6,895

Chestertown, MD Homes

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  • /36

    $660,000 Sold Dec 16, 2024

    • 3,444 Sq Ft
    • $192/SF
    • 56 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    8774 Orchard Dr, Chestertown, MD 21620

    First time to ever be offered on the market. Nestled in a picturesque neighborhood, this contemporary home is a testament to luxury and functionality. Spanning over 3,400 square feet, this meticulously maintained home has so much to offer. Spacious Living Areas: Open-concept layout with hard wood floors, high ceilings and abundant natural light, complemented by 2 gas fireplaces for cozy

    Jennifer Thomas RE/MAX Executive

    8774 Orchard Dr, Chestertown, MD 21620
    • /28

      Est $275,451 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      124 Edmore Rd, Chestertown, MD 21620

      124 Edmore Rd, Chestertown, MD 21620
  • /2

    $30,000

    • Land
    • 1.05 Acres
    • $28,571 per Acre

    206 Burchard Sawmill Rd, Chestertown, MD 21620

    Prime 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd, this versatile property offers a fantastic opportunity to build your dream home or investment property in a peaceful, scenic setting. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown!

    DANIEL DEMERS Sell Your Home Services

    206 Burchard Sawmill Rd, Chestertown, MD 21620
  • /7

    $45,000 Sold Dec 16, 2024

    • 1,040 Sq Ft
    • $43/SF
    • 210 Days On Market
    • Built 1900

    23060 Old Fairlee Rd, Chestertown, MD 21620

    Rare opportunity in a great residential location. Spacious garage/workshop, was most recently used for storage, situated on a half acre triangular lot. Check out the many possibilities! Great investor opportunity in a beautiful neighborhood. It is the buyer's responsibility to verify with Kent County Planning and Zoning any building use or renovation plans. Garage is hooked up to electric, but

    Julia Hilfiker Gunther-McClary Real Estate

    23060 Old Fairlee Rd, Chestertown, MD 21620
    • /16

      Est $237,025 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft

      319 Round Top Rd, Chestertown, MD 21620

      319 Round Top Rd, Chestertown, MD 21620
  • /2

    $40,000

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • /27

    $495,000 Sold Dec 13, 2024

    • 1,416 Sq Ft
    • $350/SF
    • 7 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1880

    106 Church Alley, Chestertown, MD 21620

    Step into this beautifully renovated 1,416 sq. ft., 2 bedrooms, 1.5 bath home in the heart of Chestertown. The building operated as the Johnson General Store into the 1950s and this home now offers the perfect blend of historical charm and modern conveniences. Fully restored in 2017 down to the studs, this home retains its rich heritage while boasting high-end updates throughout. As you enter

    Cindy Genther Rock Hall Properties Real Estate

    106 Church Alley, Chestertown, MD 21620
    • /19

      Est $299,320 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,263 Sq Ft

      332 Longfellow Dr, Chestertown, MD 21620

      332 Longfellow Dr, Chestertown, MD 21620
  • /8

    $150,000

    • Land
    • 2.00 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /26

    $325,000 Sold Dec 12, 2024

    • 1,500 Sq Ft
    • $217/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1974

    228 Concord Rd, Chestertown, MD 21620

    This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow and make your own . Main level offers eat in kitchen, an oversized living room with fireplace , four bedrooms and two full baths. One of the bedrooms could make a perfect home office. This home has been freshly painted and new flooring. This will get the new owners a fresh start while they decide on

    Grace Crockett Doug Ashley Realtors, LLC

    228 Concord Rd, Chestertown, MD 21620
    • /43

      Est $312,900 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,304 Sq Ft

      537 Truslow Rd, Chestertown, MD 21620

      537 Truslow Rd, Chestertown, MD 21620
  • /2

    $40,000

    • Land
    • 0.11 Acre
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • /60

    $625,000 Sold Dec 10, 2024

    • 2,476 Sq Ft
    • $252/SF
    • 33 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2002

    1316 Ewingtown Rd, Chestertown, MD 21620

    Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquility of rural living. Nestled on nearly 3 ½ acres of pristine land (main lot is 2.33 acres and adjacent lot is 1 acre), this Art Deco Farmhouse is a private retreat surrounded by thousands of acres of preserved farmland and woodlands. Just 45 minutes from Annapolis and Easton, and a quick 10-minute drive to

