226

Dorchester, MD Homes

Section Image
  • 1312 Taylors Island Rd, Madison, MD 21648
    1312 Taylors Island Rd, Madison, MD 21648
    1312 Taylors Island Rd, Madison, MD 21648
    /76

    $1,050,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,502 Sq Ft

    1312 Taylors Island Rd, Madison, MD 21648

    ***Mortgage savings may be available for buyers of this listing***Waterfront Paradise on Madison Bay – 1312 Taylors Island Rd, Madison, MD Discover an extraordinary waterfront retreat set on nearly 10 acres with over 300 feet of protected shoreline on scenic Madison Bay. This fully renovated 3BR/3BA Cape Cod offers unmatched privacy, sweeping lawns, and panoramic water views—creating the

    Barbara McCaffrey Redfin Corp

    1312 Taylors Island Rd, Madison, MD 21648
  • 1223 Old Madison Rd, Madison, MD 21648
    1223 Old Madison Rd, Madison, MD 21648
    1223 Old Madison Rd, Madison, MD 21648
    /32

    $230,000 Sold Aug 04, 2025

    • 1,208 Sq Ft
    • $190/SF
    • 41 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1930

    1223 Old Madison Rd, Madison, MD 21648

    A Cape-style home on nearly 3 acres of Country setting gives you plenty of space, both indoors and outdoors with your oasis. First floor 1-Room currently used as a bedroom with upstair Bedroom & additional room also used as 3rd bedroom.. Property also offers new Roof installed in 2023, Oversized Detached garage/pole building & 3 additional Sheds for extra utility, whether it's for storage,

    Kristin Abbott Keller Williams Select Realtors of Cambridge

    1223 Old Madison Rd, Madison, MD 21648
    • 942 Susquehanna Rd, Madison, MD 21648
      942 Susquehanna Rd, Madison, MD 21648
      942 Susquehanna Rd, Madison, MD 21648
      /74

      Est $374,983 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,256 Sq Ft

      942 Susquehanna Rd, Madison, MD 21648

      942 Susquehanna Rd, Madison, MD 21648
  • 0 N S Route 16 - Taylors Island Rd Unit MDDO2010114, Madison, MD 21648
    0 N S Route 16 - Taylors Island Rd Unit MDDO2010114, Madison, MD 21648
    0 N S Route 16 - Taylors Island Rd Unit MDDO2010114, Madison, MD 21648
    /8

    $750,000

    • Land
    • 101 Acres
    • $7,406 per Acre

    0 N S Route 16 - Taylors Island Rd Unit MDDO2010114, Madison, MD 21648

    Premier 101± Acre Hunting & Recreation Property in Dorchester CountyAttention, all hunters and outdoor enthusiasts! This exceptional 101± acre tract in Dorchester County is a rare find, and it won't last long! It offers a diverse and thriving habitat for the Eastern Shore's most sought-after game—including sika deer, whitetail deer, wild turkeys, and waterfowl.Key

    Beth Hill The Land Group

    0 N S Route 16 - Taylors Island Rd Unit MDDO2010114, Madison, MD 21648
  • 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
    • 5119 Brooks Rd, Woolford, MD 21677
      5119 Brooks Rd, Woolford, MD 21677
      5119 Brooks Rd, Woolford, MD 21677
      /73

      Est $1,733,727 Not Listed For Sale

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

      5119 Brooks Rd, Woolford, MD 21677

      5119 Brooks Rd, Woolford, MD 21677
  • 921 Parsons Dr, Madison, MD 21648
    921 Parsons Dr, Madison, MD 21648
    921 Parsons Dr, Madison, MD 21648
    /51

    $379,900

    • 3 Beds
    • 2.5 Baths
    • 1,152 Sq Ft

    921 Parsons Dr, Madison, MD 21648

    Welcome home to this stunningly renovated raised rancher on desirable Taylors Island! This 3-bedroom, 3-bathroom home has been meticulously updated from top to bottom. Step inside to discover gleaming new luxury flooring throughout. The heart of the home is the brand-new kitchen, boasting stainless steel appliances and ample counter space. Enjoy peace of mind with a new HVAC system and new CPVC

    David Moore RE/MAX Executive

    921 Parsons Dr, Madison, MD 21648
  • 1243 Old Madison Rd, Madison, MD 21648
    1243 Old Madison Rd, Madison, MD 21648
    1243 Old Madison Rd, Madison, MD 21648
    /41

    $485,000 Sold Mar 14, 2025

    • 3,049 Sq Ft
    • $159/SF
    • 12 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1900

