317

Dorchester, MD Homes

Section Image
  • 4906 Timbermarsh Ln, Woolford, MD 21677
    4906 Timbermarsh Ln, Woolford, MD 21677
    4906 Timbermarsh Ln, Woolford, MD 21677
    /133

    $1,499,000

    • 4 Beds
    • 3 Baths
    • 4,445 Sq Ft

    4906 Timbermarsh Ln, Woolford, MD 21677

    Beautiful waterfront on Madson Bay! Rarely do you find a property with your own private beach. This exceptional property checks all the boxes. 22+ acres. 10 acres are wooded, 2 ponds, 890 ft of shoreline, a sandy beach and a 3 bedroom, 2 bath guesthouse on the end of a private cul-de-sac. This impeccable home offers 4 bedrooms, 3 full baths, upper/lower decks, large screen porch, 3 car garage and

    Penny Windsor Benson & Mangold, LLC

    4906 Timbermarsh Ln, Woolford, MD 21677
  • 1334 Bell Ln, Woolford, MD 21677
    1334 Bell Ln, Woolford, MD 21677
    /2

    $455,000 Sold Jul 23, 2025

    • 672 Sq Ft
    • $677/SF
    • 1 Bed
    • 1 Bath
    • Built 1963

    1334 Bell Ln, Woolford, MD 21677

    Listed and sold simultaneously.

    Patrick Peters Capital Reality Group LLC

    1334 Bell Ln, Woolford, MD 21677
    • 1515 Deep Water Rd, Woolford, MD 21677
      1515 Deep Water Rd, Woolford, MD 21677
      1515 Deep Water Rd, Woolford, MD 21677
      /26

      Est $477,669 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,464 Sq Ft

      1515 Deep Water Rd, Woolford, MD 21677

      1515 Deep Water Rd, Woolford, MD 21677
  • 1609 Heliport Rd, Woolford, MD 21677
    1609 Heliport Rd, Woolford, MD 21677
    1609 Heliport Rd, Woolford, MD 21677
    /25

    $337,900

    • Land
    • 1.52 Acres
    • $222,303 per Acre

    1609 Heliport Rd, Woolford, MD 21677

    THIS IS THE LOCATION!!!!This property has a current tidewater buffer setback variance to allow construction of a dwelling inside the typical 100' setback. It does not expire and transfers with the property. (This can be confirmed with Dorchester Co. Zoning and Planning by referencing BOA Case # 2109)1609 Heliport has all the plug and play attributes that a waterfront property can

    C Fred Robinson Keller Williams Realty Delmarva

    1609 Heliport Rd, Woolford, MD 21677
  • 1617 Deep Water Rd, Woolford, MD 21677
    1617 Deep Water Rd, Woolford, MD 21677
    1617 Deep Water Rd, Woolford, MD 21677
    /47

    $870,000 Sold Jul 11, 2025

    • 2,959 Sq Ft
    • $294/SF
    • 79 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2002

    1617 Deep Water Rd, Woolford, MD 21677

    Experience waterfront living on Church Creek with this impressive 4-bedroom, 2 full and 2 half-bathroom home, offering 400 +/- ft. of shoreline and breathtaking views. Built in 2002 and situated on a private 1.76-acre lot in a cul-de-sac, this 2,959 +/- sq.ft. retreat features a private boat dock with a boat lift and 3' +/- MLW. Perfect for boating, fishing, crabbing, and water sports with direct

    Peter Stark Benson & Mangold, LLC

    1617 Deep Water Rd, Woolford, MD 21677
    • 5119 Brooks Rd, Woolford, MD 21677
      5119 Brooks Rd, Woolford, MD 21677
      5119 Brooks Rd, Woolford, MD 21677
      /73

      Est $1,728,653 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 4,632 Sq Ft

      5119 Brooks Rd, Woolford, MD 21677

      5119 Brooks Rd, Woolford, MD 21677
  • 0 Laurie Ln Unit MDDO2009086, Woolford, MD 21677
    0 Laurie Ln Unit MDDO2009086, Woolford, MD 21677
    0 Laurie Ln Unit MDDO2009086, Woolford, MD 21677
    /26

    $72,000

    • Land
    • 3.33 Acres
    • $21,622 per Acre

    0 Laurie Ln Unit MDDO2009086, Woolford, MD 21677

    Beautiful 3.33 +/- acre lot in the South Dorchester School District in a wonderful location with a waterfront view to Church Creek. Lot is located in Brad-Vern Park, Part3, Lot 2C, a rural subdivision near Woolford. The property is mostly wooded in a convenient location between Taylors Island and Cambridge. This might be just the place to build that dream house you have always wanted. Here's a

