6,895

Chestertown, MD Homes

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  • /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 large

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • /7

    $12,000 Sold Jan 24, 2025

    • Land
    • 0.34 Acre
    • $35,294 per Acre
    • 239 Days On Market

    0 Vireo Rd, Chestertown, MD 21620

    Perc approved building lot - see info under documents.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually community members have access to all the community amenities.

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    0 Vireo Rd, Chestertown, MD 21620
    • /48

      Est $333,656 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,424 Sq Ft

      119 Darden Rd, Chestertown, MD 21620

      119 Darden Rd, 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
  • /39

    $625,000 Sold Jan 15, 2025

    • 3,527 Sq Ft
    • $177/SF
    • 97 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    23575 Canvasback Rd, Chestertown, MD 21620

    Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a leisurely kayak cruise down Mill Creek to the Chesapeake Bay. Conveniently located a short distance from Worton Creek Marina, Restaurants, Resort Style Marinas, Historic Chestertown, Parks and much more. Chesapeake Landing

    John Burke Gunther-McClary Real Estate

    23575 Canvasback Rd, Chestertown, MD 21620
    • /28

      Est $417,541 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft

      209 Myers Rd, Chestertown, MD 21620

      209 Myers Rd, Chestertown, MD 21620
  • /15

    $325,000

    • 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
  • /22

    $107,500 Sold Jan 10, 2025

    • 930 Sq Ft
    • $116/SF
    • 13 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1959

    7121 Quaker Neck Rd, Chestertown, MD 21620

    Great Investment Opportunity – Fixer-Upper on 1 Acre LotAttention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    7121 Quaker Neck Rd, Chestertown, MD 21620
    • /30

      Est $400,632 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,714 Sq Ft

      2771 Mcginnes Rd, Chestertown, MD 21620

      2771 Mcginnes 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
  • /43

    $355,000 Sold Jan 10, 2025

    • 1,672 Sq Ft
    • $212/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    106 Silver Heel Rd, Chestertown, MD 21620

    Looking for a Brand New home without the hassle of building? You have found it! Built in 2023 in the wonderful neighborhood known as The Villages of Chestertown. This gorgeous 3 bedroom, 2.5 bathroom home was designed with luxury and quality in mind. As soon as you step inside you will admire the open floor plan featuring a shiplap accent wall around the fireplace. The dining area connects

    Chuck Zepp EXP Realty, LLC

    106 Silver Heel Rd, Chestertown, MD 21620
    • /19

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft

      131 E Step Rd, Chestertown, MD 21620

      131 E Step 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 Room**: Added in 2001,

    Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
  • /35

    $600,000 Sold Jan 03, 2025

    • 3,300 Sq Ft
    • $182/SF
    • 151 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2013

    101 Landing Ln Unit 39, Chestertown, MD 21620

    Welcome to 101 Landing Lane, an exquisite residence offering exceptional living in the prestigious Chester River Landing Community. *Sellers will provide a credit to cover the monthly HOA fees for one year!* Boasting an expansive 3,300 square feet of meticulously designed living space, this home features luxurious amenities and elegant finishes across three levels, ensuring comfort and

    Sarah King Cross Street Realtors LLC

    101 Landing Ln Unit 39, Chestertown, MD 21620
    • /5

      Est $592,090 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,572 Sq Ft

      193 Westwood Ln, Chestertown, MD 21620

      193 Westwood Ln, Chestertown, MD 21620
  • /33

    $395,000

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

    349 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 High St, Chestertown, MD 21620
  • /34

    $612,500 Sold Jan 02, 2025

    • 1,800 Sq Ft
    • $340/SF
    • 13 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2017

    7675 Quaker Neck Rd, Chestertown, MD 21620

    The attention to detail, superior craftsmanship and high end finishes gives this home an "Oh Wow" factor! Located on a point of land overlooking the Chester River Yacht and Country Club's pond and golf course, the views are beautiful and peaceful. The backyard patio with its fire pit and grill allows you to soak up the setting and enjoy the wildlife. There are solid cherry wood floors, marble

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    7675 Quaker Neck Rd, Chestertown, MD 21620
    • /49

      Est $406,165 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,456 Sq Ft

      205 Deep Landing Rd, Chestertown, MD 21620

      205 Deep Landing Rd, Chestertown, MD 21620
  • /47

    $395,000

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • /37

    $625,000 Sold Jan 02, 2025

    • 1,782 Sq Ft
    • $351/SF
    • 81 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1937

