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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.

457 Old Lewiston Rd, Winthrop
$999,000
1646929 MLS
Here is an excellent investment opportunity, a large multi-use building that has many potential uses and a nice lot size of 5.3 acres with good road frontage, ample parking and offers good expansion opportunities! Nice area, quiet and somewhat rural, close to both Augusta and Lewiston, nice grounds and garden areas. The building has over 13,000 SF of area,(with much more available space in the basement) many individual rooms and baths, a nice entry/reception area, nurses stations and multiple offices are spread around the building, a very spacious and sunny two room dining area with lots of seating capacity and 2 fire places, there is also a beauty salon. The building is very spacious with 2 levels and an elevator, (the elevator also goes down to the basement) BBHW heat along with some heat pumps, and vinyl windows. The full basement offers plenty of usable space with a laundry, kitchen, various staff offices, storage, etc., a propane generator system, a sprinkler system, city water and sewer, ramps on the outside, plenty of parking with about 60 or so spaces, (possibly more) there are 2 parking areas - one in front of the building and the other out back. A section of the building was flooded and has been remediated. Formally a 52-bed assisted living and rehabilitation center. A good candidate for redevelopment, for an apartment building, a living facility, etc., and more. Much good potential here. Some seller bridge financing may be available to qualified buyers. Call for more info.

457 Old Lewiston Rd, Winthrop

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

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.

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.

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.

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.

48 Pine Knoll Rd, Winthrop
$677,500
3 Beds ⋅ 3 Baths ⋅ 1666606 MLS
Set on 22 private acres in Winthrop, this extraordinary early 19th century estate offers a rare convergence of craftsmanship, natural beauty, and luxury. Sweeping lawns, mature woodlands, and curated gardens provide exceptional privacy while remaining convenient to the lakes region and Central Maine. Here you will find stunning lawns framed by handcrafted fieldstone walls, perennial gardens offering vibrant color, and hardwoods casting shade. A private pond mirrors the sky in stillness, while a climbing hydrangea envelops the wall beside an arbor-covered patio, creating a focal point where beauty meets the landscape. Transformed since 2019, the residence honors comfort and timeless design. Pumpkin pine floors lend warmth and New England character, while a wood stove provides ambiance alongside central heating creating spaces for quiet evenings and lively gatherings. A masterfully designed kitchen anchors daily living. Soapstone countertops, custom cabinetry with built-in refrigerator, Miele appliances, and a pantry combine functionality with sophistication. The first-floor primary suite offers single-level living with laundry hookup, a spacious bathroom, and access to a conservatory-style sunroom. A Wolf espresso station adds indulgence each morning just outside the door and a first floor powder room adds convenience. The second floor features new spray foam insulation, Douglas fir collar ties, vaulted ceilings, two bedrooms, and a full bath. The heated three-bay, two-story garage features insulated nickel-board walls, expansive storage, and walk-up access to a cupola with panoramic 360-degree views. A single-bay garage and two sheds offer flexibility for collectors, hobbyists, and enthusiasts. Rarely does a property combine significant acreage, extensive improvements, exceptional privacy, and enduring character. This is more than a home, it is a legacy estate where refined living and Maine's landscape exist in perfect harmony.

48 Pine Knoll Rd, Winthrop

Listing courtesy of Pouliot Real Estate. 207-248-6044

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

307 Rte 41, Winthrop
$605,000
5 Beds ⋅ 3 Baths ⋅ 1655117 MLS
This meticulously maintained farmhouse has been tastefully updated to preserve it's historic charm, all while adding modern improvements for ease and peace of mind. Built in 1784, the home boasts over 3700 square feet and three stories of living space, and features a custom kitchen with quartz countertops and a Queen Ann stove, a spacious first floor primary suite, and a gorgeous sunroom with cathedral ceilings overlooking the back yard. Multiple heating and cooling sources throughout the home provide versatility, comfort and efficiency. New Owens Corning TruDefinition Duration AR Designer Shingles installed in 2024. New Heat Pump hot water heater in 2024. The on-demand generator is on standby for any power outage. The property includes over 18 acres of fields and woods, and stunning sunrise views- perfect for that morning cup of coffee on the back deck!

307 Rte 41, Winthrop

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

Selling Office: Amnet Realty.

