Winthrop, ME Homes

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  /60

  $994,999

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172-B Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY & TITLE COMPLETED and ready for quick closing! Now includes 20 sprawling acres and a 20-foot right of way to Annabessacook Lake! This custom-built executive estate blends resort-style amenities with refined finishes for the perfect mix of luxury and functionality. Originally completed in 1997 and beautifully renovated in 2019 and 2023, the home offers 6,493 SF of finely crafted

  

  Tim Dunham

  Tim Dunham Realty

  (207) 803-6219

  172-B Annabessacook Rd, Winthrop, ME 04364
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  /23

  $24,730 per month

  • 3 Beds
  • 1.5 Baths
  • Condo for Rent

  100 Woods Grove Ln Unit ID1255650P, Winthrop, ME 04364

  Welcome to this charming 3-bedroom, 1.5-bathroom retreat located on the serene Annabessacook Lake in Winthrop. This well-maintained home offers a picturesque view of the private waterfront and dock, just steps away from your doorstep. The first floor features a bunkroom with two twin beds and a futon, along with a convenient half bath and washer/dryer. On the second floor, you'll find two

  100 Woods Grove Ln Unit ID1255650P, Winthrop, ME 04364
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  /57

  $300,000 Sold Sep 15, 2025

  22 Old Route 133, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $206/SF
  • 4 Days On Market

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

  

  22 Old Route 133, Winthrop, ME 04364
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  /37

  Est $245,211 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 896 Sq Ft

  87 Woodland Rd, Winthrop, ME 04364

  

  87 Woodland Rd, Winthrop, ME 04364
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  /123

  $995,000

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172 Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY AND TITLE COMPLETED and ready for quick closing! Now includes a 20-foot right of way to Annabessacook Lake and 20 sprawling acres!! This custom-built executive estate offers unparalleled luxury and comfort. A true one-of-a-kind haven, it blends resort-style amenities with high-end finishes for the perfect combination of elegance and functionality. Originally completed in 1997 and

  

  Tim Dunham

  Tim Dunham Realty

  (207) 367-3848

  

  172 Annabessacook Rd, Winthrop, ME 04364
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  /20

  $4,900 per month

  • 2 Beds
  • 1 Bath
  • 865 Sq Ft
  • House for Rent

  7 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200423Cozy Keyes Cottage is a fully furnished, all-inclusive waterfront home located on the shores of prestigious Cobbosseecontee Lake in central Maine. Designed for mid-term stays of one month or longer, this cottage provides a comfortable, turnkey living solution for individuals and families who need a high-quality temporary residence without the complexity of managing

  7 Fire Rd W24a, Winthrop, ME 04364
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  /51

  $410,000 Sold Jun 23, 2025

  97 Pennwood Rd, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1971

  Last Sold Summary

  • 10% Above List Price
  • $204/SF
  • 4 Days On Market

  Current Estimated Value $420,722

  Last Listing Agent Pat Ladd Homestead Realty

  

  97 Pennwood Rd, Winthrop, ME 04364
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  /47

  Est $1,015,835 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  76 Pine Point Ln, Winthrop, ME 04364

  

  76 Pine Point Ln, Winthrop, ME 04364
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  /2

  $65,000

  • Land
  • 26.55 Acres
  • $2,448 per Acre

  90 Bearce Rd, Winthrop, ME 04364

  Land and privacy!! Build your dream home and belong to Maple Ridge Owners Association and have the buffer of the green space making your home even more private. This is a great building lot. Lot #23.

  

  Pat Ladd

  Homestead Realty

  (207) 640-2322

  

  90 Bearce Rd, Winthrop, ME 04364
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  /20

  $4,400 per month

  • 1 Bed
  • 1 Bath
  • 810 Sq Ft
  • House for Rent

  11 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200424Little Landing Cottage on Cobbosseecontee LakeLittle Landing Cottage is a fully furnished, all-inclusive waterfront home on the shores of prestigious Cobbosseecontee Lake — designed for comfort, convenience, and effortless living.This turnkey cottage includes every utility at no additional cost: high-speed internet (500+ Mbps), electricity, heat, hot

  11 Fire Rd W24a, Winthrop, ME 04364
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  /33

  $330,000 Sold Jun 30, 2025

  96 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Above List Price
  • $219/SF
  • 2 Days On Market

  Current Estimated Value $341,055

  Last Listing Agent Pat Ladd Homestead Realty

  

  96 Pamela Dr, Winthrop, ME 04364
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  /26

  Est $316,183 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft

  262 Metcalf Rd, Winthrop, ME 04364

  

  262 Metcalf Rd, Winthrop, ME 04364
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  /41

  $325,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,616 Sq Ft

  11 Highland Heights, Winthrop, ME 04364

  This charming 3-bedroom, 1.5-bath home has been thoughtfully updated and offers a warm, welcoming layout perfect for everyday living. Enter through the large mudroom, which leads directly into the spacious finished basement featuring a comfortable family room and convenient half bath.Upstairs, the main living area showcases wood floors flowing through the living room, dining room, kitchen,

