5,227

Chester, MD Homes

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  • /38

    $480,000

    $15K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    1848 Harbor Dr, Chester, MD 21619

    Don’t miss this charming Cape Cod-style home in the highly desirable Harbor View neighborhood of Chester. Thoughtfully designed and move-in ready, this home offers the perfect blend of comfort, style, and functionality. The main level features luxury vinyl plank flooring and a bright, open-concept layout ideal for everyday living and entertaining. The spacious kitchen boasts granite countertops,

    Colleen Smith EXP Realty, LLC

    1848 Harbor Dr, 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
    • /36

      Not Listed For Sale

      26C Piney Narrows Rd, Chester, MD 21619

      • 611 Sq Ft
      • Built 1981
      26C Piney Narrows Rd, Chester, MD 21619

      Last Sold Summary

      • 32 Days On Market

  • /21

    $776,540

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

    830 Warbler Way Unit 21, Chester, MD 21619

    Spacious great room with electric fireplace & seamless flow to the dining area.Private balcony off the main living area, ideal for outdoor relaxation.Gourmet kitchen with large island, ample cabinetry & pantry for extra storage.Included dry bar adds convenience for hosting & everyday use.Owner’s suite with direct access to a cozy sitting room.Luxurious owner’s spa bath with

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 21, Chester, MD 21619
  • /37

    $510,000

    Sold Mar 27, 2026

    112 Chessie Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft
    • Built 2000

    Last Sold Summary

    • $247/SF
    • 85 Days On Market

    Current Estimated Value $506,501

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
    • /42

      Not Listed For Sale

      261 Warbler Way, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2025
      261 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /40

    $969,990

    New Construction $130K PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    121 Kinglet Ct, Chester, MD 21619

    Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a

    Mary Anne Kowalewski KOVO Realty

    121 Kinglet Ct, 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
    • /40

      Not Listed For Sale

      246 Peregrine Dr, Stevensville, MD 21666

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2025
      246 Peregrine Dr, Stevensville, MD 21666

      Last Sold Summary

      • 44 Days On Market

  • /62

    $739,990

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

    630 Warbler Way Unit 2224, Chester, MD 21619

    Introducing the Severn Lot 2224, projected to settle in May 2026. This thoughtfully designed home offers 3 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a dry bar, electric fireplace, a spacious owner’s suite with a sitting room, and large walk-in closets. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2224, 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
    • /48

      Not Listed For Sale

      212 Switchgrass Way Unit 1642, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1642, Chester, MD 21619

      Last Sold Summary

      • 96 Days On Market

  • /63

    $659,990

    New Construction $40K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 2412, Chester, MD 21619

    The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2412, 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
    • /48

      Not Listed For Sale

      212 Switchgrass Way Unit 1632, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1632, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

  • /52

    $799,990

    New Construction $70K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 2433, Chester, MD 21619

    The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2433, Chester, MD 21619
  • /35

    $519,900

    Sold May 21, 2026

    1921 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2026

    Last Sold Summary

    • $260/SF
    • 3 Days On Market

    Current Estimated Value $405,000

    Last Listing Agent DJ Dauses Coldwell Banker Waterman Realty

    1921 Harbor Dr, Chester, MD 21619
    • /51

      Not Listed For Sale

      218 Peregrine Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      218 Peregrine Dr, Chester, MD 21619

      Last Sold Summary

      • 56 Days On Market

  • /26

    $295,000

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    Nestled in the charming Bayside Marina community, this 2nd floor condo offers a perfect blend of comfort and modern living. Built in 1999, this contemporary gem features an open floor plan that seamlessly connects the living with vaulted ceilings, dining, and kitchen areas, creating an inviting space for relaxation and entertaining. The kitchen boasts ENERGY STAR appliances, including a

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, 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
    • /42

      Not Listed For Sale

      228 Warbler Way, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2024
      228 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 9 Days On Market

