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$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.

$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.

$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.

$269,900
3 Beds ⋅ 2 Baths
Located in the heart of the Winterport Historic District, 31 Dean Street is a charming, character-filled Greek Revival home that beautifully embodies the spirit of small-town Maine living. Known as the R.P. Atwood House, it proudly holds a place on the National Register of Historic Places. From the moment you arrive, the home's classic New England architecture and period details set the tone--wide plank floors, vintage woodwork, and the unmistakable charm that only a historic property can offer. The home offers an inviting layout with plenty of room to bring your vision to life. Recent updates include a new refrigerator, range, & microwave, providing a great starting point for future improvements. A wood stove or pellet stove hookup in the living room offers the opportunity to add an efficient supplemental heat source while enhancing the cozy atmosphere that historic homes are known for. Step outside and you'll discover fruit trees dotting the property, adding to its storybook appeal and offering the simple pleasure of seasonal harvests right from your own yard. The attached barn provides excellent storage and workshop space, with the potential to be utilized as a garage for vehicles, recreational equipment, or hobby space. Whether you're drawn to restoration projects, love the character of older homes, or simply want a space with soul, this property is an exceptional canvas--inside and out. Just a short stroll from downtown Winterport and the Penobscot River, you'll enjoy a peaceful neighborhood feel with quick access to local shops, dining, and scenic riverside views. Bangor is only a short drive away, making commuting and access to larger amenities incredibly convenient. Whether you dream of modernizing the interior, blending old-world charm with contemporary finishes, or restoring the home to its classic glory, the possibilities here are endless. This is a rare opportunity to own a piece of Winterport's history while creating a home uniquely your own

31 Dean St, Winterport

Listing courtesy of NextHome Experience.

$319,000
3 Beds ⋅ 2 Baths
This charming saltbox-style home offers the perfect blend of privacy, tranquility, and convenience. Nestled in a peaceful setting near the Hampden town line and Winterport Village, you'll enjoy an easy commute while still feeling tucked away from it all. Inside, warm and inviting finishes such as custom cabinetry and beautiful wide pine floors create a cozy, timeless feel that truly makes this house feel like home. Offering 3 bedrooms, 2 bathrooms, and a detached garage, this property is ready to welcome its next owners.

7 Upper Oak Point, Winterport

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

$299,000
3 Beds ⋅ 2 Baths
This charming in-town home offers views of the Penobscot River in a convenient location! Close to Bangor shopping and jobs, but with a small town atmosphere, you can have the best of both worlds. Enjoy the view of the river from the spacious back deck, or from the sun room!

11 Church St, Winterport

Listing courtesy of Maine Country and Coast Real Estate.

$355,000
2 Beds ⋅ 2 Baths
Nestled on a generous four-acre secluded property surrounded by woods, this well-maintained, beautiful home offers the perfect cabin-style retreat. Featuring many upgrades, an open-concept kitchen-living room, and ample storage throughout. A charming wraparound porch and deck surrounds the pool area, providing a wonderful space for relaxation and entertaining. The two-car heated garage includes a finished studio above with abundant windows for natural daylight, along with plenty of garage space for storage and workspace. The grounds have been maintained with lots of perennials and raised garden beds. Come experience the peace, privacy, and warmth this special property has to feature. Schedule your showing today and see it for yourself!

12 Irish Ln, Winterport

Listing courtesy of Realty of Maine.

$310,000
3 Beds ⋅ 1 Baths
Updated Ranch with Artistic Charm in Historic Winterport Set in the picturesque Rivertown of Winterport along the Penobscot River, this beautifully updated 3-bedroom, 1-bath ranch offers a perfect mix of character, efficiency, and lifestyle flexibility. Recently repainted in a striking coastal blue with crisp white trim, the home boasts standout curb appeal and a warm welcome. Inside, the living room features new gray-tone laminate flooring and a newly installed heat pump for efficient heating and cooling--providing year-round comfort throughout the home. The inviting, functional eat-in kitchen offers easy access from the detached one-car garage, making daily routines and grocery runs seamless New Refrigerator & Stove add to these benefits. (Custom Island not included with sale.) The third bedroom has been thoughtfully converted into an art studio, ideal as a creative space, home office, or easily returned to bedroom use. For added convenience, the washer and dryer are currently located in the second bedroom closet but can be moved back to their original location in the now dry, insulated full basement. The home has seen extensive improvements: beautiful new composite decks and stairs, a freshly paved driveway, new furnace, re-lined chimney, and a comprehensive French drain system (interior and exterior) with a sump pump for peace of mind. New windows throughout are paired with custom quilted window blankets for energy efficiency and seasonal comfort. Outside, the grounds are beautifully landscaped with blooming perennial gardens and space for raised beds or a small vegetable garden. A natural spring is located on the property--another unique feature of this well-cared-for home. A complete list of upgrades is available in the MLS documents. This move-in-ready ranch is a standout in Winterport, blending modern updates with small-town charm. Just a short walk to downtown or a short drive to Bangor or Maine's Coast. Don't miss out on this one, it is a Sweet Home!

