7,034

Homes in ZIP Code 21620

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    • /28

      Est $245,923 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft

      545 High St, Chestertown, MD 21620

      545 High St, Chestertown, MD 21620
  • /66

    $5,500,000 Under Contract

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Lands End Rd, Chestertown, MD 21620

    Beautifully situated on the east fork of Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. Sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, 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
    • /47

      Est $324,870 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      9041 S Bayview Dr, Chestertown, MD 21620

      9041 S Bayview Dr, Chestertown, MD 21620
  • /37

    $309,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,272 Sq Ft

    23315 Sandpiper Rd, Chestertown, MD 21620

    Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax

    Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, 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
    • /69

      Est $1,171,094 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft

      10069 John Carvill Rd, Chestertown, MD 21620

      10069 John Carvill Rd, Chestertown, MD 21620
  • /27

    $285,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft

    100 Acorn Dr, Chestertown, MD 21620

    Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, 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
    • /45

      Est $416,734 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, 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
    • /44

      Est $400,355 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      111 Manor Ave, Chestertown, MD 21620

      111 Manor Ave, Chestertown, MD 21620
  • /4

    $5,000 Pending

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

    0 Towhee Rd 21620

    ONLINE AUCTION: Bidding begins 5/13/2025 @ 10:00 AM. Bidding ends 5/15/2025 @ 12:40 PM. List Price is Suggested Opening Bid. 4 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 Chestertown,

    Adam Shpritz Ashland Auction Group LLC

    0 Towhee Rd 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
    • /40

      Est $432,541 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      8610 Camp Rd, Chestertown, MD 21620

      8610 Camp Rd, Chestertown, MD 21620
  • /43

    $305,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft

    10705 Millbrook Dr, Chestertown, MD 21620

    Welcome to 10705 Millbrook Drive, a charming Cape Cod-style home located in the desirable Chesapeake Landing community. This 3-bedroom, 2-bathroom residence offers comfortable living with modern updates, including bamboo flooring and a high-efficiency water heater. The open floor plan is perfect for entertaining, with a spacious living area and well-appointed kitchen featuring Meganite

    Edward Kowalski EXP Realty, LLC

    10705 Millbrook Dr, Chestertown, MD 21620
  • /31

    $394,000 Sold Sep 26, 2024

    • 1,616 Sq Ft
    • $244/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    211 Byford Dr, Chestertown, MD 21620

    Welcome to a hidden oasis, just steps from Downtown Chestertown! This Byford Heights home has been meticulously maintained; featuring main level living, attached oversized garage, home office space, an ample screen porch, fully fenced back yard, and in-ground pool. And, untouched hardwood floors just begging to be uncovered! Open House on Saturday the 24th from 1-3p.

    Liddy Campbell TTR Sotheby's International Realty

    211 Byford Dr, Chestertown, MD 21620
    • /44

      Est $628,442 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft

      207 N Queen St, Chestertown, MD 21620

      207 N Queen St, Chestertown, MD 21620
  • /4

    $5,000 Pending

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

    0 Bunting Rd, 6, Fairlee, MD 21620

    ONLINE AUCTION: Bidding begins 5/13/2025 @ 10:00 AM. Bidding ends 5/15/2025 @ 12:35 PM. List Price is Suggested Opening Bid. 4 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 Chestertown,

    Adam Shpritz Ashland Auction Group LLC

    0 Bunting Rd, 6, Fairlee, MD 21620
  • /50

    $1,300,000 Sold Sep 24, 2024

    • 3,345 Sq Ft
    • $389/SF
    • 18 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1943

    10705 Tilden Ln, Chestertown, MD 21620

    Enjoy picturesque water views of Worton Creek from every room. Situated on over 2.5 acres of well maintained and landscaped property with irrigation and enjoy the water from the private pier with 5 ft. of depth and only minutes by boat to the Chesapeake Bay or relax by the water side pool. This five bedroom three bath home has an apartment above the detached 3 car garage with a full kitchen,

    Glenn Sutton TTR Sotheby's International Realty

    10705 Tilden Ln, Chestertown, MD 21620
    • /50

      Est $736,095 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,736 Sq Ft

      201 Radcliffe Dr, Chestertown, MD 21620

      201 Radcliffe Dr, Chestertown, MD 21620
  • /10

    $213,000

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    236 Merganser Dr, Chestertown, MD 21620

    Looking for that off the beaten path property, here it is! Property located in a water privileged community on the Chester River, access at end of road. Home offers a 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Subject is sold in as is condition, seller nor buyer can make any repairs. Property is owned by the US Dept. of HUD, HUD Case #241-770004. Insurability Code:

    Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
  • /24

    $250,000 Sold Sep 23, 2024

    • 864 Sq Ft
    • $289/SF
    • 115 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1930

    235 Burchard Sawmill Rd, Chestertown, MD 21620

    Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new

    John Carroll Village Real Estate Company LLC

    235 Burchard Sawmill Rd, Chestertown, MD 21620
    • /29

      Est $170,392 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft

      21715 Tolchester Beach Rd, Chestertown, MD 21620

      21715 Tolchester Beach Rd, Chestertown, MD 21620
  • /5

    $10,000 Pending

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

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Deposit: $5,000. Lot of land located in the Chestertown area of Kent County, MD.JUST MINUTES to the many attractions of the downtown Chestertown area. Easy access to major traffic artery Fairlee Rd. +/- 15,000 SF. Vacant lot of land.

    Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
  • /27

    $269,900 Sold Sep 20, 2024

    • 1,232 Sq Ft
    • $219/SF
    • 70 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    10572 Klamath Rd, Chestertown, MD 21620

    Sellers offering $10,000 credit toward cosmetic repairs or settlement!!!! Cute rancher in Chesapeake Landing. Nice front porch. Large living room with a woodstove with brick hearth and mantle. Laminate flooring throughout most of the house. 3 bedrooms and 2 full baths. Guest bathroom is a great size and also contains the washer dryer. Stainless appliances. Kitchen Island. Nice sized lot

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    10572 Klamath Rd, Chestertown, MD 21620
    • /30

      Est $351,709 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft

      215 Devon Dr, Chestertown, MD 21620

      215 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 5/13/2025 @ 10:00 AM. Bidding ends 5/15/2025 @ 12:30 PM. List Price is Suggested Opening Bid. 4 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 the

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /54

    $450,000 Sold Sep 16, 2024

    • 1,428 Sq Ft
    • $315/SF
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    109 Birch Run Rd, Chestertown, MD 21620

    This 3 bedroom 2.5 bathroom Cape Cod has been recently updated and is located on one of Chestertown’s most desired streets. The sunroom provides a wonderful connection with nature. The newly added en suite bathroom with double vanity for the primary bedroom adds convenience and luxury. Dual zoned A/C ensures a refreshing summer and the wood burning fireplace provides a great extra boost of heat

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    109 Birch Run Rd, Chestertown, MD 21620
    • /69

      Est $498,312 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft

      110 Camelot Dr, Chestertown, MD 21620

      110 Camelot Dr, 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 5/13/2025 @ 10:00 AM. Bidding ends 5/15/2025 @ 12:25 PM. List Price is Suggested Opening Bid. 4 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 Chestertown,

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /45

    $440,000 Sold Sep 16, 2024

    • 2,128 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    105 Coleman Dr, Chestertown, MD 21620

    KINGS COURT! This Colonial, sited on an acre of land, is move-in ready and boasts so many wonderful features! Here are just some that are sure to pique your interest! Freshly painted; gleaming floors; stainless steel appliances; lots of counter and cabinet space; breakfast room; separate pantry space; family room with large picture window; fireplace with stainless steel liner; newer LG washer and

    Jenn Klarman Long & Foster Real Estate, Inc.

    105 Coleman Dr, Chestertown, MD 21620
    • /31

      Est $322,317 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft

      103 Trafford Dr, Chestertown, MD 21620

      103 Trafford Dr, 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
  • /48

    $486,000 Sold Sep 13, 2024

    • 2,864 Sq Ft
    • $170/SF
    • 52 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1989

    112 Sheaffer Rd, Chestertown, MD 21620

    Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort.Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the

    Retha Arrabal Doug Ashley Realtors, LLC

    112 Sheaffer Rd, Chestertown, MD 21620
    • /41

      Est $387,547 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,537 Sq Ft

      208 N Mill St, Chestertown, MD 21620

      208 N Mill St, 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
  • /17

    $260,000 Sold Sep 13, 2024

    • 826 Sq Ft
    • $315/SF
    • 298 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    305 Pine Tree Rd, Chestertown, MD 21620

    BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main

    Kaitlyn Collins Benson & Mangold, LLC

    305 Pine Tree Rd, Chestertown, MD 21620
    • /54

      Est $580,090 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,659 Sq Ft

      123 N Queen St, Chestertown, MD 21620

      123 N Queen St, Chestertown, MD 21620

Showing Results 321 - 360, Page 9 of 18

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