5,228

Chester, MD Homes

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  • /60

    $355,000

    Sold Aug 28, 2025

    35 F Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1994

    Last Sold Summary

    • $247/SF
    • 52 Days On Market

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

    35 F Queen Anne Way, Chester, MD 21619
    • /44

      Est $536,952

      Not Listed For Sale

      545 Cross Creek Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,486 Sq Ft
      • Built 2002
      545 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

  • /25

    $929,990

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

    532 Warbler Way, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests.Ceiling detail & crown molding carry through the kitchen and great room.Stacked cabinetry with glass-front uppers brings added depth to the kitchen.Fireplace creates a warm focal point in the great room.Screened patio off the great room extends the living space outdoors.Decorative feature walls in the foyer & primary suite

    K. Hovnanian Homes Builder
    532 Warbler Way, Chester, MD 21619
  • /37

    $999,000

    Sold Jun 15, 2026

    1704 Bayside Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $546/SF
    • 147 Days On Market

    Current Estimated Value $1,036,964

    Last Listing Agent Alex Hodges Cottage Street Realty LLC

    1704 Bayside Dr, Chester, MD 21619
    • /34

      Est $396,398

      Not Listed For Sale

      117 Wright Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,337 Sq Ft
      • Built 2003
      117 Wright Rd, Chester, MD 21619

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Barry Hess Keller Williams Flagship

  • /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River.The gourmet kitchen is the heart of the home,

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • /38

    $795,000

    Sold Dec 10, 2025

    104 Woods Rd, Chester, MD 21619

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft
    • Built 2002

    Last Sold Summary

    • $259/SF
    • 95 Days On Market

    Current Estimated Value $809,570

    Last Listing Agent Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
    • /64

      Est $654,837

      Not Listed For Sale

      1326 Queen Anne Dr, Chester, MD 21619

      • 5 Beds
      • 3 Baths
      • 3,103 Sq Ft
      • Built 1990
      1326 Queen Anne Dr, Chester, MD 21619

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /97

    $375,000

    Pending
    • 3 Beds
    • 2 Baths
    • 3,128 Sq Ft

    114 Cedar Rd, Chester, MD 21619

    AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this sprawling 1-acre lot. This meticulously maintained residence with over 3,000 SF of total living space blends modern comfort with rare functional space. Inside, you’ll find fresh updates and an expanded, bespoke master suite designed for total relaxation. The true highlight is the property’s versatility:

    Tom Atwood Keller Williams Legacy

    114 Cedar Rd, Chester, MD 21619
  • /68

    $1,200,000

    Sold Sep 30, 2025

    1622 Bayside Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2009

    Last Sold Summary

    • $400/SF
    • 112 Days On Market

    Current Estimated Value $1,246,047

    Last Listing Agent Cynthia Sullivan Berkshire Hathaway HomeServices Homesale Realty

    1622 Bayside Dr, Chester, MD 21619
    • /64

      Est $554,869

      Not Listed For Sale

      1014 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 2002
      1014 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Brandon Golueke Monument Sotheby's International Realty

  • /38

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    205 Riverside Dr, Chester, MD 21619

    Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This

    Melissa Chick Engel & Völkers Annapolis

    205 Riverside Dr, Chester, MD 21619
  • /36

    $490,000

    Sold Feb 19, 2026

    906 Auckland Way, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft
    • Built 2001

    Last Sold Summary

    • $236/SF
    • 74 Days On Market

    Current Estimated Value $486,915

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    906 Auckland Way, Chester, MD 21619
    • /54

      Est $453,353

      Not Listed For Sale

      603 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,112 Sq Ft
      • Built 2000
      603 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /25

    $689,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 33, Chester, MD 21619

    Private home office with elegant French double doors.Gourmet kitchen features a center island & built-in wall oven.Dining area includes a dry bar for added convenience.Great room with an electric fireplace opens to the balcony.Owner's suite offers balcony access for a relaxing retreat.Spa bath provides comfort with dual vanities & modern design.Laundry room includes

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 33, Chester, MD 21619
  • /45

    $825,000

    Sold Dec 09, 2025

    124 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft
    • Built 2021

    Last Sold Summary

    • $319/SF
    • 87 Days On Market

    Current Estimated Value $839,513

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
    • /23

      Est $321,914

      Not Listed For Sale

      216 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,050 Sq Ft
      • Built 1993
      216 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /21

    $629,990

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

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • /52

    $900,000

    Sold May 13, 2026

    2613 Cecil Dr, Chester, MD 21619

    • 5 Beds
    • 2.5 Baths
    • 2,496 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $361/SF
    • 44 Days On Market

    Current Estimated Value $935,070

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    2613 Cecil Dr, Chester, MD 21619
    • /46

      Est $695,520

      Not Listed For Sale

      105 Barren Ridge Rd, Chester, MD 21619

      • 4 Beds
      • 4.5 Baths
      • 3,016 Sq Ft
      • Built 1995
      105 Barren Ridge Rd, Chester, MD 21619

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

  • /3

    $897,750

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft

    320 Bayberry Dr, Chester, MD 21619

    Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just

    Jeremy McDonough Mr. Lister Realty

    320 Bayberry Dr, Chester, MD 21619
  • /33

    $929,990

    Sold Jun 12, 2026

    102 Boatswain Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 3% Below List Price
    • $489/SF
    • 31 Days On Market

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

    102 Boatswain Way Unit 42, Chester, MD 21619
    • /60

      Est $562,734

      Not Listed For Sale

      1006 Auckland Way, Chester, MD 21619

      • 4 Beds
      • 4 Baths
      • 2,076 Sq Ft
      • Built 2001
      1006 Auckland Way, Chester, MD 21619

      Last Sold Summary

      Last Listing Agent Deborah Savoie Long & Foster Real Estate, Inc.