87 Memorial Dr, Winthrop
$600,000
4 Beds ⋅ 3 Baths ⋅ 1665682 MLS
Set on 2.57± private acres with seasonal views of beautiful Maranacook Lake, this distinguished Colonial offers an exceptional blend of classic New England character, modern comfort, and tremendous location. Just a short distance to the town beach, public boat launch, and downtown Winthrop's charming collection of local shops and restaurants, the setting offers the perfect balance of privacy and convenience. Spanning 2,512 square feet, the home features four bedrooms, three baths, and well designed living spaces enhanced by gleaming pre-finished wood floors with tile floors in the mudroom and bathrooms for added durability. The heart of the home is inviting and ideal for both everyday living and entertaining. Upstairs, the spacious primary suite offers a peaceful retreat with partial lake views, a large walk-in closet, and private en suite bath. Two additional bedrooms share the second floor, along with two storage closets flanking the hallway that leads to one of the home's most versatile spaces- an expansive bonus room above the garage. With its own separate access from the rear of the garage, this impressive space lends itself beautifully to a guest suite, studio, home office, fitness room, or recreation area. The heated three-car garage features a finished floor, creating a polished and functional environment for vehicles, hobbies, projects, or storage. In the basement, you'll find a great work space and custom gun room that provides secure specialty storage and could easily transition into a wine cellar for collectors and entertainers alike. Outside, the grounds offer room to roam, garden, and enjoy the changing Maine seasons, while a storage shed keeps outdoor equipment, garden tools, and seasonal furnishings neatly tucked away. Offering the charm of lake-area living, the convenience of short distance to downtown amenities, and the comfort of a designed home, this distinctive Winthrop property presents a rare opportunity to enjoy the very best of Maine.

87 Memorial Dr, Winthrop

Listing courtesy of Pouliot Real Estate. 207-248-6044

Selling Office: RE/MAX Shoreline.

956 Memorial Dr, Winthrop
$600,000
2 Beds ⋅ 2 Baths ⋅ 1657129 MLS
Spectacular lake views from this beautifully maintained 2 bedroom Maranacook Lakefront Home with 100' of prime waterfront with dock. First floor has a great kitchen with hardwood floors, fully applianced and stone counters. There is a cathedral 1/2 bath with skylight, STUNNING lakeside dining room with glass galore and two skylights and exposed beams with a door to the massive waterside deck, and a gas heating stove. There is also a living room area with wood floors and a glass slider to the 10x30 waterside deck, and a laundry room with sink and wine fridge. The second floor has two bedrooms with wood floors and a full bath. The lower level is finished with family room and wood stove and is full daylight walkout which goes to a beautiful patio/deck. There is also an efficient rinnai heater and generator hook-up. Work shop, paved drive, beautiful landscaping and sweeping views up and down the lake. An incredible place to call home.

956 Memorial Dr, Winthrop

Listing courtesy of LAER.

Selling Office: LAER.

11 Old Western Ave, Winthrop
$557,500
4 Beds ⋅ 3 Baths ⋅ 1664080 MLS
Buy with confidence-this property has been recently appraised, providing verified value and added peace of mind! Set on a beautiful 2.28-acre lot in Winthrop, this extensively renovated 1840s home blends warmth and character with meaningful upgrades. Featuring just under 3,000 square feet, the home offers room to spread out with multiple living spaces, a dedicated office space, and charming original details. The spacious kitchen is finished with quartz countertops, a propane cooktop and wall oven combo, and newer windows, while the primary suite offers a true retreat with a walk-through closet, tiled shower, standalone soaking tub, and private toilet room. With 2.5 bathrooms, dedicated office space, multiple living areas, and a covered breezeway connecting the garage to the home, there is room for both everyday living and entertaining. Outside, enjoy the backyard oasis complete with an above-ground pool, elevated back lawn, hot tub, and a generous rear deck perfect for gathering and relaxing. Additional improvements include fiber cement siding, replaced exterior doors, updated supports beneath the crawl space, city water and sewer, and a roof installed in 2012. Heating includes a propane Rinnai heater, wood stove, hot water baseboard heat, and three heat pumps throughout the home, offering comfort and flexibility year-round. Conveniently located while still offering privacy and space, this one-of-a-kind property combines the character of an older home with the updates buyers are looking for today.

11 Old Western Ave, Winthrop

Listing courtesy of LAER.

Selling Office: EXP Realty.

