5,228

Chester, MD Homes

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    • /38

      Est $419,809

      Not Listed For Sale

      1806 Chester Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 1962
      1806 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Jackie Ball Daley Northrop Realty

  • /44

    $849,990

    New Construction $90K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • /2

    $540,000

    Sold Mar 12, 2026

    114 Addison Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,342 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $231/SF
    • 12 Days On Market

    Current Estimated Value $538,902

    Last Listing Agent Jonathan Olsavsky Coldwell Banker Waterman Realty

    114 Addison Ct, Chester, MD 21619
    • /42

      Est $394,080

      Not Listed For Sale

      218 Blenny Ln, Chester, MD 21619

      • 4 Beds
      • 4 Baths
      • 1,900 Sq Ft
      • Built 1999
      218 Blenny Ln, Chester, MD 21619

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Michael Roenigk Chaney Homes, LLC

  • /22

    $789,990

    New Construction $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 43, Chester, MD 21619

    Private home office with French doors, perfect for leisure activities.Gorgeous gourment kitchen with designer cabinets & vast island.Elegant dining area featuring lovely dry bar.Beautiful great room with sleek electric fireplace.Serene owner's suite featuring access to balcony & large walk-in closet.Lavish owner's spa bath featuring dual sinks.Fabulous balcony for

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 43, Chester, MD 21619
  • /24

    $849,990

    Sold May 01, 2026

    110 Boatswain Way Unit 31, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 10% Below List Price
    • $327/SF
    • 44 Days On Market

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

    110 Boatswain Way Unit 31, Chester, MD 21619
    • /32

      Est $518,254

      Not Listed For Sale

      1402 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 1972
      1402 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /63

    $629,900

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619
  • /66

    $330,000

    Sold Sep 16, 2025

    208 Ringneck Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • $189/SF
    • 98 Days On Market

    Current Estimated Value $330,622

    Last Listing Agent Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
    • /44

      Est $568,447

      Not Listed For Sale

      1624 Calvert Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,470 Sq Ft
      • Built 1976
      1624 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Lois Alberti Alberti Realty, LLC

  • /13

    $599,990

    New Construction $64K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study.Gourmet kitchen with central island at the heart of the home.Dining area with dry bar for easy entertaining.Great room with electric fireplace for a cozy focal point.Patio off the great room with direct access to the owner's suite.Owner's suite with dual closets for added storage.Owner's bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • /2

    $542,500

    Sold Nov 13, 2025

    558 Cross Creek Ct, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,558 Sq Ft
    • Built 2002

    Last Sold Summary

    • $212/SF
    • 121 Days On Market

    Current Estimated Value $555,220

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
    • /72

      Est $1,136,541

      Not Listed For Sale

      1507 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,558 Sq Ft
      • Built 1966
      1507 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Beverly Sloane Benson & Mangold, LLC

  • /64

    $1,294,800

    New Construction Open Sun 10:30AM - 1PM
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • /61

    $668,500

    Sold Mar 31, 2026

    141 Switchgrass Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Built 2022

    Last Sold Summary

    • $257/SF
    • 108 Days On Market

    Current Estimated Value $664,236

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
    • /3

      Est $282,607

      Not Listed For Sale

      202 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,073 Sq Ft
      • Built 1998
      202 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Regina Fischer Long & Foster Real Estate, Inc.

  • /42

    $470,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    New and improved price! This beautifully updated and well maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‐acre corner lot, this 3‐bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location.Inside, you’ll love the bright, updated kitchen featuring

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • /20

    $1,069,990

    Sold Jun 25, 2026

    102 Boatswain Way Unit 44, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $411/SF
    • 35 Days On Market

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

    102 Boatswain Way Unit 44, Chester, MD 21619
    • /20

      Est $444,065

      Not Listed For Sale

      1703 Chester Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,556 Sq Ft
      • Built 1991
      1703 Chester Rd, Chester, MD 21619

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lona Todd Taylor Properties

  • /2

    $345,000

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    1609 Crab Alley Dr, Chester, MD 21619

    Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional

    Dee Dee Miller Paul Wesley Real Estate

    1609 Crab Alley Dr, Chester, MD 21619
  • /19

    $714,990

    Sold Dec 24, 2025

    630 Warbler Way Unit 24, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $275/SF
    • 28 Days On Market

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

    630 Warbler Way Unit 24, Chester, MD 21619
    • /11

      Est $279,179

      Not Listed For Sale

      107 Lee Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1984
      107 Lee Rd, Chester, MD 21619

      Last Sold Summary

      • 160 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /15

    $839,990

    New Construction $38K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    715 Warbler Way, Chester, MD 21619

    Stacked cabinetry with glass front uppers brings layered detail to the kitchen.Soaring two-story ceiling adds volume to the great room with a fireplace.Screened patio off the great room extends the living space outdoors.Primary suite features a ceiling treatment with a sliding barn door to the private bath.Primary bath with dual freestanding vanities & plus shower.Home office

    K. Hovnanian Homes Builder
    715 Warbler Way, Chester, MD 21619
  • /45

    $625,000

    Sold Feb 23, 2026

    154 Harrier Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2023

    Last Sold Summary

    • $329/SF
    • 317 Days On Market

    Current Estimated Value $635,064

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
    • /73

      Est $399,135

      Not Listed For Sale

      312 Widgeon Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,899 Sq Ft
      • Built 2001
      312 Widgeon Way, Chester, MD 21619

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

  • /47

    $829,990

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

    102 Boatswain Way Unit 2933, 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 2933, Chester, MD 21619
  • /58

    $769,900

    Sold Nov 25, 2025

    201 Switchgrass Way Unit 1443, Chester, MD 21619

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

    Last Sold Summary

    • $405/SF
    • 53 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1443, Chester, MD 21619
    • /56

      Est $464,084

      Not Listed For Sale

      6B Queen Victoria Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1983
      6B Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • /35

    $859,500

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    201 Switchgrass Way Unit 34, Chester, MD 21619

    Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The

    Brad Kappel TTR Sotheby's International Realty

    201 Switchgrass Way Unit 34, Chester, MD 21619
  • /34

    $226,000

    Sold Aug 25, 2025

    602 Dominion Rd, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1900

    Last Sold Summary

    • $126/SF
    • 49 Days On Market

    Current Estimated Value $282,250

    Last Listing Agent Janice O'Donnell Chaney Homes, LLC

    602 Dominion Rd, Chester, MD 21619
    • /35

      Est $314,800

      Not Listed For Sale

      28G Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,010 Sq Ft
      • Built 1985
      28G Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Bev Langley Coldwell Banker Realty

  • /21

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • /29

    $326,000

    Sold May 05, 2026

    204 Ringneck Ct, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • 6% Below List Price
    • $187/SF
    • 68 Days On Market

    Current Estimated Value $329,656

    Last Listing Agent Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
    • /43

      Est $394,808

      Not Listed For Sale

      1808 Chester Dr, Chester, MD 21619

      • 3 Beds
      • 1.5 Baths
      • 1,700 Sq Ft
      • Built 1978
      1808 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /45

    $499,000

    $41K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    124 Riverside Dr, Chester, MD 21619

    NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, Chester, MD 21619
  • /2

    $643,000

    Sold Apr 08, 2026

    219 Broadwater Dr, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft
    • Built 2023

    Last Sold Summary

    • 1% Below List Price
    • $336/SF
    • 3 Days On Market

    Current Estimated Value $648,808

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    219 Broadwater Dr, Chester, MD 21619
    • /137

      Est $813,673

      Not Listed For Sale

      117 Kirwans Landing Ln, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,288 Sq Ft
      • Built 1986
      117 Kirwans Landing Ln, Chester, MD 21619

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /50

    $298,000

    $2K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft

    1025 Dundee Ct, Chester, MD 21619

    Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity.

    Rick Parreco RE/MAX Executive

    1025 Dundee Ct, Chester, MD 21619
  • /2

    $750,000

    Sold Mar 06, 2026

    113 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • $350/SF

    Current Estimated Value $761,873

    Last Listing Agent Mary Lynch Cummings & Co. Realtors

    113 Kirwans Landing Ln, Chester, MD 21619
    • /63

      Est $517,953

      Not Listed For Sale

      23D Queen Victoria Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1985
      23D Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

Showing Results 281 - 320, Page 8 of 18

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