11,962

Kent County, MD Homes

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  • /50

    $1,750,000

    $225K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,915 Sq Ft

    14183 Roberts Dr, Galena, MD 21635

    Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    14183 Roberts Dr, Galena, MD 21635
  • /48

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft
    • House for Rent

    21186 Chesapeake Ave, Rock Hall, MD 21661

    Fully furnished rental!Deck was washed and stained on 5/20/26! Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    21186 Chesapeake Ave, Rock Hall, MD 21661
  • /2

    $365,000

    Sold Jul 22, 2026

    521 N Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,934 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $189/SF

    Current Estimated Value $444,216

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    521 N Kent St, Chestertown, MD 21620
    • /38

      Est $302,256

      Not Listed For Sale

      9190 N Bayview Ave, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,160 Sq Ft
      • Built 1969
      9190 N Bayview Ave, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • /64

    $575,000

    • 1 Bed
    • 1.5 Baths
    • 1,724 Sq Ft

    25133 Wymont Park Rd, Worton, MD 21678

    Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sipping your morning coffee while watching the sunrise over the water to enjoying breathtaking waterfront sunsets from your private floating dock, this unique property offers the lifestyle you dream about. Nestled on a beautiful

    Agent Photo

    Brittany Fox

    RE/MAX Chesapeake

    25133 Wymont Park Rd, Worton, MD 21678
  • /23

    Starting at $1,300 Per Month

    • 1 - 3 Beds

    101 Morgnec Rd, Chestertown, MD 21620

    Quiet community, beautifully landscaped. Close to Washington College, can walk to downtown historic Chestertown and shops. A must see.

    Kent Crossing Apartments

    101 Morgnec Rd, Chestertown, MD 21620
  • /21

    $364,900

    Sold Feb 26, 2026

    108 Flying Cloud Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2023

    Last Sold Summary

    • $188/SF
    • 67 Days On Market

    Current Estimated Value $361,480

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • /36

      Est $374,477

      Not Listed For Sale

      5708 Liberty St, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1920
      5708 Liberty St, Rock Hall, MD 21661

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Julia Hilfiker Gunther-McClary Real Estate

  • /35

    $325,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft

    10 Ericsson Ave Unit 32, Betterton, MD 21610

    Welcome to Rigbie Bluff, where coastal charm meets modern comfort. This rare furnished 2-bedroom, 2-bath end-unit top floor condominium offers panoramic views of the upper Chesapeake Bay and Sassafras River, a deeded boat slip with boat lift, and exceptional community amenities. Situated on the third floor and perfectly positioned to capture abundant southern sunlight, this move-in-ready

    Agent Photo

    Vicky Lawson

    Long & Foster Real Estate, Inc.

    10 Ericsson Ave Unit 32, Betterton, MD 21610
  • /20

    $1,300

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Condo for Rent

    200 Cannon St Unit 1A, Chestertown, MD 21620

    Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 person. No pets or smoking.

    200 Cannon St Unit 1A, Chestertown, MD 21620
  • /79

    $825,000

    Sold May 26, 2026

    25475 Turnberry Ct, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 4,145 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 9 Days On Market

    Current Estimated Value $830,284

    Last Listing Agent Lona Todd Taylor Properties

    25475 Turnberry Ct, Chestertown, MD 21620
    • /43

      Est $347,018

      Not Listed For Sale

      127 Cedarwood Dr, Galena, MD 21635

      • 3 Beds
      • 3 Baths
      • 1,872 Sq Ft
      • Built 2003
      127 Cedarwood Dr, Galena, MD 21635

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Dottie Walker Empower Real Estate, LLC

  • /2

    $219,000

    Under Contract
    • Land
    • 2.88 Acres
    • $76,042 per Acre

    14075 Crataegus Ct, Galena, MD 21635

    Located in the community of Gentle Winds just minutes from the Eastern Shore and 10 minutes to Middletown, Delaware, this 2.88-acre private lot is shaped like a baseball field (and approximately the same size as a professional baseball field). Enclosed by mature trees for maximum privacy and complimented by 2 large beautiful trees (similar to large bonsai trees), this land is the ideal setting

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    14075 Crataegus Ct, Galena, MD 21635
  • /10

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. Utilities included!!!A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately,

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • /2

    $45,000

    Sold Aug 31, 2026

    21183 W Sharp St, Rock Hall, MD 21661

    • Land
    • 8,712 Sq Ft
    • $225,000 per Acre

    Last Sold Summary

    Current Estimated Value $252,345

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    21183 W Sharp St, Rock Hall, MD 21661
    • /32

      Not Listed For Sale

      12442 Clark Rd, Worton, MD 21646

      12442 Clark Rd, Worton, MD 21646

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent BRIAN MORRIS The Land Group

  • /135

    $487,000

    $62K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,948 Sq Ft

    16 Howell Point Rd, Betterton, MD 21610

    Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000.Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach!This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    16 Howell Point Rd, Betterton, MD 21610
  • /13

    $1,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • House for Rent

    206 N Mill St, Chestertown, MD 21620

    Entire historic home in downtown Chestertown for a great price!! One block from shops, restaurants, galleries and much more. Large living room opens to eat-in kitchen with beautiful countertops and all stainless steel appliances. Half bath and laundry on main floor and 3 bedrooms and two full bathrooms upstairs. Hardwood floors throughout. Private backyard with fence and storage shed. Dead end

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    206 N Mill St, Chestertown, MD 21620
  • /33

