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34 N Heritage Woods Ln, Winthrop
$1,070,000
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.

Selling Office: Pouliot Real Estate.

11 Charles St, Winthrop
$260,000
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.

Selling Office: Homestead Realty.

38 S, Winthrop
$720,000
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

Selling Office: Your Home Sold Guaranteed Realty.

114 Rte 133, Winthrop
$232,605
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

Selling Office: Your Home Sold Guaranteed Realty.

247 Winthrop Center Rd, Winthrop
$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

Selling Office: Real Broker.

34 Maranacook Station Ln, Winthrop
$520,000
4 Beds ⋅ 1 Baths ⋅ 1681056 MLS
Wonderful sunrise views over Maranacook Lake! This three season cottage comes with 130' of waterfront and expansive views. The 1032 square foot cottage offers 2 bedrooms on the main level, Enter into the cottage and look through the sliders to the glistening water beyond. Enjoy family and friends on the open porch before spending the day on the water. The galley style kitchen has lots of natural light through the skylight and bow window which makes a pleasant place to cook meals! The living room has pine floors and is warmed by a wood burning field stone fireplace with energy efficient insert. A lakeside 8' X 28' glassed in porch for dining at water's edge or for listening to the loons while napping in the afternoons. The second story has 2 bedrooms and lake views! The cottage is heated with a monitor heater and has laundry on the main level for convenience. A two car garage is very helpful for storage of boats and water toys. Enjoy all the best of Maranacook Lake with wonderful bass fishing, boating and swimming right outside your door. Central Maine location is perfect spot for you to slow down relax and enjoy lakefront living.

34 Maranacook Station Ln, Winthrop

Listing courtesy of Homestead Realty.

Selling Office: Homestead Realty.

2576 Us-202, Winthrop
$387,000
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.

Selling Office: Redfin Corporation.

85 Woods Grove Ln, Winthrop
$710,000
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.

Selling Office: Better Homes & Gardens Real Estate/The Masiello Group.

3 Hillside Ave, Winthrop
$249,000
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.

Selling Office: Homestead Realty.

176 Upper Narrows, Winthrop
$345,000
2 Beds ⋅ 1 Baths ⋅ 1677081 MLS
Welcome to pristine Upper Narrows Pond. This 2-bedroom seasonal waterfront retreat offers wooded privacy with 150 feet on the Eastern shore. The 0.58-acre lot is located near the end of a peninsula. Take your kayaks out for some fishing or to explore the pond, swim to the island within view of your cottage or maybe come in the winter for ice fishing. Enjoy your morning coffee on the full length screened-in porch. View the sunsets from here and watch the loons swim by and the fish feeding. The cottage comes furnished including kitchen and laundry appliances, an AC unit, a ''TommyDock'' dock system, and non-motorized watercraft. The open-concept knotty-pine interior has a living room with views of the lake and an inviting woodstove to take the chill off from a rainy day.

176 Upper Narrows, Winthrop

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: Better Homes & Gardens Real Estate/The Masiello Group.

231 Narrows Pond Rd, Winthrop
$373,500
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.

Selling Office: Sprague & Curtis Real Estate.

117 Lower Diamond Farm Ln, Winthrop
$900,000
2 Beds ⋅ 1 Baths ⋅ 1674919 MLS
Fabulous waterfront cottage on highly desirable Cobbossee Lake! Situated on the lake's west shore, this exceptional property enjoys breathtaking views down the lake. Designed for entertaining and creating lifelong memories, this charming 2-bedroom, 1-bath cottage offers an impressive 230 +/- feet of excellent waterfront on a beautiful, private 1.84-acre lot. Opportunities like this are rare on Cobbossee Lake. The property features outstanding swimming and boating frontage, along with the convenience of a private boat launch right on the property. Located close to the water's edge, the cottage provides an exceptional waterfront experience with spectacular lake views from throughout. This seasonal retreat is equipped with electric heat, a fireplace, and a wood stove, making it comfortable for extended three-season enjoyment. Inside, you'll find a welcoming enclosed porch, a spacious living room with wood floors, and an open kitchen perfect for gathering with family and friends. Additional features include a detached three-car garage with storage above, offering plenty of room for vehicles, boats, and recreational equipment. Beautifully furnished and tastefully decorated, the property is being sold mostly furnished, with only a few exclusions, making it a truly turnkey waterfront retreat ready to enjoy from day one. The seller respectfully requests an offer deadline of Sunday August 9th by 5pm with a response time of August 10th by 5pm.

