3,893

Winthrop, ME Homes

Section Image
  • /5

    $85,000

    Pending
    • Land
    • 20 Acres
    • $4,250 per Acre

    M1, L28 Mount Pisgah Rd, Winthrop, ME 04364

    Spacious 20 acre surveyed lot in Winthrop with level building area and driveway established. Rolling topography with small hill creates an excellent view. Potential gravel income and lots of opportunities.

    Daren Hachey Homestead Realty

    M1, L28 Mount Pisgah Rd, Winthrop, ME 04364
  • /59

    $575,000

    Sold Sep 02, 2025

    8 S Heritage Woods Ln, Winthrop, ME 04364

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $639/SF

    Current Estimated Value $597,215

    Last Listing Agent Joshua LaVerdiere Keller Williams Realty

    8 S Heritage Woods Ln, Winthrop, ME 04364
    • /30

      Est $548,167

      Not Listed For Sale

      20 Maranacook Station Ln, Winthrop, ME 04364

      • 3 Beds
      • 1 Bath
      • 1,542 Sq Ft
      • Built 1900
      20 Maranacook Station Ln, Winthrop, ME 04364

      Last Sold Summary

      • 40 Days On Market

  • /26

    $339,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,791 Sq Ft

    23 Annabessacook Dr, Winthrop, ME 04364

    Wonderful location comes with this 3 bedroom, 2 full bath home in an established neighborhood. This home boasts hardwood floors, metal roof, heated 2 car garage and a primary bedroom with full bath. The large yard and deck add to the features of the home. The shared access to Annabessacook Lake offers a wonderful sandy beach and year round recreation.

    Daren Hachey Homestead Realty

    23 Annabessacook Dr, Winthrop, ME 04364
  • /54

    $174,500

    Sold Jul 07, 2025

    23 Woodland Rd, Winthrop, ME 04364

    • 1 Bed
    • 1 Bath
    • 408 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $428/SF
    • 12 Days On Market

    Current Estimated Value $181,123

    Last Listing Agent Heidi Libby NextHome Northern Lights Realty

    23 Woodland Rd, Winthrop, ME 04364
    • /29

      Est $195,986

      Not Listed For Sale

      19 Hazzard Ln, Winthrop, ME 04364

      • 2 Beds
      • 1 Bath
      • 756 Sq Ft
      • Built 1940
      19 Hazzard Ln, Winthrop, ME 04364

      Last Sold Summary

      • 8 Days On Market

  • /96

    $475,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,483 Sq Ft

    23 Little Cobbosee Ave, Winthrop, ME 04364

    Set on 1.5 private acres with 200+ feet of owned shoreline on Little Cobbosseecontee Lake, this fully updated year-round home offers a rare blend of tranquility and convenience. Located on a quiet, paved, town-maintained dead-end road--uncommon for Maine lake properties--this home provides easy, low-maintenance access in every season. Little Cobbossee Avenue was newly paved in April 2026.

    Kelly Webb Fontaine Family-The Real Estate Leader

    23 Little Cobbosee Ave, Winthrop, ME 04364
  • /68

    $651,000

    Sold Jul 31, 2025

    114 Cottage Rd, Winthrop, ME 04364

    • 4 Beds
    • 2 Baths
    • 1,906 Sq Ft
    • Built 1977

    Last Sold Summary

    • 9% Above List Price
    • $342/SF
    • 5 Days On Market

    Current Estimated Value $697,448

    Last Listing Agent Karen Ramsay-Boucher Better Homes & Gardens Real Estate/The Masiello Group

    114 Cottage Rd, Winthrop, ME 04364
    • /24

      Est $228,926

      Not Listed For Sale

      2555 Us Route 202, Winthrop, ME 04364

      • 2 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1950
      2555 Us Route 202, Winthrop, ME 04364

      Last Sold Summary

      • 31 Days On Market

  • /92

    $639,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,054 Sq Ft

    89 Boot Cove Ln, Winthrop, ME 04364

    This thoughtfully designed four-bedroom, three-bath ranch is tucked into a peaceful wooded setting with direct frontage on Lower Narrows Pond. This fresh and clean property creates a pleasant flow with recent updates, an expansive back deck, and hot tub overlooking the lake! A cozy wood stove in the lower level creates a memorable atmosphere! The private dock and a newly designed staircase

