6,914

Kent, MD Homes

Section Image
    • /50

      Est $488,066 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,204 Sq Ft

      246 Devon Dr, Chestertown, MD 21620

      246 Devon Dr, Chestertown, MD 21620
  • /6

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:20 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to Worton Creek Marina, and all

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /37

    $600,000 Sold Nov 01, 2024

    • 3,240 Sq Ft
    • $185/SF
    • 6 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1900

    208 N Queen St, Chestertown, MD 21620

    Welcome to this charming Colonial four square home, nestled on the north end of Queen Street in Chestertown's historic district, just two blocks from the river. Step inside to find a beautifully remodeled kitchen, updated living room, dining room, den which doubles as a library or family room, and a sunlit porch, all on the main level. With high ceilings, intricate detailing, and polished

    Jody Baker Cross Street Realtors LLC

    208 N Queen St, Chestertown, MD 21620
    • /22

      Est $213,056 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      614 High St, Chestertown, MD 21620

      614 High St, Chestertown, MD 21620
  • /7

    $5,000

    • Land
    • 0.37 Acre
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:40 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /17

    $275,000 Sold Oct 29, 2024

    • 1,317 Sq Ft
    • $209/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    24105 Chestertown Rd, Chestertown, MD 21620

    Custom quality-built 1970 brick rancher on 0.46 acre lot just outside Chestertown. House features original hardwood floors, stained woodwork, trim moldings and hand built wood kitchen cabinetry. The living room has large bay window and brick wood burning fireplace. Full unfinished basement offers lots of extra storage space with room to expand. Attached carport with storage closets and

    Yvonne Andres Keller Williams Select Realtors of Annapolis

    24105 Chestertown Rd, Chestertown, MD 21620
    • /21

      Est $204,797 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      612 High St, Chestertown, MD 21620

      612 High St, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 0.09 Acre
    • $111,111 per Acre

    0 Texas Ave, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    0 Texas Ave, Chestertown, MD 21620
  • /6

    $615,000 Sold Oct 25, 2024

    • 2,627 Sq Ft
    • $234/SF
    • 2 Beds
    • 1.5 Baths
    • Built 1998

    305 Hickory Ln, Chestertown, MD 21620

    Perfect Rabbit Creek and Chester River Get-A-Way. Ideal for an avid sportsman, outdoorsman or nature lover, offering you extensive frontage on Rabbit Creek leading out into the Chester River situated on 20 private acres. Offering a serene setting with a good mix of marshland, woods, uplands and a private pond. Bring your canoe/kayak/ john boat/ fishing pole and deer stand. These properties

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    305 Hickory Ln, Chestertown, MD 21620
    • /72

      Est $877,737 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft

      7996 Aldan Dr, Chestertown, MD 21620

      7996 Aldan Dr, Chestertown, MD 21620
  • /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /41

    $435,000 Sold Oct 24, 2024

    • 3,000 Sq Ft
    • $145/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    100 Foxview Ct, Chestertown, MD 21620

    Nestled at the end of a serene cul-de-sac in the desirable Crestview neighborhood, this expansive 3,000-square-foot home resides on a generous 0.63-acre lot, boasting a delightful fusion of comfort and sophistication. Adorned with meticulously landscaped grounds, the outdoor space features a charming fish pond complemented by water features, a convenient shed, an expansive patio, and a deck

    Sarah Ulrick Rock Hall Properties Real Estate

    100 Foxview Ct, Chestertown, MD 21620
    • /22

      Est $291,078 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft

      211 Manor Ave, Chestertown, MD 21620

      211 Manor Ave, Chestertown, MD 21620
  • /37

    $675,000 Sold Oct 21, 2024

    • 2,128 Sq Ft
    • $317/SF
    • 1 Day On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1961

    319 Fairview Dr, Chestertown, MD 21620

    Live authentically. Welcome to your dream waterfront oasis! This charming home, nestled in a serene spot near historic Chestertown, offers the perfect blend of community amenities and private retreat. Boasting three bedrooms and two beautifully designed bathrooms, this property is the epitome of move-in ready.Step inside to discover a host of updates that ensure modern convenience without