117 Lower Diamond Farm Ln, Winthrop

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: Rizzo Mattson.

172 Turkey Ln, Winthrop
$190,000
3 Beds ⋅ 2 Baths ⋅ 1673332 MLS
Opportunity awaits! This 3-bedroom home is ready for someone to build equity and make it their own. Being sold as is, the home has already seen several updates, including newer windows and partial remodeling, giving you a head start on the finishing touches. It also features an approximately 481 sq. ft. partially finished walk-out basement, providing additional flexible living or storage space. Situated on a nice wooded lot with two storage sheds, the spacious lot may have room for a future garage (subject to local approvals). Conveniently located just 2 miles from town with easy access to Route 202. Whether you're a homeowner looking to customize your next home or an investor looking to finish what's been started for a rental or resale, this property is full of potential.

172 Turkey Ln, Winthrop

Listing courtesy of EXP Realty.

Selling Office: Fontaine Family-The Real Estate Leader.

7 Carlton Pond Rd, Winthrop
$830,000
1682358 MLS

7 Carlton Pond Rd, Winthrop

Listing courtesy of Keller Williams Realty.

Selling Office: Fontaine Family-The Real Estate Leader.

281 Annabessacook Rd, Winthrop
$112,000
3 Beds ⋅ 1 Baths ⋅ 1678752 MLS
Bring your vision and make this Winthrop property your own! Situated on a spacious lot, this 3 bedroom, 1 bath home offers plenty of potential for an investor, contractor, or someone looking for a renovation project. The property is in need of repairs and updating throughout and is being offered as an opportunity for someone ready to take on a project and bring new life to the home. A seamless metal roof was installed approximately 10 years ago. Outside, you'll find a great lot featuring a large fenced in yard, spacious storage shed, and detached 2 car garage. Conveniently located on Annabessacook Road in Winthrop, this property offers a nice setting, plenty of usable outdoor space, and lots of possibilities. Bring your ideas and see the potential!

281 Annabessacook Rd, Winthrop

Listing courtesy of Coldwell Banker Realty.

Selling Office: Integrity Homes Real Estate Group, PC.

81 Merganser Ln, Winthrop
$475,000
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.

Selling Office: Your Home Sold Guaranteed Realty.

45 Pleasant St, Winthrop
$250,000
3 Beds ⋅ 2 Baths ⋅ 1668717 MLS
Welcome to 45 Pleasant Street located right in the heart of Winthrop, Maine. This 3-bedroom, 1.5 bath, well maintained, cozy cape is perfect for those looking for in-town living, while still having ample indoor and outdoor space to call your own. Located just minutes from local shops, the town beach, and public schools, come see for yourself all this home has to provide in the desirable Town of Winthrop.

45 Pleasant St, Winthrop

Listing courtesy of Meservier & Associates.

Selling Office: Hearth & Key Realty.

1 Black Island & 93 Birchwood Lane, Winthrop
$700,000
3 Beds ⋅ 1 Baths ⋅ 1670012 MLS
Having been in the same family since the early 1900s, Black Island on Cobbossee Lake is for sale, a very rare gem and opportunity. If you have ever boated to Horseshoe Cove you've been by it; it creates the entrances on both the east and west sides. The 9.5+/- acre island features a beautifully crafted 1989 post and beam 3 BR, 1 BA home finished in V-matched pine and wide pine floors. The house has three generous bedrooms, one on the first floor and two upstairs. The kitchen is open to the large living room and dining room with a brick fireplace. It's a great layout to gather family and friends. The south facing screened porch is large enough for a crowd or a peaceful place to listen to the loons with a cup of coffee or to kick back and enjoy a book. Black Island is surrounded by mostly preserved islands owned by the Kennebec Land Trust which means they aren't developed. The island is a tranquil refuge with two beaches and trails around the island including a rock outcropping which is a favorite swimming spot. Picnic Rock is also part of the property. Access to the island is from Birchwood Association on the west shore in Winthrop. There is a building lot that the sellers own that once had a small seasonal cottage before a tree fell on it; the cottage can be rebuilt to the exact dimensions of the original cottage. Birchwood offers parking and dock space plus trash disposal and drinking water for the Black Island owners. The island house has a three-bedroom septic system and water is piped from the lake; drinking water is brought over. A washer and dryer are also included. Although electric power currently exists via easement, the easement expires with the sale of the property. Buyers may want to explore solar and generator options. The cottage comes furnished and includes an older pontoon boat with 60 hp motor, 16' skiff w/ 25 hp motor, two kayaks and a dock. Island living at its best with permanent mainland access.

