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Newest Homes for Sale in Woolford, MD

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  • /2

    $349,000

    • 4 Beds
    • 1 Bath
    • 1,728 Sq Ft

    4707 Steamboat Rd, Woolford, MD 21677

    Experience the timeless charm of Maryland's Eastern Shore at 4707 Steamboat Road in the peaceful community of Woolford MD. Just steps from the shores of beautiful Church Creek, this beautifully updated traditional farmhouse offers picturesque water views from the screened front porch and the perfect blend of classic Eastern Shore character and modern comfort. Inside, you'll find a bright,

    Phillip Anderson Keller Williams Realty

    4707 Steamboat 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
  • /53

    $695,000

    Coming Soon
    • 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
  • /37

    $719,900

    Open Sun 1PM - 3PM $80K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    1514 Deep Point Rd, Woolford, MD 21677

    Welcome to your private piece of paradise! Freshly painted, new thermopane windows, newer roof, and priced to sell quickly! Once you step through the front door, the captivating view through the living room bay window will leave you breathless. Not only is this 2-bedroom, 2-full-bath home well-maintained, but it also sits on half an acre, giving you plenty of room for entertaining. As much as the

    Theresalaina Barnett Long & Foster Real Estate, Inc.

    1514 Deep Point Rd, Woolford, MD 21677
  • /80

    $849,500

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,615 Sq Ft

    4712 Steamboat Rd, Woolford, MD 21677

    Price adjustment! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the

    Carol Baker-Jones Benson & Mangold, LLC

    4712 Steamboat Rd, Woolford, MD 21677
  • /56

    $1,400,000

    • 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
  • /32

    $475,000

    • 1 Bed
    • 1 Bath
    • 1,040 Sq Ft

    5023 Russell Rd, Woolford, MD 21677

    Exceptional waterfront opportunity with gorgeous water views, deep water access, and extensive boating amenities in a welcoming, waterfront neighborhood known for its friendly and laid-back atmosphere. This fully ADA-compliant 1-bedroom home features a thoughtfully renovated full bath with roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of

    Sydney Johnson Cohee Sharon Real Estate P.C.

    5023 Russell 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
  • /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
  • /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
  • /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
  • /39

    $849,500

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,120 Sq Ft

    1318 Bell Ln, Woolford, MD 21677

    Improved Pricing! Was $875,000 now $849,500. Major Interior Renovations completed in 2022 (see attachment for full list). This beautifully updated and meticulously maintained, 3-bedroom, 2-bath home offers over 2,300 square feet of bright living space designed to capture the beauty of waterfront living. Panoramic water views greet you from nearly every room, with the living room highlighting

    Debbie McQuaid TTR Sotheby's International Realty

    1318 Bell Ln, Woolford, MD 21677

Frequently Asked Questions

What are the most popular zip codes in Woolford, MD?
The most popular zip codes in Woolford, MD include 21677, 21613, 21622, 21648 and 21669.
What are the most popular neighborhoods near Woolford, MD?
The most popular neighborhood near Woolford, MD is Port Republic.
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