5,186

Chester, MD Homes

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  • /37

    $799,990 Pending

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    259 Redstart Dr, Chester, MD 21619

    The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors

    Mary Anne Kowalewski KOVO Realty

    259 Redstart Dr, Chester, MD 21619
  • /55

    $649,900 Sold Jul 15, 2025

    218 Switchgrass Way Unit 1711, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2024

    Last Sold Summary

    • $324/SF
    • 8 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1711, Chester, MD 21619
    • /98

      Est $756,290 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

      • $310/SF
      • 1 Day On Market

      Last Sold Price $755,000

      Last Listing Agent Carrie Rosela Curtis Real Estate Company

  • /37

    $1,456,462 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
  • /71

    $895,000 Sold Feb 26, 2026

    115 Cedar Rd, Chester, MD 21619

    • 5 Beds
    • 4 Baths
    • 4,275 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $209/SF
    • 11 Days On Market

    Current Estimated Value $931,069

    Last Listing Agent Kathleen Higginbotham Samson Properties

    115 Cedar Rd, Chester, MD 21619
    • /42

      Est $312,574 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

      • 2% Above List Price
      • $212/SF
      • 95 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Donna Wisniewski Long & Foster

  • /48

    $644,990 Pending

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

    630 Warbler Way Unit 2232, Chester, MD 21619

    The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2232, Chester, MD 21619
  • /58

    $659,900 Sold Feb 20, 2026

    121 Wheelhouse Way Unit 2132, Chester, MD 21619

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

    Last Sold Summary

    • 3% Below List Price
    • $347/SF
    • 26 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2132, Chester, MD 21619
    • /34

      Est $707,141 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

      • 16% Above List Price
      • $248/SF
      • 69 Days On Market

      Last Sold Price $610,000

      Last Listing Agent Paul Mcintye EXIT First Realty

  • /52

    $699,990 New Construction

    • 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
  • /58

    $669,900 Sold Nov 17, 2025

    201 Switchgrass Way Unit 1433, Chester, MD 21619

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

    Last Sold Summary

    • $353/SF
    • 26 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1433, Chester, MD 21619
    • /55

      Est $684,149 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

      • 7% Above List Price
      • $267/SF
      • 15 Days On Market

      Last Sold Price $637,500

      Last Listing Agent Pamela Ackermann-Doll RE/MAX

  • /26

    $375,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    9B Queen Victoria Way, Chester, MD 21619

    Jennifer Thomas RE/MAX Executive

    9B Queen Victoria Way, Chester, MD 21619
  • /86

    $545,000 Sold Sep 04, 2025

    24 D Queen Elizabeth Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1985

    Last Sold Summary

    • $324/SF
    • 36 Days On Market

    Last Listing Agent The Williams Home Team Douglas Realty, LLC

    24 D Queen Elizabeth Ct, Chester, MD 21619
    • /59

      Est $863,954 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

      • 8% Above List Price
      • $259/SF
      • 15 Days On Market

      Last Sold Price $797,000

      Last Listing Agent Tara Trout Samson Properties

  • /61

    $684,950 Under Contract

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

    141 Switchgrass Way Unit 34, Chester, MD 21619

    **** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL**** K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an expansive open floor plan with over 2600

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • /24

    $320,000 Sold Jul 30, 2025

    34B Queen Anne Way Unit B, Chester, MD 21619

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Built 1983

    Last Sold Summary

    • $400/SF
    • 79 Days On Market

    Last Listing Agent Mary Stevens Long & Foster Real Estate, Inc.

    34B Queen Anne Way Unit B, Chester, MD 21619
    • /60

      Est $542,649 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

      • 7% Above List Price
      • $247/SF
      • 35 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Lawrence Doyle Long & Foster

  • /67

    $694,500

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -------------------------------------Immediate Move In Ready. Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of sliding doors assure that this condo is drenched in sunshine, water

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • /66

    $824,900 Sold Apr 17, 2025

    166 Warbler Way Unit 31, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Built 2024

    Last Sold Summary

    • $317/SF
    • 68 Days On Market

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

    166 Warbler Way Unit 31, Chester, MD 21619
    • /69

      Est $626,584 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

      • 4% Above List Price
      • $226/SF
      • 0 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Pamela Ackermann-Doll RE/MAX

  • /13

    $701,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second floor with 2 secondary bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • /87

    $989,000 Sold Aug 18, 2025

    132 Wheelhouse Way Unit 21, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2023

    Last Sold Summary

    • $380/SF
    • 27 Days On Market

    Last Listing Agent Kathleen Higginbotham Samson Properties

    132 Wheelhouse Way Unit 21, Chester, MD 21619
    • /72

      Est $926,334 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

      • 2% Below List Price
      • $301/SF
      • 3 Days On Market

      Last Sold Price $950,000

      Last Listing Agent Edward Beres RE/MAX

  • /44

    $669,900 Open Sun 12PM - 3PM

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

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • /22

    $699,900 Sold Aug 28, 2025

    509 Warbler Way, Chester, MD 21666

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $351/SF
    • 5 Days On Market

