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144 Clinton Ave, Winslow
$339,900
4 Beds ⋅ 2 Baths
Welcome to 144 Clinton Avenue---A warm and inviting Multilevel Cape Cod. This classic well-built home sits on a rare double lot with an attached 2 car garage. There is a 21 x21 foot area above the garage that has new electrical, insulation and cut out windows, that await your finishing touches if you want additional living space. The property is fenced in with lovely landscaping, and a private backyard. There are mature raspberry blackberry and rhubarb plants, and grapes that can be harvested for a delicious treat. There is a deck off the 1st floor kitchen where you can relax and enjoy your morning coffee or host that family barbeque, and an additional deck to the right of the home. There is a washer and dryer hookup in Unit 1, and the washer and dryer for Unit 2 are in the basement. The windows are adorned with wood blinds. The home combines period charm with modern updates and is currently configured into two separate 2-bedroom, 1 bath units. Live in one unit and rent out the other, use it as a multigenerational property, or convert it back to a single-family residence. Lots of possibilities here, come take a look!

144 Clinton Ave, Winslow

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: Brookewood Realty.

15 Cushman Rd, Winslow
$313,000
3 Beds ⋅ 2 Baths
This 3-bedroom, 2-bath bungalow is the perfect place to settle in and feel at home. Full of historic charm, the property features original hardwood floors, beautiful woodwork, and a thoughtful layout designed for everyday living. The first floor offers a convenient bedroom and full bathroom, along with a flexible den or office space. Step through the glass doors into a sun-filled room, the perfect place for starting seedlings, enjoying hobbies, or simply soaking in the natural light. Grab a cup of coffee and relax on the welcoming front porch overlooking a desirable in-town lot with plenty of space for gardens or vibrant flower beds. Upstairs, you'll find two additional bedrooms and another full bathroom. With a brand-new roof, walkability to downtown, and just minutes from local shopping and eateries, this home blends space, functionality, and timeless character without compromise. The perfect place to plant roots. Book your private showing today!

15 Cushman Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Dream Home Realty LLC.

5 Robert St, Winslow
$310,000
3 Beds ⋅ 2 Baths
Well-maintained mid-century ranch, which has been thoughtfully updated with a modern feel while providing significant potential for expansion in the full unfinished basement. The home features a convenient single-level layout with an open-concept kitchen and dining area equipped with newer appliances. The spacious living room includes a wood stove, and the entire interior was recently painted. Additionally, the property features a large primary bedroom with ample closet space, an updated full bathroom, and a half bath with laundry facilities. Situated on a rare, private double corner lot near a local golf course, the exterior includes a garage and a dual driveway for easy access. Whether you are looking for a quiet location with modern updates or a home with room to grow, this property presents a fantastic opportunity.

5 Robert St, Winslow

Listing courtesy of Hoang Realty.

Selling Office: Coldwell Banker Plourde Real Estate.

51 N Reynolds Rd, Winslow
$305,000
2 Beds ⋅ 1 Baths
Extensively updated in 2024 and 2025, this 2-3 bedroom home, on 2.28 acres, is not your ordinary mobile home. It's been updated from top to bottom, offering quality craftsmanship, new systems, and new additions that sets it apart. A spacious 18' x 30' addition provides substantial extra living space. This addition was built on a full foundation with exterior foam insulation, finished interior walls featuring beautiful hemlock boards, and accented with solid hemlock support posts. With just a few finishing touches, it would make a great man-cave, craft room, office etc. This entire section was topped with a new roof structure and standing-seam metal roof. Inside, you'll find new flooring throughout the addition area, along with new paint. The inviting new entryway, built on tapered piers, features a tile floor, full insulation, pine shiplap interior, and its own standing-seam roof. A warm, welcoming space to arrive home. Major system upgrades include a new propane-fired forced hot air furnace, all new propane lines, and a new propane tank. The fully renovated bathroom was completely reimagined, including reinforced flooring to support the tiled shower, a new layout, tile shower and flooring, and a new toilet. All electrical work in the bathroom and both additions is brand new, plus there's a new generator hookup conveniently located at the front of the home. There's a perfect spot for a back deck and it's all ready for installation. With its upgrades, expanded living space, and quality finishes throughout, this special property offers the comfort and functionality of a traditional home, while proving it's anything but ordinary.