    Terri Levesque Amnet Realty

    89 Boot Cove Ln, Winthrop, ME 04364
  • /84

    $464,630

    Sold Jul 03, 2025

    372 Memorial Dr, Winthrop, ME 04364

    • 1 Bed
    • 1 Bath
    • 520 Sq Ft
    • Built 1951

    Last Sold Summary

    • 3% Below List Price
    • $894/SF
    • 12 Days On Market

    Current Estimated Value $472,616

    Last Listing Agent Trisha Cheney Portside Real Estate Group

    372 Memorial Dr, Winthrop, ME 04364
    • /54

      Est $502,193

      Not Listed For Sale

      41 N Shore Ln, Winthrop, ME 04364

      • 3 Beds
      • 2 Baths
      • 3,064 Sq Ft
      • Built 1932
      41 N Shore Ln, Winthrop, ME 04364

      Last Sold Summary

      • 82 Days On Market

  • /35

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    41 Birch St, Winthrop, ME 04364

    Well-maintained 3-bedroom, 2-bath Cape situated on a private 1.62-acre lot on a public dead-end road, offering a peaceful setting while still being conveniently close to town. Built in 2003, this home offers approximately 1,850 square feet of living space plus an unfinished basement with excellent storage or expansion potential. The first floor features a large eat-in kitchen, spacious living

    Cameron Rizzo Rizzo Mattson

    41 Birch St, Winthrop, ME 04364
  • /38

    $105,000

    Sold Jul 31, 2025

    73 Fellows Rd, Winthrop, ME 04364

    • 1 Bed
    • 114 Sq Ft
    • Built 2023

    Last Sold Summary

    • 16% Below List Price
    • $921/SF
    • 16 Days On Market

    Current Estimated Value $102,631

    Last Listing Agent Meghan Glover Down To Earth Real Estate

    73 Fellows Rd, Winthrop, ME 04364
    • /53

      Est $631,080

      Not Listed For Sale

      69 Welch Point Rd, Winthrop, ME 04364

      • 2 Beds
      • 1 Bath
      • 903 Sq Ft
      • Built 1904
      69 Welch Point Rd, Winthrop, ME 04364

      Last Sold Summary

      • 6 Days On Market

  • /43

    $499,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,416 Sq Ft

    104 Memorial Dr, Winthrop, ME 04364

    Lakefront -waterfront- home facing west on the shores of Maranacook Lake. A great sunset location close to town with public water and sewer. This Cape has easy access and is waiting for your personal touches. The yard is a nice gentle slope to the water. Room for gardening and boats. Shorefront is a mix of some gravel and some sand. Beautiful swimming in summertime. Some of the best ice skating

    Sam Lambert Keller Williams Realty

    104 Memorial Dr, Winthrop, ME 04364
  • /15

    $197,100

    Sold Apr 24, 2026

    2549 US Route 202, Winthrop, ME 04364

    • 3 Beds
    • 1 Bath
    • 858 Sq Ft
    • Built 1935

    Last Sold Summary

    • 34% Below List Price
    • $230/SF
    • 150 Days On Market

    Current Estimated Value $212,407

    Last Listing Agent Chris Vallee LAER

    2549 US Route 202, Winthrop, ME 04364
    • /47

      Est $442,656

      Not Listed For Sale

      37 Turtle Run Rd Unit 24, Winthrop, ME 04364

      • 2 Beds
      • 2 Baths
      • 1,350 Sq Ft
      • Built 1987
      37 Turtle Run Rd Unit 24, Winthrop, ME 04364

      Last Sold Summary

      • 6 Days On Market

  • /89

    $515,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 2,136 Sq Ft

    64 Annabessacook Dr, Winthrop, ME 04364

    This is the kind of property people wait for--and rarely find. Set on 7.7 private acres just minutes from downtown Winthrop, this property offers space, flexibility, and access to Annabessacook Lake without paying waterfront taxes. Keep your boat on the lake, head out for a last-minute sunset cruise, and come back to your own private setting. No hauling, no hassle, no waterfront tax bill. The

    Heidi Libby NextHome Northern Lights Realty

    64 Annabessacook Dr, Winthrop, ME 04364
  • /54

    $325,000

    Sold Jun 27, 2025

    25 Holmes Rd, Winthrop, ME 04364

    • 4 Beds
    • 1 Bath
    • 1,498 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $217/SF
    • 50 Days On Market

