16

Caroline County MD Homes for Sale with Basement

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  • /54

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an .85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding,

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /71

    $434,500

    • 4 Beds
    • 3 Baths
    • 4,304 Sq Ft

    122 Lister Ln, Ridgely, MD 21660

    Welcome to 122 Lister Lane in the charming town of Ridgely, MD, nestled on a picturesque corner lot in the highly coveted Lister Estates community. This delightful home is a treasure trove of possibilities, catering to a diverse range of lifestyles.As you approach the property, you'll be greeted by its stunning brick facade that exudes classic elegance, complemented by a fully fenced

    Chris Rosendale CR Realty

    122 Lister Ln, Ridgely, MD 21660
  • /59

    $399,500

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft

    502 N Academy St, Greensboro, MD 21639

    Welcome to 502 Academy Street, Greensboro, MD, a charming retreat that embodies the essence of cozy cottage living. This turnkey property has been meticulously cared for and spans almost 2,400 square feet of thoughtfully designed space on a beautifully landscaped lot.Inside, you'll find three inviting bedrooms, with two located on the lower level for added privacy and convenience. Each of the two

    Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
  • /70

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft

    3871 Laurel Grove Rd, Federalsburg, MD 21632

    Great Opportunity to own a Farm! 20 Acres plus Pole building to store your farm equipment, 2-car garage with a recreation room on the second floor. Great for hunting and fishing or to admire the wildlife.In-ground swimming pool with private fencing. Four season room, separate dining room, breakfast nook,Pellet stove, Fireplace with gas insert.This 1890 home needs some TLC.Call to schedule your

    Dawn Shorter McClain-Williamson Realty, LLC

    3871 Laurel Grove Rd, Federalsburg, MD 21632
  • /70

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft

    3871 Laurel Grove Rd, Federalsburg, MD 21632

    Great Opportunity to own a Farm! 20 Acres plus Pole building to store your farm equipment, 2-car garage with a recreation room on the second floor. Great for hunting and fishing or to admire the wildlife.In-ground swimming pool with private fencing. Four season room, separate dining room, breakfast nook,Pellet stove, Fireplace with gas insert.This 1890 home needs some TLC.Call to schedule your

    Dawn Shorter McClain-Williamson Realty, LLC

    3871 Laurel Grove Rd, Federalsburg, MD 21632
  • /73

    $545,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle.The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /95

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 2,968 Sq Ft

    25305 Sandy Point Rd, Greensboro, MD 21639

    Discover this stunning three-story waterfront home on the Choptank River, just five minutes from downtown Denton and Route 404. The main level features an eat-in kitchen, formal dining room, and a living room and sunroom—both offering breathtaking river views. You'll also find a spacious primary suite, an additional half bath, and a laundry room. Upstairs, two additional bedrooms, a full bath,

    Janet Larson Benson & Mangold, LLC

    25305 Sandy Point Rd, Greensboro, MD 21639
  • /2

    $465,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 3,408 Sq Ft

    135 Walnut St, Ridgely, MD 21660

    Welcome to this Grande Home in Lister Estates. This home offer Three Full Levels of living space. Main floor features the Owners Primary with En Suite and two closets. 2 additional bedrooms and full bath. Dining Room or Office, Large open kitchen overlooks Great Room and added Morning Room for additional dining or needed space. Exterior backyard offers deck for entertaining and area for garden

    Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Walnut St, Ridgely, MD 21660
  • /2

    $399,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,267 Sq Ft

    306 S 2nd St, Denton, MD 21629

    Welcome to 306 S 2nd St, a lovingly restored colonial farmhouse style home on a private lane in a great neighborhood. Situated on a large in-town lot, the home features gleaming hardwood floors, new carpeting, and well-maintained gardens. From roof to basement, nearly everything in this home has been updated or upgraded. New architectural shingles were replaced, and the basement received new

