Winthrop, ME Homes

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  /122

  $1,177,000

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

  172 Annabessacook Rd, Winthrop, ME 04364

  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 beautifully renovated in 2019 and 2023, the residence boasts

  

  Tim Dunham

  Tim Dunham Realty

  (207) 386-9358

  

  172 Annabessacook Rd, Winthrop, ME 04364
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  /20

  $5,900 per month

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

  7 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200423Cozy Keyes Cottage 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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  /42

  $394,500 Sold Jun 11, 2025

  • 1,344 Sq Ft
  • $294/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  573 Sturtevant Hill Rd, Winthrop, ME 04364

  Welcome to this beautifully crafted ranch-style home located in Winthrop's newest development. Boasting with comfort and ease, this home is perfect for those looking for close proximity to all of Winthrop's amenities. This spacious home offers 3 bedrooms and 2 full bathrooms, designed with an open floor plan that maximizes space and natural light. Enjoy the comfort of radiant floor heating

  Jackson Ladd Homestead Realty

  

  573 Sturtevant Hill Rd, Winthrop, ME 04364
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  /37

  Est $217,877 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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  /58

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  39 Turtle Run Rd Unit 8, Winthrop, ME 04364

  Lakeside Village waterfront Condo on coveted Cobbossee . Central Maine 's only year round condo situated on 7 acres in a sheltered cove with fabulous southern exposure on 700 feet of waterfrontage. Enter the reception foyer area where your mailbox is and intercom system to contact owners for axcess .Take the elevator to your second floor end unit that has 2 bedrooms and 2 full baths .Cook's

  

  John Blouin

  LAER

  (207) 690-6153

  

  39 Turtle Run Rd Unit 8, Winthrop, ME 04364
• 

  

  /20

  $4,900 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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  /10

  $615,000 Sold Jun 10, 2025

  • 5,964 Sq Ft
  • $103/SF
  • 0 Days On Market

  • 3 Baths
  • Built 1970

  29 Tappan Farm Rd, Winthrop, ME 04364

  Exceptional Three-Unit Townhouse in Prime Location. This fully updated and remodeled three-unit townhouse offers a rare opportunity for investors or savvy buyers seeking a premium property with high-end finishes and remarkable amenities. Situated on 2.05 acres of land, this multi-family property includes: - A beautifully furnished Airbnb-ready unit featuring a home movie theater, back deck,

  Jennifer Sumrall The Maine Real Estate Experience

  

  29 Tappan Farm Rd, Winthrop, ME 04364
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  /47

  Est $1,038,375 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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  /53

  $695,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  103 Lower Diamond Farm Ln, Winthrop, ME 04364

  Tucked along the shores of Cobbosseecontee Lake, this rare waterfront property offers a front-row seat to one of Maine's most cherished lakes. Known for its clean, deep water, legendary bass fishing, and boater-friendly shoreline dotted with islands and coves, Cobbossee delivers everything lake life should be: adventure, serenity, and natural beauty, all in one.This isn't just a lake view; it's

  Tasha Massey On Point Realty

  

  103 Lower Diamond Farm Ln, Winthrop, ME 04364
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  /17

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  2540 Us-202 Unit Ground Floor East, Winthrop, ME 04364

  What used to be the Cobbossee Cash Market is now both commercial and residential rental spaces. Close to Cobbosseecontee Lake - convenient to shopping, schools and dining (might we suggest the White Duck?).

  2540 Us-202 Unit Ground Floor East, Winthrop, ME 04364
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  /27

  $219,500 Sold Jun 10, 2025

  • 1,064 Sq Ft
  • $206/SF
  • 13 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  361 Turkey Ln, Winthrop, ME 04364

  Not many mobile homes that sit on a full foundation! Look at this one! Spacious layout and the kitchen has plenty of cupboards. The primary bedroom suite has a jacuzzi soaking tub! On the other end, is a 2nd full bath and 2nd bedroom, newly carpeted. The basement is huge and has daylight windows and exterior door access. The property sits back off the road allowing privacy. Back yard has a

  Geri Doyle Rizzo Mattson

  