  Kelly Webb Fontaine Family-The Real Estate Leader

  

  11 Highland Heights, Winthrop, ME 04364
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  /6

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  3 Nason Dr, Winthrop, ME 04364

  Single wide mobile home on private lot. 1200 sq. ft. 2 bedrooms, 1 bath. Livingroom and kitchen combination. 3 season porch. Washer and dryer hookup. Beautiful lot. Close to town. NO SMOKING IN OR AROUND PROPERTY. NO PETS OF ANY KIND. $1500.00 a month. $300 for fuel already in tank. $300 cleaning fee

  3 Nason Dr, Winthrop, ME 04364
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  /7

  $950,000 Sold Aug 08, 2025

  1385 U S 202, Winthrop, ME 04364

  • 19 Baths
  • 6,789 Sq Ft
  • Built 1958

  Last Sold Summary

  • 21% Below List Price
  • $140/SF
  • 11 Days On Market

  Last Listing Agent Benjamin Spencer CORE

  

  1385 U S 202, Winthrop, ME 04364
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  /48

  Est $565,780 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,136 Sq Ft

  298 Metcalf Rd, Winthrop, ME 04364

  

  298 Metcalf Rd, Winthrop, ME 04364
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  /60

  $500,000

  • 4 Beds
  • 2 Baths
  • 3,081 Sq Ft

  974 Sturtevant Hill Rd, Winthrop, ME 04364

  Imagine all the space you will have with this 10 room home. This home has been expanded over the years and provides one with so many options. There is even an insulated unfinished basement just waiting for your creative ideas. You have a spacious eat in kitchen, formal dining room, large living room and a den on the lower level. All bedrooms are on the main level. The primary bedroom with its own

  Merline Douglas Lakehome Group Real Estate

  

  974 Sturtevant Hill Rd, Winthrop, ME 04364
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  /200

  $900,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,672 Sq Ft

  427 Mount Pisgah Rd, Winthrop, ME 04364

  Cranberry Rock Farm, built in 1815, is a colonial-style farmhouse nestled on 32 private, picturesque acres. This certified-organic farm provides endless possibilities as a private retreat, wedding venue, equestrian property, or more. Perched atop a hillside with southwesterly exposure, it boasts panoramic views of the Presidential Range & Mt. Washington. Enjoy easy entertaining in the open

  Rick Bisson Keller Williams Realty

  

  427 Mount Pisgah Rd, Winthrop, ME 04364
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  /73

  Est $523,675 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  91 Wedgewood Dr, Winthrop, ME 04364

  

  91 Wedgewood Dr, Winthrop, ME 04364
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  /52

  $559,900 Open Sat 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,395 Sq Ft

  476 Winthrop Center Rd, Winthrop, ME 04364

  Step into the perfect blend of historic character and modern comfort in this beautifully restored 1917 late‑Edwardian farmhouse, set proudly on a stunning Hallowell granite foundation. This 2,382 sq ft home showcases meticulously preserved original details, including restored pine floors throughout most of the first level, complemented by new matching pine in the kitchen and family room.

  Robert Whisenant RE/MAX Riverside

  

  476 Winthrop Center Rd, Winthrop, ME 04364
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  /29

  $250,000 Sold May 09, 2025

  57 Dexter Pond Rd, Winthrop, ME 04364

  • 1 Bed
  • 1 Bath
  • 489 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $511/SF
  • 85 Days On Market

  Current Estimated Value $257,045

  Last Listing Agent Mark Michaud Fontaine Family-The Real Estate Leader

  

  57 Dexter Pond Rd, Winthrop, ME 04364
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  /36

  Est $359,601 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,913 Sq Ft

  108 Pamela Dr, Winthrop, ME 04364

  

  108 Pamela Dr, Winthrop, ME 04364
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  /98

  $649,000

  • 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
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  /3

  $259,000 Sold Apr 24, 2025

  32 Winthrop Center Rd, Winthrop, ME 04364

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1963

  Last Sold Summary

  • $245/SF

  Current Estimated Value $266,945

  Last Listing Agent Ellen Wells Coldwell Banker Plourde Real Estate

  

  32 Winthrop Center Rd, Winthrop, ME 04364
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  /59

  Est $404,188 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,878 Sq Ft

  17 Pamela Dr, Winthrop, ME 04364

  

  17 Pamela Dr, Winthrop, ME 04364
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  /43

  $499,000

  • 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
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  /45

  $325,000 Sold Jul 03, 2025

  39 Case Rd, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 1,874 Sq Ft
  • Built 1957

  Last Sold Summary

  • 8% Above List Price
  • $173/SF
  • 4 Days On Market

  Current Estimated Value $332,737

  Last Listing Agent Jessica Fike Brookewood Realty

  

