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$400,000
3 Beds ⋅ 3 Baths ⋅ 1680267 MLS
Perched at the top of Spruce Street, this contemporary post and beam home features gorgeous elevated views and a private setting on 1.46 wooded acres. Step inside to an open, light filled layout with vaulted ceilings, a dramatic two story atrium, and living room with wood burning brick fireplace. The spacious primary suite features a full bath and balcony overlooking the atrium. The four season sunroom and deck are wonderful spaces to relax and enjoy the scenery. Recent updates include all new flooring, heat pumps on each level, re-insulated attic, new 320 gallon oil tank, new water softener system, and new garage doors. An attached two car garage adds convenience. Enjoy a peaceful mountaintop setting while still being close to Winthrop shopping and dining, nearby lakes and recreation, and convenient access to major routes for travel throughout Central Maine. A special property combining beautiful views, character, updates, and convenience. OPEN HOUSE - Sept 19th 2026, Saturday, 12 pm to 2 pm.

39 Spruce St, Winthrop

Listing courtesy of EXP Realty.

$259,900
3 Beds ⋅ 1 Baths ⋅ 1679077 MLS
If you've been dreaming of owning your own home, this charming Cape-style property is ready to make that dream a reality! Tucked into a quiet neighborhood just minutes from downtown Winthrop, it offers the perfect blend of comfort, convenience, and affordability. Step inside to a freshly renovated first floor with a bright, inviting feel. The updated kitchen features new cabinets, countertops, and modern appliances, creating a welcoming space to cook and gather. Fresh paint and updated flooring make the home feel clean, comfortable, and move-in ready. The first floor also features original wood floors, a bedroom offering flexible living options, and a spacious sitting area warmed by a pellet stove — perfect for relaxing on chilly Maine evenings. The updated full bathroom includes a stylish tile shower surround. Upstairs, you'll find two additional bedrooms and convenient crawl-space storage. The full basement, accessible both inside and outside, provides plenty of room for storage, hobbies, or projects. A pool table is included with the sale! Outside, enjoy a flat, fenced-in backyard with a gazebo platform — perfect for summer gatherings, gardening, or simply relaxing outdoors. The detached one-car garage provides protection from Maine winters and additional storage. A low-maintenance metal roof adds another great benefit for easy homeownership. And the location is hard to beat! The public beach and boat launch are less than a mile away, while local schools are also conveniently located within a mile. Downtown Winthrop is just a short distance away, offering shops, restaurants, and everyday amenities. Bright, updated, affordable, and move-in ready — this is a wonderful opportunity to put down roots and start building your future in Winthrop!

11 Charles St, Winthrop

Listing courtesy of Keller Williams Realty.

$249,900
3 Beds ⋅ 1 Baths ⋅ 1678998 MLS
Winthrop - Charming and inviting 3-bedroom, 1-bath home in a convenient Winthrop location. This well-kept property features beautiful hardwood floors, a comfortable layout, and a full basement offering plenty of storage space and potential for additional use. Enjoy relaxing outdoors around the fire pit, surrounded by a peaceful, wooded setting. Conveniently located close to local amenities, shopping, dining, and recreation, this home offers a great combination of comfort, charm, and convenience.

3 Hillside Ave, Winthrop

Listing courtesy of Brookewood Realty.

$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.

$336,000
3 Beds ⋅ 3 Baths ⋅ 1676700 MLS
Bring your vision and color palette to this spacious **3-bedroom, 2-bath ranch in Winthrop!** Set on **1.30 acres**, this property offers **1,586 sq. ft. of living space on the main level** plus an additional **858 sq. ft. of finished walk-out daylight basement**, giving you plenty of room to spread out. The main level features a comfortable layout with a **fireplace**, three bedrooms, and two baths. The finished lower level provides excellent additional living space and easy access to the large yard. Outside, you'll enjoy a **nice, spacious yard** with plenty of room for gardening, recreation, entertaining, or simply enjoying the peaceful setting. The home is ready for some updating, offering an opportunity to make it your own. The bathrooms could use updating, along with fresh paint and some new flooring. Bring your ideas, choose your colors, and add your personal touches to create the home you've been looking for. **With its generous acreage, finished lower level, and solid ranch-style layout, this Winthrop property offers plenty of potential!** Home is being 'Sold As Is where Is'