  361 Turkey Ln, Winthrop, ME 04364
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  /26

  Est $295,613 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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  /84

  $479,000

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  372 Memorial Dr, Winthrop, ME 04364

  MARANACOOK LAKE - Get ready for summer fun! This turn-key cottage is just steps from the lake with a flat, level lot with 125' on one of central Maine's best lakes! Memorial Drive has a low speed limit, offers public sewer & water and coveted sunsets each evening. This property is one of the best on the lake with long views across the water and a huge grassy lawn for games, fire pit & nice

  Trisha Cheney Portside Real Estate Group

  

  372 Memorial Dr, Winthrop, ME 04364
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  /21

  $1,300 per month

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

  33 Welch Point Rd, Winthrop, ME 04364

  Cozy one bedroom one bath single family home . Property features a beautiful stone gas fireplace, two enclosed porches one of which is seasonal , back deck , open loft area on 2nd floor with spiral stair case which is used for the bedroom . , cathedral ceilings, New propane furnace. Washer and dryer in unit. . Tenants will have limited access to the lake frontage but public access is available at

  33 Welch Point Rd, Winthrop, ME 04364
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  /15

  $177,000 Sold Jun 09, 2025

  • 1,248 Sq Ft
  • $142/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  109 Pineland Dr, Winthrop, ME 04364

  2022 Double Wide Mobile Home

  Derek Eisenberg Continental Real Estate Group, Inc.

  

  109 Pineland Dr, Winthrop, ME 04364
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  /35

  Est $285,695 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  282 Metcalf Rd, Winthrop, ME 04364

  

  282 Metcalf Rd, Winthrop, ME 04364
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  /60

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  363 Winthrop Center Rd, Winthrop, ME 04364

  A Hillside Retreat with Impeccable Craftsmanship and Modern Comforts. Welcome to 363 Winthrop Center Road - a beautifully maintained 3-bedroom, 2-bath home set on a private, well-landscaped lot just minutes from downtown Winthrop and only 10 minutes to Augusta. This inviting hillside retreat offers the perfect blend of quality craftsmanship and peaceful living. Step inside to an open-concept

  Taylor Tarbox Better Homes & Gardens Real Estate/The Masiello Group

  

  363 Winthrop Center Rd, Winthrop, ME 04364
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  /25

  $85,000 Sold Jun 04, 2025

  • 998 Sq Ft
  • $85/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2018

  103 Fellows Rd, Winthrop, ME 04364

  Off Grid Living! 1.65 acre private lot offers fenced in gardens, blueberry and elderberry bushes and a short commute to town. Spring fed dug well, chemical toilet and privy, wind and solar power by Natures Generator and power pods. 2'X6' Hemlock construction this property has been this families year round home since 2018. Bonus-out door kitchen, screened and open porches, outbuildings for wood

  Pat Ladd Homestead Realty

  

  103 Fellows Rd, Winthrop, ME 04364
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  /48

  Est $528,556 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

  $650,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  8 S Heritage Woods Ln, Winthrop, ME 04364

  Turnkey Lakefront Camp on Cobbossee! Ready to skip the hassle and jump straight into lake life? Welcome to 8 South Heritage Woods Lane—a lovingly updated, fully furnished 2-bedroom seasonal camp on the highly sought-after Cobbosseecontee Lake, complete with 114 feet of owned waterfront, a dock, boat lift, and even a bonus bunkhouse! Nestled on a private, wooded 0.50-acre lot, this renovated

  Joshua LaVerdiere Sprague & Curtis Real Estate

  

  8 S Heritage Woods Ln, Winthrop, ME 04364
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  /33

  $528,000 Sold May 30, 2025

  • 2,856 Sq Ft
  • $185/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 1800

  246 Route 133, Winthrop, ME 04364

  Welcome to this charming and spacious antique historic home, offering modern conveniences with period-specific details. The formal front entry features the original door with leaded glass in the transom and sidelights, while the side entry incorporates multiple closets for storage and a nearby laundry area. Get inspired in a kitchen adorned with cherry cabinetry and a layout that will bring out

  Charlene Hamiwka Harcourts Waterfront & Fine Properties

  