90 Whig St, Winterport

Listing courtesy of NextHome Experience.

$598,000
4 Beds ⋅ 2 Baths
This enchanting cottage-style 4BR, 2 Bath Farmhouse with Penobscot River views has just become available for the first time in 50 years! The incredible craftsmanship that was thoughtfully designed and carried out is rarely seen anymore. Go ahead and open the beautiful Ash cabinets in the kitchen to fully view the attention to detail. The Cherry built-in the dining room was done by a local boat builder and the maple cabinets in the living room are equally impressive. The veranda wraps around the front, where you will be greeted by fragrant honeysuckle vines, native plantings and a view of the Penobscot during most seasons. The bluebirds and wrens currently reside here! Upon entering, you will feel the warmth and beauty of this well-loved home. The stone fireplaces in the dining and living room are estimated to be close to 180 years old! Both rooms are spacious and offer hardwood floors. The kitchen is full of light, great workspace, storage, nice appliances, tiled counters and Mexican tile floors. The back stairway in the kitchen leads to the upstairs where you will find a luxurious full bath with radiant heat, Keniston tile flooring, concrete vanity deep soaking tub and walk-in tiled shower. A bedroom or office and the primary BR with 4 closets are on either side. The formal front entry leads you into the foyer with tiled floor, antique ceiling fixture, coat closet and direct access to the 2-car attached garage and basement. The front stairway has impressive hardwood treads and a tasteful carpet runner leading to 2 additional bedrooms, the laundry area and another high-end full bath with radiant heat, tiled shower and double vanities. The large yard is bordered in the back by a peaceful stream and a wooded back ridge just waiting to be explored. This property dates back to when Winterport was still part of Frankfort and the river was bustling with tradesmen, workers and merchants. Located between Bangor and Belfast, and just 4 miles from Hampden Academy.

11 Baker Rd, Winterport

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

$105,000
2024 Baths
This versatile standalone building offers a unique opportunity for business owners or creatives looking for a highly visible location in Winterport. With its welcoming exterior and efficient interior layout, the property is well-suited for a boutique shop, salon, photography studio, office, or other small business ventures. The current setup demonstrates the space's potential as a creative studio, but the property can easily be tailored to meet a wide variety of business needs. Its size, layout, and location make it a low-maintenance investment or an affordable option for an owner-operator ready to establish their presence in the community.

111 W Main St, Winterport

Listing courtesy of Trinity Business Brokers.

$339,000
3 Beds ⋅ 1 Baths
Nestled at the back of a beautifully landscaped 2 acre lot, this inviting 3 bedroom 1 bathroom ranch style home offers privacy, space, and comfort. This home is thoughtfully positioned to maximize the peaceful surroundings, with a long paved driveway leading to an attached garage for added convenience. Inside, the home features a practical and cozy layout, perfect for everyday living. The living area flows into the eat in kitchen, while the three bedrooms offer flexibility for family, guests, or a home office. The full bathroom is centrally located and accessible directly from the master bedroom. Off the kitchen is a glassed in porch that connects to a wrap around deck off the front of the home. This home is located 30 minutes to Bangor & Belfast, 1 hour to Augusta, and 2 hours to Portland. Home is handicap accessible with direct access via ramp to master bedroom.

437 Stream Rd, Winterport

Listing courtesy of Worth Clark, Inc..

$494,900
4 Beds ⋅ 2 Baths
Set on open, rolling fields with views of the pasture and woods, this beautifully updated 4-bedroom, 2-bath Cape offers the kind of space and versatility that's getting harder to find. Whether you're dreaming of a working farm, hobby homestead, or simply room to spread out, this property delivers. The home blends comfort and function with a layout that supports both everyday living and long-term flexibility. A first-floor bedroom and full bath, complete with a new vanity (2022), provide convenient one-level living. The kitchen has been thoughtfully updated with custom Design Living cabinetry, a farmhouse sink, island, and new appliances, opening seamlessly to the living area where a wood stove creates a warm, inviting heart of the home. A den or library rounds out the main level. Upstairs, you'll find three additional bedrooms and a full bath, including a spacious primary with a walk-in closet and its own heat pump. Two of the bedrooms take in views over the back fields, adding to the peaceful, tucked-away feel. The second floor offers generous ceiling height, creating a sense of space rarely found in Cape-style homes. Two heat pumps, one on each level, provide efficient heating and cooling alongside multiple heating options. Outside is where this property truly shines. The impressive 200' x 36' barn is equipped with a new electrical panel (2022) and offers endless potential for livestock, storage, or creative use. A newly added 160' x 60' fenced arena (2025), currently registered with Sniffspot for rental income as a dog park, adds both function and opportunity. A 25' x 40' raspberry patch, expansive open land, and a 4-bay, 50' x 25' detached garage further support a variety of uses. Additional features include a whole-house automatic generator, plus a separate generator at the barn dedicated to water access, providing peace of mind year-round. A rare offering with the infrastructure already in place, just waiting for your vision to take it further.

25 & 26 Rancourt Rd, Winterport

Listing courtesy of EXP Realty.

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