2 Partridge Run Dr, Winthrop
$525,000
3 Beds ⋅ 3 Baths ⋅ 1657801 MLS
This exceptional, energy-efficient Raised Ranch built in 2019 and set on 2.18 private acres offers a refined blend of modern elegance, comfort, and sustainability. Thoughtfully designed, this 3-bedroom, 2.5-bath residence features a serene primary suite complete with a full bath and a spacious walk-in closet. The heart of the home is the stunning open-concept living space, where the kitchen, dining, and living areas seamlessly connect beneath vaulted ceilings. Bathed in natural light, this inviting space is enhanced by beautiful tile and hardwood flooring and is perfectly suited for both intimate gatherings and effortless entertaining. The lower level expands the home's versatility with a well finished bonus room ideal for a private office, fitness studio, or guest retreat, complemented by an additional bath and direct access to the insulated two-car garage. Outdoors, a generous deck extends from the dining area, offering tranquil views of the surrounding landscape and a charming fire pit, an ideal setting for elevated outdoor living and entertaining under the stars. Designed with efficiency and innovation in mind, the home is equipped with two heat pumps, a nice propane hot water baseboard heating system, and a solar photovoltaic system generating an average of 5,700 kWh annually, delivering remarkable energy savings without compromising comfort. With high-end appliances, thoughtful upgrades, and meticulous attention to detail throughout, this is a rare opportunity to experience modern luxury living in a peaceful, private setting.

2 Partridge Run Dr, Winthrop

Listing courtesy of NextHome Northern Lights Realty. Office@NextHomeNLR.com

Selling Office: Your Home Sold Guaranteed Realty.

64 Annabessacook Dr, Winthrop
$525,000
3 Beds ⋅ 2 Baths ⋅ 1659788 MLS
This is the kind of property people wait for--and rarely find. Set on 7.7 private acres just minutes from downtown Winthrop, this property offers space, flexibility, and access to Annabessacook Lake without paying waterfront taxes. Keep your boat on the lake, head out for a last-minute sunset cruise, and come back to your own private setting. No hauling, no hassle, no waterfront tax bill. The large barn adds another layer most homes simply do not offer--ideal for storing recreational equipment, projects, gatherings, or creating additional usable space beyond the home itself. Inside, the home offers multiple living areas, including a bright sitting area off the kitchen, an open-concept living room with pellet stove insert, and a finished lower level currently used as a family room and gym. Recent improvements include a remodeled bathroom, updated sitting area, finished basement space, kitchen shelving upgrades, tree removal to improve safety and usable yard space, and a recently replaced roof. Major infrastructure updates are also being completed by the seller, including a new septic system and water treatment improvements, giving buyers confidence in some of the property's most important long-term systems. Outside is where this property truly stands apart--privacy, usable acreage, hot tub, and lake access combine to create a lifestyle that is increasingly difficult to find in this area. If you've been looking for land, storage, flexibility, and access to the water without the cost of waterfront ownership, this is a property worth seeing in person.

64 Annabessacook Dr, Winthrop

Listing courtesy of NextHome Northern Lights Realty. Office@NextHomeNLR.com

Selling Office: Tim Dunham Realty.

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.

8 Horseshoe Is, Winthrop
$515,000
2 Beds ⋅ 1 Baths ⋅ 1663631 MLS
There simply is no better escape than this incredibly rare 9 acres on Horseshoe island in the middle of Cobbosseecontee. Enjoy the ability to get away from the day to day demands and unwind just 20 minutes and less from major amenities by boat and car. The residence has been meticulously cared for and in the same family since it's construction in the 90's and offers two solar panels that aid in notably comfortable off-grid seasonal living. As it stands, the residence boasts privacy from the water, with the strategic evergreen growth. Come take a look today for yourself. This property as a whole is a rarity on the market - as these Horseshoe Island residences are typically generationally inherited on one of the most desirable bodies of water in central Maine.

8 Horseshoe Is, Winthrop

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: Rizzo Mattson.

246 Carlton Pond Rd, Winthrop
$515,000
2 Beds ⋅ 2 Baths ⋅ 1662129 MLS
Discover effortless single-level living in this beautifully designed contemporary ranch set on 2 private acres in a highly desirable location. Thoughtfully crafted for comfort and convenience, this home features 2 spacious bedrooms, 2 full bathrooms, and an inviting open-concept layout filled with natural light. Additional space used as an office could be another bedroom as the septic design is for 3 bedrooms. The well-appointed kitchen flows seamlessly into the dining and living areas, creating the perfect space for everyday living and entertaining. A dedicated laundry room adds practicality, while the heated 2+ car garage offers abundant space for vehicles, storage, hobbies, or workshop needs year-round. Relax outside on the back patio to enjoy the peace & quiet from the hot tub while you watch the stars. Enjoy the peace and privacy of country-style living without sacrificing convenience. Ideally located just minutes from the town beach, golf course, shopping, dining, a quick drive to the interstate exit, and other local amenities, this property offers the perfect balance of recreation and accessibility!

246 Carlton Pond Rd, Winthrop

Listing courtesy of Meservier & Associates.

Selling Office: Homestead Realty.