    Jana Meredith Meredith Fine Properties

    306 S 2nd St, Denton, MD 21629
  • /59

    $374,000

    • 4 Beds
    • 1.5 Baths
    • 2,974 Sq Ft

    107 Butler Dr, Denton, MD 21629

    Charming Home with Timeless Character, Modern Updates & Expansion PotentialStep into this beautifully maintained 4-bedroom, 1.5-bath home that perfectly blends classic charm with thoughtful modern updates. Nestled on a generous 1/3-acre fenced-in town lot, this property offers the privacy and space you’ve been looking for, complete with mature shade trees that create a peaceful,

    Justin Pokrywka Meredith Fine Properties

    107 Butler Dr, Denton, MD 21629
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    1010 S 2nd Street offers in-town living WITHOUT in-town Taxes!!! This home rests at the edge of town on 1.06 acres with mature plantings. This 3-bed 2-bath home boasts hardwood, LVP, and tile floors. A fireplace insert for the pellet stove for heat, while the seller uses the Hot water baseboard as a backup. Full basement for additional entertaining or storage. Screened-in porch overlooks

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /12

    $125,000

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

    529 Oldtown Rd, Goldsboro, MD 21636

    1900 Brick home that is solid but needs rehab done inside. Nice hardwood floors. Owner had started renovation. For the price could be a great home for your family. Large in town lot with several outbuildings for storage, hobbies or garage. Wooded behind home for privacy in town. Convenient to Delaware, Denton, Centreville and all in between.

    Barbara Wallace Long & Foster Real Estate, Inc.

    529 Oldtown Rd, Goldsboro, MD 21636
  • /83

    $995,500 Open Sat 9AM - 11AM

    • 4 Beds
    • 3 Baths
    • 2,119 Sq Ft

    23274 Holly Park Dr, Preston, MD 21655

    Experience Waterfront Living Like Never Before on the Choptank River! Welcome to “One Sweet World", where breathtaking sunsets and expansive sky views await you just 50 feet from the river’s edge. This extraordinary waterfront retreat features a beautifully designed 2-bedroom, 2-bathroom main house, complemented by a cozy 2-bedroom, 1-bathroom guest house and a separate guest room/tackle room

    Rick Parreco RE/MAX Executive

    23274 Holly Park Dr, Preston, MD 21655
  • /54

    $250,000

    • 4 Beds
    • 1.5 Baths
    • 2,406 Sq Ft

    108 S 2nd St, Denton, MD 21629

    Historic charm meets endless potential in this spacious corner-lot home in the heart of downtown Denton—formerly home to the beloved local flower shop! With 4 bedrooms and 1.5 bathrooms, this well-maintained property offers incredible space, character, and small-town walkability.From the welcoming front porch to the large family room that opens to an oversized deck, this home is perfect

    Crystal Smith RE/MAX Executive

    108 S 2nd St, Denton, MD 21629
  • /17

    $299,900

    • 3 Beds
    • 2 Baths
    • 2,546 Sq Ft

    14706 Cherry Ln, Ridgely, MD 21660

    Are you looking for a diamond in the rough with endless potential at a great price? Here is your opportunity! Make this home shine again and create your own retreat! Leave the stress of every day life behind in this 3 bedrooms, 2 baths rambler with basement, on a beautiful lot and outside of all the hustle and bustle. Come and see for yourself! Hurry! Don't let this one get away! Needs work. Sold

    Ingrid Butler CENTURY 21 New Millennium

    14706 Cherry Ln, Ridgely, MD 21660
  • /52

    $344,900 Coming Soon

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

    7881 Dyer Rd, Denton, MD 21629

    Country location - 3BR, 2BA Home on Private 1± Acre Lot!This beautifully maintained home offers comfort, updates, and space both inside and out. Enjoy peace of mind with recent upgrades including a new well, septic system, HVAC, roof, and driveway. The home features gleaming wood floors, a bright, updated kitchen and bathrooms, and flexible living spaces – potential for a first-floor

    Valerie Brown Charles C. Powell, Inc. Realtors

    7881 Dyer Rd, Denton, MD 21629
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