5,227

Chester, MD Homes

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    • /72

      Est $1,120,726

      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

  • /66

    $780,000

    • 4 Beds
    • 3.5 Baths
    • 2,185 Sq Ft

    134 Richard Ingle Way, Chester, MD 21619

    Nestled in the sought-after Gibson's Grant at Waters Edge community on Kent Island, this beautifully maintained and thoughtfully upgraded home offers picturesque pond views and is just a short stroll from the community clubhouse, pool, private pier, and easily accessible kayak ramp. Built in 2017 and carefully enhanced over the years, this property combines quality craftsmanship, functional

    Courtney Gallagher Keller Williams Realty Central-Delaware

    134 Richard Ingle 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 $647,815

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
    • /3

      Est $293,057

      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

  • /52

    $749,990

    New Construction $110K PRICE DROP
    • 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

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, 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
    • /20

      Est $443,245

      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

  • /94

    $1,100,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,017 Sq Ft

    2812 Harvest Ct, Chester, MD 21619

    Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan

    Darlene Winegardner RE/MAX Executive

    2812 Harvest Ct, Chester, MD 21619
  • /43

    $495,000

    Sold Jul 31, 2025

    2614 Ellicott Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2023

    Last Sold Summary

    • $354/SF
    • 2 Days On Market

    Current Estimated Value $502,426

    Last Listing Agent Wendy Oliver Coldwell Banker Realty

    2614 Ellicott Dr, Chester, MD 21619
    • /73

      Est $402,457

      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

  • /29

    $729,999

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

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Adjusted price and ready for new owners!! Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way is arguably one of the most sought-after locations in the community, offering fantastic water views and

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, 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 $266,338

    Last Listing Agent Janice O'Donnell Chaney Homes, LLC

    602 Dominion Rd, Chester, MD 21619
    • /56

      Est $487,200

      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

  • /40

    $569,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    206 Anchor Ln, Chester, MD 21619

    KENT ISLAND ** CUSTOM RANCHER ** Welcome to the sought-after neighborhood of Castle Marina. There are No HOA or Association fees in this established community. You can walk to your boat in the marina, stroll to the local pub for dinner or hit the Cross Island Trail to get in your steps for the day. So close to all of the amenities Kent Island has to offer, yet tucked away behind Four Seasons,

    Suzanne Hitt Coldwell Banker Waterman Realty

    206 Anchor Ln, Chester, MD 21619
  • /45

    $650,000

    Sold Jun 26, 2025

    106 Woods Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2000

    Last Sold Summary

    • $255/SF
    • 21 Days On Market

    Current Estimated Value $678,268

    Last Listing Agent Jackie Ball Daley Northrop Realty

    106 Woods Rd, Chester, MD 21619
    • /35

      Est $323,075

      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

  • /59

    $899,990

    New Construction $80K PRICE DROP Pending
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    307 Kingfisher Ln, Chester, MD 21619

    Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private

    Mary Anne Kowalewski KOVO Realty

    307 Kingfisher Ln, Chester, MD 21619
  • /47

    $435,000

    Sold Aug 04, 2025

    2707 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Built 1995

    Last Sold Summary

    • $277/SF
    • 34 Days On Market

    Current Estimated Value $452,869

    Last Listing Agent Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
    • /34

      Est $447,726

      Not Listed For Sale

      306 Blenny Ln, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,899 Sq Ft
      • Built 1998
      306 Blenny Ln, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

  • /84

    $999,000

    $46K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    233 Kingfisher Ln, Stevensville, MD 21666

    Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living

    Tara Trout Samson Properties

    233 Kingfisher Ln, Stevensville, MD 21666
  • /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 $335,648

    Last Listing Agent Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
    • /43

      Est $406,975

      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

  • /61

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, 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 $645,476

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    219 Broadwater Dr, Chester, MD 21619
    • /137

      Est $831,551

      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

  • /28

    $929,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    532 Warbler Way, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests.Ceiling detail & crown molding carry through the kitchen and great room.Stacked cabinetry with glass-front uppers brings added depth to the kitchen.Fireplace creates a warm focal point in the great room.Screened patio off the great room extends the living space outdoors.Decorative feature walls in the foyer & primary suite

    K. Hovnanian Homes Builder
    532 Warbler Way, Chester, MD 21619
  • /44

    $295,000

    Sold Jul 21, 2025

    513 Teal Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1996

    Last Sold Summary

    • $275/SF
    • 22 Days On Market

    Current Estimated Value $309,994

    Last Listing Agent April Heim Rosendale Realty

    513 Teal Ct, Chester, MD 21619
    • /63

      Est $476,534

      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

  • /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, 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 $747,644

    Last Listing Agent Mary Lynch Cummings & Co. Realtors

    113 Kirwans Landing Ln, Chester, MD 21619
    • /39

      Est $511,788

      Not Listed For Sale

      405 Widgeon Way, Chester, MD 21619

      • 2 Beds
      • 3.5 Baths
      • 2,112 Sq Ft
      • Built 2000
      405 Widgeon Way, Chester, MD 21619

      Last Sold Summary

      • 14 Days On Market

  • /48

    $479,900

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,542 Sq Ft

    1331 Calvert Rd, Chester, MD 21619

    Welcome to this spacious 4 bedroom, 3 bathroom split-level home in Chester, MD, filled with natural light and offering a flexible layout perfect for everyday living. The first floor features a comfortable living area, large utility room, full bathroom, and two bedrooms. Upstairs, you’ll find a large kitchen with plenty of cabinet space, a dining room located just off the kitchen, and a bright

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    1331 Calvert Rd, 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
    • /55

      Est $482,169

      Not Listed For Sale

      905 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 2001
      905 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 54 Days On Market

  • /21

    $589,990

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

    Severn Plan at Four Seasons at Kent Island Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • /32

    $779,900

    Sold Sep 11, 2025

    121 Wheelhouse Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $410/SF
    • 16 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    121 Wheelhouse Way Unit 42, Chester, MD 21619
    • /35

      Est $373,702

      Not Listed For Sale

      44B Queen Neva Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,312 Sq Ft
      • Built 1996
      44B Queen Neva Ct, Chester, MD 21619

      Last Sold Summary

      • 19 Days On Market

  • /73

    $649,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,639 Sq Ft

    190 Harrier Way Unit 21, Chester, MD 21619

    Impeccably finished and immediately available, this corner residence provides the ease and comfort of luxury condo living surrounded by the natural beauty of the Chesapeake Bay landscape. Windows on three sides fill more than 2600 square feet with natural light, while the peaceful pond-to-river setting creates a backdrop of fountains, wildlife, and winter water views beyond. Secure building

    Timothy McIntyre The KW Collective

    190 Harrier Way Unit 21, 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 Condos

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

      Est $291,337

      Not Listed For Sale

      509 Teal Ct, Chester, MD 21619

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

      Last Sold Summary

      • 52 Days On Market

Showing Results 281 - 320, Page 8 of 18

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