  246 Route 133, Winthrop, ME 04364
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  /50

  Est $688,243 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,198 Sq Ft

  83 Wedgewood Dr, Winthrop, ME 04364

  

  83 Wedgewood Dr, Winthrop, ME 04364
• 

  

  /54

  $475,000

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  156 Gayton Ln, Winthrop, ME 04364

  Pristine waters and lakeside living! This classic Maine cottage sits just at the waters edge and is ready for your memories to be made! Located on the shores of Lower Narrows Pond with 100' of frontage and endless water views this 2-3 bedroom cottage has it all. Many recent improvements including drainage added to uphill side of the cottage, jacked and leveled with new posts and pads, spray foam

  Pat Ladd Homestead Realty

  

  156 Gayton Ln, Winthrop, ME 04364
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  /25

  $58,000 Sold May 30, 2025

  • Land
  • 7 Acres
  • $8,227 per Acre

  • 22 Days On Market

  lot # 6 Sturtevant Hill Rd, Winthrop, ME 04364

  A Perfect Setting for Your Dream Home!Just over 7-acre lot in a serene country subdivision offers the perfect blend of convenience and tranquility. Located just outside of town, it's far enough to enjoy the peacefulness of nature, yet close enough for easy access to local amenities. Ready for you to build your dream home, this lot provides ample space to create your ideal retreat in a quiet,

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

  

  lot # 6 Sturtevant Hill Rd, Winthrop, ME 04364
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  /40

  Est $514,216 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,860 Sq Ft

  33 Ledgemere Dr, Winthrop, ME 04364

  

  33 Ledgemere Dr, Winthrop, ME 04364
• 

  

  /5

  $449,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft

  Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364

  Welcome to this modern ranch style home- to be built in the Mountain View Subdivision in Winthrop. Open floor plan in the kitchen, dining & living room area. French doors open to the large back yard and 3.7 acres of wooded land. Three spacious bedrooms- primary bedroom suite, two more bedrooms and second full bath. Separte first floor laundry. Attached garage, nice front porch, full basement,

  Ann Castonguay Sprague & Curtis Real Estate

  

  Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364
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  /54

  $532,000 Sold May 29, 2025

  • 1,308 Sq Ft
  • $407/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1947

  545 Memorial Dr, Winthrop, ME 04364

  Lovely year round home with 100' Maranacook Lake frontage. Completely renovated with expansive windows to take in the sunset views. Large wrap around deck is a wonderful place to relax, entertain and over water frontage, lawns and gardens. Beautifully remodeled kitchen with stainless appliances, propane cookstove, tiled back splash, center island, granite counters all open to dining area and

  Pat Ladd Homestead Realty

  

  545 Memorial Dr, Winthrop, ME 04364
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  /42

  Est $349,548 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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  /44

  $415,000 Pending

  • 2 Beds
  • 3 Baths
  • 1,264 Sq Ft

  27 Mace Ave, Winthrop, ME 04364

  Escape to this cozy, year-round or seasonal retreat nestled at the head of beautiful Cobbossee Lake. Perfect for those seeking relaxation or adventure, this charming home has it all! With shared Lake Access you'll can enjoy fishing, kayaking, or lounging by the water with ease. Updated from the bottom up, this home offers modern comforts while maintaining its rustic charm. Year-round lake views

  Shelley Nadeau Your Home Sold Guaranteed Realty

  

  27 Mace Ave, Winthrop, ME 04364
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  /20

  $147,000 Sold May 23, 2025

  • Land
  • 15 Acres
  • $9,545 per Acre

  • 3 Days On Market

  Lot 53 South Rd, Winthrop, ME 04364

  Opportunity meets natural beauty on South Road in Winthrop, Maine. This surveyed and soils-tested 15.4-acre parcel offers a rare blend of space, flexibility, and serene surroundings just minutes from the shores of Cobbossee Lake. With an impressive 1,324+/- feet of road frontage, the property lends itself to a variety of possibilities, including potential division into two spacious

  Sophia Rosen Sierra Boler Portside Real Estate Group

  