    7775 Waterview Ln, Chestertown, MD 21620

    Charming house in Country Club Estates. Located on the 14th hole with views of the Chester River. 3 beds and 2.5 baths. Potential for a 4th bedroom and potential for a first-floor bedroom. Lovely landscaping and cedar shake roof. Traditional floorplan. Beautiful wood floors throughout. Screened in porch and lovely brick patio. The perfect blend of classic architecture and modern convenience.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7775 Waterview Ln, Chestertown, MD 21620
    • /8

      Est $372,423 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      101 Char Nor Manor Blvd, 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
  • /12

    $212,000 Sold Dec 30, 2024

    • 1,275 Sq Ft
    • $166/SF
    • 16 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1959

    111 Elm St, Chestertown, MD 21620

    Great opportunity to own in the College Heights subdivision across from Washington College. A few improvements would make this rancher a cozy home. One level living offers a living room, kitchen, 3 bedrooms and 1 bathroom. 2 enclosed porches present additional living space for an office, family room or game room. The exterior is brick with a newer roof. The home is situated on a large, level lot,

    Andy Batch Keller Williams Select Realtors of Annapolis

    111 Elm St, Chestertown, MD 21620
    • /71

      Est $525,403 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft

      139 Church Meadow Ct, Chestertown, MD 21620

      139 Church Meadow Ct, Chestertown, MD 21620
  • /3

    $55,000

    • Land
    • 0.70 Acre
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2003624, Chestertown, MD 21620

    Exciting opportunity awaits with this open lot located in Fairlee, Md. This parcel of land offers the perfect canvas for your dream home or investment project. .69 acres provides ample space for your vision to flourish. The property is allocated for public water and sewer, so the new owner won’t have to worry about drilling a well or paying for and maintaining a septic system! Allocations are

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2003624, Chestertown, MD 21620
  • /48

    $350,000 Sold Dec 30, 2024

    • 2,102 Sq Ft
    • $167/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    125 Primrose Rd, Chestertown, MD 21620

    **Seller has purchased a new dishwasher and it will be installed in the coming days. Tucked away in a wooded setting in a quiet neighborhood just a block off the Chester River you will find this well built welcoming home. The well designed main floor layout includes a living room, dining room, and eat in kitchen plus a year round spacious sunroom overlooking the back yard and the open space

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    125 Primrose Rd, Chestertown, MD 21620
    • /28

      Est $535,500 Not Listed For Sale

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

      329 Union Church Rd, Chestertown, MD 21620

      329 Union Church Rd, Chestertown, MD 21620
  • /9

    $1,150,000

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620
  • /30

    $649,000 Sold Dec 20, 2024

    • 1,680 Sq Ft
    • $386/SF
    • 27 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    411 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around water views in a serene wooded setting. With convenient single level living, the three bedroom two bathroom home offers a flowing floor plan bright with natural light and custom upgrades. Relax and enjoy views from the private walkout

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    411 Fairview Dr, Chestertown, MD 21620
    • /49

      Est $424,800 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,792 Sq Ft

      109 Coleman Dr, Chestertown, MD 21620

      109 Coleman Dr, Chestertown, MD 21620
  • /2

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, 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
    • /29

      Est $399,915 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft

      236 Duke of Kent St, Chestertown, MD 21620

      236 Duke of Kent St, Chestertown, MD 21620
  • /2

    $12,000

    • Land
    • 0.34 Acre
    • $35,294 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, 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
    • /35

      Est $402,296 Not Listed For Sale

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

      313 River Rd, Chestertown, MD 21620

      313 River Rd, Chestertown, MD 21620
  • /2

    $19,000

    • Land
    • 0.34 Acre
    • $55,882 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    Discover your own piece of paradise in Lenapah, Chestertown, MD! This expansive 14,500 square foot lot offers endless possibilities for your dream home or investment vision. Nestled in a serene setting, this raw land is ready for your creative touch. Embrace the tranquility of nature while being just a short drive from local amenities. Whether you’re looking to build your dream oasis or a savvy

    Michael Bennett Compass

    0 Lenapah 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
    • /26

      Est $382,216 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft

      109 Essex Rd, Chestertown, MD 21620

      109 Essex Rd, Chestertown, MD 21620
  • /2

    $64,000

    • Land
    • 1.37 Acres
    • $46,715 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

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