    $375,000

    Sold Dec 01, 2025

    907 N Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft
    • Built 2002

    Last Sold Summary

    • $204/SF
    • 83 Days On Market

    Current Estimated Value $382,771

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • /57

      Est $1,106,907

      Not Listed For Sale

      13931 Eagles Nest Farm Ln, Still Pond, MD 21667

      • 4 Beds
      • 2 Baths
      • 1,848 Sq Ft
      • Built 1987
      13931 Eagles Nest Farm Ln, Still Pond, MD 21667

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

  • /3

    $699,900

    $50K PRICE DROP
    • Land
    • 41,817 Sq Ft
    • $729,062 per Acre

    5738 Beach Rd, Rock Hall, MD 21661

    Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breathtaking panoramic views stretching across the Chesapeake Bay to the iconic Bay Bridge and the distant Baltimore skyline, creating an ever-changing backdrop of stunning sunrises, sailboats, and shimmering waterfront

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    5738 Beach Rd, Rock Hall, MD 21661
  • /7

    $1,495 Per Month

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

    104 Maple Ave Unit 3, Chestertown, MD 21620

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 3, Chestertown, MD 21620
  • /16

    $150,000

    Sold May 15, 2026

    107 Conley Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $132/SF
    • 32 Days On Market

    Current Estimated Value $159,425

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, Chestertown, MD 21620
    • /59

      Est $1,463,147

      Not Listed For Sale

      28808 Belchester Rd, Kennedyville, MD 21645

      • 4 Beds
      • 3 Baths
      • 2,508 Sq Ft
      • Built 1933
      28808 Belchester Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Patricia Kern Gunther-McClary Real Estate

  • /8

    $55,000

    • 1 Bed
    • 1 Bath
    • 180 Sq Ft

    34155 Bradford Johnson Rd, Galena, MD 21635

    Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

    Agent Photo

    Joe Howerton

    Taylor Properties

    34155 Bradford Johnson Rd, Galena, MD 21635
  • /12

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Condo for Rent

    104 Maple Ave Unit 4, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm.This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 4, Chestertown, MD 21620
  • /41

    $525,000

    Sold Aug 16, 2026

    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,824 Sq Ft
    • Built 2000

    Last Sold Summary

    • $186/SF
    • 1 Day On Market

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620
    • /21

      Est $346,953

      Not Listed For Sale

      11219 Station Rd, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 2006
      11219 Station Rd, Worton, MD 21678

      Last Sold Summary

      • 115 Days On Market

      Last Listing Agent Scott Saunders Coldwell Banker Waterman Realty

  • /33

    $398,000

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    200 School St, Millington, MD 21651

    Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite.Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial, tucked into a peaceful country setting while still offering convenient access to points north. From quiet mornings to busy afternoons and relaxed evenings, this home provides a warm, easy-flowing layout designed for everyday

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    200 School St, Millington, MD 21651
  • /16

    $350,000

    Sold Mar 05, 2026

    21111 Texas Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $354,405

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • /39

      Est $277,488

      Not Listed For Sale

      389 Cypress St, Millington, MD 21651

      • 3 Beds
      • 1.5 Baths
      • 2,296 Sq Ft
      • Built 1900
      389 Cypress St, Millington, MD 21651

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /2

    $59,000

    $5K PRICE DROP
    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Unsuccessful land evaluation

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • /36

    $1,095,000

    Sold Jun 02, 2026

    12400 Woods Rd, Worton, MD 21678

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft
    • Built 1985

    Last Sold Summary

    • $563/SF
    • 4 Days On Market

    Current Estimated Value $1,073,299

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12400 Woods Rd, Worton, MD 21678
    • /54

      Est $523,920

      Not Listed For Sale

      14180 Kentmore Park Rd, Kennedyville, MD 21645

      • 4 Beds
      • 2 Baths
      • 2,103 Sq Ft
      • Built 1958
      14180 Kentmore Park Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Patricia Kern Gunther-McClary Real Estate

  • /32

    $897,000

    • 3 Beds
    • 2.5 Baths
    • 2,448 Sq Ft

    25411 Paradise Point Ln, Worton, MD 21678

    Waterfront Living at the Head of Still Pond CreekWell-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay.Conveniently located with very easy access to Chestertown and

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    25411 Paradise Point Ln, Worton, MD 21678
  • /2

    $85,000

    Sold Jun 30, 2026

    108 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1957

    Last Sold Summary

    • 40% Below List Price
    • $93/SF
    • 6 Days On Market

    Current Estimated Value $117,450

    Last Listing Agent David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
    • /29

      Est $302,714

      Not Listed For Sale

      7425 Wilkins Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,341 Sq Ft
      • Built 1962
      7425 Wilkins Ln, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

  • /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    108 Little Harbor Way, Chestertown, MD 21620
  • /2

    $1,825,000

    Sold Jul 30, 2026

    11500 Possum Hollow Rd, Worton, MD 21678

    • 3 Beds
    • 3.5 Baths
    • 3,138 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Above List Price
    • $582/SF
    • 3 Days On Market

    Current Estimated Value $1,510,685

    Last Listing Agent Brett Schrader Taylor Properties

    11500 Possum Hollow Rd, Worton, MD 21678
    • /6

      Est $41,438

      Not Listed For Sale

      31612 Olivet Cir, Galena, MD 21635

      31612 Olivet Cir, Galena, MD 21635

      Last Sold Summary

      • 153 Days On Market

      Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

Showing Results 1 - 40, Page 1 of 18

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