5,224

Homes in ZIP Code 21619

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  • /61

    $379,900

    $20K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    2645 Cox Neck Rd, Chester, MD 21619

    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 with a stylish tile backsplash, ample cabinetry, and luxury

    Agent Photo

    Gretchen Wichlinski

    Compass

    2645 Cox Neck Rd, 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
  • /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
    • /88

      Not Listed For Sale

      211 Switchgrass Way Unit 1531, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2025
      211 Switchgrass Way Unit 1531, Chester, MD 21619

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /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

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    126 Watermans Cove Ln, Chester, MD 21619
  • /20

    Starting at $1,904 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
  • /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
    • /49

      Not Listed For Sale

      211 Switchgrass Way Unit 1512, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2024
      211 Switchgrass Way Unit 1512, Chester, MD 21619

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /78

    $1,195,000

    $55K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • /45

    $4,200 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    4000 Herons Nest Way Unit 42, Chester, MD 21619

    Four Seasons @ Kent Island -- Offered Fully Furnished to Include TV, All Bed Linens, Towels, Kitchen Dishes and Flatware -- Luxurious Penthouse Condo with Garage in the Upscale 55+ Kent Island Community of Four Seasons. First Time Offering of This Tastefully Decorated 1900 sq ft, 2 Bedroom, 2.5 Bath Condo in Elevator Building. Owner to Include Monthly Maid Service & Use of All Community

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 42, 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
    • /55

      Not Listed For Sale

      211 Switchgrass Way Unit 1511, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2024
      211 Switchgrass Way Unit 1511, Chester, MD 21619

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /70

    $499,000

    $61K 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 - Reduced! * 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 featuring a beautiful white Kitchen with quartz counters, propane gas

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /2

    $1,950 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 210, Chester, MD 21619

    Property Id: 2256460 SENIOR APTS 62+ AT VILLAGE AT CHESTER. ALL APTS ARE TWO BR, ONE BA. ALL APPLIANCES INCLUDED. PETS ALLOWED. STORAGE SPACE COMES WITH LEASE. ONE YEAR LEASE. ELECTRIC AND CABLE ARE TENANTS BILLS. CLOSE TO ALL YOUR NEEDS. AVAILABLE 10/1/2026. CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE. BLYTHE LARRIMORE OSM

    1540 Postal Rd Unit 210, 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
    • /50

      Est $835,973

      Not Listed For Sale

      121 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,760 Sq Ft
      • Built 2010
      121 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Tara Trout Samson Properties

  • /26

    $389,900

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    108 Blenny Ln, Chester, MD 21619

    Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    108 Blenny Ln, Chester, MD 21619
  • /2

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Townhouse for Rent

    321 Piney Narrows Rd Unit 1, Chester, MD 21619

    Everything Is brand new! This unique little apartment has been freshly created inside of a building right near a marina. Enjoy all that the Kent Island lifestyle has to offer. You are close to everything. This unit is offered furnished or not-your choice. Check out this bright, cheerful and newly renovated unit. Six month lease available for $2400/mo.

    Terri Gable Chesapeake Real Estate Associates, LLC

    321 Piney Narrows Rd Unit 1, 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
    • /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

  • /4

    $595,000

    Coming Soon Sep 22
    • 6 Beds
    • 6.5 Baths
    • 2,100 Sq Ft

    1010 Auckland Way, Chester, MD 21619

    Professional Photos Coming Soon - PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    1010 Auckland Way, Chester, MD 21619
  • /2

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 107, Chester, MD 21619

    Property Id: 2841646 Great location to fit all your needs. Restaurants, shopping, parks and the Bay are close. Great spot to hang your hat! Call today!

    1540 Postal Rd Unit 107, 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
    • /68

      Est $236,329

      Not Listed For Sale

      7C Queen Victoria Way, Chester, MD 21619

      • Studio
      • 1 Bath
      • 724 Sq Ft
      • Built 1983
      7C Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /93

    $2,400,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 4,331 Sq Ft

    2882 Cox Neck Rd, Chester, MD 21619

    Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    2882 Cox Neck Rd, 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
  • /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
    • /46

      Est $315,637

      Not Listed For Sale

      31C Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      31C Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /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
  • /8

    $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
  • /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
    • /44

      Est $702,927

      Not Listed For Sale

      1773 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,142 Sq Ft
      • Built 1987
      1773 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jessica Busch Keller Williams Flagship

  • /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
  • /35

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 645 Sq Ft
    • House for Rent

    215 Parks Rd, Chester, MD 21619

    Craving a WATERFRONT rental with pier, 15,000 lb boat lift, jet-ski lift, nearly 200 feet of shoreline, & sandy beach area on .4 acres just 5 mins from Bay Bridge? Welcome home! Enjoy this 6-Month WATERFRONT playground! Nearly 200' of shoreline with Private, sandy beach, 120' Pier with Boat Lift AND Jet-ski lift, panoramic views of coveted Cox Creek. With generous water depth, ideal location with

    Jennifer Chaney Chaney Homes, LLC

    215 Parks Rd, 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
    • /86

      Not Listed For Sale

      24 D Queen Elizabeth Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1985
      24 D Queen Elizabeth Ct, Chester, MD 21619

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent The Williams Home Team Douglas Realty, LLC

  • /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
  • /44

    $4,800 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • House for Rent

    215 Kingfisher Ln, Chester, MD 21619

    Try Before You Buy in Four Seasons at Kent Island! Experience the resort-style lifestyle of one of Kent Island’s most sought-after 55+ communities before making a purchase commitment.This nearly new Tuscaloosa model offers 5 bedrooms, 4.5 baths, a bright open floor plan, premium Café appliances, custom closets and window treatments, an oversized garage, and peekaboo Chester River views from

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, 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
    • /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

Showing Results 1 - 40, Page 1 of 18

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