    1243 Old Madison Rd, Madison, MD 21648

    EASTERN SHORE RETREAT- Wake-up to stunning Madison Bay views in this renovated 5 bedroom, 3 bathroom home on 8.51+/- acres. Perfect for outdoor enthusiasts or an Airbnb investment. This property combines comfort, nature and modern amenities.KEY FEATURES: Open living areas, and a large country kitchen with pantry and mudroom. RECENT UPGRADES: New HVAC, New roof, wood stove and ultra

    Bill Hubbard Charles C. Powell, Inc. Realtors

    1243 Old Madison Rd, Madison, MD 21648
    • 1224 Old Madison Rd, Madison, MD 21648
      1224 Old Madison Rd, Madison, MD 21648
      1224 Old Madison Rd, Madison, MD 21648
      /25

      Est $468,672 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,224 Sq Ft

      1224 Old Madison Rd, Madison, MD 21648

      1224 Old Madison Rd, Madison, MD 21648
  • 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
  • 1058 Taylors Island Rd, Madison, MD 21648
    1058 Taylors Island Rd, Madison, MD 21648
    1058 Taylors Island Rd, Madison, MD 21648
    /24

    $79,900 Sold Mar 14, 2025

    • 1,804 Sq Ft
    • $44/SF
    • 147 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    1058 Taylors Island Rd, Madison, MD 21648

    This Colonial Farm House sits on over half an acre lot with a circular driveway. Screened in Porch. Spacious bedrooms with 2 full bathrooms.

    Stephana Riha Century 21 Harbor Realty

    1058 Taylors Island Rd, Madison, MD 21648
    • 1207 Old Madison Rd, Madison, MD 21648
      1207 Old Madison Rd, Madison, MD 21648
      1207 Old Madison Rd, Madison, MD 21648
      /17

      Est $206,454 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,308 Sq Ft

      1207 Old Madison Rd, Madison, MD 21648

      1207 Old Madison Rd, Madison, MD 21648
  • 1242 Old Madison Rd, Madison, MD 21648
    1242 Old Madison Rd, Madison, MD 21648
    1242 Old Madison Rd, Madison, MD 21648
    /80

    $423,000

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

    1242 Old Madison Rd, Madison, MD 21648

    ***MOTIVATED SELLER SAYS "GET IT SOLD!" REASONABLE OFFERS CONSIDERED***EXPANSIVE WATER VIEWS - DEEDED RIGHT-OF-WAY TO THE WATER - REMODELED 2023 - SDPreK-8 SCHOOL DISTRICT - EXCELLENT AIRBNB PROPERTY OR PERFECT PRIMARY HOMEThis tastefully remodeled home is situated on a 1+/- acre lot in the heart of Madison where country living near the water soothes the soul. Every room in this

    Michelle Ruark McClain-Williamson Realty, LLC

    1242 Old Madison Rd, Madison, MD 21648
  • 1226 Taylors Island Rd, Madison, MD 21648
    1226 Taylors Island Rd, Madison, MD 21648
    1226 Taylors Island Rd, Madison, MD 21648
    /26

    $122,000 Sold Jan 09, 2025

    • 816 Sq Ft
    • $150/SF
    • 84 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1966

    1226 Taylors Island Rd, Madison, MD 21648

    HUNTERS!!!!!!Turn-key THREE BEDROOM ready for Dorchester County's 2024-2025 hunting season. 3 acres able to accommodate seasonal campers. RECENT UPGRADES- roof, laminate floors throughout, refrigerator, bathroom. That's not all, on PUBIC SEWER SERVICE. Well recently installed. Also IDEAL as a family residence, second home, quick weekend getaway as a VACATION RENTAL.

    C Fred Robinson Keller Williams Realty Delmarva

    1226 Taylors Island Rd, Madison, MD 21648
    • 924 Parsons Dr, Madison, MD 21648
      924 Parsons Dr, Madison, MD 21648
      924 Parsons Dr, Madison, MD 21648
      /81

      Est $350,950 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,992 Sq Ft

      924 Parsons Dr, Madison, MD 21648

      924 Parsons Dr, Madison, MD 21648
  • 4820 Madison Canning House Rd, Madison, MD 21648
    4820 Madison Canning House Rd, Madison, MD 21648
    4820 Madison Canning House Rd, Madison, MD 21648
    /74

    $699,000

    • 3 Beds
    • 2 Baths
    • 2,254 Sq Ft

    4820 Madison Canning House Rd, Madison, MD 21648

    Spectacular Water-View Retreat in Madison, MD- Discover this expansive raised residence, perfectly situated on 5 picturesque acres with sweeping views of the water, harbor, and surrounding woodlands. Designed for both comfort and functionality, this home invites you to embrace the best of coastal Maryland living. Enjoy breathtaking views from nearly every room, with decks at both the front and

    Sydney Johnson Cohee Sharon Real Estate P.C.