  • /5

    $149,900

    • Land
    • 12,632 Sq Ft
    • $516,897 per Acre

    0 Harley Ln, Chester, MD 21619

    Lot 1 of two newly formed building lots on Kent Island in Chester just off Dominion Road. Sewer Allocation has been paid (a $11,800 value!) and this lot has a working well! The site work has been done. Right around the corner from the Goodhands Creek Landing to launch your boat. Close to Rt 50/301 & Main Street for convenient commuting and shopping!

    Jason Dey Kevin Dey Realty

    0 Harley Ln, Chester, MD 21619
  • /62

    $789,000

    Sold Aug 27, 2025

    103 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,602 Sq Ft
    • Built 2012

    Last Sold Summary

    • $303/SF
    • 120 Days On Market

    Current Estimated Value $836,229

    Last Listing Agent Edward Beres RE/MAX Executive

    103 John Gibson Dr, Chester, MD 21619
    • /39

      Est $555,047

      Not Listed For Sale

      1905 Roberta Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 1976
      1905 Roberta Dr, Chester, MD 21619

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Tammi Clark Clark & Co Realty, LLC

  • /122

    $747,900

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft

    209 Harrier Way, Chester, MD 21619

    Welcome Home! JUST LISTED & OPEN Saturday 8/8 11am-1pm and Sunday 8/9 9am-11am OR by APPT DAILY! Barely lived in, this home still looks like new, offering all the benefits of new construction without the wait. The thoughtfully designed floor plan of the Simone model offers exceptional flexibility. The main level features a stunning gourmet kitchen with crisp white cabinetry, a large center

    Violeta Aguirre Long & Foster Real Estate, Inc.

    209 Harrier Way, Chester, MD 21619
  • /30

    $370,000

    Sold Oct 07, 2025

    413 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • Built 1896

    Last Sold Summary

    • $275/SF
    • 103 Days On Market

    Current Estimated Value $372,172

    Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

    413 Dominion Rd, Chester, MD 21619
    • /3

      Est $523,109

      Not Listed For Sale

      106 Logan Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 2001
      106 Logan Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kay Gatling Long & Foster Real Estate, Inc.

  • /31

    $929,990

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

    102 Boatswain Way Unit 43, Chester, MD 21619

    Beautiful gourmet kitchen featuring designer cabinetry & an efficient layout for everyday living.Bright great room with an electric fireplace adding warmth & character.Dining area complemented by a convenient dry bar for easy entertaining.Private owner’s suite with walk-in closet & direct access to the spa bath.Home office with double doors ideal for work or quiet

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 43, Chester, MD 21619
  • /20

    $849,990

    Sold Jan 07, 2026

    519 Warbler Way, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $307/SF
    • 35 Days On Market

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

    519 Warbler Way, Chester, MD 21619
    • /21

      Est $414,951

      Not Listed For Sale

      1926 Sherman Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1991
      1926 Sherman Dr, Chester, MD 21619

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent Michael Rosendale Rosendale Realty

  • /44

    $949,990

    New Construction $30K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Warbler Way Unit 3034, Chester, MD 21619

    The Severn combines an open floorplan with thoughtful design elements, with a projected settlement date of November 2026. Designed for comfortable and modern living, this home features 3 bedrooms, 2.5 baths, and a 1-car garage. The owner’s suite includes a sitting room, large walk-in closets, and a spa-inspired bath with a shower featuring a seat and handheld shower wand, double sinks, and quartz

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3034, Chester, MD 21619
  • /49

    $880,000

    Sold Jul 28, 2026

    127 Flycatcher Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 2022

    Last Sold Summary

    • $442/SF
    • 233 Days On Market

    Current Estimated Value $910,921

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    127 Flycatcher Way, Chester, MD 21619
    • /67

      Est $550,355

      Not Listed For Sale

      910 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft
      • Built 2001
      910 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Ryan Lancaster Long & Foster Real Estate, Inc.

  • /41

    $856,000

    • 3 Beds
    • 3 Baths
    • 2,527 Sq Ft

    193 Spinnaker Way, Chester, MD 21619

    Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious

    Alex Estill Long & Foster Real Estate, Inc.

    193 Spinnaker Way, Chester, MD 21619
  • /33

    $569,000

    Sold Dec 03, 2025

    306 Skipper Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,610 Sq Ft
    • Built 1974

    Last Sold Summary

    • $218/SF
    • 9 Days On Market

    Current Estimated Value $591,245

    Last Listing Agent Elizabeth Arentz Coldwell Banker Realty

    306 Skipper Ln, Chester, MD 21619
    • /23

      Est $394,888

      Not Listed For Sale

      2608 Harrington Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1967
      2608 Harrington Rd, Chester, MD 21619

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Brenda Sarver Maryland Realty Connection

  • /15

    $789,990

    New Construction $40K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    723 Warbler Way, Chester, MD 21619

    Elegant kitchen with white cabinetry & center island.Open concept living spaces featuring cozy fireplace.Serene primary suite with stylish ceiling treatment & feature wall.Polished primary bath featuring brushed nickel finishes & walk-in closet.Formal home office provides a quiet space for working remotely.Versatile screened patio for relaxing with friends.Functional

    K. Hovnanian Homes Builder
    723 Warbler Way, Chester, MD 21619
  • /2

    $735,000

    Sold Jul 28, 2026

    212 Switchgrass Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • 33 Days On Market

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    212 Switchgrass Way Unit 34, Chester, MD 21619

Showing Results 361 - 400, Page 10 of 18

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