5,229

Chester, MD Homes

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    • /30

      Est $562,305

      Not Listed For Sale

      230 Cross Creek Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,332 Sq Ft
      • Built 1999
      230 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /2

    $779,900

    Under Contract
    • 2 Beds
    • 2 Baths
    • 2,394 Sq Ft

    169 Harrier Way, Chester, MD 21619

    Dorothea Slaughter CENTURY 21 New Millennium

    169 Harrier Way, Chester, MD 21619
  • /45

    $925,000

    Sold Jul 24, 2026

    132 Kestrel Ln, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $255/SF
    • 88 Days On Market

    Current Estimated Value $949,466

    Last Listing Agent Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
    • /30

      Est $444,859

      Not Listed For Sale

      2709 Sherman Dr, Chester, MD 21619

      • 3 Beds
      • 1.5 Baths
      • 1,512 Sq Ft
      • Built 1986
      2709 Sherman Dr, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

  • /65

    $2,450,000

    Under Contract
    • 4 Beds
    • 5 Baths
    • 4,717 Sq Ft

    2832 Cox Neck Rd, Chester, MD 21619

    Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space.The gourmet kitchen is appointed

    Dee Dee McCracken Coldwell Banker Realty

    2832 Cox Neck Rd, Chester, MD 21619
  • /79

    $680,000

    Sold Nov 03, 2025

    157 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft
    • Built 2010

    Last Sold Summary

    • $302/SF
    • 26 Days On Market

    Current Estimated Value $694,610

    Last Listing Agent Ryan Briggs Anne Arundel Properties, Inc.

    157 John Gibson Dr, Chester, MD 21619
    • /36

      Est $527,979

      Not Listed For Sale

      300 Skyler Ave, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,250 Sq Ft
      • Built 1991
      300 Skyler Ave, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Mike Altobelli RE/MAX Realty Services

  • /35

    $840,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    232 Evelyne St, Chester, MD 21619

    Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

    Courtney Chipouras TTR Sotheby's International Realty

    232 Evelyne St, Chester, MD 21619
  • /51

    $365,000

    Sold Apr 29, 2026

    402 Blenny Ln, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $209/SF
    • 74 Days On Market

    Current Estimated Value $370,339

    Last Listing Agent Thomas Welch Long & Foster Real Estate, Inc.

    402 Blenny Ln, Chester, MD 21619
    • /73

      Est $694,788

      Not Listed For Sale

      104 Sunset Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,096 Sq Ft
      • Built 1993
      104 Sunset Dr, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Nicki Palermo RE/MAX One

  • /5

    $139,900

    • Land
    • 12,632 Sq Ft
    • $482,414 per Acre

    0 Harley Ln, Chester, MD 21619

    Lot 2 of two newly formed building lots on Kent Island in Chester just off Dominion Road. Sewer Allocation has been paid (a $11,800 value)! The site work has been done. Right around the corner from the Goodhand's Creek Landing to launch your boat or go fishing. Close to Rt 50/301 & Main Street for convenient commuting and shopping!

    Jason Dey Kevin Dey Realty

    0 Harley Ln, Chester, MD 21619
  • /25

    $784,900

    Sold Aug 20, 2025

    201 Switchgrass Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $413/SF
    • 31 Days On Market

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

    201 Switchgrass Way Unit 42, Chester, MD 21619
    • /39

      Est $537,312

      Not Listed For Sale

      1617 Chester Rd, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,976 Sq Ft
      • Built 1990
      1617 Chester Rd, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Christine Schumaker Douglas Realty LLC

  • /24

    $1,100,000

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

    123 Flycatcher Way, Chester, MD 21619

    Well-equipped kitchen with stacked dark stained cabinetry & glass uppers. Cozy fireplace adds warmth & character to spacious great room. Tranquil primary suite with generous walk-in closet. Productive home office for studying or reading. Private Extra Suite, great for overnight guests. Inviting screened patio for outdoor entertaining. Second floor loft provide addtionial living space.

    K. Hovnanian Homes Builder
    123 Flycatcher Way, Chester, MD 21619
  • /20

    $1,119,990

    Sold May 19, 2026

    102 Boatswain Way Unit 41, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 2% Below List Price
    • $430/SF
    • 7 Days On Market

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

    102 Boatswain Way Unit 41, Chester, MD 21619
    • /50

      Est $390,066

      Not Listed For Sale

      106 Blenny Ln, Chester, MD 21619

      • 3 Beds
      • 4 Baths
      • 1,899 Sq Ft
      • Built 2000
      106 Blenny Ln, Chester, MD 21619

      Last Sold Summary

      • 183 Days On Market

      Last Listing Agent Annie Eaton Coldwell Banker Realty

  • /57

    $680,000

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

    111 Marshgrass Way Unit 21, Chester, MD 21619

    A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake

    Marisol Cardona Samson Properties

    111 Marshgrass Way Unit 21, Chester, MD 21619
  • /26

    $799,990

    Sold Apr 03, 2026

    110 Boatswain Way Unit 43, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 7% Below List Price
    • $421/SF
    • 16 Days On Market