51 N Reynolds Rd, Winslow

Listing courtesy of The Maine Real Estate Experience.

Selling Office: The Maine Real Estate Experience.

14 Paine St, Winslow
$305,000
2 Beds ⋅ 1 Baths
Welcome home to easy one-floor living in this beautifully maintained 2-bedroom, 1-bath ranch nestled in one of Winslow's desirable neighborhoods. Just minutes from downtown Waterville, I95, and local shopping, this area offers both convenience and a comfortable neighborhood feel. Originally built during Winslow's growth era of the 1950s and 60s, this home was thoughtfully renovated in 2016, giving it fresh life for modern living. The open-concept kitchen and living room create a bright, welcoming space perfect for everyday living and easy entertaining, while the oversized laundry room and bath add practicality and comfort. The attached 2-car garage provides excellent space for vehicles and storage, with additional room above for even more flexibility. Downstairs, the expansive basement offers plenty of room for storage, hobbies, or recreation, with exciting potential for future finished space since it is already zoned for heating. Step outside and enjoy the cozy yard with mature fruit trees including cherry, pear, and apple, plus a blackberry bush. Out back you'll find an inviting spot for relaxing, gardening, or entertaining. Move-in ready and full of charm, this is a home you'll want to see with your own eyes!

14 Paine St, Winslow

Listing courtesy of Your Home Sold Guaranteed Realty.

Selling Office: Your Home Sold Guaranteed Realty.

12 Harry St, Winslow
$302,000
2 Beds ⋅ 2 Baths
Opportunity meets charm in this well-located Winslow ranch. Whether you're a first-time buyer or a savvy investor, 12 Harry St delivers immediate livability with serious upside -- all under $300K. The main level offers a comfortable layout with a delightful 3-season porch overlooking a level, usable backyard -- perfect for morning coffee or evening unwinding. The attached 2-car garage adds everyday convenience that's hard to find at this price point. The real story is in the basement. It is currently partially finished following recent water remediation from a leaking spigot, a buyer can easily finish the space into 2 additional bedrooms plus a family room -- potentially adding 1,000+ sq ft of living space and significant equity. Priced to reflect the opportunity, this home rewards the buyer willing to invest a little sweat equity into something lasting. Schedule your showing today.

12 Harry St, Winslow

Listing courtesy of EXP Realty.

Selling Office: LAER.

6 Victor Ter, Winslow
$290,000
3 Beds ⋅ 1 Baths
This charming brick ranch, built in 1966, offers comfortable one-floor living in a quiet and established Winslow neighborhood. Located within walking distance to Winslow schools, this mid-century modern home boasts 3 spacious bedrooms and 1 bathroom. The open concept floor plan combines the kitchen, dining and living room areas making the home feel, welcoming, cozy and comfortable. The fenced-in backyard off of the covered patio offers a lovely private space for entertaining or hanging out with friends and family and an oversized 1-car garage is the perfect spot for all of your toys and hobbies. This home is also in close proximity to the historical Two Cent Bridge offering easy walkable access to Waterville's thriving downtown. This home has the allure of convenience and the practicality of easy living all rolled into one. Come check it out! *New roof to be done by closing*

6 Victor Ter, Winslow

Listing courtesy of Coldwell Banker Realty.

Selling Office: Coldwell Banker Realty.

88 Augusta Rd, Winslow
$287,000
3 Beds ⋅ 2 Baths
Attention Investors! Welcome to 88 Augusta Road in Winslow! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort, versatility, and convenience. Once a two-family residence (the garage was once a 1 bed 1 bath), this property can easily be converted back with proper town permitting and a certificate of occupancy—offering great potential for rental income or multi-generational living. Step inside to find a bright and inviting living space filled with natural light and thoughtful updates throughout. The kitchen provides ample cabinet space and opens seamlessly to the dining and living areas—ideal for both everyday living and entertaining. The first floor features a convenient primary bedroom and a half bath for guests, while upstairs offers two additional bedrooms, a bonus room, and a full bath—providing plenty of space for everyone. Significant updates in 2024 include a brand-new roof, solar panels, a 200 amp electrical panel and a hybrid hot water tank, adding efficiency and long-term value to the home. Situated on a corner lot with a driveway on the side road, this property also offers the option to convert the garage (which had previously been a 1 bed, 1 bath apartment) back to a two-car garage, adding even more functionality. Outside, enjoy a spacious yard ready for gardening, play, or relaxation. Perfectly located near local schools, shopping, and downtown Waterville, this home combines small-town charm with easy access to modern amenities.