    Rob Freyer Charis Realty Group

    0 Laurie Ln Unit MDDO2009086, Woolford, MD 21677
  • 5012 Cherry Point Rd, Woolford, MD 21677
    5012 Cherry Point Rd, Woolford, MD 21677
    5012 Cherry Point Rd, Woolford, MD 21677
    /21

    $360,000 Sold Jun 30, 2025

    • Land
    • 4.30 Acres
    • $83,721 per Acre
    • 3 Days On Market

    5012 Cherry Point Rd, Woolford, MD 21677

    Nestled at McKeil Pointe, this stunning wooded waterfront lot boasts one of the prime locations in Dorchester County. Featuring 530 feet of shoreline along Fishing Creek, a tributary of the Little Choptank River, this exceptional property offers an ideal setting for your dream home. The lot includes an elevated building pad and road base installed in 1999, with a new sewer connection available.

    Sharon Spedden Sharon Real Estate P.C.

    5012 Cherry Point Rd, Woolford, MD 21677
    • 4707 Steamboat Rd, Woolford, MD 21677
      4707 Steamboat Rd, Woolford, MD 21677
      4707 Steamboat Rd, Woolford, MD 21677
      /52

      Est $329,526 Not Listed For Sale

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

      4707 Steamboat Rd, Woolford, MD 21677

      4707 Steamboat Rd, Woolford, MD 21677
  • 0 Taylors Island Rd Unit MDDO2000516, Woolford, MD 21677
    0 Taylors Island Rd Unit MDDO2000516, Woolford, MD 21677
    0 Taylors Island Rd Unit MDDO2000516, Woolford, MD 21677
    /4

    $239,900

    • Land
    • 3.75 Acres
    • $63,973 per Acre

    0 Taylors Island Rd Unit MDDO2000516, Woolford, MD 21677

    Beautiful point of land with panoramic view of Church Creek. Health Dept. approved. Stoned driveway in place.

    Valerie Brown Charles C. Powell, Inc. Realtors

    0 Taylors Island Rd Unit MDDO2000516, Woolford, MD 21677
  • 1604 Deep Point Rd, Woolford, MD 21677
    1604 Deep Point Rd, Woolford, MD 21677
    1604 Deep Point Rd, Woolford, MD 21677
    /49

    $825,000 Sold Jun 03, 2025

    • 2,327 Sq Ft
    • $355/SF
    • 7 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1966

    1604 Deep Point Rd, Woolford, MD 21677

    Waterfront Paradise – Boating, Crabbing & Fishing on Fishing Creek!Embrace the ultimate Eastern Shore waterfront lifestyle in this beautifully renovated (2023) ranch on Fishing Creek, offering 4 feet MLW (mean low water)—perfect for boating, fishing, and crabbing right from your backyard! All renovations have been completed—just move in and start enjoying life on the water. (See full list of

    Susan Lamont Howard Hanna Real Estate Services-Shrewsbury

    1604 Deep Point Rd, Woolford, MD 21677
    • 1620 Taylors Island Rd, Woolford, MD 21677
      1620 Taylors Island Rd, Woolford, MD 21677
      1620 Taylors Island Rd, Woolford, MD 21677
      /63

      Est $707,668 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 2,352 Sq Ft

      1620 Taylors Island Rd, Woolford, MD 21677

      1620 Taylors Island Rd, Woolford, MD 21677
  • 4334 Buttons Neck Rd, Woolford, MD 21677
    4334 Buttons Neck Rd, Woolford, MD 21677
    4334 Buttons Neck Rd, Woolford, MD 21677
    /11

    $70,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    4334 Buttons Neck Rd, Woolford, MD 21677

    Located on a private road just minutes from the renowned Blackwater National Wildlife Refuge, this 3-bedroom, 2-bathroom mobile home sits on a quiet, wooded lot offering peace, privacy, and endless potential. The home is in need of significant renovation and is being sold as-is—ideal for experienced investors, DIY renovators, or those looking to build new in a serene, natural setting. Whether

    Carlo Washington Samson Properties

    4334 Buttons Neck Rd, Woolford, MD 21677
  • 1738 Taylors Island Rd, Woolford, MD 21677
    1738 Taylors Island Rd, Woolford, MD 21677
    1738 Taylors Island Rd, Woolford, MD 21677
    /36

