5,231

Chester, MD Homes

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  • /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
    • /51

      Est $488,741

      Not Listed For Sale

      412 Hanna Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 1,840 Sq Ft
      • Built 2001
      412 Hanna Ct, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sarah Miller Hubble Bisbee Christie's International Real Estate

  • /63

    $599,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    REDUCED!!! 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
  • /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
    • /47

      Est $385,410

      Not Listed For Sale

      30F Queen Mary Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1999
      30F Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Karen Clark Clark & Co 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
  • /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 $657,262

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
    • /33

      Est $459,730

      Not Listed For Sale

      1809 Stevens Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 1,896 Sq Ft
      • Built 1975
      1809 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Greg Koch Taylor Properties

  • /64

    $1,194,800

    New Construction
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT ****Schedule showoing today!New Home, New Pier,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 lifestyle in this

    George Bailey Keller Williams Flagship

    1757 Harbor 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
    • /85

      Est $423,860

      Not Listed For Sale

      28J Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,660 Sq Ft
      • Built 1985
      28J Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /49

    $345,000

    Pending
    • 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
    • /40

      Est $471,546

      Not Listed For Sale

      2709 Cox Neck Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,286 Sq Ft
      • Built 1975
      2709 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jessica Garrison LPT Realty, LLC

  • /47

    $819,990

    New Construction $10K PRICE DROP
    • 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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2933, 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 $647,812

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
    • /48

      Est $355,889

      Not Listed For Sale

      5002 Bridgepointe Dr, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1995
      5002 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /41

    $835,000

    $25K PRICE DROP
    • 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

    Brad Kappel TTR Sotheby's International Realty

    201 Switchgrass Way Unit 34, 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
    • /44

      Est $295,757

      Not Listed For Sale

      513 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,073 Sq Ft
      • Built 1996
      513 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent April Heim Rosendale 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
  • /12

    $1,510,604

    Sold Aug 06, 2026

    216 Kingfisher Ln, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $752/SF
    • 9,714 Days On Market

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

    216 Kingfisher Ln, Chester, MD 21619
    • /24

      Est $278,859

      Not Listed For Sale

      314 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1998
      314 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

  • /45

    $499,000

    $41K PRICE DROP Under Contract
    • 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

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, 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
    • /68

      Est $236,329

      Not Listed For Sale

      7C Queen Victoria Way, Chester, MD 21619

      • Studio
      • 1 Bath
      • 724 Sq Ft
      • Built 1983
      7C Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /54

    $619,990

    New Construction $10K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    110 Boatswain Way Unit 3012, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3012, 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 $658,407

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    219 Broadwater Dr, Chester, MD 21619
    • /27

      Est $343,688

      Not Listed For Sale

      15G Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      15G Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Mackenzie Hoffer CENTURY 21 New Millennium

  • /32

    $369,900

    $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    2004 Bridgepointe Dr, Chester, MD 21619

    REDUCED!! Welcome to one of the most desirable Homes in the Bridgepointe Community! ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after

    Sheryl Carmody RE/MAX Executive

    2004 Bridgepointe Dr, 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
    • /45

      Est $693,128

      Not Listed For Sale

      106 Woods Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,551 Sq Ft
      • Built 2000
      106 Woods Rd, Chester, MD 21619

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Jackie Ball Daley Northrop Realty

  • /35

    $819,990

    New Construction $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island.Spacious great room featuring electric fireplace.Charming dining area with dry bar for efficient serving.Serene owner's suite & spa bath with frameless shower door.Convenient home office for working remotely.Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • /54

    $570,000

    Sold Jun 19, 2026

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $300/SF
    • 42 Days On Market

    Last Listing Agent Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
    • /39

      Est $355,431

      Not Listed For Sale

      7003 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1994
      7003 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent April Heim Rosendale Realty

  • /11

    $709,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

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

    Private home office for working from home.Spacious great room with slider to covered patio.Beautiful kitchen with large island and roomy pantry.Luxurious primary suite with triple windows.Relaxing primary bath with spacious shower and walk-in closet.Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • /10

    $659,990

    Sold Mar 11, 2026

    176 Flagstaff Way Unit 12, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 6% Below List Price
    • $330/SF
    • 5 Days On Market

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

    176 Flagstaff Way Unit 12, Chester, MD 21619
    • /22

      Est $387,327

      Not Listed For Sale

      500 Dominion Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2000
      500 Dominion Rd, Chester, MD 21619

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Kelly Alvarez Pugliese Metas Realty Group, LLC

  • /77

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft

    1717 Harbor Dr, Chester, MD 21619

    Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality.Inside, you'll

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    1717 Harbor Dr, Chester, MD 21619
  • /2

    $629,990

    Sold Sep 09, 2026

    110 Boatswain Way Unit 12, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $315/SF
    • 8 Days On Market

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

    110 Boatswain Way Unit 12, Chester, MD 21619

Showing Results 281 - 320, Page 8 of 18

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