Winthrop, ME Homes

• 

  

  

  /54

  $515,000

  Pending

  • 2 Beds
  • 2 Baths
  • 2,018 Sq Ft

  246 Carlton Pond Rd, Winthrop, ME 04364

  Discover effortless single-level living in this beautifully designed contemporary ranch set on 2 private acres in a highly desirable location. Thoughtfully crafted for comfort and convenience, this home features 2 spacious bedrooms, 2 full bathrooms, and an inviting open-concept layout filled with natural light. Additional space used as an office could be another bedroom as the septic design is

  

  Sarah Foster

  Meservier & Associates

  

  246 Carlton Pond Rd, Winthrop, ME 04364
• 

  

  

  /11

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  23 Green St Unit 2-B, Winthrop, ME 04364

  Beautiful 2 Bed - 1 Bath Apartment in Winthrop! Rent: $1,500Bedrooms: 2 Bathrooms: 1 Available: Late June Lease Term: 12 Months Utilities Included: Heat, water and sewer Tenant Responsibilities: Electricity Pets: Pets are Negotiable (Monthly Pet Fee Applies) Parking: 2 off-street spots Laundry: In Unit W/D Hookups Smoking: Non-smoking unit

  23 Green St Unit 2-B, Winthrop, ME 04364
• 

  

  /2

  $450,000

  Sold May 26, 2026

  569 Stanley Rd, Winthrop, ME 04364

  • 2 Baths
  • 1,792 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $251/SF
  • 0 Days On Market

  Current Estimated Value $412,209

  Last Listing Agent Pat Ladd Homestead Realty

  

  569 Stanley Rd, Winthrop, ME 04364
• 

  

  

  /102

  Est $1,098,812

  Not Listed For Sale

  24 Loch Ln, Winthrop, ME 04364

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

  

  24 Loch Ln, Winthrop, ME 04364

  Last Sold Summary

  • 173 Days On Market
• 

  

  

  /65

  $305,000

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  22 Woodland Rd, Winthrop, ME 04364

  Escape to your own waterfront retreat on the shores of Berry Pond. With 100 feet of private waterfrontage and stunning sunset views, this charming cottage offers the perfect place to relax, recharge, and enjoy all that Maine has to offer. Spend your days swimming in the lake, kayaking across the peaceful pond, unwinding in the private sauna, gathering around the outdoor fire pit, or simply

  

  Pat Ladd

  Homestead Realty

  

  22 Woodland Rd, Winthrop, ME 04364
• 

  

  /3

  $1,200 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  26 High St Unit A, Winthrop, ME 04364

  Property Id: 1594440Welcome to your new home at 26 High Street in Winthrop, ME! This single unit features modern amenities such as a oven, refrigerator, and more. Enjoy the convenience of off-street parking, a large picnic area, and a block from lake Winthrop. Pets are welcome, and utilities such as sewage, water, and garbage are included. Don't miss out on this amazing opportunity for

  26 High St Unit A, Winthrop, ME 04364
• 

  /2

  $65,000

  Sold Feb 23, 2026

  Lot 6 Holmes Brook Ln, Winthrop, ME 04364

  • Land
  • 10 Acres
  • $6,500 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 7 Days On Market

  Last Listing Agent Jane Gravel Blue Lobster Real Estate

  

  Lot 6 Holmes Brook Ln, Winthrop, ME 04364
• 

  

  /37

  Est $215,040

  Not Listed For Sale

  87 Woodland Rd, Winthrop, ME 04364

  • 1 Bed
  • 2 Baths
  • 896 Sq Ft
  • Built 2004

  

  87 Woodland Rd, Winthrop, ME 04364

  Last Sold Summary

  • 27 Days On Market
• 

  

  /57

  $359,900

  Open Sun 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,424 Sq Ft

  196 Holmes Rd, Winthrop, ME 04364

  Welcome to 196 Holmes Road! Set on nearly two sunny, landscaped acres, this move-in ready home has been extensively updated since 2023, including a fully refreshed kitchen, updated flooring, remodeled bathroom, and new decking on the wraparound deck.Inside, you'll find a bright and efficient layout featuring a spacious primary bedroom with a walk-in closet, a full bath, and an inviting living

  

  Brett Davis

  EXP Realty

  

  196 Holmes Rd, Winthrop, ME 04364
• 

  

  /20

  $16,965

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • Condo for Rent

  100 Woods Grove Ln Unit SI ID1255650P, Winthrop, ME 04364

  The advertised rate of $16,965/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  100 Woods Grove Ln Unit SI ID1255650P, Winthrop, ME 04364
• 

  

  /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
• 

  

  /47

  Est $1,071,130

  Not Listed For Sale

  76 Pine Point Ln, Winthrop, ME 04364

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft
  • Built 1975

  

  76 Pine Point Ln, Winthrop, ME 04364

  Last Sold Summary

  • 6 Days On Market
• 

  /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

  

  90 Bearce Rd, Winthrop, ME 04364
• 

  

