12,095

Kent County, MD Homes

Section Image
  • /90

    $585,000 Sold Nov 13, 2025

    • 5,576 Sq Ft
    • $105/SF
    • 54 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2008

    103 Adela Way, Chestertown, MD 21620

    Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which flows directly into the rest of the house. Moving forward is the very large den/ family room that

    Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • /9

      Est $359,170 Not Listed For Sale

      10578 Chesterville Forest Rd, Millington, MD 21651

      10578 Chesterville Forest Rd, Millington, MD 21651
  • /29

    $470,000

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • /59

    $775,000 Sold Nov 08, 2025

    • 2,836 Sq Ft
    • $273/SF
    • 0 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1900

    8293 Brices Mill Rd, Chestertown, MD 21620

    Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • /35

      Not Listed For Sale

      • 2 Beds

      11430 Lynch Rd, Worton, MD 21678

      11430 Lynch Rd, Worton, MD 21678
  • /50

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 2,944 Sq Ft

    21163 Chesapeake Ave, Rock Hall, MD 21661

    This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split

    Doug Ashley Doug Ashley Realtors, LLC

    21163 Chesapeake Ave, Rock Hall, MD 21661
  • /29

    $306,000 Sold Nov 07, 2025

    • 1,312 Sq Ft
    • $233/SF
    • 117 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    26959 Branchtown Rd, Worton, MD 21678

    Updated in 2024 by a loving family member & their licensed professional! This charming 3-bedroom, 2-bath home offers a perfect blend of modern updates and country serenity. The main level features a convenient first-floor bedroom and full bath, ideal for aging in place. Enjoy stylish & durable vinyl plank flooring throughout and soaring cathedral ceilings upstairs that create an airy, open feel.

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    26959 Branchtown Rd, Worton, MD 21678
    • /52

      Est $431,468 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,520 Sq Ft

      5785 Liberty St, Rock Hall, MD 21661

      5785 Liberty St, Rock Hall, MD 21661
  • /43

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 3,046 Sq Ft

    25999 Lambs Meadow Rd, Worton, MD 21678

    Originally built with handcrafted bricks in 1782, this Flemish Bond Georgian Colonial home is the embodiment of simple elegance. Restored with the utmost historical respect in the mid-1980’s with handcrafted oak windows and mahogany doors with period hardware and modernized with preservation-sensitive practices and materials over the past eight years by the current stewards of the home, step into

    Liddy Campbell TTR Sotheby's International Realty

    25999 Lambs Meadow Rd, Worton, MD 21678
  • /36

    $795,000 Sold Nov 07, 2025

    • 2,736 Sq Ft
    • $291/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    201 Radcliffe Dr, Chestertown, MD 21620

    Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
    • /35

      Est $275,036 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft

      120 N Main St, Galena, MD 21635

      120 N Main St, Galena, MD 21635
  • /24

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Cross Street Realtors LLC

    109 S College Ave, Chestertown, MD 21620
  • /93

    $1,550,000 Sold Nov 07, 2025

    • 4,167 Sq Ft
    • $372/SF
    • 150 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1952

    7961 Quaker Neck Rd, Chestertown, MD 21620

    **Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of

    Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
    • /24

      Est $296,112 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,220 Sq Ft

      5788 Liberty St, Rock Hall, MD 21661

      5788 Liberty St, Rock Hall, MD 21661
  • /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /37

    $380,000 Sold Nov 06, 2025

    • 1,600 Sq Ft
    • $238/SF
    • 63 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    1 Bayview Rd Unit 11A, Betterton, MD 21610

    FULLY-FURNISHED WATERFRONT HOME FOR SALE: Enjoy the best of Eastern Shore living in this fully furnished 2-bedroom, 2-bath waterfront home, just steps from a 600-foot sandy beach and the association dock. A 30-foot-wide veranda offers panoramic Chesapeake Bay views—perfect for morning coffee, a crab feast, or sunset cocktail gatherings. Inside, hardwood floorings flow through the main living

    Thomas Lee EXP Realty, LLC

    1 Bayview Rd Unit 11A, Betterton, MD 21610
    • /44

      Est $531,272 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,932 Sq Ft

      218 Camelot Dr, Chestertown, MD 21620

      218 Camelot Dr, Chestertown, MD 21620
  • /46

    $619,000

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • /23

    $317,000 Sold Nov 06, 2025

    • 1,300 Sq Ft
    • $244/SF
    • 214 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    4921 Piney Neck Rd, Rock Hall, MD 21661

    Welcome to your new home in the historic harbor town of Rock Hall! Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and color palette. Every appliance and ammenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen

    Andy Batch Keller Williams Select Realtors of Annapolis

    4921 Piney Neck Rd, Rock Hall, MD 21661
    • /33

      Est $678,845 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      209 Landing Ln, Chestertown, MD 21620

      209 Landing Ln, Chestertown, MD 21620
  • /56

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,234 Sq Ft

    32155 River Rd, Millington, MD 21651

    Welcome to your thoughtfully renovated and updated waterfront retreat on the Chester River! This spacious 3–4 bedroom, 2,234square foot, home sitting on 0.587 acres with 75 feet of direct waterfront, offering a rare blend of privacy, natural beauty, andconvenience.The property delivers the best of Eastern Shore living—perfect for boating, fishing, kayaking, or simply relaxing

    Lawrence Lessin Save 6, Incorporated

    32155 River Rd, Millington, MD 21651
  • /39

    $695,000 Sold Nov 05, 2025

    • 2,492 Sq Ft
    • $279/SF
    • 7 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1900

    110 S Mill St, Chestertown, MD 21620

    Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront.The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for