  39 Case Rd, Winthrop, ME 04364
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  /35

  Est $472,449 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft

  310 Route 41, Winthrop, ME 04364

  

  310 Route 41, Winthrop, ME 04364
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  /87

  $655,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,086 Sq Ft

  183 Loon Cove Ln, Winthrop, ME 04364

  Welcome to this 4 bedroom, 2 bath home on pristine Upper Narrows Pond in Winthrop. 183 Loon Cove Lane is at the end of a well maintained private road. It has great privacy and even greater views of all Mother Nature has to offer. Inside is open concept living with beautiful cherry kitchen cabinets and quartz countertops. The home is freshly painted throughout, with natural wood trim. There are

  Dylan Armstrong Sprague & Curtis Real Estate

  

  183 Loon Cove Ln, Winthrop, ME 04364
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  /20

  $14,000 Sold Oct 23, 2025

  35A-12 Woodland Rd, Winthrop, ME 04364

  • Land
  • 0.49 Acre
  • $28,571 per Acre

  Last Sold Summary

  • 49% Below List Price
  • 91 Days On Market

  Last Listing Agent Kimberly Granholm LAER

  

  35A-12 Woodland Rd, Winthrop, ME 04364
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  /23

  Est $451,953 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,170 Sq Ft

  105 Nottingham Rd, Winthrop, ME 04364

  

  105 Nottingham Rd, Winthrop, ME 04364
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  /74

  $699,900 Under Contract

  • 3 Beds
  • 3 Baths
  • 3,292 Sq Ft

  77 Holmes Rd, Winthrop, ME 04364

  Your search stops here! This year-round waterfront home comes with an open concept kitchen/dining/living room with a butcher block island and granite countertops, vaulted ceilings, and sunset views on the deck overlooking Annabessacook Lake. Built in 2006, the property has 4.3 acres, 205 ft. of owned waterfrontage, and over 3200 square ft. The home features a first floor primary suite with a full

  Lori Dube Sprague & Curtis Real Estate

  

  77 Holmes Rd, Winthrop, ME 04364
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  /102

  $1,225,000 Sold Feb 21, 2025

  24 Loch Ln, Winthrop, ME 04364

  • 4 Beds
  • 3.5 Baths
  • 3,712 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $330/SF
  • 173 Days On Market

  Current Estimated Value $1,097,115

  Last Listing Agent Stephanie Yeaton Gardner Portside Real Estate Group

  

  24 Loch Ln, Winthrop, ME 04364
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  /32

  Est $271,008 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 907 Sq Ft

  1006 Sturtevant Hill Rd, Winthrop, ME 04364

  

  1006 Sturtevant Hill Rd, Winthrop, ME 04364
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  /84

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 3,728 Sq Ft

  336 Main St, Winthrop, ME 04364

  Exceptional home with possible home business with a one floor layout! This property offers gorgeous landscaping, and a private fenced-in backyard retreat with an in-ground 18x36 heated pool with a slide, water fountain, and pool cover. The pool is heated by 6 solar panels has a depth of 4' - 9'. Just off the patio is a hot tub room which completes the oasis. This versatile 3-bed, 2.5-bath ranch

  Kimberly Hawkes OWN REAL ESTATE

  

  336 Main St, Winthrop, ME 04364
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  /53

  $415,000 Sold May 21, 2025

  345 Main St, Winthrop, ME 04364

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 1964

  Last Sold Summary

  • $182/SF
  • 10 Days On Market

  Current Estimated Value $429,162

  Last Listing Agent Shawn McKillop Maine Real Estate Co

  

  345 Main St, Winthrop, ME 04364
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  /36

  Est $357,532 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,798 Sq Ft

  30 Route 41, Winthrop, ME 04364

  

  30 Route 41, Winthrop, ME 04364
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  /92

  $859,000

  • 2 Beds
  • 2 Baths
  • 2,470 Sq Ft

  882 Memorial Dr, Winthrop, ME 04364

  Maranacook Lake Living! Sunsets over the 165' of waterfront on this +/- 7 mile central Maine lake. The home sits at waters edge and comes with dock system, several decks and terraces all for year round lakefront enjoyment. Beautiful home with tiled entries. The open custom oak kitchen/dining area is filled with sunlight and warmed by a propane fireplace. The main level offers full bath with

  Daren Hachey Homestead Realty

  

  882 Memorial Dr, Winthrop, ME 04364
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  /47

  $320,000 Sold Oct 27, 2025

  170 Hathaway Rd, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 2,575 Sq Ft
  • Built 1850

  Last Sold Summary

  • 11% Below List Price
  • $124/SF
  • 210 Days On Market

  Current Estimated Value $335,824

  Last Listing Agent Heidi Libby NextHome Northern Lights Realty

  

  170 Hathaway Rd, Winthrop, ME 04364
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  /30

  Est $558,850 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,542 Sq Ft

  20 Maranacook Station Ln, Winthrop, ME 04364

  

  20 Maranacook Station Ln, Winthrop, ME 04364

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