    Travis Gray Engel & Völkers Annapolis

    1316 Ewingtown Rd, Chestertown, MD 21620
    • /31

      Est $354,811 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      707 Round Top Rd, Chestertown, MD 21620

      707 Round Top Rd, Chestertown, MD 21620
  • /2

    $28,000

    • Land
    • 2.00 Acres
    • $14,000 per Acre

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • /22

    $342,000 Sold Dec 09, 2024

    • 1,200 Sq Ft
    • $285/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1997

    218 Concord Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher located in the desirable Chester Harbor neighborhood! This move-in-ready home features a recently updated kitchen with quartz counters and new flooring in the bedrooms. New heat pump. Enjoy the spacious, fenced-in backyard complete with a screened-in porch and fire pit. A large shed offers extra storage. Conveniently situated just minutes from downtown

    Courtney Chipouras TTR Sotheby's International Realty

    218 Concord Rd, Chestertown, MD 21620
    • /25

      Est $322,317 Not Listed For Sale

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

      324 Longfellow Dr, Chestertown, MD 21620

      324 Longfellow Dr, Chestertown, MD 21620
  • /2

    $38,000

    • Land
    • 0.34 Acre
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • /33

    $329,000 Sold Dec 06, 2024

    • 1,473 Sq Ft
    • $223/SF
    • 35 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    23055 Parsons Rd, Chestertown, MD 21620

    Well Maintained rancher with major renovations. Updating Kitchen including recently new stainless steel appliances and cabinets, Bathrooms, HW flooring refinished, fresh Paint throughout, move-in condition. New boiler, new water heater & new central A/c in 2011. Full basement -Office/den in basement w/ built-in book shelves and tile floor that has a separate entrance. Laundry area in basement.

    Sharon Clark Clark & Co Realty, LLC

    23055 Parsons Rd, Chestertown, MD 21620
    • /35

      Est $294,017 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,144 Sq Ft

      121 Tuxedo Rd, Chestertown, MD 21620

      121 Tuxedo Rd, Chestertown, MD 21620
  • /2

    $24,000

    • Land
    • 0.50 Acre
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23710 L Rd, Chestertown, MD 21620
  • /33

    $250,000 Sold Dec 06, 2024

    • 1,632 Sq Ft
    • $153/SF
    • 88 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    305 Lincoln Dr, Chestertown, MD 21620

    Looking for extra space? This home has a large extra room that could be a primary bedroom & bath with walk-in closet, a den/playroom, office with a separate private entrance, gym, or whatever your lifestyle needs! The original primary bedroom includes an attached half bath and the original hardwood floors gleam throughout most of the home! Easy access to multiple public ramps & just a short drive

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    305 Lincoln Dr, Chestertown, MD 21620
    • /6

      Est $288,988 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      210 Creston Rd, Chestertown, MD 21620

      210 Creston Rd, Chestertown, MD 21620
  • /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /22

    $374,900 Sold Dec 06, 2024

    • 1,512 Sq Ft
    • $248/SF
    • 223 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    481 Pear Tree Point Rd, Chestertown, MD 21620

    Major Price Reduction - Brand New Home ready ready for ALL your Holiday Celebrations! Lawn has been freshly seeded and new shrubs planted for the fall. Three generous bedrooms and 2.5 baths! Enjoy beautiful water views of the Chester River... just across the street! Open floor plan, stainless steel appliances, main-level master suite with a walk-in closet and ensuite. Upstairs, you'll find two

    Clint Evans Cross Street Realtors LLC

    481 Pear Tree Point Rd, Chestertown, MD 21620
    • /33

      Est $458,169 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,900 Sq Ft

      118 Harlan Loop, Chestertown, MD 21620

      118 Harlan Loop, Chestertown, MD 21620
  • /2

    $38,000

    • Land
    • 0.56 Acre
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, Chestertown, MD 21620
  • /24

    $355,000 Sold Dec 02, 2024

    • 1,536 Sq Ft
    • $231/SF
    • 64 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    24291 Chestertown Rd, Chestertown, MD 21620

    Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square feet of comfortable, inviting living space. This home boasts 3 spacious bedrooms and 2 full baths, perfectly designed to accommodate a variety of lifestyles. Step inside and be greeted by the open floor plan, where the brick fireplace in the living room adds both charm and warmth—an ideal gathering spot for

