MD 21619
  • /30

    $1,350,000

    Sold Feb 24, 2026

    132 Wheelhouse Way Unit 43, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $711/SF
    • 9,551 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    132 Wheelhouse Way Unit 43, Chester, MD 21619
    • /56

      Not Listed For Sale

      212 Switchgrass Way Unit 1641, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1641, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /15

    $275,000

    $25K PRICE DROP
    • Land
    • 29,620 Sq Ft
    • $404,412 per Acre

    0 Parks Rd, Chester, MD 21619

    Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is

    Linda Austin Long & Foster Real Estate, Inc.

    0 Parks Rd, Chester, MD 21619
  • /41

    $685,000

    Sold May 11, 2026

    1700 Saint Marys Rd, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,898 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Above List Price
    • $361/SF
    • 5 Days On Market

    Current Estimated Value $693,905

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1700 Saint Marys Rd, Chester, MD 21619
    • /58

      Not Listed For Sale

      218 Switchgrass Way Unit 1744, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      218 Switchgrass Way Unit 1744, Chester, MD 21619

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /48

    $425,500

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • /38

    $480,000

    Sold Jun 24, 2026

    1848 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Below List Price
    • $266/SF
    • 35 Days On Market

    Current Estimated Value $483,764

    Last Listing Agent Colleen Smith EXP Realty, LLC

    1848 Harbor Dr, Chester, MD 21619
    • /55

      Not Listed For Sale

      218 Switchgrass Way Unit 1711, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,003 Sq Ft
      • Built 2024
      218 Switchgrass Way Unit 1711, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /46

    $364,900

    Open Sun 10:30AM - 12PM $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    5011 Bridgepointe Dr, Chester, MD 21619

    Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that

    Nick Waldner Keller Williams Realty Centre

    5011 Bridgepointe Dr, Chester, MD 21619
  • /24

    $224,000

    Sold Sep 04, 2025

    2653 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1975

    Last Sold Summary

    • 52% Below List Price
    • $144/SF
    • 94 Days On Market

    Current Estimated Value $314,903

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    2653 Cox Neck Rd, Chester, MD 21619
    • /42

      Not Listed For Sale

      510 Warbler Way, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2025
      510 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /19

    $749,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 24, Chester, MD 21619

    Charming gourmet kitchen with designer cabinetry & sprawling island.Elegant dining area with dry bar perfect for hosting.Beautiful great room with electric fireplace for cozy evenings.Private owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish frameless shower.Serene balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 24, Chester, MD 21619
  • /106

    $630,000

    Sold Oct 30, 2025

    204 Skipper Ln, Chester, MD 21619

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $168/SF
    • 40 Days On Market

    Current Estimated Value $665,704

    Last Listing Agent Andy Schweigman Douglas Realty, LLC

    204 Skipper Ln, Chester, MD 21619
    • /73

      Not Listed For Sale

      170 Harrier Way Unit 32, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2022
      170 Harrier Way Unit 32, Chester, MD 21619

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Scott Swahl Redfin Corp

  • /63

    $599,990

    New Construction $50K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Warbler Way Unit 2912, Chester, MD 21619

    Welcome to the Magothy, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2912, Chester, MD 21619
  • /71

    $965,000

    Sold May 07, 2026

    102 Carriage Heath, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Above List Price
    • $328/SF
    • 1 Day On Market

    Current Estimated Value $971,932

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    102 Carriage Heath, Chester, MD 21619
    • /33

      Not Listed For Sale

      24 C Queen Elizabeth Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,760 Sq Ft
      • Built 1985
      24 C Queen Elizabeth Ct, Chester, MD 21619

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Jennifer Thomas RE/MAX Executive

  • /33

    $544,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    Chester Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owner’s suite with spa bath and access to balcony. Large secondary bedroom with access to balcony. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
  • /30

    $644,990

    Sold Jan 13, 2026

    630 Warbler Way Unit 33, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $339/SF
    • 39 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    630 Warbler Way Unit 33, Chester, MD 21619
    • /39