1 Black Island & 93 Birchwood Lane, Winthrop

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: Rizzo Mattson.

260 Narrows Pond Rd, Winthrop
$315,000
2 Beds ⋅ 1 Baths ⋅ 1669084 MLS
Quality-built and low maintenance, this charming two-bedroom, one-bath home offers comfortable one-level living with thoughtful features throughout. Enjoy radiant heat, a heated one-car garage, and an open-concept kitchen, dining, and living area highlighted by vaulted ceilings that create a bright and spacious feel. The primary bedroom features a walk-in closet, while the private backyard and deck provide the perfect setting for relaxing or entertaining. Additional highlights include vinyl siding, a paved driveway, and easy-care living in a home designed for comfort and convenience.

260 Narrows Pond Rd, Winthrop

Listing courtesy of Brookewood Realty.

Selling Office: Sprague & Curtis Real Estate.

392 Memorial Dr, Winthrop
$325,000
1 Beds ⋅ 1 Baths ⋅ 1676624 MLS
Want to extend your summer a little longer? This cottage on Maranacook Lake may be the perfect fit for you. Charming features, efficient layout, and a stunning lake with a sandy beach area. Swimming, fishing, sunsets, and rest & relaxation are calling! The living area showcases hardwood flooring, exposed wooden ceiling beams, cozy furnishings, and large window frames for a scenic waterfront view and natural light throughout. A combination living room and bedroom with propane stove and eat-in kitchen with cooktop and ample cupboards making the compact space highly functional. Full bathroom with walk-in shower and a sunroom that could be used for additional sleeping space. Together, the rooms create a cohesive rustic-cottage ambiance, ideal for an intimate lakeside retreat on Maranacook Lake. Stone patio perfect for outdoor dining, granite steps to the water, stone wall, log siding, metal roof, aluminum dock, Rinnai on demand water heater, insulated attic, and basement / storage area with poured concrete. This home away from home has so much to offer, so don't miss out!

392 Memorial Dr, Winthrop

Listing courtesy of The Dot Fernald Team, Inc..

Selling Office: Hoang Realty.

714 Mount Pisgah Rd, Winthrop
$335,000
2 Beds ⋅ 2 Baths ⋅ 1671550 MLS
Love spending time outdoors? This charming Winthrop ranch offers everything you've been looking for! Set on a beautiful 4.3-acre lot, this well-maintained 2-bedroom, 2-bath home features scenic nature trails and direct access to snowmobile trails, with opportunities for cross-country skiing and snowshoeing during the winter months. Enjoy peaceful mornings with a cup of coffee on the deck just off the living room while listening to the birds, or spend your evenings relaxing on the pergola-covered terrace surrounded by beautifully landscaped gardens. It's the perfect setting for outdoor dining, entertaining friends, or simply unwinding in nature. Inside, the spacious living room features hardwood floors, generous closet space, and lovely views of the surrounding property. The updated kitchen is a cook's dream, complete with a farmhouse sink, granite countertops, and stainless steel appliances. A bright and versatile dining room with a sitting area offers built-in shelving, abundant natural light, and gleaming oak floors. The front-to-back primary bedroom provides double closets and a heat pump, allowing you to maintain year-round comfort. The recently renovated lower level expands the living space with a guest room, full bath, and a convenient summer kitchen. Sliding patio doors open directly to the pergola-covered terrace and backyard, creating an ideal indoor-outdoor lifestyle. Move-in ready and available for immediate occupancy, this exceptional property is conveniently located midway between Augusta and Lewiston/Auburn, offering the perfect balance of privacy and accessibility. Come experience all this special home has to offer--and make it yours! Front door entry area coat rack and small antique shelf in lower kitchen. Lower kitchen gas stove to be replaced with similar aged gas stove.

714 Mount Pisgah Rd, Winthrop

Listing courtesy of Homestead Realty.

Selling Office: Coldwell Banker Team Real Estate.