    Current Estimated Value $342,078

    Last Listing Agent Tracie Pooley Pooley Realty Group

    25 Holmes Rd, Winthrop, ME 04364
    • /33

      Est $462,761

      Not Listed For Sale

      37 Turtle Run Rd Unit 22, Winthrop, ME 04364

      • 2 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1989
      37 Turtle Run Rd Unit 22, Winthrop, ME 04364

      Last Sold Summary

      • 45 Days On Market

  • /44

    $328,000

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,312 Sq Ft

    247 Winthrop Center Rd, Winthrop, ME 04364

    Step into the charm of this classic Cape Cod-style home, with town records dating it to 1910, though it is believed to be circa 1850s, offering 2,312 square feet of character, space, and thoughtful updates. This inviting property blends timeless details with modern improvements, including a new metal roof, all new interior doors, two new exterior doors, and nearly all new windows (with the

    Rebecca Wilson Better Homes & Gardens Real Estate/The Masiello Group

    247 Winthrop Center Rd, Winthrop, ME 04364
  • /52

    $539,000

    Sold Dec 22, 2025

    50 Robin Hood Dr, Winthrop, ME 04364

    • 4 Beds
    • 2.5 Baths
    • 3,128 Sq Ft
    • Built 1986

    Last Sold Summary

    • $172/SF
    • 30 Days On Market

    Current Estimated Value $556,733

    Last Listing Agent Michael Roddy Your Home Sold Guaranteed Realty

    50 Robin Hood Dr, Winthrop, ME 04364
    • /32

      Est $470,962

      Not Listed For Sale

      39 Turtle Run Rd Unit 7, Winthrop, ME 04364

      • 2 Beds
      • 2 Baths
      • 1,760 Sq Ft
      • Built 1986
      39 Turtle Run Rd Unit 7, Winthrop, ME 04364

      Last Sold Summary

      • 77 Days On Market

  • /60

    $614,000

    $11K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,512 Sq Ft

    87 Memorial Dr, Winthrop, ME 04364

    Set on 2.57± private acres with seasonal views of beautiful Maranacook Lake, this distinguished Colonial offers an exceptional blend of classic New England character, modern comfort, and tremendous location. Just a short distance to the town beach, public boat launch, and downtown Winthrop's charming collection of local shops and restaurants, the setting offers the perfect balance of privacy and

    Matt Pouliot Pouliot Real Estate

    87 Memorial Dr, Winthrop, ME 04364
  • /40

    $480,000

    Sold May 15, 2026

    100 Route 133, Winthrop, ME 04364

    • 4 Baths
    • 3,606 Sq Ft
    • Built 1890

    Last Sold Summary

    • $133/SF
    • 26 Days On Market

    Last Listing Agent Tyler Janelle Maine Real Estate Co

    100 Route 133, Winthrop, ME 04364
    • /40

      Est $440,863

      Not Listed For Sale

      39 Turtle Run Rd Unit 5, Winthrop, ME 04364

      • 2 Beds
      • 2 Baths
      • 1,350 Sq Ft
      • Built 1988
      39 Turtle Run Rd Unit 5, Winthrop, ME 04364

      Last Sold Summary

      • 1 Day On Market

  • /44

    $550,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,016 Sq Ft

    8 Horseshoe Rd, Winthrop, ME 04364

    There simply is no better escape than this incredibly rare 9 acres on Horseshoe island in the middle of Cobbosseecontee. Enjoy the ability to get away from the day to day demands and unwind just 20 minutes and less from major amenities by boat and car. The residence has been meticulously cared for and in the same family since it's construction in the 90's and offers two solar panels that aid in

    Spencer Hazzard Rizzo Mattson

    8 Horseshoe Rd, Winthrop, ME 04364
  • /49

    $650,000

    Sold Jul 10, 2025

    11 Green St, Winthrop, ME 04364

    • 6 Baths
    • 7,994 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $81/SF
    • 7 Days On Market

    Last Listing Agent James Pepin Sprague & Curtis Real Estate

    11 Green St, Winthrop, ME 04364
    • /29

      Est $340,941

      Not Listed For Sale

      46 Beechwood Rd, Winthrop, ME 04364

      • 3 Beds
      • 1 Bath
      • 1,800 Sq Ft
      • Built 1976
      46 Beechwood Rd, Winthrop, ME 04364