      Not Listed For Sale

      33 H Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      33 H Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Peter Ayerle Cummings & Co. Realtors

  • /38

    $355,000

    $25K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,804 Sq Ft

    2008 Bridgepointe Dr, Chester, MD 21619

    Looking for more space than you might expect on Kent Island? This spacious end-unit home offers over 1,800 square feet with a flexible layout designed to give you plenty of room to make it your own. At the heart of the home, the oversized kitchen provides an abundance of cabinetry and countertop space, making it ideal for everyday living, entertaining, or anyone who simply appreciates having room

    Crystal Smith RE/MAX Executive

    2008 Bridgepointe Dr, Chester, MD 21619
  • /55

    $500,900

    Sold Sep 05, 2025

    211 Switchgrass Way Unit 1511, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2024

    Last Sold Summary

    • $250/SF
    • 12 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1511, Chester, MD 21619
    • /47

      Not Listed For Sale

      3 Queen Victoria Way, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1985
      3 Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Carol Tinnin RE/MAX Leading Edge

  • /78

    $1,195,000

    $55K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Tricia Wilson Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • /62

    $699,990

    Sold Jul 01, 2026

    630 Warbler Way Unit 2224, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2025

    Last Sold Summary

    • $269/SF
    • 248 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2224, Chester, MD 21619
    • /38

      Not Listed For Sale

      200 Harrier Way Unit 44, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • Built 2023
      200 Harrier Way Unit 44, Chester, MD 21619

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Ralph Kennedy RE/MAX Executive

  • /32

    $749,990

    New Construction $110K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island.Inviting great room featuring a cozy electric fireplace.Dry bar creates a polished space for serving & entertaining.Peaceful owner's suite with stylish tray ceiling & private bath.Home office with double doors offers a quiet, flexible workspace.Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • /38

    $370,000

    Sold Oct 03, 2025

    204 Dominion Ln, Chester, MD 21619

    • 4 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1965

    Last Sold Summary

    • $248/SF
    • 13 Days On Market

    Current Estimated Value $383,258

    Last Listing Agent James Real Estate Group EXP Realty, LLC

    204 Dominion Ln, Chester, MD 21619
    • /51

      Not Listed For Sale

      148 Nighthawk Dr, Stevensville, MD 21666

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      148 Nighthawk Dr, Stevensville, MD 21666

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /2

    $868,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    113 Bentons Pleasure Rd, Chester, MD 21619

    A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining

    Temple Peirce Cummings & Co. Realtors

    113 Bentons Pleasure Rd, Chester, MD 21619
  • /40

    $969,990

    Sold Jun 16, 2026

    121 Kinglet Ct, Chester, MD 21619

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 12% Below List Price
    • $301/SF
    • 20 Days On Market

    Current Estimated Value $977,635

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    121 Kinglet Ct, Chester, MD 21619
    • /24

      Not Listed For Sale

      201 Switchgrass Way Unit 33, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      201 Switchgrass Way Unit 33, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

  • /18

    $749,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 21, Chester, MD 21619

    Spacious great room with electric fireplace & seamless flow to the dining area.Private balcony off the main living area, ideal for outdoor relaxation.Gourmet kitchen with large island, ample cabinetry & pantry for extra storage.Included dry bar adds convenience for hosting & everyday use.Owner’s suite with direct access to a cozy sitting room.Luxurious owner’s spa bath with

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 21, Chester, MD 21619
  • /30

    $689,990

    Sold Jun 03, 2026

    110 Boatswain Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 13% Below List Price
    • $363/SF
    • 22 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 32, Chester, MD 21619
    • /36

      Not Listed For Sale

      26C Piney Narrows Rd, Chester, MD 21619

      • 611 Sq Ft
      • Built 1981
      26C Piney Narrows Rd, Chester, MD 21619

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Lisa Lynch Keller Williams Realty

Showing Results 41 - 80, Page 2 of 18

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