    Joelle Dolch Cross Street Realtors LLC

    24291 Chestertown Rd, Chestertown, MD 21620
    • /58

      Est $759,136 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft

      105 S Water St, Chestertown, MD 21620

      105 S Water St, Chestertown, MD 21620
  • /2

    $120,000

    • Land
    • 1.80 Acres
    • $66,667 per Acre

    0 Rd, Chestertown, MD 21620

    Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Rd, Chestertown, MD 21620
  • /73

    $675,000 Sold Nov 26, 2024

    • 2,400 Sq Ft
    • $281/SF
    • 27 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2011

    6270 Quaker Neck Landing Rd, Chestertown, MD 21620

    From the moment you drive up to this beautiful home, you are struck by the beautiful landscaping that complements the home, includes a rain garden, cutting garden, wildflower garden and a walkway that leads to an outdoor patio that provides such a great space for outdoor living. The orchard has peaches, plum, apple trees as well as berries and grapes. The enclosed screen porch overlooks the

    Retha Arrabal Doug Ashley Realtors, LLC

    6270 Quaker Neck Landing Rd, Chestertown, MD 21620
    • /39

      Est $244,506 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft

      114 School Rd, Chestertown, MD 21620

      114 School Rd, Chestertown, MD 21620
  • /2

    $9,500

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

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /6

    $152,881 Sold Nov 25, 2024

    • 1,232 Sq Ft
    • $124/SF
    • 14 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21345 Persimmon Dr, Chestertown, MD 21620

    Join the small Tolchester Village community in a nice two bedroom and one bath town house. Remodeled in 2021 this modern home features low maintenance living. It could use a little tlc to make it your own. Outdoor storage areas are located in the front and back. There is a small back patio where you can sit and enjoy your morning coffee. Never worry about mowing the grass as the small HOA

    Vince Raimond Doug Ashley Realtors, LLC

    21345 Persimmon Dr, Chestertown, MD 21620
    • /28

      Est $525,552 Not Listed For Sale

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

      101 Birch Run Rd, Chestertown, MD 21620

      101 Birch Run Rd, Chestertown, MD 21620
  • /19

    $335,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    10578 Tonopah Rd, Chestertown, MD 21620

    Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living—featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite

    David Moore RE/MAX Executive

    10578 Tonopah Rd, Chestertown, MD 21620
  • /32

    $239,000 Sold Nov 25, 2024

    • 1,202 Sq Ft
    • $199/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    5 Rolling Rd, Chestertown, MD 21620

    Brick rancher located in College Heights! There are 3 bedrooms and living room, all with wood floors. There is a large family room with built-ins. There is a full unfinished basement with connecting interior stairs and exterior stairs. The rear porch is ready to be screened in. Property backs up to woods. Close to hospital, parks and schools. This home will require a little TLC however the

    Doug Ashley Doug Ashley Realtors, LLC

    5 Rolling Rd, Chestertown, MD 21620
    • /28

      Est $538,432 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,067 Sq Ft

      116 Harlan Loop, Chestertown, MD 21620

      116 Harlan Loop, Chestertown, MD 21620
  • /37

    $285,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    7483 Shortall St, Chestertown, MD 21620

    Discover this delightful, move-in-ready ranch-style home in a peaceful Chestertown setting. Featuring three bedrooms and two bathrooms, this residence boasts recent updates including fresh paint, new flooring, modern stainless steel appliances, and stunning Beechwood butcher block countertops. Enjoy abundant natural light through the beautiful front door and Anderson windows, relax on the back

    David Moore RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
  • /27

    $405,000 Sold Nov 22, 2024

    • 1,426 Sq Ft
    • $284/SF
    • 39 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    142 Church Meadow Ct, Chestertown, MD 21620

    Conveniently located between Church Hill and Chestertown this home sits on a quiet cul de sac with 1.25 acre lot backing to farm fields. Fenced rear yard is great for 2 or 4 legged family members and provides ample room to play, garden, or just relax. Inside features over 1400 SQFT of finished space with 3 bedrooms, 2.5 bathrooms and great lower level family room with walk out to rear yard

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    142 Church Meadow Ct, Chestertown, MD 21620

Showing Results 241 - 280, Page 7 of 18

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