    K. Hovnanian Homes K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series

    509 Warbler Way, Chester, MD 21666
    • /31

      Est $352,773 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

      • 2% Above List Price
      • $322/SF
      • 1 Day On Market

      Last Sold Price $347,500

      Last Listing Agent Toni McDowell Keller Williams Select Realtors of Annapolis

  • /73

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Coming Soon... Get ready for this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this community and the upcoming Spring and Summer on

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • /19

    $739,900 Sold Jul 24, 2025

    211 Switchgrass Way Unit 31, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $284/SF
    • 5 Days On Market

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

    211 Switchgrass Way Unit 31, Chester, MD 21619
    • /22

      Est $1,136,153 Not Listed For Sale

      2012 Chester Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 780 Sq Ft
      • Built 1959
      2012 Chester Rd, Chester, MD 21619

      Last Sold Summary

      • 50% Below List Price
      • $2,917/SF
      • 220 Days On Market

      Last Sold Price $2,275,000

      Last Listing Agent William White Monument Sotheby's International Realty

  • /41

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft

    7009 Bridgepointe Dr, Chester, MD 21619

    Bridgepoint - This is a great end unit that is private and overlooking the pond with the fountain. The unit offers a first floor primary bedroom and bath. Open floor plan for entertaining and sunroom you will enjoy. Upstairs is two large bedrooms and a bath. Storage space in the attic. The one garage offers room for your car and some storage. Call today for your showing appointment.

    Linda Austin Long & Foster Real Estate, Inc.

    7009 Bridgepointe Dr, Chester, MD 21619
  • /2

    $475,000 Sold Aug 08, 2025

    1017 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1952

    Last Sold Summary

    • $333/SF
    • 14 Days On Market

    Current Estimated Value $477,204

    Last Listing Agent Lisa Lynch Keller Williams Realty

    1017 Dominion Rd, Chester, MD 21619
    • /54

      Est $620,561 Not Listed For Sale

      143 Carriage Heath, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,241 Sq Ft
      • Built 2009
      143 Carriage Heath, Chester, MD 21619

      Last Sold Summary

      • 5% Above List Price
      • $475/SF
      • 55 Days On Market

      Last Sold Price $590,000

      Last Listing Agent Tara Trout Samson Properties

  • /13

    $889,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    719 Warbler Way, Chester, MD 21619

    Polished kitchen with white cabinets & glass-front uppers. Vast island & quartz countertops for prep & dining. Welcoming great room featuring elegant fireplace. Screened patio with direct access to the great room. Charming dining area for mealtime enjoyment. Lavish primary suite & bath with dual vanities & feature wall. Private home office for leisure activities.

    K. Hovnanian Homes Builder
    719 Warbler Way, Chester, MD 21619
  • /48

    $714,900 Sold May 01, 2025

    212 Switchgrass Way Unit 1642, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2024

    Last Sold Summary

    • $376/SF
    • 96 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    212 Switchgrass Way Unit 1642, Chester, MD 21619
    • /26

      Est $330,689 Not Listed For Sale

      200 Church St, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,274 Sq Ft
      • Built 1922
      200 Church St, Chester, MD 21619

      Last Sold Summary

      • 6% Above List Price
      • $245/SF
      • 2 Days On Market

      Last Sold Price $312,000

      Last Listing Agent Phil Gerdes Real Broker, LLC - Annapolis

  • /27

    $699,990 New Construction

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

    110 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Exquisite dining area with dry bar, perfect for entertaining. Gorgeous great room with cozy electric fireplace. Sophisticated owner's suite with triple windows. Stunning owner's spa bath featuring split vanities. Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 33, Chester, MD 21619
  • /74

    $651,000 Sold Apr 18, 2025

    200 Harrier Way Unit 31, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2023

    Last Sold Summary

    • $250/SF
    • 26 Days On Market

    Current Estimated Value $662,989

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

    200 Harrier Way Unit 31, Chester, MD 21619
    • /35

      Est $404,634 Not Listed For Sale

      28A Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1985
      28A Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 1% Above List Price
      • $317/SF
      • 15 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

  • /63

    $825,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    202 Mchenny Ct, Chester, MD 21619

    Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car GarageWelcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage.No need to worry about stairs — a full elevator

    Dee Dee McCracken Coldwell Banker Realty

    202 Mchenny Ct, Chester, MD 21619

Showing Results 81 - 120, Page 3 of 18

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