    Michelle Schwab Krauss Real Property Brokerage

    319 Fairview Dr, Chestertown, MD 21620
    • /56

      Est $800,343 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,414 Sq Ft

      10258 Mill Hollow Ln, Chestertown, MD 21620

      10258 Mill Hollow Ln, Chestertown, MD 21620
  • /22

    $287,000 Sold Oct 18, 2024

    • 1,420 Sq Ft
    • $202/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    235 Island Lark Way, Chestertown, MD 21620

    Village at Chestertown end-unit two-story townhome with 3 bedrooms and 2.5 bathrooms. The spacious first floor is open-concept consisting of a kitchen, living, and dining area. The thoughtfully designed kitchen comes with stylish gray cabinets, stainless steel appliances, a storage closet and a peninsula island that seats three. The first floor also offers a spacious living area and powder room.

    Derek Eisenberg Continental Real Estate Group

    235 Island Lark Way, Chestertown, MD 21620
    • /12

      Est $760,525 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft

      8042 Brices Mill Rd, Chestertown, MD 21620

      8042 Brices Mill Rd, Chestertown, MD 21620
  • /4

    $422,000 Sold Oct 18, 2024

    • 1,600 Sq Ft
    • $264/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    231 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM 2 BATH RANCHER. OPEN FLOOR PLAN. NEW CONSTRUCTION TO START 2024. 1600SF ON 1 ACRE LOT

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    231 Blakefield Dr, Chestertown, MD 21620
    • /20

      Est $338,929 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      5772 Johnsontown Rd, Chestertown, MD 21620

      5772 Johnsontown Rd, Chestertown, MD 21620
  • /48

    $260,000 Sold Oct 18, 2024

    • 1,150 Sq Ft
    • $226/SF
    • 263 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1949

    9020 Cumberland St, Chestertown, MD 21620

    Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    9020 Cumberland St, Chestertown, MD 21620
    • /17

      Est $268,601 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,237 Sq Ft

      10755 Glenola Rd, Chestertown, MD 21620

      10755 Glenola Rd, Chestertown, MD 21620
  • /65

    $950,000 Sold Oct 17, 2024

    • 4,730 Sq Ft
    • $201/SF
    • 110 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    7755 Waterview Ln, Chestertown, MD 21620

    This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7755 Waterview Ln, Chestertown, MD 21620
    • /25

      Est $361,367 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      8550 Caulks Field Rd, Chestertown, MD 21620

      8550 Caulks Field Rd, Chestertown, MD 21620
  • /76

    $1,362,500 Sold Oct 16, 2024

    • 5,195 Sq Ft
    • $262/SF
    • 457 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1760

    201 N Water St, Chestertown, MD 21620

    SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified

    Nancy McGuire Maryland Heritage Properties

    201 N Water St, Chestertown, MD 21620
    • /42

      Est $335,509 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,855 Sq Ft

      626 High St, Chestertown, MD 21620

      626 High St, Chestertown, MD 21620
  • /22

    $565,000 Sold Oct 07, 2024

    • 1,146 Sq Ft
    • $493/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1870

    125 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience.Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just

    John Burke Gunther-McClary Real Estate

    125 High St, Chestertown, MD 21620
    • /28

      Est $272,683 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      403 E Campus Ave, Chestertown, MD 21620

      403 E Campus Ave, Chestertown, MD 21620
  • /27

    $165,000 Sold Oct 04, 2024

    • 1,232 Sq Ft
    • $134/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21320 Persimmon Dr, Chestertown, MD 21620

    Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just the answer. Close to the Bay and all Tolchester offers from it's marina, Shanty beach bar and the best spot for an incredible sunset. Tolchester Village offers the perfect location for those looking for a summer retreat or full

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    21320 Persimmon Dr, Chestertown, MD 21620
    • /8

      Est $453,959 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      219 Philosophers Terrace, Chestertown, MD 21620

