89

Homes for Sale in 21620

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  • /57

    $699,000

    • 2 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    100 Little Harbor Way, Chestertown, MD 21620

    Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom (with the possibility of both a main level 3rd bedroom or upper level 3rd bedroom), 2 bath home offers the perfect blend of comfort and modern living and is ideal for quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find

    Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
  • /3

    $15,000

    • Land
    • 0.69 Acre
    • $21,739 per Acre

    23683 L Rd, Chestertown, MD 21620

    This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront attractions just minutes from the town of Chestertown, Worton Creek Marina, and Great Oak Landing.

    Alyson Anderson Allfirst Realty, Inc.

    23683 L Rd, Chestertown, MD 21620
  • /20

    $220,000

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • /2

    $25,000

    • Land
    • 0.34 Acre
    • $73,529 per Acre

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
  • /2

    $25,000

    • Land
    • 0.34 Acre
    • $73,529 per Acre

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
  • /52

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /22

    $199,900

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    110 Philosophers Terrace, Chestertown, MD 21620

    Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

    Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • /11

    $49,900

    • Land
    • 1.51 Acres
    • $33,046 per Acre

    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620
  • /26

    $274,000

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

    118 Tuxedo Rd, Chestertown, MD 21620

    Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

    Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
  • /16

    $232,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • /52

    $845,000

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft

    24576 Langford Rd, Chestertown, MD 21620

    Designed by noted architectural historian and restoration consultant, Michael Bourne, Highfield exemplifies a deep appreciation and intimate knowledge of historic architectural composition and its elements. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, in form and style, Highfield is reminiscent of the vernacular farmhouses of southeastern

    Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
  • /16

    $449,000

    • Land
    • 2.02 Acres
    • $222,277 per Acre

    0 Walnut Point Rd, Chestertown, MD 21620

    Extremely Rare offering! 2 acre recorded waterfront parcel in Quaker Neck on Walnut Point Road with 211 feet of frontage on the East Fork Of Langford Creek. Parcel was perc evaluated years ago and require re-evaluation which has been applied for, please see documents. Partially wooded and partially cleared with gorgeous views of the Langford Creek. Dock is allowed by the County. Possibility of 4"

    William Norris Select Land & Homes, LLC

    0 Walnut Point Rd, Chestertown, MD 21620
  • /22

    $299,000

    • 3 Beds
    • 2 Baths
    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /2

    $25,000

    • Land
    • 0.34 Acre
    • $73,529 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
  • /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
  • /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
  • /2

    $10,000

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

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678

    The HO Assocation is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community. Lot failed perc in 2005 and cannot be built on but a great place to use your boat!

    Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
  • /2

    $10,000

    • Land
    • 0.11 Acre
    • $90,909 per Acre

    0 Montgomery Unit MDKE2004196, Chestertown, MD 21620

    Property in Tolchester Estates! Walking distance to the Chesapeake Bay, Tolchester beach, marina and Shanty. The county says sewer allocation is available. Buyer to confirm lot is buildable regarding setbacks, sewer allocation, and utility hookups. Buyer responsible for sewer allocation fees estimated to be $12,800. Lot next door is also for sale MDKE2003418. All offers considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Montgomery Unit MDKE2004196, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

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