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$899,500
4 Beds ⋅ 2 Baths ⋅ 1679578 MLS
A rare find on desirable Lake Cobbossee. This beautifully landscaped and meticulously maintained property has privacy, comfort, a gorgeous view, and one of the largest shorelines and best locations on the lake. Relax into the sound of loons from sunrise to sunset on the large screened porch. Walk just a few steps down the natural granite steps to the dock and enjoy the convenience of your own boat launch, and oversized garage for storing watercraft or vehicles. Inside are 4 bedrooms, 2 bathrooms, and a large family space with a cathedral ceiling and warm wood interior with windows all around. A fireplace insert will ensure coziness on cooler evenings. This one-of-a-kind property and home is a must see!

34 N Heritage Woods Ln, Winthrop

Listing courtesy of Homestead Realty.

$524,000
4 Beds ⋅ 2 Baths ⋅ 1679526 MLS
Space, storage & location come together in this expansive, move-in-ready Winthrop Saltbox! Set on a peaceful 1.13-acre country setting, this spacious 4-bedroom, 2-bath home offers a flexible layout with room for everyone and storage, storage, storage! Enter from the attached 2-bay garage into a convenient mudroom that leads to the kitchen and flows naturally into the dining and living areas. Cathedral ceilings add to the open feel, while a heat pump provides year-round comfort. The main floor also features a bedroom with a bonus cedar closet, bath, laundry, pantry and direct access to the back deck. Upstairs you'll find additional bedrooms, a full bath and generous closet space. The finished lower level adds even more possibilities with the 4th bedroom, recreation room and office. A sliding glass door provides walkout access from the recreation room, while the office offers an additional walkout beneath the deck. Storage is truly a standout here, with closets throughout, extensive storage above and below the garage, plus a generator hookup in the garage for added convenience. Outside, enjoy established landscaping, a paved driveway and plenty of space to relax. The location gives you the best of both worlds, country living while remaining close to Winthrop amenities. Hiking trails are within walking distance, and the public beach on beautiful Cobbosseecontee Lake is just minutes away. Spacious, well cared for and truly move-in ready, come see everything this Winthrop home has to offer! This is a home you won't outgrow anytime soon!

196 Case Rd, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. 2073956063
$239,000
3 Beds ⋅ 2 Baths ⋅ 1678988 MLS
Welcome to this beautiful double wide mobile just waiting for you to move in within walking distance to downtown Winthrop. This home offers 3 bedrooms, two full baths and an open concept kitchen/living room that will make hosting holiday gatherings or family game nights comfortable and roomy. If you like gardening or just want to relax, you will have plenty of opportunity to spend time in the privacy of your own backyard. You have a one car garage along with convenient off-site parking right next door for any large gatherings. You are just a few minutes from downtown Winthrop offering you plenty of shopping and restaurants. Don't miss out on this easy maintenance home leaving you years of worry-free living.

114 Rte 133, Winthrop

Listing courtesy of Maine Real Estate Experts. Kellyatmainehomes@gmail.com
$375,000
3 Beds ⋅ 2 Baths ⋅ 1677476 MLS
Welcome to this charming single-family home, lovingly cared for by the same owners for 40 years. Set on approximately 4 acres, this 3-bedroom, 2-bath property offers a wonderful blend of comfort, privacy, and convenience. Inside, you'll find approximately 2,300 square feet of living space featuring beautiful hardwood floors and a comfortable layout. A heat pump provides efficient heating and cooling, while a whole-house generator offers peace of mind year-round. Nature lovers and outdoor enthusiasts will appreciate having Narrows Pond just down the road, providing easy access to the beauty and recreation of the area. With four acres to enjoy, there's plenty of room for gardening, outdoor activities, or simply relaxing in your own private setting. After four decades of ownership, this well-loved home is ready for its next chapter. A wonderful opportunity to own a property with land, character, and desirable features in a peaceful setting.

231 Narrows Pond Rd, Winthrop

Listing courtesy of Sprague & Curtis Real Estate.