88 Augusta Rd, Winslow

Listing courtesy of Keller Williams Realty.

Selling Office: EXP Realty.

680 Maple Ridge Rd, Winslow
$285,000
2 Beds ⋅ 1 Baths
Welcome to a property that truly captures the beauty of Maine living at a reasonable price. Set on 9 picturesque acres, this charming home combines single floor living, privacy, usable land, and timeless character in a way that is becoming increasingly difficult to find. From the moment you arrive, the peaceful setting and expansive backyard immediately stand out. Mature trees, open lawn space, and the natural surroundings create a setting that feels private, relaxing, and full of possibility. Whether you envision gardening, entertaining, enjoying quiet evenings outdoors, or simply having room to breathe, this property delivers the lifestyle buyers are searching for. Inside, the home is filled with warmth and character. Beautiful wood accents, hardwood floors, and a classic brick fireplace create an inviting atmosphere that feels comfortable and authentic. The spacious kitchen features abundant cabinetry and a timeless country feel, while the overall layout offers practical everyday living with two bedrooms and one full bathroom. One of the property's rare and highly valuable features is the presence of two separate garages, providing exceptional flexibility for vehicles, storage, workshop space, recreational equipment, or hobbies. Properties offering this combination of acreage, multiple outbuildings, and a beautiful setting are increasingly limited in today's market. If you have been searching for a property with land, privacy, charm, and long-term value potential, this is the kind of opportunity that buyers wait for.

680 Maple Ridge Rd, Winslow

Listing courtesy of Keller Williams Realty. jlaverdiere@gmail.com

Selling Office: Townsend Real Estate.

6 Hemlock St, Winslow
$281,000
3 Beds ⋅ 2 Baths
This spacious multi-level home offers both comfort and versatility with generously sized rooms throughout and a layout that fits a wide range of lifestyles. Featuring a durable standing seam metal roof, the home combines low-maintenance living with long-term value. Inside, the multi-level floorplan creates a natural flow through the living spaces, with oversized rooms perfect for gatherings, relaxing evenings, or working from home. The partially finished basement includes two completed rooms ready to be transformed into a home office, gym, hobby area, or guest suite — truly whatever your heart desires. Step outside to enjoy a private backyard retreat with a charming patio and hot tub that backs up to the woods, offering peaceful seclusion and the perfect space to entertain, garden, or simply unwind. Whether you're seeking more room to grow, flexible living spaces, or a quiet outdoor escape, this home delivers all that and more in a tranquil setting. Close to Schools, Downtown Waterville for dinning and shopping, Colby College and Thomas College.

6 Hemlock St, Winslow

Listing courtesy of OWN REAL ESTATE.

Selling Office: Real Broker.

168 Augusta Rd, Winslow
$280,000
3 Beds ⋅ 1 Baths
This well-maintained 3-bedroom, 1-bath ranch offers comfortable one-level living with the added bonus of finished space in the basement. The lower level features an exercise room and additional flexible living space perfect for a family room, home office, hobby area, or playroom. The home includes an attached two-car garage for added convenience and storage. Recent updates provide peace of mind, including a new boiler installed in 2024 and are-shingled roof completed in 2020. Inside, you'll find some hardwood floors that add warmth and character to the living spaces. Conveniently located with easy access to local amenities, this move-in-ready home offers a great combination of comfort, functionality, and value.

168 Augusta Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Brookewood Realty.

17 Sam St, Winslow
$280,000
3 Beds ⋅ 2 Baths
Welcome home to this well-maintained 3-bedroom, 2 full bath ranch nestled in a desirable Winslow neighborhood. As you enter, you'll be greeted by a bright and inviting sunroom featuring sliding doors that lead to the back deck and fenced backyard, creating the perfect space to relax or entertain. Inside, beautiful hardwood floors flow throughout much of the home, adding warmth and character, complemented by neutral, peaceful colors throughout. The finished basement offers a spacious family room with custom cabinetry, built-in storage, and generous closet space, along with a full bathroom and a convenient laundry area, providing plenty of additional living space. An attached one-car garage adds everyday convenience, while the backyard is a private retreat complete with perennial gardens that provide seasonal color and charm.

