5,182

Homes in ZIP Code 21619

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  • /42

    $749,500 Open Sun 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • /42

    $2,995 per month

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft
    • Townhouse for Rent

    106 Blenny Ln, Chester, MD 21619

    Welcome to this beautifully updated 3-level interior townhome located in the highly sought-after Bayside community on Kent Island. This move-in ready home features 3 spacious bedrooms, 2 full bathrooms, and 2 half baths, offering both comfort and functionality across every level. The main living area showcases gleaming hardwood floors, a gas fireplace, and an open layout perfect for everyday

    Jose Matos Chaney Homes, LLC

    106 Blenny Ln, Chester, MD 21619
  • /52

    $553,000 Sold Apr 30, 2025

    1106 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • Built 1975

    Last Sold Summary

    • $209/SF
    • 53 Days On Market

    Current Estimated Value $564,011

    Last Listing Agent April Heim Rosendale Realty

    1106 Cox Neck Rd, Chester, MD 21619
    • /65

      Est $866,484 Not Listed For Sale

      151 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,156 Sq Ft
      • Built 2010
      151 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 1% Above List Price
      • $272/SF
      • 12 Days On Market

      Last Sold Price $860,000

      Last Listing Agent Michele Naish BHHS PenFed (actual)

  • /40

    $419,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft

    27 Queen Mary Ct Unit F, Chester, MD 21619

    Fabulous Adriatic Grande unit ( largest end unit and 1 of 4) in the desirable Queens Landing community. With 1,380 sq. ft. of meticulously maintained space, this home features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. FIRST FLOOR BEDROOM suite features a private patio while second floor owner suite has an adjoining loft with a

    Agent Photo

    Deborah Shiley

    Long & Foster Real Estate, Inc.

    (667) 249-7796

    27 Queen Mary Ct Unit F, Chester, MD 21619
  • /19

    $3,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • House for Rent

    113 Henry Stoupe Way, Chester, MD 21619

    The "Gibson's Grant" Waterfront Community has a new Rental Home available! They don't come on the market that often in this desired neighborhood... so don't delay! This Stunning 3 BR, 2.5BA, single family home is ready for you to move right in! Full of upgrades to include a Custom Stone Fireplace Surround and Mantel, Hardwood floors, Granite Countertops, SS Appliances, Beautiful Tiled Backsplash,

    Pamela Ackermann-Doll RE/MAX Executive

    113 Henry Stoupe Way, 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 $494,781

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
    • /48

      Est $519,121 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

      • 3% Below List Price
      • $258/SF
      • 167 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Pamela Ackermann-Doll RE/MAX

  • /8

    $275,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    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 in the bedroom. Queens Landing is a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 888-0022

    3 D Queen Victoria Ct, Chester, MD 21619
  • /49

    $4,500 per month

    • 4 Beds
    • 3 Baths
    • 2,876 Sq Ft
    • House for Rent

    226 Bentons Pleasure Rd, Chester, MD 21619

    Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water

    Michael Roenigk Chaney Homes, LLC

    226 Bentons Pleasure 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 $1,028,974

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, Chester, MD 21619
    • /76

      Est $470,260 Not Listed For Sale

      51D Queen Caroline Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1995
      51D Queen Caroline Ct, Chester, MD 21619

      Last Sold Summary

      • 3% Below List Price
      • $337/SF
      • 0 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /34

    $443,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features a fenced yard for kids and pets, screened porch, large yard with concrete pad, and small storage shed. Temperature-controlled concrete crawl space, new sump pump, and septic contract for easy, worry-free living. Conveniently located near shopping and everything Kent Island has to offer.Make sure you see

    Agent Photo

    Linda Moran

    Berkshire Hathaway HomeServices PenFed Realty-WOC

    (410) 650-8215

    200 Newtown Rd, Chester, MD 21619
  • /10

    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,272 Sq Ft
    • House for Rent

    2626 Cecil Dr, Chester, MD 21619

    Welcome to this charming home located in the quiet, established community of Harbor View in Chester. This well-maintained property features a bright and open floor plan with a cozy fireplace—perfect for relaxing evenings. The kitchen comes fully equipped with modern appliances. Enjoy the convenience of an attached garage and a spacious 0.34-acre lot with plenty of outdoor space. Situated just

    Kevin Waterman Coldwell Banker Waterman Realty

    2626 Cecil Dr, Chester, MD 21619
  • /46

    $350,000 Sold Apr 04, 2025

    1833 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1986

    Last Sold Summary

    • $342/SF
    • 106 Days On Market

    Current Estimated Value $359,542

    Last Listing Agent Janice O'Donnell Chaney Homes, LLC

    1833 Harbor Dr, Chester, MD 21619
    • /68

      Est $1,128,648 Not Listed For Sale

      116 Kirwans Landing Ln, Chester, MD 21619

      • 5 Beds
      • 4.5 Baths
      • 3,736 Sq Ft
      • Built 2000
      116 Kirwans Landing Ln, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $294/SF
      • 17 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Michelle Abplanalp Rosendale Realty