161 Pamela Dr, Winthrop
$315,000
3 Beds ⋅ 3 Baths ⋅ 1664559 MLS
Welcome to this charming Cape Cod-style home in a sought-after neighborhood in Winthrop -- offering the perfect blend of comfort, convenience, and classic New England charm. Ideally located just minutes from local schools, the public library, shopping, restaurants, the boat landing, and the public beach on beautiful Maranacook Lake, this home puts recreation and everyday essentials right at your fingertips. Set on over a half-acre lot, the property features a spacious 2-car garage, ample yard space for entertaining or relaxing, and a welcoming setting in one of Winthrop's desirable in-town neighborhoods. Inside, the main level offers a warm and functional layout with a kitchen, dining room, living room, full bathroom, and convenient first-floor bedroom. Upstairs, you'll find two additional bedrooms and a half bath, providing comfortable space for family or guests. The partially finished basement expands the home's versatility with a cozy family room, kitchenette, full bathroom, and a bonus room perfect for a home office, guest room, hobby space, or activity room. Whether you're looking for extra living space, multi-generational possibilities, or room to work from home, this home offers flexibility to fit your lifestyle.

161 Pamela Dr, Winthrop

Listing courtesy of LAER.

Selling Office: Hearth & Key Realty.

27 Ruby Ridge Rd, Winthrop
$449,999
3 Beds ⋅ 3 Baths ⋅ 1674528 MLS
Welcome to this private Maine retreat offering the perfect combination of peaceful country living and convenience. Situated on 2.5 acres, this well-maintained property features a private backyard with a patio area, making it the perfect place to relax, entertain, or enjoy the surrounding wildlife. Inside, you'll find the ease of one-floor living with a bright, open floor plan designed for comfortable everyday living. The home offers 4 bedrooms and 3 full baths, including a spacious finished primary suite in the lower level that provides a private escape for homeowners or guests. The beautifully appointed kitchen features granite countertops and flows seamlessly into the main living areas. Step outside to the inviting outdoor entertainment space, perfect for evenings with family and friends. Surrounded by nature yet just minutes from town and local amenities, this property offers the best of both worlds--privacy, space, and convenience. If you've been searching for a move-in ready home with room to enjoy both indoors and out, this one is a must see.

27 Ruby Ridge Rd, Winthrop

Listing courtesy of Coldwell Banker Realty.

Selling Office: Fontaine Family-The Real Estate Leader.

57 Metcalf Rd, Winthrop
$445,000
4 Beds ⋅ 4 Baths ⋅ 1672559 MLS
Welcome home to this charming Cape Cod nestled on a beautiful 0.60-acre lot in the heart of Winthrop. This lovingly maintained home has 3-4 bedrooms and 3.5 baths, offering 1,644 square feet of warm, inviting living space with classic New England character throughout. Step inside to a bright first floor featuring a spacious living room, a comfortable dining area, and a beautiful kitchen boasting stylish cabinetry, Corian countertops, and tile flooring -- all warmed by a cozy wood stove perfect for enjoying Maine's four distinct seasons. Gorgeous wood floors flow through much of the main level, with tile flooring continuing into the bathrooms and hallway, while updated Anderson and Pella windows fill the home with natural light and add year-round energy efficiency. The first floor also hosts a private primary suite complete with a jetted tub and separate steam shower for the ultimate in relaxation, along with a convenient half bath/laundry combo. Upstairs, you'll find two additional bedrooms and a full bath, ideal for family, guests, or a home office setup. Efficient heat pump technology delivers both heating and cooling, complemented by baseboard hot water heat and multi-fuel flexibility for year-round comfort, along with an automatic generator transfer switch for the home and garage provides such important peace of mind. Step outside to a large deck, perfect for morning coffee or evening sunsets. This deck connects to a heated 2-car 20x24 detached garage, which is topped by a versatile 480-square-foot bonus room complete with its own heat pump combo for heating and cooling--ideal for guests, a studio, or additional living space. The backyard offers room to garden, play, or simply relax in a peaceful, rural setting. Located just minutes from downtown Winthrop, area schools, shopping, dining, and Maine's beautiful lakes region, this home offers the perfect blend of small-town charm and everyday convenience. Don't miss your chance to make this Cape home yours today.

57 Metcalf Rd, Winthrop

Listing courtesy of Hoang Realty.

Selling Office: Home At Last Realty.

M1, L28 Mt Pisgah Rd, Winthrop
$80,000
1657080 MLS
Spacious 20 acre surveyed lot in Winthrop with level building area and driveway established. Rolling topography with small hill creates an excellent view. Potential gravel income and lots of opportunities.

M1, L28 Mt Pisgah Rd, Winthrop

Listing courtesy of Homestead Realty.

Selling Office: Meservier & Associates.

