5,228

Chester, MD Homes

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  • /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
  • /124

    $784,400

    Sold Nov 24, 2025

    129 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,630 Sq Ft
    • Built 1988

    Last Sold Summary

    • $298/SF
    • 23 Days On Market

    Current Estimated Value $817,485

    Last Listing Agent Noah Mumaw Monument Sotheby's International Realty

    129 Kirwans Landing Ln, 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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /78

    $2,840,000

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft

    300 Woods Point Rd, Chester, MD 21619

    Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the guest cottage (2BR, 1.5 BA) has a fabulous screened porch

    Elinor Warring Tidewater Properties

    300 Woods Point Rd, 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 $904,532

    Last Listing Agent Kathleen Higginbotham Samson Properties

    115 Cedar Rd, 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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /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
  • /2

    $338,000

    Sold Jun 18, 2026

    34 Queen Anne Way Unit F, Chester, MD 21619

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

    Last Sold Summary

    • 3% Below List Price
    • $467/SF
    • 52 Days On Market

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, Chester, MD 21619
    • /26

      Not Listed For Sale

      218 Switchgrass Way Unit 32, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      218 Switchgrass Way Unit 32, Chester, MD 21619

      Last Sold Summary

      • 22 Days On Market

  • /25

    $300,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    509 Teal Ct, Chester, MD 21619

    Welcome to your perfect island retreat in the sought-after waterfront community of Bayside! This beautifully positioned end-unit condominium offers the ideal blend of comfort, convenience, and breathtaking scenery. Enjoy tranquil pond views with a charming fountain, along with glimpses of the Chester River and marina—all from the privacy of your own deck. Whether you're sipping your morning

    Darlene Winegardner RE/MAX Executive

    509 Teal Ct, 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
    • /26

      Not Listed For Sale

      211 Switchgrass Way Unit 42, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      211 Switchgrass Way Unit 42, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

  • /27

    $287,500

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Hardwood floors, soaring vaulted ceilings, and a cozy gas fireplace create a warm and inviting atmosphere throughout the main living area.The spacious primary suite offers a peaceful retreat

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, 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 $503,953

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    112 Chessie 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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /70

    $995,000

    Under Contract
    • 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
  • /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
    • /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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /17

    $849,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 31, Chester, MD 21619

    Beautiful great room with electric fireplace & acccess to balcony.Serene balcony off the main living area, ideal for outdoor relaxation.Gourmet kitchen with large island, ample cabinetry & pantry.Included dry bar adds convenience for hosting & everyday use.Owner’s suite with direct access to a cozy sitting room.Polished owner’s spa bath with dual sinks & frameless shower door.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 31, 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
    • /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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /8

    $969,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    118 Kinglet Ct, Chester, MD 21619

    Home office with sliding doors for added privacy.Vaulted ceiling with stunning beams spans the great room, dining area & kitchen.Fireplace adds a warm focal point to the great room.Screened patio extends directly from the great room.Spacious central island anchors the kitchen.Walk-in closet provides generous storage in the primary suite.Dual freestanding vanities & Plus

    K. Hovnanian Homes Builder
    118 Kinglet Ct, Chester, MD 21619
  • /87

    $1,300,000

    Sold Jul 17, 2026

    1719 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 5 Baths
    • 4,208 Sq Ft
    • Built 2006

    Last Sold Summary

    • 13% Below List Price
    • $309/SF
    • 28 Days On Market

    Current Estimated Value $1,374,153

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    1719 Harbor Dr, 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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /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
  • /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 $504,527

    Last Listing Agent DJ Dauses Coldwell Banker Waterman Realty

    1921 Harbor Dr, Chester, MD 21619
    • /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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /44

    $969,990

    New Construction $20K PRICE DROP Pending
    • 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
  • /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
    • /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

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /77

    $895,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,579 Sq Ft

    2810 Harvest Ct, Chester, MD 21619

    Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully

    Deb Laite Blackwell Real Estate, LLC

    2810 Harvest Ct, 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
    • /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

      Last Listing Agent Creig Northrop Northrop Realty

  • /52

    $515,000

    $34K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    WATERFRONT Condo! Open House dates scheduled. 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, fresh paint throughout (ceilings, walls, trim, and

    Lona Todd Taylor Properties

    34 Queen Anne Way, 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 $483,560

    Last Listing Agent Lisa Lynch Keller Williams Realty

    1017 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

      Last Listing Agent Peter Ayerle Cummings & Co. Realtors

  • /51

    $869,990

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

    102 Boatswain Way Unit 2921, 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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2921, 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 $352,844

    Last Listing Agent Elaina Bellas LPT Realty, LLC

    1905 Keister Dr, Chester, MD 21619
    • /49

      Est $393,925

      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

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /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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