    $264,500 Sold May 23, 2025

    • 1,616 Sq Ft
    • $164/SF
    • 77 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    1738 Taylors Island Rd, Woolford, MD 21677

    Church Creek - located just a short drive from Cambridge, this home offers all the advantages of country living. New roof, new well, new HVAC - all the expensive project are done! Stick built home loved by one family. You will enjoy the cozy living room with the fireplace and warmth of the gas logs. Large primary bedroom with bath. Two additional bedrooms and bath. Additional room can be a

    Valerie Brown Charles C. Powell, Inc. Realtors

    1738 Taylors Island Rd, Woolford, MD 21677
    • 4920 Laurie Ln, Woolford, MD 21677
      4920 Laurie Ln, Woolford, MD 21677
      4920 Laurie Ln, Woolford, MD 21677
      /28

      Est $330,355 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft

      4920 Laurie Ln, Woolford, MD 21677

      4920 Laurie Ln, Woolford, MD 21677
  • 4926 Timbermarsh Ln, Woolford, MD 21677
    4926 Timbermarsh Ln, Woolford, MD 21677
    4926 Timbermarsh Ln, Woolford, MD 21677
    /39

    $449,000 Under Contract

    • Land
    • 21 Acres
    • $21,828 per Acre

    4926 Timbermarsh Ln, Woolford, MD 21677

    Private 20 acre plus lot with broad westerly views over Madison and Chesapeake Bay’s in Bromwell's Adventure. Designated building area on lot, shared sewage system for subdivision and lane in place. Privacy, wildlife, views & hunting! Property is accessed by a private drive, security in place, no access without an appointment. Call listing agent for access.

    Mark McGuire Benson & Mangold, LLC

    4926 Timbermarsh Ln, Woolford, MD 21677
  • 1326 Bell Ln, Woolford, MD 21677
    1326 Bell Ln, Woolford, MD 21677
    1326 Bell Ln, Woolford, MD 21677
    /28

    $358,200 Sold May 05, 2025

    • 816 Sq Ft
    • $439/SF
    • 39 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    1326 Bell Ln, Woolford, MD 21677

    WATERFRONT Opportunity! This is a great vacation home and has a lot of potential. Whether you want to crab or fish off your own pier or hop on your boat and cruise out to the Little Choptank, your excursions are endless. This large lot is 2.52 Acres NW of Deep Point Road. You must see this adorable 816 sq ft cottage - two-bedroom and one full bath. The interior offers a surprisingly open flow

    Lona Todd Taylor Properties

    1326 Bell Ln, Woolford, MD 21677
    • 4905 Longview Rd, Woolford, MD 21677
      4905 Longview Rd, Woolford, MD 21677
      4905 Longview Rd, Woolford, MD 21677
      /34

      Est $813,751 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,935 Sq Ft

      4905 Longview Rd, Woolford, MD 21677

      4905 Longview Rd, Woolford, MD 21677
  • 4739 Harrisville Rd, Woolford, MD 21677
    4739 Harrisville Rd, Woolford, MD 21677
    4739 Harrisville Rd, Woolford, MD 21677
    /24

    $300,000 Sold Mar 25, 2025

    • 1,242 Sq Ft
    • $242/SF
    • 30 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    4739 Harrisville Rd, Woolford, MD 21677

    Woolford - brand new 3 bedroom, 2 bath home located on a quiet country lot. Close to the Madison boat ramp. South Dorchester K-8. Worry free.Room for an outbuilding.

    Valerie Brown Charles C. Powell, Inc. Realtors

    4739 Harrisville Rd, Woolford, MD 21677
    • 4915 Mallard Cove, Woolford, MD 21677
      4915 Mallard Cove, Woolford, MD 21677
      4915 Mallard Cove, Woolford, MD 21677
      /53

      Est $1,005,245 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,000 Sq Ft

      4915 Mallard Cove, Woolford, MD 21677

      4915 Mallard Cove, Woolford, MD 21677
  • 4903 Mallard Cove, Woolford, MD 21677
    4903 Mallard Cove, Woolford, MD 21677
    4903 Mallard Cove, Woolford, MD 21677
    /55

    $1,295,000 Sold Feb 14, 2025

    • 3,853 Sq Ft
    • $336/SF
    • 3 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    4903 Mallard Cove, Woolford, MD 21677

