5,230

Chester, MD Homes

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  • /68

    $924,000

    • 3 Beds
    • 3 Baths
    • 2,745 Sq Ft

    214 Bayberry Dr, Chester, MD 21619

    Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney 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 primary

    Jim Corson Benson & Mangold, LLC

    214 Bayberry Dr, Chester, MD 21619
  • /61

    $379,900

    Sold Sep 16, 2026

    2645 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Below List Price
    • $319/SF
    • 51 Days On Market

    Current Estimated Value $393,593

    Last Listing Agent Gretchen Wichlinski Compass

    2645 Cox Neck Rd, Chester, MD 21619
    • /72

      Est $341,184

      Not Listed For Sale

      202 Ringneck Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,956 Sq Ft
      • Built 1995
      202 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Sheila Washburn Benson & Mangold, LLC

  • /32

    $374,900

    $84K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    NEW AMAZING PRICE!! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • /61

    $704,900

    Sold Feb 19, 2026

    121 Wheelhouse Way Unit 2124, Chester, MD 21619

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

    Last Sold Summary

    • 2% Below List Price
    • $271/SF
    • 0 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2124, Chester, MD 21619
    • /69

      Est $830,056

      Not Listed For Sale

      215 Mcguckin St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2008
      215 Mcguckin St, Chester, MD 21619

      Last Sold Summary

      • 81 Days On Market

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

  • /63

    $989,800

    New Construction Pending
    • 5 Beds
    • 3.5 Baths
    • 3,036 Sq Ft

    203 Riverside Dr, Chester, MD 21619

    Construction Complete, QUICK MOVE IN! Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • /44

    $764,000

    Sold Jul 27, 2026

    126 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,276 Sq Ft
    • Built 2011

    Last Sold Summary

    • 3% Below List Price
    • $336/SF
    • 56 Days On Market

    Current Estimated Value $773,420

    Last Listing Agent Tara Trout Samson Properties

    126 Claiborne St, Chester, MD 21619
    • /28

      Est $370,218

      Not Listed For Sale

      206 Church St, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1935
      206 Church St, Chester, MD 21619

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Jim Keating Keller Williams Realty Centre

  • /24

    $639,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    641 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry, center island, & brushed nickel finishes.Expansive great room for spending time with family & friends.Charming dining area with access to covered patio.Peaceful primary suite with stylish ceiling treatment.Polished primary bath featuring dual sinks & barn door.Formal home office provides a quiet space to work remotely.Attached

    K. Hovnanian Homes Builder
    641 Warbler Way, Chester, MD 21619
  • /45

    $492,500

    Sold Oct 06, 2025

    312 Hanna Ct, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 2001

    Last Sold Summary

    • $248/SF
    • 4 Days On Market

    Current Estimated Value $515,875

    Last Listing Agent Justin Kennedy Samson Properties

    312 Hanna Ct, Chester, MD 21619
    • /55

      Est $1,194,623

      Not Listed For Sale

      2802 Cox Neck Rd, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,692 Sq Ft
      • Built 1997
      2802 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Biana Arentz Coldwell Banker Realty

  • /54

    $374,900

    $13K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,885 Sq Ft

    6010 Bridgepointe Dr, Chester, MD 21619

    Welcome to this beautifully situated two-story townhome overlooking a tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient access to Route 50, and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort,

    April Heim Rosendale Realty

    6010 Bridgepointe Dr, Chester, MD 21619
  • /23

    $335,000

    Sold Jan 02, 2026

    206 Ringneck Ct Unit 78, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • $192/SF
    • 3 Days On Market

    Current Estimated Value $349,144

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    206 Ringneck Ct Unit 78, Chester, MD 21619
    • /45

      Est $656,515

      Not Listed For Sale

      2608 Cecil Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,336 Sq Ft
      • Built 1976
      2608 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Violeta Aguirre Long & Foster Real Estate, Inc.

