5,235

Chester, MD Homes

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  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $515,000

    $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    /53

    $4,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Condo for Rent

    190 Harrier Way Unit 24, Chester, MD 21619

    This is What You Have Been Looking For + More! You'll love this Gorgeous 2600 sf Condo in Four Seasons @ Kent Island, a Premiere 55+ Community! This is a rare and quality offering of this modern and bright 2nd Floor end unit condo in a resort style, waterfront community. This is the largest condo model built here by K.Hovnanian called The Severn with 3 Bedrooms and 2.5 Baths. It is being offered

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    190 Harrier Way Unit 24, Chester, MD 21619
  • 203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    /53

    $475,000

    Sold Sep 29, 2025

    203 Barren Ridge Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft
    • Built 1988

    Last Sold Summary

    • $229/SF
    • 38 Days On Market

    Current Estimated Value $512,204

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
    • 203 Anchor Ln, Chester, MD 21619
      203 Anchor Ln, Chester, MD 21619
      203 Anchor Ln, Chester, MD 21619
      /27

      Est $519,245

      Not Listed For Sale

      203 Anchor Ln, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1977
      203 Anchor Ln, Chester, MD 21619

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

  • 2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    /61

    $379,900

    Open Sat 11AM - 1PM $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    2645 Cox Neck Rd, Chester, MD 21619

    Price Reduced & Open House, Saturday, Aug 8, 11:00am - 1:00pm; Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and is priced to sell. Inside, you'll find a bright and inviting floor plan featuring a kitchen

    Agent Photo

    Gretchen Wichlinski

    Compass

    2645 Cox Neck Rd, Chester, MD 21619
  • 800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    /20

    Starting at $1,879 Per Month

    • 1 - 3 Beds

    800 Abruzzi Dr, Chester, MD 21619

    Make your new home on Kent Island at The Promenade at Red Apple Town Center, and you will have found the ideal setting that combines the best of city and beach living. With easy access to Route 50 and just a short drive from Annapolis, Easton, and Centreville, adventure is always right around the corner.When you’re not exploring the surrounding area, at home you’ll enjoy premium interior finishes

    The Promenade

    800 Abruzzi Dr, Chester, MD 21619
  • 318 Old Point Rd, Chester, MD 21619
    318 Old Point Rd, Chester, MD 21619
    318 Old Point Rd, Chester, MD 21619
    /43

    $1,025,000

    Sold Nov 26, 2025

    318 Old Point Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,656 Sq Ft
    • Built 2024

    Last Sold Summary

    • $619/SF
    • 6 Days On Market

    Current Estimated Value $1,062,317

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, Chester, MD 21619
    • 2707 Cox Neck Rd, Chester, MD 21619
      2707 Cox Neck Rd, Chester, MD 21619
      2707 Cox Neck Rd, Chester, MD 21619
      /47

      Est $445,178

      Not Listed For Sale

      2707 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1995
      2707 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Samantha Hernandez Douglas Realty, LLC

  • 3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    /9

    $249,000

    $26K PRICE DROP Under Contract
    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    Price improvement and ready to move in! Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    3 D Queen Victoria Ct, Chester, MD 21619
  • 1712 Main St, Chester, MD 21619
    1712 Main St, Chester, MD 21619
    1712 Main St, Chester, MD 21619
    /11

    $1,500 Per Month

    • Studio
    • 2 Baths
    • 875 Sq Ft
    • House for Rent

    1712 Main St, Chester, MD 21619

    Property Id: 2619180 Office space available approximately 875 square feet. Features two separate offices plus common area, Two individual private bath rooms . This is a second floor office with outside entry but no elevator. A shared kitchenette is also available for your use. NO CAM nor utility charges. Building is well maintained and office staff available during the week to answer any

    1712 Main St, Chester, MD 21619
  • 1407 Calvert Rd, Chester, MD 21619
    1407 Calvert Rd, Chester, MD 21619
    /2

    $430,000

    Sold Jan 23, 2026

    1407 Calvert Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 1,693 Sq Ft
    • Built 1966

    Last Sold Summary

    • $254/SF
    • 2 Days On Market

    Current Estimated Value $451,186

    Last Listing Agent Dina Baxter Rosendale Realty

    1407 Calvert Rd, Chester, MD 21619
    • 136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      /81

      Est $822,016

      Not Listed For Sale

      136 Evelyne St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,771 Sq Ft
      • Built 2014
      136 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • 126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    /44

    $559,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    126 Watermans Cove Ln, Chester, MD 21619

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    126 Watermans Cove Ln, Chester, MD 21619
  • 1606 Postal Rd Unit B, Chester, MD 21619
    1606 Postal Rd Unit B, Chester, MD 21619
    1606 Postal Rd Unit B, Chester, MD 21619
    /13

    $1,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 5,128 Sq Ft
    • House for Rent

    1606 Postal Rd Unit B, Chester, MD 21619

    2 bedroom 1.5 bath apartment unit. Entrance off rear deck. Home built into 3 apartments. To be freshly painted. LVP flooring, large parking lot. Dumpster available for trash. Easy access to Rt 50, close to shopping, restaurants. Pets welcome on a case-by-case basis. Prefer small pets under 35lbs. Water & Sewer included. Tenants pay electric.