$379,500
3 Beds ⋅ 2 Baths ⋅ 1677161 MLS
Your Maine waterfront lifestyle starts here! Set along the scenic shores of Little Cobbosseecontee Lake, this inviting Winthrop home offers the perfect setting for swimming, kayaking, fishing, entertaining, or simply relaxing by the water. Enjoy all four seasons, with winter bringing the added opportunity for ice fishing and the peaceful beauty. With 1,800+ square feet of comfortable living space, the home features 3 bedrooms, 2 bathrooms, an additional sleeping area, gleaming hardwood floors, a cozy fireplace, and a dedicated laundry room. Numerous recent updates--including the kitchen, bathrooms, appliances, doors, and fresh interior paint--make this home move-in ready while maintaining its comfortable Maine character. A unique hideaway door cleverly conceals the mechanical room, adding both character and functionality to the home. A home office space and workshop provide valuable flexibility for remote work, hobbies, projects, or additional storage. Outside, the expansive open backyard offers plenty of room for entertaining, gardening, outdoor games, or enjoying peaceful afternoons beside the water. A durable metal roof provides added longevity and peace of mind, while the property's convenient location puts you just minutes from Augusta for shopping, dining, entertainment, golf, and area attractions. Portland also less than an hour away, making it an easy commute to Jetport or enjoy the city's restaurants, shopping, waterfront, arts, and entertainment. Whether you're looking for a year-round home, a four-season Maine getaway, or your own piece of waterfront property, 2576 US Route 202 offers a rare combination of waterfront recreation, recent updates, usable outdoor space, unique character, and classic Maine living. SHOWINGS TO BEGIN 8/30 WITH OPEN HOUSE 11A-2P

2576 Us-202, Winthrop

Listing courtesy of Keller Williams Realty.

$470,000
3 Beds ⋅ 2 Baths ⋅ 1675236 MLS
Lake views fill every room, creating a serene backdrop throughout the home. The spacious living room features cathedral ceilings and a cozy propane stove, making it the perfect gathering place on cool evenings. Enjoy meals on the expansive screened porch or in the sunny breakfast nook, both offering beautiful water views just steps from the kitchen. The walk-out lower level includes two private guest bedrooms, providing family and friends with easy access to the waterfront. Upstairs, the primary suite offers a peaceful escape with sliding glass doors leading to its own private lakeside deck--the ideal spot to enjoy your morning coffee while taking in the tranquil views. Outside, a dock system is ready for all your waterfront adventures, while a separate workshop provides space for hobbies, projects, and convenient winter storage. With breathtaking sunsets, exceptional privacy, and direct access to one of the area's most desirable lakes, this property is a true Maine waterfront getaway.

81 Merganser Ln, Winthrop

Listing courtesy of Homestead Realty.

$725,000
3 Beds ⋅ 2 Baths ⋅ 1673596 MLS
Own your own peninsula on beautiful Annabessacook Lake and experience a combination of privacy, panoramic water views, and exceptional waterfront. As the last home at the end of the road, this year-round property includes 672 feet of private frontage, surrounding you with water and creating the feeling of a secluded lakeside retreat while remaining just minutes from the amenities of Winthrop. Designed to capture the beauty of the lake from nearly every room, the home features 3 bedrooms, 2 full baths, a spacious living room with lake views and a wood-burning stove that creates the perfect gathering space in every season. The fully equipped kitchen offers granite countertops, tile flooring, and opens to inviting dining and living spaces ideal for entertaining. Step outside and experience the best of Maine lake life--from morning coffee overlooking the water to afternoons spent swimming, boating, kayaking, and fishing from your own shoreline. The dock conveys, and the sandbar just off the point is a wonderful spot to anchor, swim, and enjoy long summer days on the lake. Whether you're searching for a year-round residence, a vacation getaway, or a legacy property to enjoy for generations, opportunities like this are exceptionally rare. Properties with this much waterfront, this level of privacy, and the unique opportunity to truly own your own peninsula seldom come to market. Please note: The new lakeside deck will require modifications to complete the permitted project. The approved building permit and plans are in hand and will convey with the property.

