6,895

Chestertown, MD Homes

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  • /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
    • /41

      Est $398,920 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

    $5,000

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

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 7/15/2025 @ 10:00 AM. Bidding ends 7/17/2025 @ 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 Worton Creek Marina, and all the

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, 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
    • /54

      Est $585,641 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
  • /7

    $5,000

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

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 7/15/2025 @ 10:00 AM. Bidding ends 7/17/2025 @ 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 all the attractions in Chestertown,

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, 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
    • /36

      Est $349,799 Not Listed For Sale

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

      10656 Millbrook Dr, Chestertown, MD 21620

      10656 Millbrook 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
  • /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
    • /34

      Est $403,804 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      202 Byford Dr, Chestertown, MD 21620

      202 Byford 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
  • /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
    • /69

      Est $1,256,646 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      9088 Point Ln, Chestertown, MD 21620

      9088 Point Ln, 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
    • /22

      Est $482,907 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft

      7920 Carriage Ln, Chestertown, MD 21620

      7920 Carriage Ln, 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
    • /34

      Est $439,590 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft

      209 E Campus Ave, Chestertown, MD 21620

      209 E Campus Ave, 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
    • /55

      Est $630,194 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,952 Sq Ft

      25819 Collins Ave, Chestertown, MD 21620

      25819 Collins Ave, Chestertown, 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
    • /64

      Est $1,660,407 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      9545 Chantilly Farm Ln, 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
    • /46

      Est $564,900 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,264 Sq Ft

      7898 Radcliffe Rd, Chestertown, MD 21620

      7898 Radcliffe Rd, 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
    • /44

      Est $654,295 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      5564 Quaker Neck Landing 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
    • /27

      Est $315,402 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      10791 Foreston Rd, Chestertown, MD 21620

      10791 Foreston Rd, 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
    • /24

      Est $422,231 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,316 Sq Ft

      247 Devon Dr, Chestertown, MD 21620

      247 Devon Dr, 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
    • /49

      Est $822,497 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,382 Sq Ft

      10761 Kasota Rd, Chestertown, MD 21620

      10761 Kasota 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
    • /50

      Est $726,942 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,147 Sq Ft

      8930 Orchard Dr, Chestertown, MD 21620

      8930 Orchard Dr, Chestertown, MD 21620
  • /25

    $430,000 Sold Sep 11, 2024

    • 2,240 Sq Ft
    • $192/SF
    • 42 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2014

    8500 Broad Neck Rd, Chestertown, MD 21620

    This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2 pantry's. This home has a Large living and Dining room too! The 'Florida Sunroom' allows could be an office or a place to read a book in the sunshine and the

    Ginny Dauses Coldwell Banker Waterman Realty

    8500 Broad Neck Rd, Chestertown, MD 21620
    • /50

      Est $462,370 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
  • /29

    $345,000 Sold Sep 10, 2024

    • 1,566 Sq Ft
    • $220/SF
    • 28 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    21199 Iowa Ave, Chestertown, MD 21620

    Charming Renovated Ranch Home in Tolchester EstatesWelcome to this beautifully renovated ranch home nestled in Tolchester Estates. Recently updated, this home offers a perfect blend of modern amenities and tranquil surroundings.As you step inside, you'll notice the new flooring throughout and fresh paint that creates a bright and inviting atmosphere. The remodeled kitchen is a chef's

    Thomas Huston Real Broker LLC

    21199 Iowa Ave, Chestertown, MD 21620
    • /26

      Est $521,756 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,216 Sq Ft

      207 E Campus Ave, Chestertown, MD 21620

      207 E Campus Ave, Chestertown, MD 21620
  • /26

    $355,000 Sold Sep 06, 2024

    • 1,344 Sq Ft
    • $264/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2015

    10719 Mallard Point Rd, Chestertown, MD 21620

    Welcome to this charming raised rancher, built in 2015and located in the water-privileged community of Chesapeake Landing. This beautiful home features 3 spacious bedrooms and a desirable split bedroom floor plan, offering privacy and comfort for all. The open floor plan creates a seamless flow from room to room, enhancing both functionality and style, and offers a large kitchen with stainless

    Sarah King Cross Street Realtors LLC

    10719 Mallard Point Rd, Chestertown, MD 21620
    • /22

      Est $212,249 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

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