5,227

Chester, MD Homes

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  • /50

    $812,500

    Sold Sep 15, 2025

    121 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft
    • Built 2010

    Last Sold Summary

    • $294/SF
    • 7 Days On Market

    Current Estimated Value $845,578

    Last Listing Agent Tara Trout Samson Properties

    121 John Gibson Dr, Chester, MD 21619
    • /3

      Not Listed For Sale

      lot 16 & 17 Cecil Dr, Chester, MD 21619

      lot 16 & 17 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /42

    $575,000

    Open Sat 11AM - 2PM $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    115 Gibson Cir, Chester, MD 21619

    Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both

    Lawrence Doyle Long & Foster Real Estate, Inc.

    115 Gibson Cir, Chester, MD 21619
  • /64

    $550,000

    Sold Jun 08, 2026

    200 Schooner Way, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • Built 1996

    Last Sold Summary

    • $262/SF
    • 15 Days On Market

    Current Estimated Value $540,960

    Last Listing Agent Michele Cordle Long & Foster Real Estate, Inc.

    200 Schooner Way, Chester, MD 21619
    • /9

      Not Listed For Sale

      26K Queen Anne Way Unit 26K, Chester, MD 21619

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft
      • Built 1983
      26K Queen Anne Way Unit 26K, Chester, MD 21619

      Last Sold Summary

  • /59

    $935,990

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    176 Flagstaff Way Unit 2424, Chester, MD 21619

    The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2424, Chester, MD 21619
  • /10

    $539,900

    Sold Sep 08, 2025

    121 Wheelhouse Way Unit 11, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $270/SF
    • 40 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    121 Wheelhouse Way Unit 11, Chester, MD 21619
    • /28

      Not Listed For Sale

      33 F Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1988
      33 F Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 68 Days On Market

  • /44

    $1,049,500

    $51K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666
  • /40

    $899,990

    Sold Mar 25, 2026

    311 Kingfisher Ln, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 7% Below List Price
    • $279/SF
    • 8 Days On Market

    Current Estimated Value $899,207

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

    311 Kingfisher Ln, Chester, MD 21619
    • /98

      Est $771,880

      Not Listed For Sale

      184 Evelyne St, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,437 Sq Ft
      • Built 2013
      184 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

  • /21

    $869,990

    New Construction $32K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, Chester, MD 21619
  • /26

    $679,900

    Sold Sep 18, 2025

    121 Wheelhouse Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $358/SF
    • 23 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    121 Wheelhouse Way Unit 32, Chester, MD 21619
    • /42

      Est $335,034

      Not Listed For Sale

      300 Drake Tail Place, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1992
      300 Drake Tail Place, Chester, MD 21619

      Last Sold Summary

      • 95 Days On Market

  • /30

    $240,000

    $9K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, Chester, MD 21619
  • /29

    $829,990

    Sold Mar 11, 2026

    176 Flagstaff Way Unit 33, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 5% Below List Price
    • $437/SF
    • 5 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    176 Flagstaff Way Unit 33, Chester, MD 21619
    • /34

      Est $744,438

      Not Listed For Sale

      104 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,464 Sq Ft
      • Built 2010
      104 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 69 Days On Market

  • /68

    $574,900

    $24K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,425 Sq Ft

    29A Queen Mary Ct, Chester, MD 21619

    Experience "Paradise" in Queen’s Landing. This rare, end-unit waterfront gem offers an unparalleled livingexperience overlooking the serene Lake Amleto. Boasting a 2019 full-gut renovation by a customcontractor, this 1,425 sq. ft. residence (including a 145 sq. ft. sunroom) blends sophisticated design withresort-style tranquility. The interior showcases master-level craftsmanship:

    Jorge Zea Jorge A. Zea

    29A Queen Mary Ct, Chester, MD 21619
  • /27

    $789,990

    Sold Apr 01, 2026

    539 Warbler Way, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 7% Below List Price
    • $285/SF
    • 9,587 Days On Market

    Current Estimated Value $784,636

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

    539 Warbler Way, Chester, MD 21619
    • /55

      Est $702,183

      Not Listed For Sale

      243 Evelyne St, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,386 Sq Ft
      • Built 2011
      243 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

  • /37

    $1,200,000

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

    111 Flycatcher Way, Chester, MD 21619

    Beautiful kitchen with wood-stained cabinetry & pendant lighting. Open concept living spaces with vaulted ceiling & elegant fireplace. Private primary suite & bath with generous walk-in closet. Productive home office for working remotely. Secluded Extra Suite, ideal for overnight guests. Stunning screened patio for outdoor entertaining. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    111 Flycatcher Way, Chester, MD 21619
  • /48