      219 Philosophers Terrace, Chestertown, MD 21620
  • /36

    $380,000 Sold Oct 03, 2024

    • 1,625 Sq Ft
    • $234/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    23118 Raleigh Rd, Chestertown, MD 21620

    Welcome to this beautifully updated rancher, offering a perfect blend of classic charm and modern amenities. This home boasts an oversized detached 2-car garage and an inviting in-ground saltwater pool. Inside, you'll find two fully remodeled bathrooms, stunning hardwood floors, and a back screened-in porch where you can relax and enjoy serene country views. Recent upgrades include a newer HVAC

    Kaitlyn Collins Benson & Mangold, LLC

    23118 Raleigh Rd, Chestertown, MD 21620
    • /4

      Est $499,846 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,693 Sq Ft

      928 Gateway Dr, Chestertown, MD 21620

      928 Gateway Dr, Chestertown, MD 21620
  • /13

    $749,000 Sold Oct 01, 2024

    • 3,322 Sq Ft
    • $225/SF
    • 3 Beds
    • 2 Baths
    • Built 1966

    7694 Waterview Ln, Chestertown, MD 21620

    Prepare to be wowed! Stunning house in Country Club Estates. Less than 2 miles from Chestertown and close to the Chester River. One floor living. Large rear and side yards. Easy flow floor plan with spacious rooms. Plenty of storage space. Nothing needed, just bring your suitcase!

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7694 Waterview Ln, Chestertown, MD 21620
    • /34

      Est $751,925 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft

      112 S Mill St, Chestertown, MD 21620

      112 S Mill St, Chestertown, MD 21620
  • /46

    $279,000 Sold Sep 27, 2024

    • 1,456 Sq Ft
    • $192/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    9769 Augustine Herman Hwy, Chestertown, MD 21620

    Panoramic farmland views and a peaceful rural setting invite you to enjoy all that this traditional brick home has to offer. Original oak hardwood floors add classic charm to the spacious traditional floor plan, perfect for both entertaining and everyday living. A large rear-facing garage compliments the home's livability and enhances it's curb appeal. Situated on 1.38 acres, the surrounding yard

    Rosella Hunter Remax Vision

    9769 Augustine Herman Hwy, Chestertown, MD 21620
    • /40

      Est $380,211 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,790 Sq Ft

      7653 Broad Neck Rd, Chestertown, MD 21620

      7653 Broad Neck Rd, Chestertown, MD 21620
  • /26

    $398,000 Sold Sep 27, 2024

    • 1,776 Sq Ft
    • $224/SF
    • 45 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    209 Princess Anne Dr, Chestertown, MD 21620

    Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foyer, you'll immediately appreciate the spaciousness and elegance this home offers.This meticulously maintained residence boasts three comfortable bedrooms that provide ample space for relaxation and privacy. The property

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    209 Princess Anne Dr, Chestertown, MD 21620
    • /41

      Est $474,434 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft

      203 Leeds Ct, Chestertown, MD 21620

      203 Leeds Ct, Chestertown, MD 21620
  • /9

    $250,000 Sold Sep 27, 2024

    • 1,234 Sq Ft
    • $203/SF
    • 36 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    631 High St, Chestertown, MD 21620

    Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of the few homes on High Street to come with off street parking (up to 4 spaces) accessed by alley way in back. Partially fenced in back yard with privacy

    Michele Palmer Doug Ashley Realtors, LLC

    631 High St, Chestertown, MD 21620
    • /15

      Est $232,539 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft

      7509 Sunburst Ave, Chestertown, MD 21620

      7509 Sunburst Ave, Chestertown, MD 21620
  • /24

    $350,000 Sold Sep 27, 2024

    • 2,472 Sq Ft
    • $142/SF
    • 85 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    213 Devon Dr, Chestertown, MD 21620

    Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower – 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible – Be sure to step outside from the dining room through the sliding glass door into the large screened-in deck

    Christopher Buss Weichert Realtors - Blue Ribbon

    213 Devon Dr, Chestertown, MD 21620

Showing Results 401 - 440, Page 11 of 18

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