260 Memorial Dr, Winthrop
$482,000
2 Beds ⋅ 1 Baths ⋅ 1668870 MLS
Escape to this charming waterfront cottage on beautiful Maranacook Lake, nestled in an exceptionally private peninsula setting with breathtaking sunset views. Perched right at the water's edge, this rare property offers the quintessential Maine lakefront experience. Relax and unwind on the covered front and back porches, both perfectly positioned to take in stunning lake vistas and cooling summer breezes. Step inside and appreciate the timeless character of this cottage, originally built in the 1920s, featuring a cozy living room and charming galley-style kitchen that evoke a simpler, more peaceful era. Fall asleep to the haunting call of loons and the gentle sound of waves lapping along the shore. Spend your days swimming from your doorstep, boating across Maranacook Lake's 1,673 acres, or exploring its 22 miles of scenic shoreline and countless hidden coves. Seasonal public water and sewer services provide added convenience and peace of mind. Ideally located in Central Maine, the property offers easy access to Augusta, the mountains, the Maine coast, and Portland International Jetport. This is a rare opportunity to own a truly special waterfront retreat and create lasting memories on one of Maine's most beloved lakes. Waterfront was measured on town website using Parcel Viewer & GIS Web Map.

260 Memorial Dr, Winthrop

Listing courtesy of Homestead Realty.

Selling Office: Homestead Realty.

100 Rte 133, Winthrop
$480,000
4 Baths ⋅ 1655273 MLS
4-Unit property in Winthrop seeks new owner! Excellent investment or owner-occupied opportunity in the desirable Town of Winthrop within minutes to Maranacook Lake public beach and town amenities. Great location close to Auburn, Lewiston, Augusta and only an hour to Portland. Property has a brand new roof and new vinyl siding. Solid rental history, Unit A is a first floor unit with one bedroom and a large, enclosed sun porch. This unit has access to the basement which has washer/dryer hook-ups. Unit B is a third floor unit with 1 bedroom and 1 bathroom. This unit was entirely renovated approximately 6 years ago and has a new kitchen and bathroom. Unit C is the second floor unit with 2 bedrooms, 1 bathroom and a good sized living room and kitchen. Unit D is a two-level unit, this unit has a front entry and rear entry with a large hallway for storage space, its own first floor laundry, a large living room and sun porch along with two bedrooms and a bathroom upstairs. Home is fully rented and notice is required prior to showings.

100 Rte 133, Winthrop

Listing courtesy of Maine Real Estate Co.

Selling Office: Ferraro Realty LLC.

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.

24 Winthrop Center Rd, Winthrop
$470,100
3 Beds ⋅ 3 Baths ⋅ 1657143 MLS
Enjoy the best of Central Maine's recreational lifestyle from this conveniently located Colonial, with at least 10 different lakes and ponds situated within a 10-minute drive. Outdoor enthusiasts will appreciate direct access to nearby snowmobile trails and the expansive two-acre lot featuring an open, flat lawn and rear deck. Positioned just off well-maintained Route 202, this property offers a straightforward commute to Augusta and I-95, providing a rural feel with efficient access to city amenities and services at a great value. The home features a functional layout including a kitchen with granite countertops, a center island, and a breakfast nook that opens into a living room with built-in cabinetry. The first floor also provides a formal dining room, a dedicated office, and the practical additions of a large mudroom and separate laundry room. Upstairs, the primary suite includes a walk-in closet and a private bathroom with a jetted tub, alongside two additional bedrooms with ample natural light. A standout feature of the property is the oversized three-car heated and insulated garage, which includes a substantial storage loft above offering potential for a workshop or future expansion. This property offers a versatile combination of living space, significant storage, and proximity to the region's most popular lakes and trail systems.

24 Winthrop Center Rd, Winthrop

Listing courtesy of Androvise Realty.

Selling Office: Allied Real Estate.

104 Memorial Dr, Winthrop
$460,000
3 Beds ⋅ 2 Baths ⋅ 1647275 MLS
Lakefront -waterfront- home facing west on the shores of Maranacook Lake. A great sunset location close to town with public water and sewer. This Cape has easy access and is waiting for your personal touches. The yard is a nice gentle slope to the water. Room for gardening and boats. Shorefront is a mix of some gravel and some sand. Beautiful swimming in summertime. Some of the best ice skating and ice fishing in winter. This is a Deep water location and great for all types of boats. The South Basin of the Lake is managed by inland fish and wildlife for Trout Species: Brown trout, Landlocked Salmon, Brook Trout and Lake Trout-Togue and smelt. Tremendous ice fishing within steps onto the ice in winter. The Winthrop Lakes Region is known for being the playground of Central Maine. Town is a few blocks from the home or a boat ride down the lake to the public boat ramp. A historic stone public library is close by. Relocate to your waterfront home in time for summer. This home is dated. Bring your vision. Great potential for your waterfront getaway.