565 Old Lewiston Rd, Winthrop
$265,000
3 Beds ⋅ 1 Baths ⋅ 1669618 MLS
Great location! You have to see this 3 bedroom 1 bath split level ranch! The property is situated on a large level lot with close access to Rte. 202 in Winthrop. Commuting to Augusta or L/A is quick and easy. The main level of the house is open and inviting. Plenty of room to entertain on the back deck. The livingroom has a pellet stove insert to keep you warm in the winter. The basement opportunities are endless. With walkout access, it would make a nice entertainment room, with enough space to add a fourth bedroom, an extra bathroom or home office. The detached 2 car garage has high ceilings, and a finished space on the second floor. Be sure to check this one out.

565 Old Lewiston Rd, Winthrop

Listing courtesy of Meservier & Associates.

Selling Office: Better Homes & Gardens Real Estate/The Masiello Group.

28 Beechwood Dr, Winthrop
$347,500
4 Beds ⋅ 1 Baths ⋅ 1662173 MLS
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 move-in ready space that feels both fresh and inviting. Step outside to the patio fire pit area, perfect for relaxing summer evenings with family and friends. With broad financing appeal, this property is an excellent fit for all loan types and a wonderful opportunity to enjoy neighborhood living with water access at an affordable price point. This Certified Pre-Owned Home has been thoroughly inspected by a professional home inspector, and you'll receive the detailed building inspection at no cost - no surprises here! Plus, enjoy peace of mind with a 12-month Home Warranty and a 12-month Satisfaction Guarantee: Love this home, or we will sell it for you for free! Conditions Apply. A pre-listing title search was also performed, and clear title was confirmed. This property is ready to go!

28 Beechwood Dr, Winthrop

Listing courtesy of Your Home Sold Guaranteed Realty.

Selling Office: Listings Direct.

90 Bearce Rd, Winthrop
$45,000
1441955 MLS
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.

90 Bearce Rd, Winthrop

Listing courtesy of Homestead Realty.

Selling Office: Elevate Maine Realty.

132 N Shore Ln, Winthrop
$317,000
2 Beds ⋅ 2 Baths ⋅ 1668484 MLS
Welcome to 132 North Shore Lane in Winthrop, Maine, a beautifully renovated year-round home located near the shores of Cobbosseecontee Lake, one of Maine's most desirable freshwater lakes. Thoughtfully updated throughout, this move-in-ready property combines modern improvements with convenient access to outdoor recreation and local amenities. Recent renovations include new siding, all-new flooring, updated kitchen cabinetry, countertops, and lighting, renovated bathroom(s), and a newly constructed retaining wall that created two dedicated parking spaces on the property. Inside, bright and comfortable living spaces are complemented by seasonal views of Cobbosseecontee Lake from the kitchen and living room. The home's layout is designed for easy everyday living while embracing the natural beauty of its surroundings. Just steps away, deeded right-of-way access to Cobbosseecontee Lake provides convenient enjoyment of boating, fishing, kayaking, paddleboarding, swimming, and memorable sunrises and sunsets along the water's edge. Conveniently situated minutes from the Augusta Country Club, local marinas, restaurants, shopping, and other area amenities, the location supports both year-round living and seasonal enjoyment. Whether you're seeking a primary residence, vacation property, or investment in the Cobbosseecontee Lake region, 132 North Shore Lane represents a rare chance to own a fully renovated home with lake access in one of Central Maine's most sought-after waterfront communities. Experience the lifestyle that makes Cobbosseecontee Lake a destination for recreation, relaxation, and four-season enjoyment.

132 N Shore Ln, Winthrop

Listing courtesy of Salt Real Estate Co.

Selling Office: LAER.

63 Upper Narrows, Winthrop
$317,000
2 Beds ⋅ 2 Baths ⋅ 1669383 MLS
Log cabin style living meets modern function in this 2 bed, 2 bath Winthrop home set in the heart of the lakes. Cathedral ceilings and authentic log construction give the main living area warmth and character, with an efficient heat pump for year round comfort. The updated kitchen delivers on both style and use, with quartz counters and a center island featuring a dedicated prep sink. Down the hall is a side deck, bedroom, and full bathroom with laundry. Upstairs, a loft-style primary bedroom offers a private retreat with full en-suite bath, double vanity, and a balcony overlooking the property. Outdoor space is a standout: a wraparound deck and a fully fenced backyard framed by mature landscaping with established lilies and hostas. Move-in ready and thoughtfully maintained, this home blends rustic charm with everyday ease in one of Central Maine's most desirable lake communities.

63 Upper Narrows, Winthrop

Listing courtesy of Portside Real Estate Group.

Selling Office: Signature Homes Real Estate Group, LLC.

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