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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  /20

  $21,359 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 $267,675 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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  /124

  $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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  /10

  $1,150 per month

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

  2 Cloverleaf St, Winthrop, ME 04364

  Completely Renovated 2 bed/1 bath Mobile Home in Winthrop! Available Now!- Fully Remodeled Bathroom and Kitchen- Newer Furnace- Newer Flooring Throughout- Washer/Dryer Hookups in the unit! When Applying: Choose "Breton's Lakeside" as Your Property.Rent To Own - Terms are $2,500 down. Lot rent of $500. Home payment of $650 for 84 months. Monthly Payment of

  2 Cloverleaf St, Winthrop, ME 04364
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  /24

  $99,000 Sold Jun 24, 2025

  64 Pineland Dr, Winthrop, ME 04364

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 2020

  Last Sold Summary

  • $118/SF
  • 53 Days On Market

  Last Listing Agent Daren Hachey Homestead Realty

  

  64 Pineland Dr, Winthrop, ME 04364
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  /47

  Est $1,025,318 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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  /47

  $349,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  3 Gayton Ln, Winthrop, ME 04364

  Welcome to this charming 2-bedroom, 1 bath home offering an inviting open-concept with exceptional potential for building instant equity. The mail level features a sunny, spacious kitchen flowing seamlessly into the living room--perfect for everyday living and effortless entertaining. Two comfortable bedrooms with hardwood floors and a well- appointed bath with tiled floor and walk in shower for

  

  Pat Ladd

  Homestead Realty

  (207) 630-2401

  

  3 Gayton Ln, Winthrop, ME 04364
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  /20

  $3,200 per month

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

  7 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200423Cozy Keyes Cottage on Cobbosseecontee LakeWelcome to Cozy Keyes Cottage, a charming lakeside retreat located on the shores of the prestigious Cobbosseecontee Lake. This beautiful property offers an ideal setting for those seeking both adventure and tranquility, with breathtaking lake views and access to a variety of outdoor activities.Perfectly situated

  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 $409,965

  Last Listing Agent Pat Ladd Homestead Realty

  

  97 Pennwood Rd, Winthrop, ME 04364
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  /26

  Est $311,720 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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  /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

  $1,600 per month

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • House for Rent

  19 Pond View Rd, Winthrop, ME 04364

  Large 4 Bed - 2 Bath Mobile Home in Winthrop. Available Now!- Minutes away from Manchester/Augusta with easy access to I-95 - Large Eat-In Kitchen and living room! - Master Bedroom features a spacious private bathroom with a double vanity! - Many recent updates throughout the home!When Applying: Choose "Breton's Lakeside" as Your Property. $1,600/Month. 9 Month

  19 Pond View Rd, Winthrop, ME 04364
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  $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 $335,313

  Last Listing Agent Pat Ladd Homestead Realty

  

  96 Pamela Dr, Winthrop, ME 04364
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  /48

  Est $551,882 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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  /57

  $539,000 Pending

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

  50 Robin Hood Dr, Winthrop, ME 04364

  With over 6 Acres come discover more than you'd expect in this beautiful 4-bedroom, 2.5-bath —3,100 Square Foot home-perfect for a growing family—nestled on a private 6.11 - acre lot. This is the home for you, especially if you're looking for a great community suited to families, outdoor recreation, and a quieter, more semi-rural lifestyle. Step inside to a modern kitchen featuring beautiful

  Michael Roddy Your Home Sold Guaranteed Realty

  

  50 Robin Hood Dr, Winthrop, ME 04364
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  /20

  $1,950 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • House for Rent

  220 Me-133, Winthrop, ME 04364

  Property Id: 1320038This brand new, family-friendly, 2-bedroom cozy, modern cottage packed full of amenities is nestled in the village of Winthrop w/ lake views. There is a large yard with fire pit, snowmobile & walking trail access out back. A 10-minute walk to the beach & boat launch on Maranacook lake, as well as multiple local eateries and shops. A massage studio and sauna are located

  220 Me-133, 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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  /73

  Est $517,963 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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  $325,000 Coming Soon

  • 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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  /20

  $2,900 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 LakeNestled on the shores of the prestigious Cobbosseecontee Lake, Little Landing Cottage offers breathtaking water views and direct access to all the lake has to offer. With its charming design and idyllic setting, this property is perfect for those seeking a balance of outdoor adventure and peaceful

  11 Fire Rd W24a, Winthrop, ME 04364
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  $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 $256,032

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

  

  57 Dexter Pond Rd, Winthrop, ME 04364
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  /42

  Est $392,749 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  192 Metcalf Rd, Winthrop, ME 04364

  

  192 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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  /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. 1st and last. Plus utilities.

  3 Nason Dr, Winthrop, ME 04364
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  $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 $321,466

  Last Listing Agent Jessica Fike Brookewood Realty

  

  39 Case Rd, Winthrop, ME 04364
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  Est $358,130 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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  /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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  /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 $261,175

  Last Listing Agent Ellen Wells Coldwell Banker Plourde Real Estate

  

  32 Winthrop Center Rd, Winthrop, ME 04364
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  /59

  Est $405,267 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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  /12

  $230,000

  • Land
  • 64.81 Acres
  • $3,549 per Acre

  616 Stanley Rd, Winthrop, ME 04364

  Buildable lot with 1.8 acre clearing of land to have a homestead, hunt and recreational activities. Septic, drilled well and electricity already at the property. currently enrolled in Tree Growth with a great Tax Break plus opportunity to harvest plenty of timber! Lakes close by for fishing and boating. This property is enrolled in the Maine Tree Growth Program except for 1.8 ac. Land can be

  Dawn Lopez Hearth & Key Realty

  

  616 Stanley Rd, 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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  /35

  Est $461,133 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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  /19

  $89,900

  • Land
  • 3.11 Acres
  • $28,907 per Acre

  0 U S Highway 202, Winthrop, ME 04364

  Incredible opportunity to live or build right next to Winthrop High School and Middle School—walk to both! This former apple orchard offers 3.1 acres with two access points: one through Apple Farm Crossing and the other directly off Route 202. Zoned for residential use, with public water and sewer available, it's a prime location with great visibility and road frontage on Route 202. Ideal for a

  Brian Rizzo Rizzo Mattson

  

  0 U S Highway 202, Winthrop, ME 04364
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  /72

  $480,000 Sold Jan 13, 2025

  299 Case Rd, Winthrop, ME 04364

  • 3 Beds
  • 2.5 Baths
  • 2,569 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $187/SF
  • 62 Days On Market

  Current Estimated Value $520,044

  Last Listing Agent Ashleigh Rolfson Real Broker

  

  299 Case Rd, Winthrop, ME 04364
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  /23

  Est $444,626 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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  /15

  $250,000

  • 3 Beds
  • 1 Bath
  • 858 Sq Ft

  2549 US Route 202, Winthrop, ME 04364

  What a spot. Extremely visible property on Rt. 202 in E. Winthrop. This 1.5-acre corner lot has a well maintained small 3-bedroom ranch. Tiled oak kitchen, living room with wood floors and heat pump, 3 bedrooms and small bathroom. Full basement with HWBB oil heat. There is a detached 'extremely visible' out building that was formerly a rock and mineral store. It's great space for someone looking

  Chris Vallee LAER

  

  2549 US Route 202, 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 $1,074,324

  Last Listing Agent Stephanie Yeaton Gardner Portside Real Estate Group

  

  24 Loch Ln, Winthrop, ME 04364
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  /32

  Est $268,376 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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