3

Woolford, MD Houses for Sale

Section Image Section Image
  • 4825 Madison Canning House Rd, Madison, MD 21648
    4825 Madison Canning House Rd, Madison, MD 21648
    4825 Madison Canning House Rd, Madison, MD 21648
    /117

    $765,000

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

    4825 Madison Canning House Rd, Madison, MD 21648

    A must-see if you're looking for Eastern Shore Waterfront charm! Beautiful waterfront with expansive sunrise views of Madison Bay! Recently renovated primary residence or weekend getaway 15 minutes off of Route 50 outside Cambridge. Four bedroom, three bathroom two-story on 2.2 Acres. 800 ft of wrap around rip rap, pier with deep water docking for 2 to 3 boats. Detached shed/ one car garage for

    Agent Photo

    Wayne Phillips

    Coastal Life Realty Group LLC

    (410) 618-4673

    4825 Madison Canning House Rd, Madison, MD 21648
  • 1318 Bell Ln, Woolford, MD 21677
    1318 Bell Ln, Woolford, MD 21677
    1318 Bell Ln, Woolford, MD 21677
    /38

    $875,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 2 Baths
    • 2,120 Sq Ft

    1318 Bell Ln, Woolford, MD 21677

    Prepare to fall in love! More than just a house- this is a home, lovingly cared for and thoughtfully designed. It offers the perfect blend of comfort, character and privacy. Experience the peace, and tranquility of this secluded, move-in-ready waterfront retreat. Ideally located, just a short distance from historic Cambridge, the Hyatt Regency Chesapeake Bay Golf Resort and within an easy reach

    Debbie McQuaid TTR Sotheby's International Realty

    1318 Bell Ln, Woolford, MD 21677
  • 1252 Old Madison Rd, Madison, MD 21648
    1252 Old Madison Rd, Madison, MD 21648
    1252 Old Madison Rd, Madison, MD 21648
    /90

    $1,600,000

    • 4 Beds
    • 4.5 Baths
    • 5,037 Sq Ft

    1252 Old Madison Rd, Madison, MD 21648

    **THIS OPPORTUNITY IS FOR THE COMBINED PURCHASE OF 1252 OLD MADISON RD, MADISON, MD 21648 - TAX ID 1016008176 AND 1250 OLD MADISION RD, MADISON, MD 21648 - 1016001406** End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound featuring 268 feet of protected shoreline and approximately 2.83 acres of combined privacy, perfectly positioned with an ideal east-west

    Barbara McCaffrey Redfin Corp

    1252 Old Madison Rd, Madison, MD 21648
Maryland Dorchester County Woolford

Houses for Sale in Woolford, MD

How to Buy a Home How to Finance a Home How to Sell a Home

In Woolford, there are currently 3 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Woolford, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group