    Stunning Waterfront Oasis on 2.47 acres with 475+/- feet on Churck Creek where Fishing Creek and Church Creek meet. This 5/6 Bedroom 3.5Bath home w/large Great Room, Living Room, Dining Room, Kitchen, Office and Sitting Area has incredible waterviews from almost every room . The layout of this home makes it perfect for large gatherings of friends and family. Come enjoy the indoor/outdoor

    Craig Linthicum Benson & Mangold, LLC

    4903 Mallard Cove, Woolford, MD 21677
    • 5219 Brooks Rd, Woolford, MD 21677
      5219 Brooks Rd, Woolford, MD 21677
      5219 Brooks Rd, Woolford, MD 21677
      /41

      Est $1,087,616 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,170 Sq Ft

      5219 Brooks Rd, Woolford, MD 21677

      5219 Brooks Rd, Woolford, MD 21677
  • 4641 Harrisville Rd, Woolford, MD 21677
    4641 Harrisville Rd, Woolford, MD 21677
    /2

    $20,000 Sold Feb 11, 2025

    • Land
    • 1.61 Acres
    • $12,422 per Acre
    • 174 Days On Market

    4641 Harrisville Rd, Woolford, MD 21677

    Build your dream home on 1.61 acres in Country living setting. Property offers multiple possibilities - No HOA or Covenants & Restrictions. Buyer to do due diligence- Seller has not applied for Perc

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    4641 Harrisville Rd, Woolford, MD 21677
    • 1624 Deep Water Rd, Woolford, MD 21677
      1624 Deep Water Rd, Woolford, MD 21677
      1624 Deep Water Rd, Woolford, MD 21677
      /19

      Est $342,407 Not Listed For Sale

      1624 Deep Water Rd, Woolford, MD 21677

      1624 Deep Water Rd, Woolford, MD 21677
  • 4913 Lee Terrace, Woolford, MD 21677
    4913 Lee Terrace, Woolford, MD 21677
    4913 Lee Terrace, Woolford, MD 21677
    /68

    $900,000 Sold Jan 10, 2025

    • 5,784 Sq Ft
    • $156/SF
    • 66 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2003

    4913 Lee Terrace, Woolford, MD 21677

    Stunning 4-bedroom, 3 and 1/2 bath waterfront home on scenic Church Creek! MOST FUNISHINGS CONVEY!!!!This spacious residence boasts an open floor plan perfect for entertaining, with abundant natural light and open, airy rooms. Kitchen, dining room and great room with fireplace afford stunning waterviews of the river. The first floor primary bedroom offers convenience and privacy as well as

    Debbie Luthy Benson & Mangold, LLC

    4913 Lee Terrace, Woolford, MD 21677
    • 5228 Brooks Rd, Woolford, MD 21677
      5228 Brooks Rd, Woolford, MD 21677
      5228 Brooks Rd, Woolford, MD 21677
      /59

      Est $1,206,118 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,140 Sq Ft

      5228 Brooks Rd, Woolford, MD 21677

      5228 Brooks Rd, Woolford, MD 21677
  • 1554 Taylors Island Rd, Woolford, MD 21677
    1554 Taylors Island Rd, Woolford, MD 21677
    1554 Taylors Island Rd, Woolford, MD 21677
    /64

    $825,000 Sold Nov 15, 2024

    • 3,420 Sq Ft
    • $241/SF
    • 103 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1948

    1554 Taylors Island Rd, Woolford, MD 21677

    Unbelievably great opportunity to assume a $510k mortgage at just 2.25% through 10/1/2051! Ownersneed to relocate and have just reduced the price to $825K which is under the recent appraisal. Welcome to Crystal Cove...1554 Taylors Island Road! If you are looking for a tranquil, bucolic refuge on the water and a great house...look no farther. This beautiful home sited on 3.5 acres

    Mary Losty Compass

    1554 Taylors Island Rd, Woolford, MD 21677
    • 1508 Deep Point Rd, Woolford, MD 21677
      1508 Deep Point Rd, Woolford, MD 21677
      1508 Deep Point Rd, Woolford, MD 21677
      /34

      Est $419,347 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,200 Sq Ft

      1508 Deep Point Rd, Woolford, MD 21677

      1508 Deep Point Rd, Woolford, MD 21677
  • 5130 Brooks Rd, Woolford, MD 21677
    5130 Brooks Rd, Woolford, MD 21677
    /2

