Winterport Real Estate

Welcome to Winterport, a charming town nestled in the heart of Waldo County, Maine. Known for its picturesque landscapes and friendly community, Winterport offers a peaceful retreat for those looking to escape the hustle and bustle of city life.

With a rich history dating back to the 18th century, Winterport boasts a quaint downtown area lined with historic buildings and local shops. Residents enjoy a close-knit community where neighbors quickly become friends, creating a warm and welcoming atmosphere for all who call Winterport home.

Nature lovers will appreciate the abundance of outdoor activities available in Winterport, from hiking and fishing to snowshoeing and cross-country skiing in the winter months. The town's proximity to the Penobscot River also provides opportunities for boating and kayaking, allowing residents to explore the natural beauty of the region.

For those seeking a slower pace of life without sacrificing modern conveniences, Winterport offers the perfect balance of rural charm and urban amenities. With easy access to nearby cities like Bangor and Belfast, residents can enjoy the best of both worlds – small-town living with big-city convenience.

Come discover the magic of Winterport and find your perfect home in this idyllic Maine town.

Newest Listings in Winterport

$284,900

3 Beds ⋅ 2 Baths

Step into the timeless charm of this beautiful 1880s New England home, where historic character meets modern comfort. Featuring 3 bedrooms and 2 full baths, this inviting property showcases hardwood floors, stunning original details, and classic gingerbread trim that enhances the home's picturesque exterior. A true local celebrity, this iconic home was featured on the cover of Downeast magazine, a testament to its exceptional beauty and enduring New England charm. The completely renovated upper level blends seamlessly with the home's historic appeal, while numerous updates throughout provide peace of mind and everyday convenience. Outside, you'll find beautiful gardens that create a picturesque setting, along with a classic barn offering endless possibilities for storage, hobbies, or a workshop. Every corner of this property reflects pride of ownership. If you've been searching for a home with rich history, distinctive architectural details, modern updates, and a story all its own, this one-of-a-kind Winterport gem is ready to welcome its next chapter.

49 Lebanon Rd, Winterport

Listing courtesy of Signature Group Real Estate.

$575,000

Opportunity has a way of finding the right location, and for more than two decades this landmark commercial property, home to Winterport Winery, has been a place where people gathered to enjoy handcrafted beverages, dining, celebrations, and community events. Today, it stands ready for its next chapter. The spacious commercial building provides exceptional flexibility for a wide variety of business ventures. Expansive interior spaces with established hospitality areas, production space, retail opportunities, outdoor deck seating, and ample room for gatherings create endless possibilities for entrepreneurs, investors, or business owners looking to bring a new vision to life. Whether your plans include continuing its celebrated legacy or re-imagining the property for restaurant, event venue, brewery, winery, distillery, retail, specialty food production, professional offices, or other commercial use, this property is ready to inspire. Buyers are encouraged to verify any intended use with local municipal officials. Located in the heart of Winterport with convenient access to Bangor, Belfast, and surrounding Midcoast communities, the property enjoys excellent visibility and has long served as a destination for both residents and visitors traveling throughout the region. The existing wine and distillery production equipment is not included in the listing price but is available for separate purchase, providing the opportunity to continue beverage production while allowing buyers the flexibility to tailor the investment to their own business goals. But restaurant kitchen equipment will convey with the sale of the property. Whether you're expanding an existing business, launching a new venture, or investing in one of Midcoast Maine's recognizable commercial properties, this exceptional opportunity offers flexibility, visibility, and foundation to bring your vision to life.

279 S Main St, Winterport

Listing courtesy of RE/MAX JARET & COHN. belfast@jaretcohn.com

$119,000

Discover 35.48 acres of opportunity at 0 Harmony Lane in Winterport! Tucked away off Stream Road, this expansive parcel offers privacy, space, and endless potential for those looking to create their own Maine retreat. Whether you envision a secluded homesite, recreational getaway, hunting property, or off-grid escape, this wooded acreage provides a beautiful natural setting to bring your ideas to life. Enjoy the peace and quiet of rural Maine while still being within reach of Winterport, Bangor, and surrounding communities. With over 35 acres to explore, the possibilities are yours to imagine. Come walk the land and see what makes this property so special!