    Cindy Jacobs Maryland Residential Management Co

    1606 Postal Rd Unit B, Chester, MD 21619
  • 211 Switchgrass Way Unit 1524, Chester, MD 21619
    211 Switchgrass Way Unit 1524, Chester, MD 21619
    211 Switchgrass Way Unit 1524, Chester, MD 21619
    /88

    $624,900

    Sold Sep 19, 2025

    211 Switchgrass Way Unit 1524, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $240/SF
    • 147 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1524, Chester, MD 21619
    • 232 Shopping Center Rd, Stevensville, MD 21666
      232 Shopping Center Rd, Stevensville, MD 21666
      /2

      Est $990,113

      Not Listed For Sale

      232 Shopping Center Rd, Stevensville, MD 21666

      • 1 Bed
      • 1 Bath
      • 1,000 Sq Ft
      • Built 2009
      232 Shopping Center Rd, Stevensville, MD 21666

  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /27

    $819,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    Kerr Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 2201 Main St Unit 104, Chester, MD 21619
    2201 Main St Unit 104, Chester, MD 21619
    /2

    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Chester Centre Apartments

    2201 Main St Unit 104, Chester, MD 21619

    1500 square feet, 3 bedrooms, 1.5 baths. Large rooms. Kitchen with pantry and full dining area. New carpet and laminate flooring. Secured entrance. Townhouse-style apartment (living space downstairs, bedrooms upstairs) located on the second and third floors of the Chester Centre building.

    2201 Main St Unit 104, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /2

    $445,000

    Sold Jul 31, 2026

    1872 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft
    • Built 1961

    Last Sold Summary

    • 8% Below List Price
    • $299/SF
    • 49 Days On Market

    Current Estimated Value $452,572

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
    • 316 Macum Creek Dr, Chester, MD 21619
      316 Macum Creek Dr, Chester, MD 21619
      316 Macum Creek Dr, Chester, MD 21619
      /79

      Est $873,199

      Not Listed For Sale

      316 Macum Creek Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,901 Sq Ft
      • Built 2015
      316 Macum Creek Dr, Chester, MD 21619

      Last Sold Summary

      • 38 Days On Market

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

  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $848,990

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    Tuscaloosa Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 1606 Postal Rd Unit C, Chester, MD 21619
    1606 Postal Rd Unit C, Chester, MD 21619
    1606 Postal Rd Unit C, Chester, MD 21619
    /17

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 5,128 Sq Ft
    • House for Rent

    1606 Postal Rd Unit C, Chester, MD 21619

    Apartment #C-Upstairs all on one level 4-bedroom, 2 bath unit, just painted and new LVP flooring & carpet added. Plenty of parking in building lot. Easy access to Rt 50, close to shopping, restaurants. Trash, parking, grounds maintenance and water sewer included in rent. One pet under 35lbs allowed with pet rent.

    Cindy Jacobs Maryland Residential Management Co

    1606 Postal Rd Unit C, Chester, MD 21619
  • 117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    /8

    $849,990

    Sold Dec 10, 2025

    117 Redstart Dr, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $423/SF
    • 7 Days On Market

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

    117 Redstart Dr, Chester, MD 21619
    • 163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      /46

      Est $621,892

      Not Listed For Sale

      163 Claiborne St, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,824 Sq Ft
      • Built 2012
      163 Claiborne St, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Dave Luptak Long & Foster Real Estate, Inc.

  • 134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    /63

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 2,185 Sq Ft

    134 Richard Ingle Way, Chester, MD 21619

    Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the

    Barbara McCaffrey Redfin Corp

    134 Richard Ingle Way, Chester, MD 21619
  • 41A Queen Catherine Ct, Chester, MD 21619
    41A Queen Catherine Ct, Chester, MD 21619
    41A Queen Catherine Ct, Chester, MD 21619
    /63

    $3,000 Per Month

    • 2 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Townhouse for Rent

    41A Queen Catherine Ct, Chester, MD 21619

    Welcome to Kent Island living at its finest! This beautifully maintained end-unit townhome offers the perfect blend of coastal charm and modern comfort. The upper level features two spacious primary bedroom suites, each with its own private full bathroom, providing an ideal layout for homeowners and guests alike. Enjoy peaceful mornings and relaxing evenings from one of two private exterior decks

