6,883

Chestertown, MD Homes

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    • /55

      Est $372,023 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,746 Sq Ft

      304 Truslow Rd, Chestertown, MD 21620

      304 Truslow Rd, Chestertown, MD 21620
  • /20

    $299,000

    • Studio
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • /59

    $1,450,000 Sold Dec 20, 2024

    • 3,788 Sq Ft
    • $383/SF
    • 4 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1953

    10262 John Carvill Rd, Chestertown, MD 21620

    This beloved waterfront property has been a treasured family gathering place for over twenty four years. There have been numerous updates throughout that time, including the spectacular shoreline area which offers a private dock with about 5 feet MLW, bulk-headed shoreline, several boat lifts, water slide and sandy beach. From the homesite, you can walk down the well constructed stairs or you

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10262 John Carvill Rd, Chestertown, MD 21620
    • /31

      Est $296,262 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      201 Farwell Rd, Chestertown, MD 21620

      201 Farwell Rd, Chestertown, MD 21620
  • /6

    $8,000

    • Land
    • 0.42 Acre
    • $19,048 per Acre

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek. Lot failed percolation Test in March of 1989.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
  • /80

    $385,000 Sold Dec 20, 2024

    • 2,240 Sq Ft
    • $172/SF
    • 35 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1969

    221 River Rd, Chestertown, MD 21620

    Hidden within the wandering gardens, you will find this meticulously maintained home with seasonal water views of the Chester River in a quiet family-friendly community just minutes from Chestertown. The spacious front and back yards are private oases with just about every tree or plant one can think of; a true gardner's dream. Enjoy the fall colors from the back screened-in porch. Inside you

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    221 River Rd, Chestertown, MD 21620
    • /5

      Est $112,667 Not Listed For Sale

      201 Duke of Kent St, Chestertown, MD 21620

      201 Duke of Kent St, Chestertown, MD 21620
  • /30

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • /27

    $247,500 Sold Dec 18, 2024

    • 1,260 Sq Ft
    • $196/SF
    • 30 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 2022

    117 Chester Arms Dr, Chestertown, MD 21620

    Discover this nearly new, beautifully maintained home in Chestertown. Featuring luxury vinyl flooring throughout, white cabinets, granite countertops, a spacious living room, an eat-in kitchen area, and a covered patio, this home offers a comfortable and stylish living space. The large primary bedroom suite and additional spacious bedrooms provide ample room for relaxation and

    David Moore RE/MAX Executive

    117 Chester Arms Dr, Chestertown, MD 21620
    • /24

      Est $300,919 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft

      2607 Mcginnes Rd, Chestertown, MD 21620

      2607 Mcginnes Rd, Chestertown, MD 21620
  • /37

    $309,000

    • 3 Beds
    • 1 Bath
    • 1,698 Sq Ft

    909 Round Top Rd, Chestertown, MD 21620

    Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 23’8 X 18’4 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    909 Round Top Rd, Chestertown, MD 21620
  • /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
    • /23

      Est $282,954 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      208 Central Dr, Chestertown, MD 21620

      208 Central Dr, Chestertown, MD 21620
  • /5

    $225,000

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, 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
    • /31

      Est $383,088 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,080 Sq Ft

      225 Burchard Sawmill Rd, Chestertown, MD 21620

      225 Burchard Sawmill Rd, Chestertown, MD 21620
  • /15

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    107 Dutchess Rd, Chestertown, MD 21620

    Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

    Jo Ann Edwards The Hogans Agency

    107 Dutchess 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
    • /25

      Est $383,394 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft

      224 Fey Rd, Chestertown, MD 21620

      224 Fey Rd, Chestertown, MD 21620
  • /7

    $250,000

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, 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
    • /5

      Est $221,542 Not Listed For Sale

      • Studio
      • 1,008 Sq Ft

      327 Pine Tree Rd, Chestertown, MD 21620

      327 Pine Tree Rd, Chestertown, MD 21620
  • /49

    $950,000

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft

    26865 Mallard Rd, Chestertown, MD 21620

    A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles,

    Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, 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
    • /22

      Est $222,962 Not Listed For Sale

      • Studio
      • 1,080 Sq Ft

      340 Pine Tree Rd, Chestertown, MD 21620

      340 Pine Tree Rd, Chestertown, MD 21620
  • /44

    $1,450,000

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    **Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman-style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately150 feet of shoreline and a sandy beach, this property is a true waterfront gem.**Key Features:**- **Spacious Great

    Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, 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
    • /16

      Est $367,327 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft

      206 Tamarack Rd, Chestertown, MD 21620

      206 Tamarack Rd, Chestertown, MD 21620
  • /3

    $20,000

    • Land
    • 0.14 Acre
    • $142,857 per Acre

    0 Tolchester Beach Rd Unit MDKE2004198, Chestertown, MD 21620

    SEVEN separate lots for sale in Tolchester Estates. These lots are not currently buildable since sewer allocations are not available and septic systems not permitted. Four of these lots (Tolchester Beach Rd, Oak Rd, and two on Poplar) are accessible by car and three ( Texas, Georgia, and Kansas) are not since the intended roads were never built. All are walking distance to the Chesapeake Bay,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Tolchester Beach Rd Unit MDKE2004198, 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
    • /40

      Est $306,253 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft

      310 Central Dr, Chestertown, MD 21620

      310 Central Dr, Chestertown, MD 21620
  • /33

    $395,000

    • 7 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    349 High St, Chestertown, MD 21620

    Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 High St, 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
    • /38

      Est $476,750 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,285 Sq Ft

      105 Holly Ct, Chestertown, MD 21620

      105 Holly Ct, Chestertown, MD 21620
  • /47

    $395,000

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike.Situated on a generous lot,

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, 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
    • /28

      Est $464,141 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,188 Sq Ft

      118 Hilltop Dr, Chestertown, MD 21620

      118 Hilltop Dr, Chestertown, MD 21620
  • /3

    $20,000

    • Land
    • 0.09 Acre
    • $222,222 per Acre

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, 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
    • /11

      Est $507,054 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,619 Sq Ft

      300 Gatling Dr, Chestertown, MD 21620

      300 Gatling Dr, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 18

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