94 Harmony Ln, Winterport

Listing courtesy of RE/MAX JARET & COHN. belfast@jaretcohn.com

$225,000

3 Beds ⋅ 1 Baths

Cheaper than rent and packed with potential! If you've been waiting for an affordable opportunity to own a home instead of paying your landlord's mortgage, this could be the one. Located in the desirable town of Winterport, you'll enjoy the benefit of school choice, giving your family added flexibility when it comes to education. This 3-bedroom, 1-bath ranch sits on a beautiful wooded lot along a quiet country road, offering the privacy and peaceful setting that's hard to find at this price. The home is completely livable as-is, with just a little TLC like fresh paint and new flooring to make it truly your own and build instant equity. Inside, you'll find a functional kitchen with plenty of cabinet space, a comfortable living area, and three well-sized bedrooms that can easily accommodate family, guests, or a home office. The single-level layout makes everyday living simple and convenient. Step outside and enjoy your own private backyard surrounded by mature trees, with plenty of room for gardens, outdoor entertaining, or simply relaxing in nature. Whether you're a first-time home owner, someone looking to downsize, or an investor searching for value, this property offers an affordable path to homeownership with room to personalize and grow. Opportunities like this don't last long!

642 Stream Rd, Winterport

Listing courtesy of NextHome Experience.

$259,900

Discover the possibilities with this stunning 16.88-acre parcel on Monroe Road! Currently used as productive pastureland for cattle, this beautiful property features a blend of open fields, rolling terrain, and elevated building sites with breathtaking long-range views. A large pond enhances the property's natural beauty while providing a peaceful setting for recreation, wildlife, or livestock. With ample road frontage and expansive usable acreage, this property offers endless opportunities to build your dream home, establish a hobby farm, create a private homestead, continue agricultural use, or enjoy as a recreational retreat. The gently rolling hillside provides multiple potential building locations designed to capture the spectacular countryside vistas. Whether you're seeking privacy, space for animals, investment potential, or the perfect place to build in rural Maine, this exceptional parcel delivers the best of country living while remaining conveniently accessible. Rarely does a property offer this combination of acreage, scenic views, open pasture, a large pond, and endless potential. Don't miss your opportunity to own a truly remarkable piece of Maine.

Lot # 96-2 Monroe, Winterport

Listing courtesy of RE/MAX JARET & COHN. belfast@jaretcohn.com

$469,000

5 Baths

Situated within the Winterport Historical District, with scenic views of Penobscot River and Penobscot Narrows Bridge and Observatory. Located 11 miles from Bangor and 16 to Belfast. This apartment home has been well maintained by same owners for 39 years. The roof is one year old and paint is recent. Currently has a Two Bedroom, A Studio/Efficiency, and Three one bedroom units with an additional space presently an office but could be an additional apartment with a shower.. The attic also has potential as an apartment but is empty space at present. Plenty of off street parking. Owners have only one apartment rented so new owners can select new tenants. Heat is economical Empire Propane Heaters and most units pay their own electric and heat. Additonal features include Public Water and Sewer, Three new refrigerators, New carpeting but has nice wood floors underneath, New Kitchen Cabinets, New Interior Painting, Newly insulated. This is a Landmark Property with Multi Commercial or Residential Options, or Ideal for a Residence and Home Office with Additional Rental Income. With parks, Winterport Dragway, and iconic attractions like Fort Knox, Sandy Beach, 60 miles to Acadia National Park,, you''ll enjoy a lively mix of a great location and Great Business Opportunity. With a boat can go to Bangor, Bucksport, access to Penobscot Bay to Belfast or Acadia.

4 Whig St, Winterport

Listing courtesy of Berkshire Hathaway HomeServices Northeast Real Estate.

$125,000

Looking for room to roam? This 68± acre parcel offers the privacy and potential you've been searching for. Recently harvested, the land provides a blank canvas for your vision while maintaining the peaceful rural setting that outdoor enthusiasts appreciate. With a small amount of road frontage and expansive acreage beyond, this property is ideal for building your dream home, creating a private hunting retreat, establishing a recreational getaway, or investing for the future. Abundant wildlife, excellent hunting opportunities, and plenty of space to explore make this a rare opportunity for those seeking privacy and the freedom to enjoy Maine's outdoors. Whether you're looking for a secluded homesite, weekend escape, or land to make your own, this property is ready for its next chapter.

532 Lebanon Rd, Winterport

Listing courtesy of Realty of Maine.