  • /70

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /29

    $2,950 per month

    • 4 Beds
    • 2.5 Baths
    • 1,852 Sq Ft
    • House for Rent

    2605 Harrington Rd, Chester, MD 21619

    Beautiful, four-bedroom, ranch-style home on level lot with spacious, fenced backyard. Kitchen has stainless steel appliances and granite counters/island. Hardwood floors. Energy efficiency improvements include a fully encapsulated, insulated crawlspace and R49 attic insulation. Quiet street. One small dog considered on case-by-case-basis, additional fee and deposit will apply. PROPERTY AVAILABLE

    Raj Mirani Taylor Properties

    2605 Harrington 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 $425,901

    Last Listing Agent Dina Baxter Rosendale Realty

    1407 Calvert Rd, Chester, MD 21619
    • /46

      Est $570,307 Not Listed For Sale

      2612 Cecil Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,392 Sq Ft
      • Built 2017
      2612 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $240/SF
      • 10 Days On Market

      Last Sold Price $575,000

      Last Listing Agent April Heim Rosendale Realty

  • /81

    $814,900

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

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • /59

    $3,200 per month

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • Townhouse for Rent

    907 Auckland Way, Chester, MD 21619

    Showings begin Sunday! Rare waterview end-unit townhouse for rent on Kent Island. Located in Bayside, a sought-after waterfront community on Maryland’s Eastern Shore, this tucked-away property offers true Chesapeake Bay resort-style living. Residents enjoy a community pool with hot tub, tennis courts, lawn volleyball, scenic walking trails, and a renovated clubhouse with fitness center, kitchen,

    Jennifer Snead Long & Foster Real Estate, Inc.

    907 Auckland Way, 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
    • /48

      Not Listed For Sale

      212 Switchgrass Way Unit 1612, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1612, Chester, MD 21619

      Last Sold Summary

      • $262/SF
      • 8 Days On Market

      Last Sold Price $524,900

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • /24

    $669,990 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • /16

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 6,338 Sq Ft
    • Condo for Rent

    107 Dundee Ave Unit 201, Chester, MD 21619

    1 bedroom 1 bath apartment in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with pet rent of $50 per month. Closet on balcony is mechanical room and not

    Cindy Jacobs Maryland Residential Management Co

    107 Dundee Ave Unit 201, Chester, MD 21619
  • /52

    $365,000 Sold Mar 25, 2025

    6004 Bridgepointe Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,885 Sq Ft
    • Built 1992

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $364,178

    Last Listing Agent Kathleen Higginbotham Samson Properties

    6004 Bridgepointe Dr, Chester, MD 21619
    • /14

      Est $27,598 Not Listed For Sale

      3C Piney Narrows Rd, Chester, MD 21619

      • Studio
      • 540 Sq Ft
      • Built 1492
      3C Piney Narrows Rd, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $52/SF
      • 1 Day On Market

      Last Sold Price $28,000

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /27

    $858,990 New Construction

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

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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
  • /39

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    29D Queen Mary Ct, Chester, MD 21619

    Wonderful Queens Landing on Kent Island! Totally updated kitchen area with center island and bar stools! *Hardwood floors on main living area! Enclosed sun-room with beautiful views of the lake. Spacious living room with fireplace and built in book cases. Kitchen with Breakfast Bar. Main Bedroom, with Main Bath, also over looks the lake. *This town home is a must see in Queens Landing* Community

    Michael Roenigk Chaney Homes, LLC

    29D Queen Mary Ct, Chester, MD 21619
  • /30

    $465,000 Sold Jun 10, 2025

    1713 Bayside Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • Built 1972

    Last Sold Summary

    • $235/SF
    • 42 Days On Market

    Current Estimated Value $481,043

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    1713 Bayside Dr, Chester, MD 21619
    • /14

      Est $24,641 Not Listed For Sale

      27C Piney Narrows Rd, Chester, MD 21619

      • Studio
      • 540 Sq Ft
      • Built 1492
      27C Piney Narrows Rd, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $46/SF
      • 8 Days On Market

      Last Sold Price $25,000

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /12

    $886,990 New Construction

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

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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
  • /42

    $649,900 Sold Apr 24, 2025

    228 Warbler Way, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2024

    Last Sold Summary

    • $233/SF
    • 9 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    228 Warbler Way, Chester, MD 21619
    • /13

      Est $509,427 Not Listed For Sale

      115 Watermans Cove Ln, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,536 Sq Ft
      • Built 2019
      115 Watermans Cove Ln, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $336/SF
      • 3 Days On Market

      Last Sold Price $516,000

      Last Listing Agent Kevin Waterman Coldwell Banker Waterman Realty

  • /10

    $752,990 New Construction

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

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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
  • /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 K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series

    117 Redstart Dr, Chester, MD 21619
    • /81

      Est $805,674 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

      • 6% Above List Price
      • $274/SF
      • 102 Days On Market

      Last Sold Price $760,000

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /12

    $499,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    Magothy Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, 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 $658,078

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    132 Claiborne St, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 18

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