    4820 Madison Canning House Rd, Madison, MD 21648
  • 1236 Pennsylvania Ave, Madison, MD 21648
    1236 Pennsylvania Ave, Madison, MD 21648
    1236 Pennsylvania Ave, Madison, MD 21648
    /47

    $705,000 Sold Oct 07, 2024

    • 2,030 Sq Ft
    • $347/SF
    • 52 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    1236 Pennsylvania Ave, Madison, MD 21648

    Stunning Madison Bay sunsets, and that’s not all!! This lovely custom contemporary home greets you with a bright and spacious open floor plan, with the amazement and beauty of an entire wall of floor to ceiling windows as you enter …. It’s spectacular! The cathedral ceilings and gas fireplace add warmth and charm to the large great room; and the sliding glass doors leading out to the rambling

    Alma Fitzgerald Long & Foster Real Estate, Inc.

    1236 Pennsylvania Ave, Madison, MD 21648
    • 932 Parsons Dr, Madison, MD 21648
      932 Parsons Dr, Madison, MD 21648
      932 Parsons Dr, Madison, MD 21648
      /27

      Est $294,883 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft

      932 Parsons Dr, Madison, MD 21648

      932 Parsons Dr, Madison, MD 21648
  • 0 Parsons Dr Unit MDDO2000640, Madison, MD 21648
    0 Parsons Dr Unit MDDO2000640, Madison, MD 21648
    0 Parsons Dr Unit MDDO2000640, Madison, MD 21648
    /21

    $35,000

    • Land
    • 0.94 Acre
    • $37,234 per Acre

    0 Parsons Dr Unit MDDO2000640, Madison, MD 21648

    Lot for sale in quiet water privileged community which includes sandy beach, pier and pavilion for residents use

    Levin Elzey Long & Foster Real Estate, Inc.

    0 Parsons Dr Unit MDDO2000640, Madison, MD 21648
    • 4804 Saltmarsh Rd, Madison, MD 21648
      4804 Saltmarsh Rd, Madison, MD 21648
      4804 Saltmarsh Rd, Madison, MD 21648
      /53

      Est $880,178 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft

      4804 Saltmarsh Rd, Madison, MD 21648

      4804 Saltmarsh Rd, Madison, MD 21648
  • 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
    • 1260 Old Madison Rd, Madison, MD 21648
      1260 Old Madison Rd, Madison, MD 21648
      1260 Old Madison Rd, Madison, MD 21648
      /72

      Est $826,384 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,008 Sq Ft

      1260 Old Madison Rd, Madison, MD 21648

      1260 Old Madison Rd, Madison, MD 21648
    • 5219 Brooks Rd, Woolford, MD 21677
      5219 Brooks Rd, Woolford, MD 21677
      5219 Brooks Rd, Woolford, MD 21677
      /41

      Est $1,076,651 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
    • 5228 Brooks Rd, Woolford, MD 21677
      5228 Brooks Rd, Woolford, MD 21677
      5228 Brooks Rd, Woolford, MD 21677
      /59

      Est $1,304,507 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
    • 1254 Old Madison Rd, Madison, MD 21648
      1254 Old Madison Rd, Madison, MD 21648
      1254 Old Madison Rd, Madison, MD 21648
      /35

      Est $522,106 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 594 Sq Ft

      1254 Old Madison Rd, Madison, MD 21648

      1254 Old Madison Rd, Madison, MD 21648
    • 0 Parsons Dr Unit MDDO2004418, Madison, MD 21648
      0 Parsons Dr Unit MDDO2004418, Madison, MD 21648
      0 Parsons Dr Unit MDDO2004418, Madison, MD 21648
      /4

      Not Listed For Sale

      0 Parsons Dr Unit MDDO2004418, Madison, MD 21648

      0 Parsons Dr Unit MDDO2004418, Madison, MD 21648
    • 0 Parsons Dr Unit MDDO2004292, Madison, MD 21648
      0 Parsons Dr Unit MDDO2004292, Madison, MD 21648
      0 Parsons Dr Unit MDDO2004292, Madison, MD 21648
      /5