549 Old Lewiston Rd, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. DonnaPinkham@Masiello.com
$389,750
3 Beds ⋅ 1 Baths ⋅ 1675951 MLS
Coveted and sought after Memorial drive location with Marancook lake shared waterfront , The best of both worlds Waterfront views from your side deck and just 97 steps to the shared waterfront. Nice gradual waterfront for swimming and enjoyment Stunning sun sets and affordable taxes .Three bedrooms, and one full bath with 960 square feet of living. An open concept kitchen -dining room and lakeside living room that is 17.9 by 11.5 . Your composite deck is 24.4 by 8.7 and the perfect place to entertain grille and relax. Multiple heat pumps provide efficient whisper quiet heating and cooling, keeping the home comfortable through every season, The heated walkout basement adds to the flexible workshop, recreation area, storage hobbies, or whatever suits your needs. Possible to add more bedrooms and baths if you prefer . An additional back lot is included and all ready for a garage or accessory dwelling unit .This properties location is ideal .Enjoy this wonderful waterfront community and level front lawn . This home is flexible and you can use your imagination for what it could be Finish the basement and add a garage . You could also reconfigure the layout to meet your desires .Easy to do .Whether you're looking for a year round home , a place to enjoy the lake, an investment property , or the opportunity to own in one of Winthrop's most desirable neighborhoods. 147 Memorial drive offers it all .See it now on -line with the Matterport tour or schedule your showing now

147 Memorial Dr, Winthrop

Listing courtesy of LAER.

$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.

$579,000
3 Beds ⋅ 3 Baths ⋅ 1674236 MLS
Nestled in a wonderful, quiet neighborhood, this beautifully maintained Cape/Contemporary home offers the perfect blend of comfort, style and natural beauty. Set on the shores of scenic 18-acre Kezar Pond, this exceptional property provides a peaceful waterfront lifestyle where you can canoe, kayak, fish, swim, or simply enjoy the abundant wildlife right from your own backyard. Inside, you'll find a thoughtfully designed floor plan with room for everyone. The spacious kitchen features classic oak cabinetry, granite countertops, and plenty of workspace for cooking and entertaining. The dining room showcases beautiful hardwood floors, while the inviting living room offers a comfortable place to relax. A separate three-season porch provides the perfect spot to enjoy the changing season and tranquil pond views. The main level includes a convenient first-floor bedroom and full bath, making single-level living an option. Upstairs are two additional bedrooms and another full bath. The finished lower level offers outstanding flexibility with a home office, a spacious family room featuring a charming brick fireplace, and a half bath with laundry. Additional highlights include an attached three-car garage, automatic whole-house generator, and a recently installed roof for added peace of mind. Beautiful landscaping enhances the home's curb appeal and creates an inviting outdoor setting. Located just 10 minutes from Augusta and Interstate 95, this home offers the serenity of country living with easy access to shopping, dining, and commuting. In wonderful condition and set in an exceptional waterfront location, the is a rare opportunity to own a home that combines quality, convenience, and the beauty of Maine living.

77 Wedgewood Dr, Winthrop

Listing courtesy of Sprague & Curtis Real Estate. earle@spragueandcurtis.com
$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.

$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
$445,000
3 Beds ⋅ 3 Baths ⋅ 1664292 MLS
Move right into this beautifully updated and meticulously maintained Colonial, where modern comforts and thoughtful design come together in a peaceful setting just minutes from town. The inviting open-concept kitchen and dining area is the heart of the home, featuring abundant cabinetry, granite countertops, and a large center island that's perfect for everyday living, entertaining, or gathering with family and friends. Offering three bedrooms and three bathrooms, this home provides a functional layout with plenty of space to spread out. The spacious primary suite serves as a private retreat with a walk-in closet and an ensuite bath. A standout feature is the dedicated first-floor laundry room with direct access to the backyard, making it easy to enjoy the fenced area designed with pets, gardening, or outdoor convenience in mind. Step outside to the back porch overlooking inviting outdoor living spaces, including a firepit area that's perfect for relaxing evenings or entertaining guests. A generously sized storage shed provides extra space for tools, lawn equipment, and seasonal items. Set on a picturesque .46-acre lot, this property offers the perfect balance of privacy and convenience, with downtown, local boat launches, shopping, dining, and other amenities just minutes away. Whether you're hosting friends around the firepit, enjoying a quiet morning on the porch, or heading out for a day on the water, this home is ready to complement the way you live!

256 Narrows Pond Rd, Winthrop

Listing courtesy of Sprague & Curtis Real Estate. lori@spragueandcurtis.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

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