104 Memorial Dr, Winthrop

Listing courtesy of Keller Williams Realty.

Selling Office: Lash Realty Group.

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.

23 Little Cobbossee Ave, Winthrop
$446,500
2 Beds ⋅ 2 Baths ⋅ 1660636 MLS
Set on 1.5 private acres with 200+ feet of owned shoreline on Little Cobbosseecontee Lake, this fully updated year-round home offers a rare blend of tranquility and convenience. Located on a quiet, paved, town-maintained dead-end road--uncommon for Maine lake properties--this home provides easy, low-maintenance access in every season. Little Cobbossee Avenue was newly paved in April 2026. Extensive upgrades make this home truly move-in ready. Recent improvements include a new metal roof on both the home and garage, new dock, and significant tree removal. The home has been modernized with closed-cell spray foam insulation, updated plumbing throughout, renovated bathrooms, new vanities, and a new water heater. The primary bedroom was remodeled with a new sliding glass door, and comfort is enhanced with a Mitsubishi heat pump system and efficient Rinnai heaters. Additional updates include new Maytag washer/dryer, Whirlpool refrigerator and dishwasher, and the removal of the garbage disposal for optimal septic performance. In 2026, the home received new some Pella windows, upgraded trim and baseboards, faux stone skirting, full interior paint, plus a freshly painted porch and stained deck. Serviced by public water and private septic, the property is just steps from a marina, public boat launch, bait shop, and local favorites restaurants and Augusta Country Club is less than a mile away. Located under 15 minutes from Augusta and Hallowell--''The Little Easy''--you'll enjoy top dining, live music, and nightlife nearby. Known for calm waters and excellent bass fishing, the lake is largely protected by the Kennebec Land Trust, preserving its natural beauty. Ideal as a year-round home, getaway, or Airbnb, this property feels like a private retreat--yet is minutes from everything.

23 Little Cobbossee Ave, Winthrop

Listing courtesy of Fontaine Family-The Real Estate Leader.

Selling Office: Your Home Sold Guaranteed Realty.

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.

43 Holmes Rd, Winthrop
$430,000
3 Beds ⋅ 2 Baths ⋅ 1662721 MLS
Discover the perfect blend of rustic charm and year-round comfort in this inviting 3-bedroom, 2-bath home, ideally located in Winthrop just minutes from Lake Annabessacook, Maranacook Lake, and Upper and Lower Narrows Ponds. Outdoor enthusiasts will love the private 1.9-acre lot featuring a serene terrace overlooking beautifully landscaped grounds, raised-bed gardens, and fruit-bearing bushes. Enjoy peaceful mornings with coffee on the covered front porch while soaking in the sunshine and natural surroundings. Inside, the home offers a spacious family room perfect for entertaining and gatherings. The cozy kitchen features a breakfast area and flows seamlessly into the open dining room, creating an ideal space for everyday living and family meals. A large living room with a propane fireplace provides instant warmth and comfort during the winter months. The oversized primary bedroom includes double closets and a private en suite full bath. With laundry conveniently located on the main level, this home offers the ease and convenience of true one-level living. Take the worry out with the whole house generator and attached two car garage and workshop area. Lovingly maintained you can move in and start living.

43 Holmes Rd, Winthrop

Listing courtesy of Homestead Realty.

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

38 Pamela Dr, Winthrop
$387,500
4 Beds ⋅ 2 Baths ⋅ 1662225 MLS
Step into a home designed for the way you live today. Set on 1.1 private acres and offering over 2,200 square feet of versatile living space, this move-in ready 4-bedroom, 2 full bath home combines comfort, functionality, and flexibility. A practical mudroom and breezeway welcome you inside, where durable vinyl plank flooring flows through the main living areas and cozy carpeted bedrooms create inviting retreats. Thoughtfully designed with multi-zone heating, second-floor laundry, generous under-eave storage, and an attached 2-car garage, the layout easily supports both busy daily routines and relaxed living. The soundproofed basement offers endless possibilities for entertaining, hobbies, creative space, remote work, or additional living area. Outside, enjoy the privacy and freedom of a spacious 1.1-acre lot with room to garden, play, entertain, or simply unwind. This home is just minutes to public beaches, shopping, and everyday conveniences, offering the perfect balance of privacy and accessibility. A home that truly delivers the space and flexibility to fit a variety of lifestyles for years to come.

38 Pamela Dr, Winthrop

Listing courtesy of Fontaine Family-The Real Estate Leader.

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.

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