  • /84

    $697,900

    $22K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    121 Merlin Dr, Chester, MD 21619

    Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a

    Yael Beckman Coldwell Banker Realty

    121 Merlin Dr, Chester, MD 21619
  • /2

    $360,000

    Sold Mar 27, 2026

    9B Queen Victoria Way, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $214/SF
    • 24 Days On Market

    Current Estimated Value $352,851

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    9B Queen Victoria Way, Chester, MD 21619
    • /37

      Est $760,423

      Not Listed For Sale

      121 Mcguckin St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2008
      121 Mcguckin St, Chester, MD 21619

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Peggy Stancavage Long & Foster Real Estate, Inc.

  • /48

    $400,000

    Open Sat 12PM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    List price is Opening Bid at the Online auction to be conducted on Auctioneers website.- Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the

    Carley Cooper Alex Cooper Auctioneers, Inc.

    1868 Roberta Dr, Chester, MD 21619
  • /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 $2,341,573

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1901 Cox Neck Rd, Chester, MD 21619
    • /48

      Est $524,189

      Not Listed For Sale

      1004 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 2001
      1004 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 167 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, 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 - Luxury Condos

    630 Warbler Way Unit 21, Chester, MD 21619
    • /61

      Est $746,443

      Not Listed For Sale

      244 Bentons Pleasure Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1948
      244 Bentons Pleasure Rd, Chester, MD 21619

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent John McGlannan Meredith Fine Properties

  • /44

    $225,000

    Pending
    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    26 Queen Anne Way, Chester, MD 21619

    Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is priced well below its tax-assessed value to reflect its original interior condition, giving buyers the flexibility to update and personalize the space to suit their own style.The condo overlooks Lake Amletto, offering a

    Julia Stevens Realty Navigator

    26 Queen Anne Way, 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 $332,683

    Last Listing Agent Chris Craddock EXP Realty, LLC

    206 Blenny Ln, Chester, MD 21619
    • /46

      Est $487,702

      Not Listed For Sale

      915 Auckland Way, Chester, MD 21619

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

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Jenn Bonk Cummings & Co. Realtors

  • /50

    $595,000

    $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

    Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment.Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, 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 $782,169

    Last Listing Agent Kathleen Higginbotham Samson Properties

    314 Thomas White Blvd, Chester, MD 21619
    • /27

      Est $340,703

      Not Listed For Sale

      306 Drake Tail Place, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1992
      306 Drake Tail Place, Chester, MD 21619

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Melissa Murray Compass

  • /29

    $999,990

    New Construction $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    114 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests or extended living.Home office with sliding doors for added privacy.Crown molding adds a refined touch to the great room & kitchen.Screened patio extends directly from the great room.Stacked cabinetry with glass-front uppers brings layered detail to the kitchen.Decorative feature walls add custom character to the foyer &

    K. Hovnanian Homes Builder
    114 Kinglet Ct, 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 $384,052

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1150 Little Creek Rd, Chester, MD 21619
    • /66

      Est $384,672

      Not Listed For Sale

      2747 Cecil Dr, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1992
      2747 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Ryan Briggs Anne Arundel Properties, Inc.

  • /44

    $849,990

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

    110 Warbler Way Unit 3031, 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 3031, 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 $500,837

    Last Listing Agent Jorge Zea Jorge A. Zea

    1221 Cox Neck Rd, Chester, MD 21619
    • /19

      Est $278,031

      Not Listed For Sale

      413 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1999
      413 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Cindy Jacobs Maryland Residential Management Co

  • /24

    $789,990

    New Construction $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 43, Chester, MD 21619

    Private home office with French doors, perfect for leisure activities.Gorgeous gourment kitchen with designer cabinets & vast island.Elegant dining area featuring lovely dry bar.Beautiful great room with sleek electric fireplace.Serene owner's suite featuring access to balcony & large walk-in closet.Lavish owner's spa bath featuring dual sinks.Fabulous balcony for

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 43, 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 $538,902

    Last Listing Agent Jonathan Olsavsky Coldwell Banker Waterman Realty

    114 Addison Ct, Chester, MD 21619
    • /51

      Est $526,838

      Not Listed For Sale

      2008 Palm Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,283 Sq Ft
      • Built 1997
      2008 Palm Dr, Chester, MD 21619

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Marilyn Hendley EXP Realty, LLC

  • /63

    $599,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619

Showing Results 241 - 280, Page 7 of 18

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