5,227

Chester, MD Homes

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  • /95

    $2,350,000

    Sold May 28, 2026

    1901 Cox Neck Rd, Chester, MD 21619

    • 4 Beds
    • 4.5 Baths
    • 5,510 Sq Ft
    • Built 1997

    Last Sold Summary

    • $426/SF
    • 0 Days On Market

    Current Estimated Value $2,308,639

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1901 Cox Neck Rd, Chester, MD 21619
    • /33

      Est $484,337

      Not Listed For Sale

      1852 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,238 Sq Ft
      • Built 1953
      1852 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /52

    $829,990

    New Construction $20K 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 office

    Mary Anne Kowalewski KOVO Realty

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • /17

    $724,900

    Sold Nov 10, 2025

    630 Warbler Way Unit 21, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $279/SF
    • 19 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    630 Warbler Way Unit 21, Chester, MD 21619
    • /12

      Est $361,729

      Not Listed For Sale

      1303 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1955
      1303 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 16 Days On Market

  • /49

    $464,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    1906 Stevens Dr, Chester, MD 21619

    Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full baths, including a large bonus room that can easily function as a fourth bedroom, home office, or second living area. A welcoming front porch sets the tone, while the screened back porch provides the perfect space to relax or

    Terri Murray RE/MAX Executive

    1906 Stevens Dr, Chester, MD 21619
  • /30

    $332,500

    Sold Feb 20, 2026

    206 Blenny Ln, Chester, MD 21619

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $175/SF
    • 4 Days On Market

    Current Estimated Value $348,573

    Last Listing Agent Chris Craddock EXP Realty, LLC

    206 Blenny Ln, Chester, MD 21619
    • /48

      Est $301,242

      Not Listed For Sale

      1905 Cecil Ct, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,108 Sq Ft
      • Built 1983
      1905 Cecil Ct, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

  • /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
  • /73

    $760,000

    Sold Oct 30, 2025

    314 Thomas White Blvd, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2013

    Last Sold Summary

    • $317/SF
    • 47 Days On Market

    Current Estimated Value $789,328

    Last Listing Agent Kathleen Higginbotham Samson Properties

    314 Thomas White Blvd, Chester, MD 21619
    • /53

      Est $459,038

      Not Listed For Sale

      205 Newtown Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1992
      205 Newtown Rd, Chester, MD 21619

      Last Sold Summary

      • 54 Days On Market

  • /64

    $1,283,780

    New Construction
    • 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
  • /51

    $500,000

    Sold Aug 22, 2025

    2008 Palm Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,283 Sq Ft
    • Built 1997

    Last Sold Summary

    • $219/SF
    • 64 Days On Market

    Current Estimated Value $513,953

    Last Listing Agent Marilyn Hendley EXP Realty, LLC

    2008 Palm Dr, Chester, MD 21619
    • /65

      Est $320,668

      Not Listed For Sale

      53B Queen Caroline Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1998
      53B Queen Caroline Ct, Chester, MD 21619

      Last Sold Summary

      • 118 Days On Market

  • /15

    $849,990

    New Construction $28K 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
  • /28

    $375,000

    Sold Jun 03, 2026

    1150 Little Creek Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft
    • Built 1896

    Last Sold Summary

    • 12% Below List Price
    • $170/SF
    • 55 Days On Market

    Current Estimated Value $380,408

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1150 Little Creek Rd, Chester, MD 21619
    • /35

      Est $546,541

      Not Listed For Sale

      511 Skipper Ct, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,754 Sq Ft
      • Built 1972
      511 Skipper Ct, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /44

    $989,990

    New Construction $145K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Boatswain Way Unit 3044, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3044, Chester, MD 21619
  • /35

    $500,000

    Sold Feb 02, 2026

    1221 Cox Neck Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Built 2012

    Last Sold Summary

    • $337/SF
    • 77 Days On Market

    Current Estimated Value $512,296

    Last Listing Agent Jorge Zea Jorge A. Zea

    1221 Cox Neck Rd, Chester, MD 21619
    • /53

      Est $388,489

      Not Listed For Sale

      102 Ringneck Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,747 Sq Ft
      • Built 1995
      102 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 21 Days On Market

  • /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
  • /2

    $295,000

    Sold Jul 18, 2025

    204 Teal Ct Unit B, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1993

    Last Sold Summary

    • $275/SF
    • 5 Days On Market

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    204 Teal Ct Unit B, Chester, MD 21619
    • /27

      Est $333,967

      Not Listed For Sale

      1304 Little Creek Rd, Chester, MD 21619

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1979
      1304 Little Creek Rd, Chester, MD 21619

      Last Sold Summary

      • 72 Days On Market

  • /45

    $545,000

    $5K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    124 Riverside Dr, Chester, MD 21619

    Gorgeous, like-new home on Kent Island! VA ASSUMABLE at 2.75% Interest!! Call for details!Fresh interior paint and new carpet throughout make this home truly move-in ready. The spacious living and dining areas offer plenty of room for relaxing and entertaining, while the inviting fireplace adds warmth and charm. The kitchen features a breakfast bar, pantry, abundant cabinetry, and plenty of

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, 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 $540,167

    Last Listing Agent Jonathan Olsavsky Coldwell Banker Waterman Realty

    114 Addison Ct, Chester, MD 21619
    • /17

      Est $493,218

      Not Listed For Sale

      2616 Cecil Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • Built 1984
      2616 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 354 Days On Market

  • /35

    $829,990

    New Construction $35K 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
  • /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 Condos

    110 Boatswain Way Unit 31, Chester, MD 21619
    • /38

      Est $422,579

      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

  • /29

    $939,990

    New Construction $31K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    540 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & glass-front uppers.Vast center island, perfect for prepping family meals.Stunning fireplace adds character & warmth to spacious great room.Lavish primary suite & bath featuring bath barn door.Secluded Extra Suite for overnight guests.Functional home office for leisure activities.Cozy screened patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    540 Warbler Way, 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 $346,030

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

    208 Ringneck Ct, Chester, MD 21619
    • /42

      Est $411,626

      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

  • /11

    $774,990

    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
  • /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 $565,341

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
    • /32

      Est $503,156

      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

  • /52

    $979,900

    New Construction $42K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, 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 $676,891

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
    • /44

      Est $598,478

      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

  • /44

    $749,990

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

    110 Warbler Way Unit 3021, 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 3021, 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 Condos

    630 Warbler Way Unit 24, Chester, MD 21619

Showing Results 241 - 280, Page 7 of 18

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