85 Woods Grove Ln, Winthrop

Listing courtesy of EXP Realty.

$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1672392 MLS
Two year-round lake cottages, one exceptional Cobbossee offering. With two fully renovated, independent homes on one waterfront lot, the flexibility is rare: a private family compound, multi-generational living, the ability to comfortably host family and friends in their own private cottage, or the opportunity to offset ownership costs by renting one cottage while enjoying the other. Both homes have been thoughtfully renovated and are move-in ready with modern finishes while preserving the charm of a classic Maine lakefront retreat. One cottage offers two bedrooms, a full basement that is partially finished, and a spacious living room. The second features an open-concept first floor, a loft bedroom, and a stunning wall of windows showcasing panoramic lake views. The setting is private, yet easily accessible, on the desirable north side of Cobbossee Lake, a 9-mile lake renowned for boating, kayaking, seaplanes, islands, an active lake association, and some of Maine's finest bass fishing, including professional tournaments. Wake each morning to breathtaking south-facing views, with sunshine filling the property throughout the day. Outside, the property is beautifully appointed with underground LED lighting, landscaped perennial gardens, stone riprap along the shoreline, three private docks, and multiple outdoor gathering spaces designed for evenings around the fire, family cookouts, and relaxing after a day on the lake. The expansive side yard offers additional flexibility for lawn games, a tent for special gatherings, or even a camper for visiting family and friends. Enjoy every season Maine has to offer-from summer boating and swimming to spectacular fall foliage, winter ice fishing, and peaceful year-round escapes. Despite its tranquil waterfront setting, the property is just minutes from a full-service marina, golf, dining, shopping, MaineGeneral Medical Center, the State Capitol, and all the conveniences of Augusta.

7 & 11 Keyes Landing Ln, Winthrop

Listing courtesy of Your Home Sold Guaranteed Realty.

$675,000
5 Beds ⋅ 2 Baths ⋅ 1671611 MLS
Welcome Home! Experience ideal New England living with expansive views across 3.7 acres of rolling lawns to beautiful Maranacook Lake. Unwind on the spectacular 700+ square-foot deck, gather around the open fire pit for evenings of roasting marshmallows while the loons call across the water, or enjoy the changing seasons from the comfort of the glass-enclosed porch. Filled with warmth, sunlight, and timeless character, this gracious Victorian farmhouse offers the perfect blend of historic charm and modern convenience. Located just a short walk to town, you'll feel worlds away in this peaceful and picturesque setting. Enter through the sunny, south-facing breakfast porch, an inviting space to linger over morning coffee while soaking in the natural light. The charming kitchen features beadboard walls, stainless steel appliances, including a propane cookstove, and a tile floor that complements the home's classic farmhouse character. The formal dining room is designed for memorable gatherings, offering hardwood floors, built-in cabinetry, and a beautiful bay window. The front parlor is equally inviting with another bay window, hardwood floors, and abundant natural light. A convenient first-floor laundry room and full bath complete the main level. Upstairs, you'll find three to four light-filled bedrooms. The spacious primary suite features an oversized walk-in closet, an adjoining office or sitting area, and easy access to a full bath. An impressive two-story barn provides endless possibilities for storage, hobbies, or a workshop, with direct access to the deck and porch for seamless indoor-outdoor living. The barn comes with an electric car charger. This is more than a home--it's a lifestyle.

229 Rte 133, Winthrop

Listing courtesy of Homestead Realty.

$145,000
3 Beds ⋅ 2 Baths ⋅ 1669962 MLS
Well cared for 3 bedroom, 2 full bath home in desirable community. Enjoy the open concept this home offers with central air, paved driveway, and home generator. Primary bedroom with full bath. Two sheds for additional storage. Home features abundant light and private back yard with deck.

87 Pineland Dr, Winthrop

Listing courtesy of Homestead Realty.