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

    110 Boatswain Way Unit 43, Chester, MD 21619
    • /41

      Est $358,715

      Not Listed For Sale

      6008 Bridgepointe Dr, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1992
      6008 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

  • /46

    $435,000

    • 3 Beds
    • 2.5 Baths
    • 1,595 Sq Ft

    106 Bodys Neck Rd, Chester, MD 21619

    Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout

    Bill Longest Realty Navigator

    106 Bodys Neck Rd, Chester, MD 21619
  • /20

    $1,019,990

    Sold Jun 12, 2026

    102 Boatswain Way Unit 31, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $392/SF
    • 22 Days On Market

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

    102 Boatswain Way Unit 31, Chester, MD 21619
    • /24

      Est $557,698

      Not Listed For Sale

      102 Skipper Ln, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,810 Sq Ft
      • Built 2006
      102 Skipper Ln, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent SALLY KERCHNER AXEN Realty LLC

  • /52

    $699,990

    New Construction $90K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Warbler Way Unit 3033, 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 3033, Chester, MD 21619
  • /41

    $385,500

    Sold Apr 14, 2026

    7009 Bridgepointe Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft
    • Built 1993

    Last Sold Summary

    • 3% Above List Price
    • $236/SF
    • 7 Days On Market

    Current Estimated Value $383,947

    Last Listing Agent Linda Austin Long & Foster Real Estate, Inc.

    7009 Bridgepointe Dr, Chester, MD 21619
    • /40

      Est $509,497

      Not Listed For Sale

      206 Widgeon Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 1999
      206 Widgeon Way, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Carol Tinnin RE/MAX Leading Edge

  • /32

    $829,990

    New Construction $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Formal 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
    102 Boatswain Way Unit 33, Chester, MD 21619
  • /51

    $674,900

    Sold Sep 11, 2025

    516 Warbler Way, Chester, MD 21619

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

    Last Sold Summary

    • $339/SF
    • 47 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    516 Warbler Way, Chester, MD 21619
    • /30

      Est $297,740

      Not Listed For Sale

      605 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1997
      605 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jarnell Foster Samson Properties

  • /26

    $674,900

    New Construction Pending
    • 4 Beds
    • 2.5 Baths

    Lot 6 Norman Ct, Chester, MD 21619

    The Windermere combines all of the home design elements our purchasers love the most. On the main level is an open plan design with a huge kitchen, breakfast/sunroom and family room! Formal living and dining rooms, and two-story foyer complete the space. Upstairs you will find 4 spacious bedrooms to include an owner's suite with spacious walk-in closet or choose the optional super bath and get

    George Bailey Keller Williams Flagship

    Lot 6 Norman Ct, Chester, MD 21619
  • /15

    $829,990

    Sold Jun 12, 2026

    719 Warbler Way, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 7% Below List Price
    • $296/SF
    • 16 Days On Market

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

    719 Warbler Way, Chester, MD 21619
    • /35

      Est $300,175

      Not Listed For Sale

      601 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1997
      601 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /2

    $289,900

    • 1 Bed
    • 2 Baths
    • 1,260 Sq Ft

    23 Queen Victoria Way Unit 23J, Chester, MD 21619

    Pictures and details coming soon 1 bedroom with a loft and full bath.

    Deric Beckett Berkshire Hathaway HomeServices PenFed Realty

    23 Queen Victoria Way Unit 23J, Chester, MD 21619
  • /30

    $644,990

    Sold Jan 14, 2026

    630 Warbler Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $339/SF
    • 49 Days On Market

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

    630 Warbler Way Unit 32, Chester, MD 21619
    • /34

      Est $407,064

      Not Listed For Sale

      308 Blenny Ln, Chester, MD 21619

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

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /66

    $479,000

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No need to wait for new construction this unit is ready for immediate occupancy. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • /88

    $705,250

    Sold Sep 16, 2025

    211 Switchgrass Way Unit 1534, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $271/SF
    • 56 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1534, Chester, MD 21619
    • /55

      Est $283,050

      Not Listed For Sale

      607 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1997
      607 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /16

    $883,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

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

    Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities and optional freestanding tub. Private home office off foyer for working from home. Large covered patio for enjoying the outdoors.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
  • /34

    $285,000

    Sold Aug 08, 2025

    211 Golden Eye Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 2000

    Last Sold Summary

    • $266/SF
    • 10 Days On Market

    Current Estimated Value $277,508

    Last Listing Agent Brendan Noone Coldwell Banker Realty

    211 Golden Eye Ct, Chester, MD 21619
    • /62

      Est $1,124,296

      Not Listed For Sale

      1708 Bayside Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,340 Sq Ft
      • Built 1989
      1708 Bayside Dr, Chester, MD 21619

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

Showing Results 401 - 440, Page 11 of 18

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