  • /87

    $1,395,000

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 5 Baths
    • 4,208 Sq Ft

    1719 Harbor Dr, Chester, MD 21619

    Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    1719 Harbor Dr, 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 Four Seasons at Kent Island - Single Family

    509 Warbler Way, Chester, MD 21666
    • /51

      Not Listed For Sale

      111 Peregrine Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      111 Peregrine Dr, Chester, MD 21619

      Last Sold Summary

      • 60 Days On Market

  • /70

    $995,000

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 3,434 Sq Ft

    154 Bluebell Ct, Chester, MD 21619

    Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and

    Tricia Wilson Wilson Realty & Staging LLC

    154 Bluebell Ct, 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 $471,772

    Last Listing Agent Lisa Lynch Keller Williams Realty

    1017 Dominion Rd, Chester, MD 21619
    • /51

      Not Listed For Sale

      211 Warbler Way, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 2024
      211 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 86 Days On Market

  • /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • /2

    $205,000

    Sold Dec 26, 2025

    1905 Keister Dr, Chester, MD 21619

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1968

    Last Sold Summary

    • $128/SF

    Current Estimated Value $307,035

    Last Listing Agent Elaina Bellas LPT Realty, LLC

    1905 Keister Dr, Chester, MD 21619
    • /76

      Not Listed For Sale

      129 Wheelhouse Way Unit 2032, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      129 Wheelhouse Way Unit 2032, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

  • /84

    $2,049,000

    Pending
    • 5 Beds
    • 4 Baths
    • 3,250 Sq Ft

    328 Bentons Pleasure Rd, Chester, MD 21619

    Gorgeous Waterfront property on Cox Creek with stunning sunset views. Open house Friday June 19, 7:00-8:30 PM for sunset viewing This cottage-style retreat on Cox Creek offers the perfect blend of cozy charm and luxury living. Featuring a refreshing pool (grandfathered in the 100 foot buffer) with 180 degree views, fully equipped gym, 4 garage spaces, dock with 2 boat lifts and jet-ski lift, a

    Christopher Carr HomeZu

    328 Bentons Pleasure Rd, Chester, MD 21619
  • /50

    $915,000

    Sold Apr 10, 2026

    635 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 5 Baths
    • 2,818 Sq Ft
    • Built 2011

    Last Sold Summary

    • $325/SF
    • 27 Days On Market

    Current Estimated Value $920,932

    Last Listing Agent Constance Golihew Coldwell Banker Realty

    635 Dominion Rd, Chester, MD 21619
    • /53

      Not Listed For Sale

      1 F S Queen Victoria Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1983
      1 F S Queen Victoria Ct, Chester, MD 21619

      Last Sold Summary

      • 10 Days On Market

  • /44

    $969,990

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Warbler Way Unit 2934, 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 December 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 sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2934, Chester, MD 21619
  • /41

    $853,000

    Sold Mar 10, 2026

    162 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1988

    Last Sold Summary

    • $355/SF
    • 104 Days On Market

    Current Estimated Value $848,371

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    162 Kirwans Landing Ln, Chester, MD 21619
    • /49

      Est $393,406

      Not Listed For Sale

      203 Dominion Ln, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,074 Sq Ft
      • Built 2017
      203 Dominion Ln, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

  • /52

    $529,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement! Fully Remodeled Chester River Waterfront Condo! This gem won't last long! Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet,

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • /19

    $949,990

    Sold Mar 02, 2026

    110 Boatswain Way Unit 34, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 3% Below List Price
    • $365/SF
    • 11 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island Condos

    110 Boatswain Way Unit 34, Chester, MD 21619
    • /48

      Not Listed For Sale

      209 Harrier Way, Stevensville, MD 21666

      • 4 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 2024
      209 Harrier Way, Stevensville, MD 21666

      Last Sold Summary

      • 131 Days On Market

  • /52

    $799,990

    New Construction $60K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 3043, 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 3043, Chester, MD 21619

Showing Results 81 - 120, Page 3 of 18

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