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Woolford, MD Homes for Sale with Acreage

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  • 1252 Old Madison Rd, Madison, MD 21648
    1252 Old Madison Rd, Madison, MD 21648
    1252 Old Madison Rd, Madison, MD 21648
    /56

    $1,375,000

    $25K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,037 Sq Ft

    1252 Old Madison Rd, Madison, MD 21648

    End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound offering 268 feet of protected, rip-rapped shoreline and 1.12 acres of privacy, ideally positioned with a coveted east-west orientation. A private pier equipped with a boat lift and personal watercraft lift enhances the property’s appeal, delivering immediate access to the water and an effortless boating

    Barbara McCaffrey Redfin Corp

    1252 Old Madison Rd, Madison, MD 21648
  • 1648 Taylors Island Rd, Woolford, MD 21677
    1648 Taylors Island Rd, Woolford, MD 21677
    1648 Taylors Island Rd, Woolford, MD 21677
    /46

    $849,900

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    1648 Taylors Island Rd, Woolford, MD 21677

    Imagine waking up to sweeping waterfront views, launching your kayak from your private beach, and ending the day with uninterrupted sunset skies right from your own yard! This stunning, completely remodeled coastal retreat combines peace of mind with exceptional investment potential. Featuring a new roof and new HVAC system, every detail of this home has been thoughtfully updated, including fresh

    Valerie Brown Coldwell Banker Realty

    1648 Taylors Island Rd, Woolford, MD 21677
  • 5227 Brooks Rd, Woolford, MD 21677
    5227 Brooks Rd, Woolford, MD 21677
    5227 Brooks Rd, Woolford, MD 21677
    /68

    $1,795,000

    • 4 Beds
    • 2.5 Baths
    • 3,633 Sq Ft

    5227 Brooks Rd, Woolford, MD 21677

    Fabulous waterfront home with modern flair and a stunning indoor pool, ideally located in McKeil Point, offering effortless one-level living and an open floor plan designed to capture spectacular, unobstructed water views from nearly every room. The thoughtfully designed split-bedroom layout ensures privacy, featuring a serene primary suite with direct access to the indoor pool, a luxurious bath,

    Randy Staats Benson & Mangold, LLC

    5227 Brooks Rd, Woolford, MD 21677
  • 0 Taylors Island Rd Unit MDDO2012124, Woolford, MD 21677
    0 Taylors Island Rd Unit MDDO2012124, Woolford, MD 21677
    0 Taylors Island Rd Unit MDDO2012124, Woolford, MD 21677
    /21

    $585,600

    • Land
    • 91.5 Acres
    • $6,400 per Acre

    0 Taylors Island Rd Unit MDDO2012124, Woolford, MD 21677

    91± Acres – Wooded Recreational Retreat with Residential Potential (2 parcels) - Sika-Whitetail-Turkey Discover the perfect escape with this expansive 91± acre wooded property, offering a rare blend of privacy, accessibility, and versatility. Featuring established logging roads running through both parcels, the land provides excellent internal access—ideal for navigating the property by ATV,

    Craig Linthicum Benson & Mangold, LLC

    0 Taylors Island Rd Unit MDDO2012124, Woolford, MD 21677
  • 1609 Heliport Rd, Woolford, MD 21677
    1609 Heliport Rd, Woolford, MD 21677
    1609 Heliport Rd, Woolford, MD 21677
    /37

    $319,700

    • Land
    • 1.52 Acres
    • $210,329 per Acre

    1609 Heliport Rd, Woolford, MD 21677

    BACK ON THE MARKET WITH IMPROVED PRICE-THIS IS THE LOCATION!!!!***********************PUBLIC SEWER IS ON THIS PROPERTY*************************************If you’ve been searching for the perfect canvas to build your Delmarva masterpiece, look no further. This rare offering features over 1.5 acres of low-maintenance waterfront land on the Little Choptank River, comprised of two cleared,

    C Fred Robinson Keller Williams Realty Delmarva

    1609 Heliport Rd, Woolford, MD 21677
  • 4808 Saltmarsh Rd, Madison, MD 21648
    4808 Saltmarsh Rd, Madison, MD 21648
    4808 Saltmarsh Rd, Madison, MD 21648
    /119

    $1,399,999

    $100K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 5,087 Sq Ft

    4808 Saltmarsh Rd, Madison, MD 21648

    Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home—it’s a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5

    Kenneth Jester Coldwell Banker Realty

    4808 Saltmarsh Rd, Madison, MD 21648
  • 4825 Madison Canning House Rd, Madison, MD 21648
    4825 Madison Canning House Rd, Madison, MD 21648
    4825 Madison Canning House Rd, Madison, MD 21648
    /53

    $695,000

    • 4 Beds
    • 3 Baths
    • 2,128 Sq Ft

    4825 Madison Canning House Rd, Madison, MD 21648

    Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz

    Leo Kuneman Meredith Fine Properties

    4825 Madison Canning House Rd, Madison, MD 21648
Maryland Dorchester County

Homes for Sale with Acreage in Woolford, MD

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In Woolford, there are currently 7 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Woolford, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Woolford and discover the potential and freedom that comes with owning your own piece of property.

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