    Mark Milligan RE/Max Experience

    41A Queen Catherine Ct, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $787,500

    Sold Aug 07, 2026

    135 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 230 Days On Market

    Current Estimated Value $811,120

    Last Listing Agent Riley White Real Broker, LLC - Annapolis

    135 Nauset Ln, Chester, MD 21619
    • 215 John Gibson Dr, Chester, MD 21619
      215 John Gibson Dr, Chester, MD 21619
      215 John Gibson Dr, Chester, MD 21619
      /60

      Est $566,559

      Not Listed For Sale

      215 John Gibson Dr, Chester, MD 21619

      • 3 Beds
      • 4 Baths
      • 2,240 Sq Ft
      • Built 2011
      215 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Catherine Watson - Bye RE/MAX Executive

  • 1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    /46

    $599,900

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

    1012 Auckland Way, Chester, MD 21619

    Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home,

    Jerrise Spencer Redfin Corp

    1012 Auckland Way, Chester, MD 21619
  • 9 Queen Victoria Way, Chester, MD 21619
    9 Queen Victoria Way, Chester, MD 21619
    9 Queen Victoria Way, Chester, MD 21619
    /35

    $2,800 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Townhouse for Rent

    9 Queen Victoria Way, Chester, MD 21619

    Come see this freshly renovated waterview unit in Queens Landing! More photos to come, kitchen and bathrooms are being renovated. Enjoy Chester River views from all angles! The spacious first floor with a half bath has plenty of room for living, dining and whatever else you desire. The upper level features two bedrooms each with their own waterview balcony and full bathroom (one in the hall and

    Annie Eaton Coldwell Banker Realty

    9 Queen Victoria Way, Chester, MD 21619
  • 110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    /18

    $949,990

    Sold Apr 22, 2026

    110 Boatswain Way Unit 41, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 9% Below List Price
    • $365/SF
    • 35 Days On Market

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

    110 Boatswain Way Unit 41, Chester, MD 21619
    • 147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      /70

      Est $723,222

      Not Listed For Sale

      147 Carriage Heath, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft
      • Built 2015
      147 Carriage Heath, Chester, MD 21619

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Yael Beckman Coldwell Banker Realty

  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $858,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    Franklin Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /40

    $640,000

    Sold Jan 05, 2026

    132 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2011

    Last Sold Summary

    • $267/SF
    • 20 Days On Market

    Current Estimated Value $679,188

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    132 Claiborne St, Chester, MD 21619
    • 2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      /20

      Not Listed For Sale

      2629 Cecil Dr, Chester, MD 21619

      2629 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Gretchen Wichlinski Compass

  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $886,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    /40

    $540,656

    Sold Sep 19, 2025

    112 Harbour Sound Dr, Chester, MD 21619

    • 2 Beds
    • 3.5 Baths
    • 2,131 Sq Ft
    • Built 1989

    Last Sold Summary

    • $254/SF
    • 86 Days On Market

    Current Estimated Value $541,200

    Last Listing Agent Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
    • 121 Wheelhouse Way Unit 12, Chester, MD 21619
      121 Wheelhouse Way Unit 12, Chester, MD 21619
      121 Wheelhouse Way Unit 12, Chester, MD 21619
      /10

      Not Listed For Sale

      121 Wheelhouse Way Unit 12, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,003 Sq Ft
      121 Wheelhouse Way Unit 12, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $699,990

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

    Taylor Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests.Stylish home office off foyer for working from home.Open & airy great room with adjacent dining area.Striking kitchen with island & tons of cabinet space.Luxurious primary suite with oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 1337 Queen Anne Dr, Chester, MD 21619
    1337 Queen Anne Dr, Chester, MD 21619
    1337 Queen Anne Dr, Chester, MD 21619
    /77

    $488,000

    Sold Apr 17, 2026

    1337 Queen Anne Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $229/SF
    • 15 Days On Market

    Current Estimated Value $486,594

    Last Listing Agent Caitlin Prossner Long & Foster Real Estate, Inc.

    1337 Queen Anne Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 18

Maryland Queen Anne's County

Real Estate & Homes

Home Prices in Chester, MD

The median home sale price in Chester, MD is $675,438, up 18% year-over-year. Homes in Chester sell in 361 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$675,438
Median Single Family Sale Price
$749,500
Median Townhouse Sale Price
$369,950
Median 2 Bedroom Sale Price
$618,750
Median 1 Bedroom Sale Price
$289,000
Average Price Per Sq Ft
$306
Number of Homes for Sale
98
Last 12 months Home Sales
222
Months of Supply
5.30
Median List Price
$705,125
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
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