5,228

Chester, MD Homes

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  • /50

    $915,000

    Sold Apr 10, 2026

    635 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 5 Baths
    • 2,818 Sq Ft
    • Built 2011

    Last Sold Summary

    • $325/SF
    • 27 Days On Market

    Current Estimated Value $934,693

    Last Listing Agent Constance Golihew Coldwell Banker Realty

    635 Dominion Rd, Chester, MD 21619
    • /48

      Not Listed For Sale

      209 Harrier Way, Stevensville, MD 21666

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2024
      209 Harrier Way, Stevensville, MD 21666

      Last Sold Summary

      • 131 Days On Market

      Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

  • /42

    $565,900

    $19K 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
  • /41

    $853,000

    Sold Mar 10, 2026

    162 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1988

    Last Sold Summary

    • $355/SF
    • 104 Days On Market

    Current Estimated Value $1,225,605

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    162 Kirwans Landing Ln, 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

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /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
  • /19

    $949,990

    Sold Mar 02, 2026

    110 Boatswain Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 3% Below List Price
    • $365/SF
    • 11 Days On Market

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

    110 Boatswain Way Unit 34, 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

      Last Listing Agent John Cary Rosendale Realty

  • /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
  • /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 $827,403

    Last Listing Agent Tara Trout Samson Properties

    121 John Gibson Dr, 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

      Last Listing Agent Alex Martinez The Agency DC

  • /46

    $1,400,000

    New Construction Pending
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    216 Kingfisher Ln, Chester, MD 21619

    Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    216 Kingfisher Ln, Chester, MD 21619
  • /84

    $2,200,000

    Sold Jul 24, 2026

    328 Bentons Pleasure Rd, Chester, MD 21619

    • 5 Beds
    • 4 Baths
    • 3,250 Sq Ft
    • Built 1953

    Last Sold Summary

    • 7% Above List Price
    • $677/SF
    • 1 Day On Market

    Current Estimated Value $1,279,268

    Last Listing Agent Christopher Carr HomeZu

    328 Bentons Pleasure Rd, Chester, MD 21619
    • /77

      Not Listed For Sale

      4000 Herons Nest Way Unit 11, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,003 Sq Ft
      • Built 2021
      4000 Herons Nest Way Unit 11, Chester, MD 21619

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Christine Vorsteg Keller Williams Flagship

  • /39

    $490,000

    • 2 Beds
    • 2.5 Baths

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright,

    Tara Trout Samson Properties

    1000 Herons Nest Way Unit 23, 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 $544,037

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

    200 Schooner Way, Chester, MD 21619
    • /98

      Est $755,510

      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

      Last Listing Agent Carrie Rosela Curtis Real Estate Company

  • /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
  • /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 - Luxury Condos

    121 Wheelhouse Way Unit 11, Chester, MD 21619
    • /42

      Est $347,806

      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

      Last Listing Agent Donna Wisniewski Long & Foster Real Estate, Inc.

  • /68

    $559,900

    $39K 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
  • /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 $862,447

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

    311 Kingfisher Ln, Chester, MD 21619
    • /34

      Est $729,487

      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

      Last Listing Agent Paul Mcintye EXIT First Realty

  • /48

    $355,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft

    7013 Bridgepointe Dr, Chester, MD 21619

    Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath.The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and

    Dee Dee McCracken Coldwell Banker Realty

    7013 Bridgepointe Dr, 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 - Luxury Condos

    121 Wheelhouse Way Unit 32, Chester, MD 21619
    • /55

      Est $685,771

      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

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /47

    $929,990

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

    102 Boatswain Way Unit 2943, Chester, MD 21619

    Welcome to the Chester, 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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2943, 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 - Luxury Condos

    176 Flagstaff Way Unit 33, Chester, MD 21619
    • /65

      Est $892,458

      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

      Last Listing Agent Michele Naish Berkshire Hathaway HomeServices PenFed Realty

  • /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
  • /81

    $1,150,000

    Sold Jul 31, 2026

    108 Carriage Heath, Chester, MD 21619

    • 5 Beds
    • 3.5 Baths
    • 4,334 Sq Ft
    • Built 2016

    Last Sold Summary

    • 15% Below List Price
    • $265/SF
    • 41 Days On Market

    Current Estimated Value $1,248,220

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    108 Carriage Heath, Chester, MD 21619
    • /59

      Est $875,074

      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

      Last Listing Agent Tara Trout Samson Properties

  • /47

    $749,990

    New Construction Open Sat 11AM - 4PM
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 3042, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • /31

    $567,500

    Sold Jul 23, 2026

    134 Mchenny Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft
    • Built 2017

    Last Sold Summary

    • 8% Below List Price
    • $309/SF
    • 64 Days On Market

    Current Estimated Value $583,952

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    134 Mchenny Ct, Chester, MD 21619
    • /60

      Est $554,307

      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

      Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

  • /39

    $825,000

    Open Sun 2:30PM - 4:30PM
    • 4 Beds
    • 2.5 Baths
    • 3,291 Sq Ft

    313 Thomas White Blvd, Chester, MD 21619

    Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined

    Carol Snyder Monument Sotheby's International Realty

    313 Thomas White Blvd, 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 $772,787

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

    539 Warbler Way, Chester, MD 21619
    • /69

      Est $620,122

      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

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /2

    $660,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 2,473 Sq Ft

    118 Broadwater Dr, Chester, MD 21619

    Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult

    Ralph Kennedy RE/MAX Executive

    118 Broadwater Dr, Chester, MD 21619
  • /52

    $639,900

    Sold Aug 26, 2025

    524 Warbler Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft
    • Built 2025

    Last Sold Summary

    • $379/SF
    • 79 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    524 Warbler Way, Chester, MD 21619

Showing Results 121 - 160, Page 4 of 18

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