      Last Sold Summary

      • 16 Days On Market

  • /67

    $669,000

    Open Sat 10AM - 12PM
    • 5 Beds
    • 2 Baths
    • 2,759 Sq Ft

    337 Route 133, Winthrop, ME 04364

    Welcome to the ''Garden of Eden,'' a truly special property steeped in local history. In the early 1800s, this land was known for its medicinal herb gardens, where remedies were gathered, offering wellness. Today, this remarkable home blends that rich heritage with thoughtful modern updates.Meticulously restored, the home features new insulation, new windows, refined flooring, a fully

    Tiffany Libby Pamela Starnes Signature Homes Real Estate Group

    337 Route 133, Winthrop, ME 04364
  • /70

    $605,000

    Sold Jun 03, 2026

    307 Route 41, Winthrop, ME 04364

    • 5 Beds
    • 3 Baths
    • 3,704 Sq Ft
    • Built 1784

    Last Sold Summary

    • 2% Below List Price
    • $163/SF
    • 72 Days On Market

    Current Estimated Value $608,966

    Last Listing Agent Lori Dube Sprague & Curtis Real Estate

    307 Route 41, Winthrop, ME 04364
    • /30

      Est $513,296

      Not Listed For Sale

      918 Memorial Dr, Winthrop, ME 04364

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1922
      918 Memorial Dr, Winthrop, ME 04364

      Last Sold Summary

      • 4 Days On Market

  • /30

    $269,900

    Open Sat 10AM - 12PM
    • 3 Beds
    • 1.5 Baths
    • 1,176 Sq Ft

    45 Pleasant St, Winthrop, ME 04364

    Welcome to 45 Pleasant Street located right in the heart of Winthrop, Maine. This 3-bedroom, 1.5 bath, well maintained, cozy cape is perfect for those looking for in-town living, while still having ample indoor and outdoor space to call your own. Located just minutes from local shops, the town beach, and public schools, come see for yourself all this home has to provide in the desirable Town of

    Randi-Anne Langelier Meservier & Associates

    45 Pleasant St, Winthrop, ME 04364
  • /64

    $297,500

    Sold Jul 25, 2025

    20 Green St, Winthrop, ME 04364

    • 2.5 Baths
    • 1,795 Sq Ft
    • Built 1890

    Last Sold Summary

    • 1% Above List Price
    • $166/SF
    • 7 Days On Market

    Current Estimated Value $282,167

    Last Listing Agent David Marsden Marsden Real Estate

    20 Green St, Winthrop, ME 04364
    • /40

      Est $334,462

      Not Listed For Sale

      677 Memorial Dr, Winthrop, ME 04364

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 2006
      677 Memorial Dr, Winthrop, ME 04364

      Last Sold Summary

      • 3 Days On Market

  • /30

    $375,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,702 Sq Ft

    144 Highland Ave, Winthrop, ME 04364

    Welcome to this beautifully renovated three-bedroom split-entry home, where modern updates and comfortable living come together in a desirable location just minutes from downtown Winthrop and the area's renowned lakes. Offering convenient access to shopping, dining, schools, recreational opportunities, and waterfront activities, this property provides the perfect balance of privacy and

    Heidi Holley Realty of Maine

    144 Highland Ave, Winthrop, ME 04364
  • /2

    $169,000

    Sold Mar 31, 2026

    60 Case Rd, Winthrop, ME 04364

    • 4 Beds
    • 2.5 Baths
    • 2,020 Sq Ft
    • Built 1963

    Last Sold Summary

    • $84/SF
    • 13 Days On Market

    Current Estimated Value $175,762

    Last Listing Agent Jeffrey Decker EXP Realty

    60 Case Rd, Winthrop, ME 04364
    • /55

      Est $828,734

      Not Listed For Sale

      668 Memorial Dr, Winthrop, ME 04364

      • 3 Beds
      • 1.5 Baths
      • 1,872 Sq Ft
      • Built 1954
      668 Memorial Dr, Winthrop, ME 04364

      Last Sold Summary

      • 6 Days On Market

  • /112

    $575,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,852 Sq Ft

    11 Old Western Ave, Winthrop, ME 04364

    Buy with confidence-this property has been recently appraised, providing verified value and added peace of mind! Set on a beautiful 2.28-acre lot in Winthrop, this extensively renovated 1840s home blends warmth and character with meaningful upgrades. Featuring just under 3,000 square feet, the home offers room to spread out with multiple living spaces, a dedicated office space, and charming

    Maria Kempton LAER

    11 Old Western Ave, Winthrop, ME 04364

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