  Lot 53 South Rd, Winthrop, ME 04364
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  /36

  Est $311,161 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,913 Sq Ft

  108 Pamela Dr, Winthrop, ME 04364

  

  108 Pamela Dr, Winthrop, ME 04364
• 

  

  /51

  $372,500 Pending

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

  97 Pennwood Rd, Winthrop, ME 04364

  First time offered! Well maintained Winthrop Ranch in convenient in-town neighborhood. This 3 bedroom 2 bath home offers spacious kitchen and abundant cupboards/counter space for the cook of the house. Dining area is tiled and has views over private 1 acre lot and fenced in pool. West facing living room with lovely sunset views and is warmed by pellet stove. Large bonus room with red oak floors,

  Pat Ladd Homestead Realty

  

  97 Pennwood Rd, Winthrop, ME 04364
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  /119

  $465,000 Sold May 21, 2025

  • 2,411 Sq Ft
  • $193/SF
  • 9 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  166 Carlton Pond Rd, Winthrop, ME 04364

  Welcome to your private escape! Nestled on 10.9 scenic acres, on a quiet residential street, this spacious 4-bedroom, 2-bathroom home offers the perfect blend of comfort and country charm. Step inside to find a generous layout featuring a large kitchen ideal for cooking and gathering, with ample counter space and storage to make meal prep a breeze. There is also a den/office for a perfect work

  Terri Stone Redfin Corporation

  

  166 Carlton Pond Rd, Winthrop, ME 04364
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  /59

  Est $343,800 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
• 

  

  /55

  $449,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,828 Sq Ft

  229 Bearce Rd, Winthrop, ME 04364

  Welcome to 229 Bearce road in beautiful Winthrop Maine. This colonial features 4 large bedrooms, 2 1/2 bathrooms, an office, and a separate dining room with a large brick fireplace. The kitchen offers, granite countertops, lots of storage and a butcher block island with built in range. Beautiful wood and tile floors throughout. The Primary bedroom has a large walk-in closet with an unfinished

  Jeffrey Perkins Brookewood Realty

  

  229 Bearce Rd, Winthrop, ME 04364
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  /53

  $415,000 Sold May 21, 2025

  • 2,280 Sq Ft
  • $182/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  345 Main St, Winthrop, ME 04364

  Discover this beautifully maintained and thoughtfully updated four-bedroom home, perfectly situated for easy access to local shopping, amenities, and a quick commute to I-95. Step inside to experience the perfect blend of classic charm and modern comfort, with spacious living areas designed to accommodate today's lifestyle. The first floor features a well-designed layout, including a convenient

  Shawn McKillop Maine Real Estate Co

  

  345 Main St, Winthrop, ME 04364
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  /43

  Est $300,830 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,069 Sq Ft

  362 Route 41, Winthrop, ME 04364

  

  362 Route 41, Winthrop, ME 04364
• 

  

  /25

  $39,000

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft

  60 Squire Ct, Winthrop, ME 04364

  Recently renovated 1988 mobile home offering 3 bedrooms and 1.5 bathrooms in a peaceful Maine setting. This move-in-ready home features new flooring and fresh paint throughout, creating a bright and updated interior. The kitchen has been fully renovated with new clean, white cabinets. Both bathrooms have been refreshed with new toilets, and the full bath includes a new shower. Additional upgrades

  Karen Edgcombe Maine Real Estate Co

  

  60 Squire Ct, Winthrop, ME 04364
• 

  

  /23

  $190,000 Sold May 15, 2025

  • 3,000 Sq Ft
  • $63/SF
  • 229 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  379 Winthrop Center Rd, Winthrop, ME 04364

  Seller has listened to the consumer feedback and has adjusted the price accordingly. The spot is not far from a public boat launch, is close to the local apple orchards and farms. Truly a project that will be worth it in when your finish work is done. Current owner had started big plans, started and did a fabulous job cleaning out what was left by the prior owner, got the second level ready

  Julie Cromwell Cromwell Coastal Properties

  

  379 Winthrop Center Rd, Winthrop, ME 04364
• 

  

  /23

  Est $422,662 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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