17 Sam St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Coldwell Banker Plourde Real Estate.

1 Hollingsworth St, Winslow
$270,000
3 Beds ⋅ 1 Baths
Welcome to 1 Hollingsworth Street in Winslow, where timeless character meets thoughtful updates. Built in 1914, this charming 3-bedroom, 1-bath home showcases the craftsmanship and architectural details that make homes of this era so special. Newly refinished hardwood floors bring warmth and beauty, while the original kitchen cabinets and separate pantry preserve its authentic vintage appeal. The second floor features three comfortable bedrooms and a full bath, offering a practical layout for everyday living. Rich in original charm, you'll appreciate the classic woodwork, inviting spaces, and period details that have stood the test of time. Relax with your morning coffee or unwind at the end of the day on the wonderful enclosed front porch--an inviting extension of the home's living space. Conveniently located close to local Winslow schools, this home offers an easy commute for students and families alike. If you're looking for a home with history, character, and enduring style in a convenient in-town location, 1 Hollingsworth Street is ready to welcome its next owner.

1 Hollingsworth St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Your Home Sold Guaranteed Realty.

5 Lucille St, Winslow
$267,000
3 Beds ⋅ 1 Baths
Love mid-century charm? This 1961 ranch in a desirable Winslow neighborhood offers timeless character paired with thoughtful updates for today's lifestyle. Designed for easy one-level living, this home features three bedrooms and one beautifully updated full bath. Inside, you'll appreciate the warmth of hardwood flooring, complemented by newer laminate, along with fresh paint throughout that creates a bright, move-in ready feel. The kitchen is equipped with new appliances, and the convenience of a first-floor washer and dryer adds everyday practicality. Step outside to enjoy the fenced backyard -- perfect for pets, gardening, or gatherings -- along with a small deck overlooking the yard, ideal for relaxing at the end of the day. A two-car detached garage provides ample storage and parking. With its classic mid-century appeal, modern updates, and convenient location close to local amenities, this home offers comfort, character, and convenience all in one.

5 Lucille St, Winslow

Listing courtesy of Summit Real Estate.

Selling Office: Central Maine Real Estate.

313 Cushman Rd, Winslow
$265,000
3 Beds ⋅ 2 Baths
Welcome to 313 Cushman Road, where extensive renovations inside and out have transformed this home into a move-in ready retreat. The first floor features an open-concept kitchen and dining area with abundant cabinetry and counter space, creating a functional layout for both everyday living and entertaining. A bright living room and a convenient half bath with first-floor laundry complete the main level. Step outside onto the back deck, the perfect place to relax on warm summer evenings or gather with family and friends. Upstairs, you'll find three comfortable bedrooms and an updated full bathroom. Recent improvements include an expanded and newly paved driveway, a new metal roof, all new exterior siding, and all new interior and exterior doors, providing both peace of mind and lasting curb appeal. Conveniently located just minutes from local amenities and the recreational opportunities of China Lake, this beautifully updated Cape offers the perfect blend of modern updates, comfort, and convenience.

313 Cushman Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Keller Williams Realty.

364 Cushman Rd, Winslow
$265,000
2 Beds ⋅ 2 Baths
ALL OFFERS DUE 12/2 BY 5pm!!! Welcome to this move-in-ready 2-bedroom ranch home set on a beautiful 5.58-acre mix of open and wooded land with stream access. This well-maintained property offers a spacious layout featuring hardwood floors, a bright main living area, and a bonus framed in family room downstairs. The walkout basement adds excellent functionality with additional storage rooms and direct access to the yard. The extra space downstairs provided several opportunities that can be used for storage or future expansion. Car enthusiasts and hobbyists will appreciate the 2-car front garage with auto door openers plus an additional 1-car garage in the back, providing ample space for vehicles, tools, and equipment. A durable metal roof, large deck out back, oil heat, and solid construction offers long-term peace of mind. Whether you're relaxing by the stream, enjoying the privacy of the wooded areas, or making full use of the open land, this property delivers the perfect blend of comfort, utility, and natural beauty. A rare opportunity to enjoy acreage living with all the convenience of a move-in-ready home.

364 Cushman Rd, Winslow

Listing courtesy of EXP Realty.

Selling Office: Real Broker.

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