    $559,900

    Sold May 27, 2026

    630 Warbler Way Unit 2223, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $295/SF
    • 35 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2223, Chester, MD 21619
    • /65

      Est $897,356

      Not Listed For Sale

      151 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,156 Sq Ft
      • Built 2010
      151 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 12 Days On Market

  • /52

    $689,990

    New Construction $101K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Warbler Way Unit 3032, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3032, Chester, MD 21619
  • /34

    $280,000

    Sold Apr 17, 2026

    106 Merganser Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $262/SF
    • 1 Day On Market

    Current Estimated Value $283,498

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Merganser Ct, Chester, MD 21619
    • /59

      Est $884,328

      Not Listed For Sale

      134 Henry Stoupe Way, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 3,076 Sq Ft
      • Built 2010
      134 Henry Stoupe Way, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

  • /50

    $5,900,000

    • 7 Beds
    • 9 Baths
    • 9,974 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, Chester, MD 21619
  • /63

    $365,000

    Sold Oct 20, 2025

    1033 Dundee Ct Unit 5, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft
    • Built 2003

    Last Sold Summary

    • $268/SF
    • 14 Days On Market

    Current Estimated Value $381,153

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    1033 Dundee Ct Unit 5, Chester, MD 21619
    • /60

      Est $574,743

      Not Listed For Sale

      107 Gibson Cir, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,048 Sq Ft
      • Built 2009
      107 Gibson Cir, Chester, MD 21619

      Last Sold Summary

      • 35 Days On Market

  • /50

    $420,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    $25k Price Improvement + Views of Crab Alley! Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table for six, ideal for

    Kathleen Higginbotham Samson Properties

    200 Newtown Rd, Chester, MD 21619
  • /28

    $285,000

    Sold May 05, 2026

    1905 Bayside Dr, Chester, MD 21619

    • 2 Beds
    • 1.5 Baths
    • 1,220 Sq Ft
    • Built 1976

    Last Sold Summary

    • 21% Below List Price
    • $234/SF
    • 17 Days On Market

    Current Estimated Value $360,942

    Last Listing Agent Lisa Ciofani Cummings & Co. Realtors

    1905 Bayside Dr, Chester, MD 21619
    • /69

      Est $638,334

      Not Listed For Sale

      201 Gibson Cir, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2010
      201 Gibson Cir, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

  • /46

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54F Queen Caroline Ct, Chester, MD 21619

    Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan

    Lawrence Doyle Long & Foster Real Estate, Inc.

    54F Queen Caroline Ct, Chester, MD 21619
  • /9

    $849,990

    Sold Jun 05, 2026

    536 Warbler Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $423/SF
    • 16 Days On Market

    Current Estimated Value $783,667

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

    536 Warbler Way, Chester, MD 21619
    • /72

      Est $950,678

      Not Listed For Sale

      432 Macum Creek Dr, Chester, MD 21619

      • 5 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 2010
      432 Macum Creek Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /44

    $775,000

    $13K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,276 Sq Ft

    126 Claiborne St, Chester, MD 21619

    Welcome to 126 Claiborne Street in the sought-after Gibson's Grant community on Kent Island — a beautifully crafted Covell-built Sawgrass model offering the perfect blend of coastal charm and comfortable with peaceful pond and park views right outside your door This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a desirable main-level primary suite complete with a private en suite

    Tara Trout Samson Properties

    126 Claiborne St, Chester, MD 21619
  • /27

    $899,990

    Sold Mar 04, 2026

    141 Redstart Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 14% Below List Price
    • $325/SF
    • 13 Days On Market

    Current Estimated Value $894,166

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

    141 Redstart Dr, Chester, MD 21619
    • /31

      Est $362,860

      Not Listed For Sale

      1817 Stevens Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1976
      1817 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

  • /54

    $640,000

    • 3 Beds
    • 2.5 Baths
    • 2,119 Sq Ft

    265 Evelyne St, Chester, MD 21619

    Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for

    Kathleen Higginbotham Samson Properties

    265 Evelyne St, Chester, MD 21619
  • /36

    $705,000

    Sold Sep 23, 2025

    242 Peregrine Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $224/SF
    • 111 Days On Market

    Last Listing Agent Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619

Showing Results 121 - 160, Page 4 of 18

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