$380,000

4 Beds ⋅ 2 Baths

Some homes are simply lived in. Others are loved, preserved, and passed through generations with care. Captain Andrews' house was built circa 1790 and believed to be the 2nd oldest home in Winterport. This remarkable property carries more than two centuries of Maine history within its walls. Owned by the same family since 1972, the home has been thoughtfully updated and restored over the years, blending modern comfort with the timeless character that makes historic homes so special. Exposed hand cut ceiling beams in the kitchen, living room, first floor bedroom, and family room serve as beautiful reminders of the home's earliest days, while updates such as 200 amp power, two pellet stoves, a new forced air furnace, R20/R30 insulation, a four year old roof, and newer windows and doors bring peace of mind for today's living. Life here offers the rare feeling of being tucked away while still right in town. The back yard is surprisingly private, spacious, and welcoming, with a fenced in outdoor living area designed for every day enjoyment. Imagine quiet mornings in the garden, summer evenings around the grill, friends gathered on the huge patio around the fire pit, pets playing in the grass, and peaceful nights in the hot tub as the gardens change with the seasons around you. Just moments from Winterport's public landing on the Penobscot River, the park, local shopping, and an easy drive to both Bangor and Belfast / Camden areas, this home offers a lifestyle that is rooted in history, surrounded by comfort, and connected to the best of the area. This is more than an in town home with a large private yard. It is a rare opportunity to become part of a story that began over 200 years ago.

137 Main St, Winterport

Listing courtesy of Realty of Maine.

$349,900

3 Beds ⋅ 2 Baths

Located in the charming town of Winterport, this spacious Raised Ranch offers comfort, convenience, and partial views of the Penobscot River on over 2 private acres. Owned by the same family since 1992, the home is centrally located to both Bangor and the Belfast coast. The main floor features hardwood floors throughout most rooms, a spacious living room with fireplace, and an open kitchen with breakfast bar and dining area. Just off the kitchen is a bright sunroom, perfect for relaxing mornings or quiet evenings overlooking the property. The primary bedroom includes a private bath with stand-up shower, while two additional bedrooms and a second full bath provide space for family and guests. Each bedroom offers closet space, and a hallway pantry provides additional storage. The finished basement includes a large family room, office space ideal for working from home, laundry area, and direct access to the heated drive-in garage for added convenience year-round. A detached one-car garage offers additional storage for vehicles, lawn equipment, or seasonal items. Additional features include a generator, HWBB heat, wood furnace, generous parking for 10+ vehicles, and a right-of-way for future expansion or added privacy. Residents enjoy local schools through grade 8, with high school attendance at nearby Hampden Academy. Conveniently designed for everyday living with direct garage entry into the home and extra storage options throughout. Easy to show -- schedule your viewing today.

28 Marine St, Winterport

Listing courtesy of ERA Dawson-Bradford Co..

$325,000

4 Beds ⋅ 1 Baths

Charming 3-4 bedroom ranch in a convenient Winterport location! This well-maintained home offers beautiful hardwood floors, updated kitchen and bathroom flooring and several other improvements including some replacement windows, updated electrical and added zoning for better heating. The flexible floor plan features a spacious bonus area on the second level that could serve as a fourth bedroom, family room, home office, or hobby space. Enjoy relaxing on the screened rear porch overlooking the private backyard, perfect for entertaining or quiet evenings outdoors. A detached two-car garage provides ample storage and workspace. With many updates already completed and room to make it your own, this home offers comfort, versatility, and value in a desirable location close to local amenities and an easy commute to Bangor, Belfast and surrounding communities.

110 Lebanon Rd, Winterport

Listing courtesy of Signature Group Real Estate.

$359,000

3 Beds ⋅ 3 Baths

Welcome to Upper Meadows subdivision in the mid-coast town of Winterport. Here you will find equal distance to Bangor or Belfast, Hampden/Winterport school district RSU 22 and an easy walk to the village with shops, cafes, restaurants, the historical library and more. This 3BR, 2 1/2 Bath home has a great open concept kitchen, dining and living room with lots of natural light. The kitchen has plenty of cabinets, nice stainless appliances and looks out to the private back yard. The dining area is spacious and leads to the back deck, a perfect spot for the grill! The living room is also bright and sunny all year long and a great space to gather. Down the hall are 2 bedrooms and a full bath plus the primary bedroom with another full bath. Downstairs is the large family room offering so much space for a serious tv/gaming hangout or workout equipment plus a 1/2 bath, laundry and storage. The attached 2-car garage is heated, spacious and gives direct access to living space. Costly upgrades include new roof shingles and new RELO boiler. This affordable home is move-in ready!

11 Rob Clark St, Winterport

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$210,000

3 Beds ⋅ 2 Baths

This 1970's Oxford home has seen a few additions over the years, leaving you with a large dining room and livingroom area. Features 3 bedrooms and 2 full bathrooms along with a 2 car garage, solar panels and eat in kitchen. This home does need some TLC and will not go financing due to a missing HUD tag and no tie downs. Home being sold ''as is, where is''.

33 Coles Corner Rd, Winterport

Listing courtesy of Realty of Maine.

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