  /22

  $1,500

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  422 Me-41 Unit B, Winthrop, ME 04364

  **Property Listing: 422 ME-41**This 900 sq. ft. property features 2 bedrooms and 1 bathroom, ideal for small families or individuals seeking a comfortable living space. The living room offers ample space for relaxation and entertainment. The kitchen is equipped with a dishwasher for convenience and includes a washer and dryer for laundry needs. The bedrooms provide sufficient room for

  422 Me-41 Unit B, Winthrop, ME 04364
• 

  

  /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 $349,591

  Last Listing Agent Pat Ladd Homestead Realty

  

  96 Pamela Dr, Winthrop, ME 04364
• 

  

  /26

  Est $302,030

  Not Listed For Sale

  262 Metcalf Rd, Winthrop, ME 04364

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft
  • Built 1985

  

  262 Metcalf Rd, Winthrop, ME 04364

  Last Sold Summary

  • 3 Days On Market
• 

  

  /39

  $324,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  59 Route 41, Winthrop, ME 04364

  Home sweet home is the way you'll feel with this beautifully renovated 3 bedroom, 2 bath Ranch home that combines a rural feel with the ease of being just minutes to the downtown Winthrop amenities and local beach. The open concept kitchen, dining and living room has a great fit and feel to it and the fireplace adds some flare and ambience to any evening. The three bedrooms are all good-sized

  

  Tim Fortin

  NextHome Northern Lights Realty

  

  59 Route 41, Winthrop, ME 04364
• 

  

  /16

  $1,850 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  98 Main St Unit A, Winthrop, ME 04364

  Updated first-floor apartment in Winthrop offers a comfortable, move-in-ready home with thoughtful updates throughout. The kitchen features brand new stainless steel appliances and a fresh, modern feel, paired with bright living spaces that make the unit easy to settle into.The layout includes two well-sized bedrooms plus an additional smaller room that works well as a third bedroom, home

  98 Main St Unit A, Winthrop, ME 04364
• 

  

  /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
• 

  

  /73

  Est $481,393

  Not Listed For Sale

  91 Wedgewood Dr, Winthrop, ME 04364

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1986

  

  91 Wedgewood Dr, Winthrop, ME 04364

  Last Sold Summary

  • 28 Days On Market
• 

  

  /37

  $194,900

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,319 Sq Ft

  27 Royal St, Winthrop, ME 04364

  In-town opportunity with great upside. This 3-bedroom, 1-bath New Englander offers approximately 1,319 sq ft of living space on a manageable 0.10-acre lot with public water and public sewer. Featuring classic character, hardwood floors, vinyl siding, and a recently updated roof, this home is ready for its next chapter. Ideal for buyers looking to build equity, the property would benefit from

  

  Elias Leland

  Coldwell Banker Realty

  

  27 Royal St, Winthrop, ME 04364
• 

  

  /18

  $2,100 Per Month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  98 Main St Unit B, Winthrop, ME 04364

  Spacious 3-bedroom, 1-bath two-level home in the heart of Winthrop, recently updated throughout for a fresh, modern feel. The first floor features a brand-new kitchen with stainless steel appliances and an open, comfortable layout, perfect for everyday living and entertaining. Upstairs, you'll find all three generously sized bedrooms, offering a true separation between living and sleeping spaces

  98 Main St Unit B, Winthrop, ME 04364
• 

  

  /200

  $860,000

  Sold Feb 05, 2026

  427 Mount Pisgah Rd, Winthrop, ME 04364

  • 3 Beds
  • 2.5 Baths
  • 3,672 Sq Ft
  • Built 1815

  Last Sold Summary

  • 9% Below List Price
  • $234/SF
  • 87 Days On Market

  Current Estimated Value $870,476

  Last Listing Agent Rick Bisson Keller Williams Realty

  

  427 Mount Pisgah Rd, Winthrop, ME 04364
• 

  

  /36

  Est $311,620

  Not Listed For Sale

  108 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 1 Bath
  • 1,913 Sq Ft
  • Built 1984

  

  108 Pamela Dr, Winthrop, ME 04364

  Last Sold Summary

  • 2 Days On Market
• 

  

  /87

  $99,000

  • Land
  • 3.11 Acres
  • $31,833 per Acre

  0 U S Highway 202, Winthrop, ME 04364

  Incredible opportunity to own a 3.1-acre parcel in a prime Winthrop location, right next to the High School and Middle School--walk to both! You have axcess off Route 202 . This former apple orchard is a beautiful place to have your home or Multiple units up to five units providing flexibility and excellent visibility. With frontage off Route 202 and public sewer and a potential for public water

  

  John Blouin

  LAER

  

  0 U S Highway 202, Winthrop, ME 04364
• 

  

  /13

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  56 Me-133 Unit E, Winthrop, ME 04364

  Fully renovated apartment located in an updated 6-unit building in the heart of Winthrop. The home offers 1 spacious bedroom and 1 smaller bedroom that can be used as an office or bonus room. Both bedrooms include closets, refinished floors throughout the home, and plenty of natural light. The apartment features a brand-new kitchen with new cabinets and stainless steel appliances, a completely