      Not Listed For Sale

      0 Parsons Dr Unit MDDO2004292, Madison, MD 21648

      0 Parsons Dr Unit MDDO2004292, Madison, MD 21648
    • 0 Old Madison Rd Unit 1004378909, Madison, MD 21648
      0 Old Madison Rd Unit 1004378909, Madison, MD 21648
      0 Old Madison Rd Unit 1004378909, Madison, MD 21648
      /10

      Not Listed For Sale

      0 Old Madison Rd Unit 1004378909, Madison, MD 21648

      0 Old Madison Rd Unit 1004378909, Madison, MD 21648
    • 1228 Old Madison Rd, Madison, MD 21648
      1228 Old Madison Rd, Madison, MD 21648
      1228 Old Madison Rd, Madison, MD 21648
      /51

      Est $495,719 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft

      1228 Old Madison Rd, Madison, MD 21648

      1228 Old Madison Rd, Madison, MD 21648
    • 948 Parsons Dr, Madison, MD 21648
      948 Parsons Dr, Madison, MD 21648
      948 Parsons Dr, Madison, MD 21648
      /20

      Est $287,167 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,632 Sq Ft

      948 Parsons Dr, Madison, MD 21648

      948 Parsons Dr, Madison, MD 21648
    • 5040 Brooks Rd, Woolford, MD 21677
      5040 Brooks Rd, Woolford, MD 21677
      5040 Brooks Rd, Woolford, MD 21677
      /76

      Est $1,804,700 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
    • 1221 Old Madison Rd, Madison, MD 21648
      1221 Old Madison Rd, Madison, MD 21648
      1221 Old Madison Rd, Madison, MD 21648
      /49

      Est $455,803 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,580 Sq Ft

      1221 Old Madison Rd, Madison, MD 21648

      1221 Old Madison Rd, Madison, MD 21648
    • 4658 White Marsh Rd, Madison, MD 21648
      4658 White Marsh Rd, Madison, MD 21648
      4658 White Marsh Rd, Madison, MD 21648
      /38

      Est $223,735 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,060 Sq Ft

      4658 White Marsh Rd, Madison, MD 21648

      4658 White Marsh Rd, Madison, MD 21648
    • 5124 Brooks Rd, Woolford, MD 21677
      5124 Brooks Rd, Woolford, MD 21677
      5124 Brooks Rd, Woolford, MD 21677
      /70

      Est $990,545 Not Listed For Sale

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

      5124 Brooks Rd, Woolford, MD 21677

      5124 Brooks Rd, Woolford, MD 21677
    • 4918 Timbermarsh Ln, Woolford, MD 21677
      4918 Timbermarsh Ln, Woolford, MD 21677
      4918 Timbermarsh Ln, Woolford, MD 21677
      /77

      Est $1,660,055 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
    • 927 Susquehanna Rd, Madison, MD 21648
      927 Susquehanna Rd, Madison, MD 21648
      927 Susquehanna Rd, Madison, MD 21648
      /41

      Est $213,954 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,008 Sq Ft

      927 Susquehanna Rd, Madison, MD 21648

      927 Susquehanna Rd, Madison, MD 21648
    • 911 Susquehanna Rd, Madison, MD 21648
      911 Susquehanna Rd, Madison, MD 21648
      911 Susquehanna Rd, Madison, MD 21648
      /27

      Est $391,670 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,452 Sq Ft

      911 Susquehanna Rd, Madison, MD 21648

      911 Susquehanna Rd, Madison, MD 21648
    • 5227 Brooks Rd, Woolford, MD 21677
      5227 Brooks Rd, Woolford, MD 21677
      5227 Brooks Rd, Woolford, MD 21677
      /39

      Est $1,340,381 Not Listed For Sale

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

      5227 Brooks Rd, Woolford, MD 21677

      5227 Brooks Rd, Woolford, MD 21677
    • 5035 Brooks Rd, Woolford, MD 21677
      5035 Brooks Rd, Woolford, MD 21677
      5035 Brooks Rd, Woolford, MD 21677
      /60

      Est $1,034,075 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,167 Sq Ft

      5035 Brooks Rd, Woolford, MD 21677

      5035 Brooks Rd, Woolford, MD 21677
    • 1218 Old Madison Rd, Madison, MD 21648
      1218 Old Madison Rd, Madison, MD 21648
      1218 Old Madison Rd, Madison, MD 21648
      /5

      Est $253,261 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft

      1218 Old Madison Rd, Madison, MD 21648

      1218 Old Madison Rd, Madison, MD 21648

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