    $140,000 Sold Aug 15, 2024

    • Land
    • 16 Acres
    • $8,537 per Acre
    • 27 Days On Market

    5130 Brooks Rd, Woolford, MD 21677

    **New Listing: Dream Waterfront Property on 5130 Brooks Rd, Woolford, MD**Unlock the potential of this expansive 16.4-acre waterfront property located in the serene Woolford, Maryland. Perfectly situated, this vacant land offers an unparalleled opportunity to build your custom dream home overlooking approximately 1,500 feet of stunning waterfront.The property features a cleared

    Andy Schweigman Douglas Realty, LLC

    5130 Brooks Rd, Woolford, MD 21677
    • 1725 Taylors Island Rd, Woolford, MD 21677
      1725 Taylors Island Rd, Woolford, MD 21677
      1725 Taylors Island Rd, Woolford, MD 21677
      /30

      Est $329,196 Not Listed For Sale

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

      1725 Taylors Island Rd, Woolford, MD 21677

      1725 Taylors Island Rd, Woolford, MD 21677
    • 4711 Steamboat Rd, Woolford, MD 21677
      4711 Steamboat Rd, Woolford, MD 21677
      4711 Steamboat Rd, Woolford, MD 21677
      /63

      Est $880,942 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,770 Sq Ft

      4711 Steamboat Rd, Woolford, MD 21677

      4711 Steamboat Rd, Woolford, MD 21677
    • 1803 Perseus Rd, Church Creek, MD 21622
      1803 Perseus Rd, Church Creek, MD 21622
      1803 Perseus Rd, Church Creek, MD 21622
      /47

      Est $552,133 Not Listed For Sale

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

      1803 Perseus Rd, Church Creek, MD 21622

      1803 Perseus Rd, Church Creek, MD 21622
    • 1602 Deep Point Rd, Woolford, MD 21677
      1602 Deep Point Rd, Woolford, MD 21677
      1602 Deep Point Rd, Woolford, MD 21677
      /90

      Est $450,245 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,408 Sq Ft

      1602 Deep Point Rd, Woolford, MD 21677

      1602 Deep Point Rd, Woolford, MD 21677
    • 1514 Deep Point Rd, Woolford, MD 21677
      1514 Deep Point Rd, Woolford, MD 21677
      1514 Deep Point Rd, Woolford, MD 21677
      /46

      Est $508,231 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft

      1514 Deep Point Rd, Woolford, MD 21677

      1514 Deep Point Rd, Woolford, MD 21677
    • 5040 Brooks Rd, Woolford, MD 21677
      5040 Brooks Rd, Woolford, MD 21677
      5040 Brooks Rd, Woolford, MD 21677
      /76

      Est $1,819,176 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 5,000 Sq Ft

      5040 Brooks Rd, Woolford, MD 21677

      5040 Brooks Rd, Woolford, MD 21677
    • 5124 Brooks Rd, Woolford, MD 21677
      5124 Brooks Rd, Woolford, MD 21677
      5124 Brooks Rd, Woolford, MD 21677
      /70

      Est $935,815 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,066 Sq Ft

      5124 Brooks Rd, Woolford, MD 21677

      5124 Brooks Rd, Woolford, MD 21677
    • 4901 Lee Terrace, Woolford, MD 21677
      4901 Lee Terrace, Woolford, MD 21677
      4901 Lee Terrace, Woolford, MD 21677
      /58

      Est $1,186,380 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,939 Sq Ft

      4901 Lee Terrace, Woolford, MD 21677

      4901 Lee Terrace, Woolford, MD 21677
    • 4918 Timbermarsh Ln, Woolford, MD 21677
      4918 Timbermarsh Ln, Woolford, MD 21677
      4918 Timbermarsh Ln, Woolford, MD 21677
      /77

      Est $1,611,803 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,808 Sq Ft

      4918 Timbermarsh Ln, Woolford, MD 21677

      4918 Timbermarsh Ln, Woolford, MD 21677
    • 1605 Taylors Island Rd, Woolford, MD 21677
      1605 Taylors Island Rd, Woolford, MD 21677
      1605 Taylors Island Rd, Woolford, MD 21677
      /17

      Est $356,826 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,658 Sq Ft

      1605 Taylors Island Rd, Woolford, MD 21677

      1605 Taylors Island Rd, Woolford, MD 21677
    • 1516 Deep Point Rd, Woolford, MD 21677
      1516 Deep Point Rd, Woolford, MD 21677
      1516 Deep Point Rd, Woolford, MD 21677
      /50

      Est $545,965 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,184 Sq Ft

      1516 Deep Point Rd, Woolford, MD 21677

      1516 Deep Point Rd, Woolford, MD 21677

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