  56 Me-133 Unit E, Winthrop, ME 04364
• 

  

  /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 $338,555

  Last Listing Agent Jessica Fike Brookewood Realty

  

  39 Case Rd, Winthrop, ME 04364
• 

  

  /59

  Est $367,412

  Not Listed For Sale

  17 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 2,878 Sq Ft
  • Built 1976

  

  17 Pamela Dr, Winthrop, ME 04364

  Last Sold Summary

  • 7 Days On Market
• 

  

  /78

  $399,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,906 Sq Ft

  43 Holmes Rd, Winthrop, ME 04364

  Discover the perfect blend of rustic charm and year-round comfort in this inviting 3-bedroom, 2-bath home, ideally located in Winthrop just minutes from Lake Annabessacook, Maranacook Lake, and Upper and Lower Narrows Ponds. Outdoor enthusiasts will love the private 1.9-acre lot featuring a serene terrace overlooking beautifully landscaped grounds, raised-bed gardens, and fruit-bearing bushes.

  

  Pat Ladd

  Homestead Realty

  

  43 Holmes Rd, Winthrop, ME 04364
• 

  

  /20

  $14,000

  Sold Oct 23, 2025

  35A-12 Woodland Rd, Winthrop, ME 04364

  • Land
  • 21,344 Sq Ft
  • $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
• 

  

  /35

  Est $432,717

  Not Listed For Sale

  310 Route 41, Winthrop, ME 04364

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 2004

  

  310 Route 41, Winthrop, ME 04364

  Last Sold Summary

  • 35 Days On Market
• 

  

  /55

  $349,000

  • 2 Beds
  • 1 Bath
  • 803 Sq Ft

  260 Memorial Dr, Winthrop, ME 04364

  Escape to this charming waterfront cottage on beautiful Maranacook Lake, nestled in an exceptionally private peninsula setting with breathtaking sunset views. Perched right at the water's edge, this rare property offers the quintessential Maine lakefront experience. Relax and unwind on the covered front and back porches, both perfectly positioned to take in stunning lake vistas and cooling summer

  

  Pat Ladd

  Homestead Realty

  

  260 Memorial Dr, Winthrop, ME 04364
• 

  

  /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 $344,619

  Last Listing Agent Heidi Libby NextHome Northern Lights Realty

  

  170 Hathaway Rd, Winthrop, ME 04364
• 

  

  /57

  Est $406,010

  Not Listed For Sale

  15 Lakeshore Dr, Winthrop, ME 04364

  • 4 Beds
  • 1.5 Baths
  • 2,792 Sq Ft
  • Built 1974

  

  15 Lakeshore Dr, Winthrop, ME 04364

  Last Sold Summary

  • 13 Days On Market
• 

  

  /32

  $362,000

  $8K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,332 Sq Ft

  28 Beechwood Dr, Winthrop, ME 04364

  Tucked into one of the area's most desirable neighborhoods, this beautifully updated raised ranch offers the perfect blend of comfort, convenience, and summer lifestyle. Enjoy deeded shared water frontage just a private 2-minute walk around the corner -- an ideal spot for swimming, kayaking, or simply unwinding by the water. Inside, the home features numerous updates throughout, creating a

  Kasey Hewett Your Home Sold Guaranteed Realty

  

  28 Beechwood Dr, Winthrop, ME 04364
• 

  

  /12

  $190,000

  Sold Jun 19, 2026

  616 Stanley Rd, Winthrop, ME 04364

  • Land
  • 64.81 Acres
  • $2,932 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 168 Days On Market

  Last Listing Agent Dawn Lopez Hearth & Key Realty

  

  616 Stanley Rd, Winthrop, ME 04364
• 

  

  /32

  Est $257,158

  Not Listed For Sale

  1006 Sturtevant Hill Rd, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 907 Sq Ft
  • Built 1969

  

  1006 Sturtevant Hill Rd, Winthrop, ME 04364

  Last Sold Summary

  • 30 Days On Market
• 

  

  /60

  $475,000

  $25K PRICE DROP

  • 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
• 

  

  /52

  $545,000

  Sold Apr 29, 2026

  476 Winthrop Center Rd, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 2,395 Sq Ft
  • Built 1917

  Last Sold Summary

  • 3% Below List Price
  • $228/SF
  • 38 Days On Market

  Current Estimated Value $538,405

  Last Listing Agent Robert Whisenant RE/MAX Riverside

  

  476 Winthrop Center Rd, Winthrop, ME 04364
• 

  

  /36

  Est $334,604

  Not Listed For Sale

  30 Route 41, Winthrop, ME 04364

  • 4 Beds
  • 1.5 Baths
  • 1,798 Sq Ft
  • Built 1971

  

  30 Route 41, Winthrop, ME 04364

  Last Sold Summary

  • 12 Days On Market

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