$399,900
3 Beds ⋅ 2 Baths ⋅ 1665904 MLS
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 room with a wood stove, two bedrooms, and a full bath, allowing for convenient one-floor living if desired. The second floor includes a large primary bedroom with bath plus an additional open area that would make a great family room, office, or could potentially be converted into a 4th bedroom. Additional features include a second wood stove in the basement, whole house generator, good overall condition, and a nice blend of privacy and convenience. A great opportunity for anyone looking for space, flexibility, and a quiet location close to town.

41 Birch St, Winthrop

Listing courtesy of Rizzo Mattson. 207-622-9000
$799,900
2 Beds ⋅ 2 Baths ⋅ 1663823 MLS
Nestled on the shores of beautiful Upper Narrows Pond, this stunning waterfront home at 38 South Upper Narrows Lane offers breathtaking water views, spectacular sunsets, and the peaceful lifestyle you've been dreaming of. Meticulously maintained and thoughtfully designed, this spacious 2,387 sq. ft. home combines comfort, style, and functionality in a truly picturesque setting. The well-landscaped property features a paved driveway, two garages, and an additional shed, providing plenty of space for vehicles, storage, and outdoor equipment. Inside, you'll find a bright and inviting open-concept layout highlighted by cathedral ceilings, beautiful built-ins, and a striking stone fireplace that creates a warm and welcoming atmosphere. The large kitchen is perfect for entertaining and everyday living, featuring granite countertops, ample cabinetry, and generous workspace. Relax year-round in the sunroom while taking in serene pond views and natural beauty surrounding the home. The spacious primary suite offers a private retreat complete with a walk-in closet and an elegant bathroom featuring a tiled shower and double vanity. The finished lower level adds even more living space with a cozy family room warmed by a pellet stove, two additional bedrooms, a full bathroom, and laundry area -- ideal for guests or extended family. Whether you're looking for a year-round residence or a waterfront getaway, this exceptional property offers comfort, charm, and the very best of Maine waterfront living.

38 S, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. DonnaPinkham@Masiello.com
$295,000
3 Beds ⋅ 2 Baths ⋅ 1657372 MLS
Fantastic New Price! Historic Winthrop Gem Full of Character & Opportunity! If you've been searching for a home with history, timeless craftsmanship, and room to make it your own, this is your opportunity. Located in Winthrop's Historic District, this home is believed to date back to the 1850s (town records indicate 1910) and offers 2,312 square feet filled with original architectural details that have stood the test of time. From its classic character to its generous floor plan, this home offers a rare opportunity to own a piece of Winthrop's history while adding your own personal touch. Thoughtful updates include a new metal roof, nearly all new windows (with only one small bathroom window remaining), all new interior doors, two new exterior doors, and a generator hookup for added peace of mind. The spacious eat-in kitchen opens to a welcoming front deck, perfect for enjoying your morning coffee or grilling on warm summer evenings. The flexible first-floor layout includes a living room, office, formal living room, bedroom, large laundry room, and half bath, offering options for today's lifestyle. Just off the main level, the former summer kitchen provides direct access to the backyard and presents exciting possibilities. With a little vision, this area could become the perfect transition to a beautiful outdoor entertaining space or private backyard patio. Upstairs, you'll find three additional bedrooms and a spacious full bath featuring double sinks, a classic clawfoot tub, and a separate stand-up shower. With multiple living spaces, abundant storage, and endless possibilities. Enjoy the peaceful charm of a country setting while remaining just minutes from Augusta and approximately 30 minutes from the Lewiston / Auburn area.

247 Winthrop Center Rd, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. 2073956063
$465,000
4 Beds ⋅ 2 Baths ⋅ 1644187 MLS
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 bathroom and laundry has a nice balcony-the perfect place to enjoy your morning coffee and after work glass of wine. This home sits on almost an acre with lovely flower gardens and a fenced in back yard and paved drive. Just a quick drive down the hill and you're on Main Street with all of it's shopping or at the town park on the shores of Maranacook Lake. You have to see this one to appreciate all it has to offer. The town tax records indicate it is a 5 bedroom home, however, the septic design was not able to be located showing the size of the leach field.

974 Sturtevant Hill Rd, Winthrop

Listing courtesy of Lakehome Group Real Estate. info@lakehomegroup.com

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

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