    John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
    • /18

      Est $423,082 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft

      21991 Lovers Ln, Rock Hall, MD 21661

      21991 Lovers Ln, Rock Hall, MD 21661
  • /35

    $465,000

    • 3 Beds
    • 4 Baths
    • 1,881 Sq Ft

    5829 N Main St, Rock Hall, MD 21661

    Fully renovated, spacious home with commercial or residential zoning use. Extensive upgrades, all new appliances, bathrooms, engineered hardwood floors, hardiplank exterior, new roof, and much more! This home has been tastefully finished with high-end new and selective antiques, echoing a coastal antique style. You'll love cooking and entertaining in the fully updated kitchen and dining area,

    Lynn Hilfiker Gunther-McClary Real Estate

    5829 N Main St, Rock Hall, MD 21661
  • /48

    $535,000 Sold Nov 05, 2025

    • 1,148 Sq Ft
    • $466/SF
    • 168 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1890

    5179 Quaker Neck Rd, Chestertown, MD 21620

    $20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized,

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • /36

      Est $619,609 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,652 Sq Ft

      22768 McKinleyville Rd, Rock Hall, MD 21661

      22768 McKinleyville Rd, Rock Hall, MD 21661
  • /71

    $515,000

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    *Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • /31

    $435,000 Sold Nov 03, 2025

    • 2,162 Sq Ft
    • $201/SF
    • 22 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    25800 Collins Ave, Chestertown, MD 21620

    Price improvement! Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
    • /12

      Est $228,474 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,426 Sq Ft

      20790 Mercer Ave, Rock Hall, MD 21661

      20790 Mercer Ave, Rock Hall, MD 21661
  • /42

    $519,999

    • 5 Beds
    • 2.5 Baths
    • 2,660 Sq Ft

    31569 Jim Davis Rd, Galena, MD 21635

    Don't miss this incredible opportunity to own your own piece of Eastern Shore! Nestled on 2 acres at 31569 Jim Davis Rd. Galena, MD, this charming property offers peace, privacy, and plenty of room to grow. Featuring spacious living areas, a beautiful rural setting, and endless potential for outdoor enjoyment - this home is ready for it's next owner to make it their own. Welcome to your country

    Lori Cichocki-Leonardi Remax Vision

    31569 Jim Davis Rd, Galena, MD 21635
  • /36

    $395,000 Sold Nov 03, 2025

    • 2,074 Sq Ft
    • $190/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    5648 S Main St, Rock Hall, MD 21661

    Welcome to 5648 S. Main Street, a charming, original Rock Hall home. The owners took great care to throughly update the home over the years, and preserve the original style. The moulding was hand routed to match the original style of older homes in Rock Hall. Throughout the home the wood floors flow nicely with the wooden ceilings and custom built-ins. Downstairs, there is a full bathroom, and a

    Julia Hilfiker Gunther-McClary Real Estate

    5648 S Main St, Rock Hall, MD 21661
    • /44

      Est $463,495 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft

      204 N Mill St, Chestertown, MD 21620

      204 N Mill St, Chestertown, MD 21620
  • /21

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,247 Sq Ft

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to the newly renovated 21424 Catholic Ave! Situated on a large in-town parcel, the largest residential lot on Catholic Ave. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT and engineered hardwood flooring. The welcoming living space contains original wood accents, adding much charm to this newly updated home. There are three bedrooms,

    Lynn Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • /4

    $60,000 Sold Oct 31, 2025

    • Land
    • 1 Acre
    • $60,000 per Acre
    • 96 Days On Market

    0 Station Rd, 2, Kennedyville, MD 21678

    Cleared and level lot in a secluded and rural setting on the beautiful Eastern Shore. Perc approved (2015). Backs to trees. bring your plans for your dream home!

    Michele Palmer Doug Ashley Realtors, LLC

    0 Station Rd, 2, Kennedyville, MD 21678
    • /7

      Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft

      128 N Queen St, Chestertown, MD 21620

      128 N Queen St, Chestertown, MD 21620
  • /38

    $499,999 Pending

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 AcresDiscover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout.Step inside to find a

    Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
  • /56

    $520,000 Sold Oct 30, 2025

    • 1,820 Sq Ft
    • $286/SF
    • 62 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1998

    11307 Urieville Ln, Worton, MD 21678

    Your private retreat awaits! Nestled on nearly 4 acres in Worton, Maryland, this beautifully renovated Cape Cod offers the perfect blend of space, comfort, and functionality. Featuring four spacious bedrooms and two full bathrooms, this home is ideal for multi-generational living or a growing family with two main-level bedrooms and a full bath. Step inside to find new LVP flooring, brand new

    Crystal Smith RE/MAX Executive

    11307 Urieville Ln, Worton, MD 21678
    • /18

      Est $253,118 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,088 Sq Ft

      114 W Cross St, Galena, MD 21635

      114 W Cross St, Galena, MD 21635
  • /28

    $469,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,129 Sq Ft

    21090 W Sharp St Unit 112, Rock Hall, MD 21661

    Spectacular Chesapeake Bay waterview condo located in the heart of Rock Hall. Beautiful upgrades include LVP flooring, tile bathrooms, kitchen cabinets, backsplash, granite countertops and appliances, plus new electric fireplace. Relax on the recently refinished Bayview deck or cuddle up next to the fireplace. The convenience of condo living lets you enjoy all the festivals and fun Rock Hall has

    Cindy Genther Rock Hall Properties Real Estate

    21090 W Sharp St Unit 112, Rock Hall, MD 21661
  • /29

    $264,900 Sold Oct 30, 2025

    • 1,110 Sq Ft
    • $239/SF
    • 23 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1962

    24415 Chestertown Rd, Chestertown, MD 21620

    Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply

    Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

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