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593 Abbott Rd, Winslow
$345,000
3 Beds ⋅ 2 Baths ⋅ 1678220 MLS
Country Setting, Spacious Grounds & Exceptional Updates! Discover the charm and comfort of this inviting 3-bedroom home set on 3 beautiful acres in a peaceful country setting. The spacious yard is designed for enjoying the outdoors, with an in-ground pool offering the perfect spot for summer fun, entertaining, and relaxing. A carport and shed provide convenient storage for vehicles, equipment, and outdoor toys. Inside, you'll find a spacious and welcoming layout with plenty of room for everyone. The large kitchen features an abundant cabinetry, a pantry, gas range, and stainless-steel appliances. The dining room flows naturally into the living spaces, while the spacious family room provides an ideal gathering spot for movie nights, game days, or simply relaxing. A bright four-season sunroom adds even more living space and is a wonderful place to enjoy the changing Maine seasons. The spacious primary suite offers a private retreat with two walk-in closets and a large bathroom featuring a tiled walk-in shower and plenty of storage. Two additional bedrooms provide flexibility for family, guests, a home office, or hobbies. Major exterior improvements completed in 2026 make this home even more appealing, including a new metal roof, all new windows and trim, and new vinyl siding with 3/8' insulation board installed on all exterior walls. If you've been searching for room to spread out, a peaceful country setting, and a home with significant recent improvements, this property checks all the boxes. Come enjoy the space, privacy, and comfort this property has to offer!

593 Abbott Rd, Winslow

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. KarenRamsay@masiello.com

Selling Office: Realty of Maine.

77 Halifax St, Winslow
$245,000
3 Beds ⋅ 2 Baths ⋅ 1669179 MLS
**NEW PHOTOS ARE AVAILABLE!!** Freshly painted inside and out! New exterior doors and some extra finishing touches to make this home ready for you to move right in to this updated 3-bedroom, 1.5-bath New England-style home. Located on a spacious in-town lot in Winslow, nearly all of the major updates have been completed, including a brand-new kitchen with new appliances, updated bathrooms, new flooring, replacement windows, a new propane furnace, and a freshly painted metal roof. This home offers a wonderful blend of classic character and modern improvements while still leaving a few finishing touches for the next owner to make it their own. A property that has been loved by 4 generations, it is ready to begin its next chapter with its new owner.

77 Halifax St, Winslow

Listing courtesy of Summit Real Estate.

Selling Office: Tim Dunham Realty.

2 Segar Brook Ave, Winslow
$148,500
3 Beds ⋅ 2 Baths ⋅ 1679203 MLS
2020 Eagle River 3 bedroom/2 full bathroom double-wide located in Halifax Heights 55+ community in Winslow. This home offers over 1400 square feet of living space and was custom ordered with high-end features like sheet rock walls instead of paneling and a pot-filler over the oven. Halifax Heights is a recently established community with affordable lot fees and well-maintained late model homes, helping to ensure sustainable value. 2 Segar Brook also coveys with a large storage shed, providing space for tool storage and potentially a small workshop. Inside the home, the aforementioned sheet rock gives the interior a warm feel and can easily be painted or wallpapered if desired. Inviting, efficient, affordable, this might be just the spot you've been waiting for! Schedule a showing today and come check it out!

2 Segar Brook Ave, Winslow

Listing courtesy of Rizzo Mattson. 207-622-9000

Selling Office: EXP Realty.

1 Hollingsworth St, Winslow
$270,000
3 Beds ⋅ 1 Baths ⋅ 1674856 MLS
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.

168 Augusta Rd, Winslow
$280,000
3 Beds ⋅ 1 Baths ⋅ 1674668 MLS
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.

176 Garland Rd, Winslow
$355,000
2 Beds ⋅ 2 Baths ⋅ 1669922 MLS
Welcome to 176 Garland Road, a beautifully maintained 2-bedroom, 2-bath ranch located along the Sebasticook River. Thoughtfully cared for inside and out, this home offers comfortable, year-round living with a functional layout and numerous updates. The bright eat-in kitchen opens to a welcoming living room filled with natural light and anchored by a cozy brick fireplace. Heat pumps have been installed throughout the home, including the basement, providing efficient comfort in every season. The first floor features a practical mudroom, two spacious bedrooms, two full bathrooms with convenient first-floor laundry, a walk-in shower, and a classic clawfoot tub, offering both accessibility and character. An attached two-car garage provides ample space for vehicles, storage, or gardening equipment. Outside, you'll find mature landscaping, established garden beds, and a peaceful setting perfect for enjoying the outdoors. Relax under the covered seating area on warm summer evenings or unwind by the fireplace after a long day. Complete with a standby generator and a new metal roof for added peace of mind, this move-in ready property offers the perfect combination of comfort, convenience, and low-maintenance living.

176 Garland Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Your Home Sold Guaranteed Realty.

2 Lucille Ave, Winslow
$247,600
3 Beds ⋅ 2 Baths ⋅ 1666448 MLS
COMING SOON! SHOWINGS START June 13th, 2026. Welcome to 2 Lucille Avenue, a charming Cape-style home perfectly situated on a lovely 0.2-acre corner lot in a desirable Winslow, Maine neighborhood. Located right across the street from the local park, this property offers an ideal blend of cozy residential living and outdoor convenience. This delightful single-family home features a classic exterior with aluminum siding, a timeless gable roof, and an efficient hot water heating system to keep you warm through the Maine winters. Inside, you will find 1,472 square feet of bright, well-designed living space spread across 5 total rooms. The layout features 3 comfortable bedrooms, 1 full bathroom, and an additional half bath, offering plenty of space for family and guests alike. The interior boasts clean drywall finishes, providing a wonderful blank canvas ready for your personal decorative touches. Adding to the home's immense appeal is a spacious detached 2-car garage, offering excellent storage for vehicles, outdoor gear, or a potential workshop space. Whether you are looking for your first home or searching for a wonderful community to settle down in, this Winslow gem is a must-see. Don't miss your chance to tour this beautiful property--schedule your showing starting June 13th!

2 Lucille Ave, Winslow

Listing courtesy of Realty ONE Group Next Level.

Selling Office: Rizzo Mattson.

19 Cardinal Way Unit 10, Winslow
$356,000
2 Beds ⋅ 2 Baths ⋅ 1672985 MLS
Nestled in the highly sought after and well-established community, Heartland Condominium Association, this ranch style 2-bedroom, 2-bathroom unit is ready to become your new retirement home. Carefree living begins with a welcoming sun-filled open floor plan. Quality construction is evident from the eat-in-kitchen to the adjacent dining area with patio doors that lead to a composite back deck and paved patio, perfect for entertaining. The dining room flows into the living room and into the lovely sunroom. The large primary ensuite at the back of the home features a full bathroom with walk-in shower, excellent closet space, and a convenient laundry closet with side-by-side full-sized washer and dryer. A spacious guest bedroom located at the front of the home also offers large closets with the main bathroom with tub/shower at the end of the hallway. The unit's efficient floor plan features spacious and perfectly positioned linen, pantry and coat closets. There is additional storage in the attached garage with auto door opener and in the dry and partially finished basement. Call today for a showing to become part of this wonderful community in Central Maine.

19 Cardinal Way Unit 10, Winslow

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

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

15 Cushman Rd, Winslow
$313,000
3 Beds ⋅ 2 Baths ⋅ 1664159 MLS
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.

40 White Fish Rd, Winslow
$255,000
1 Beds ⋅ 1 Baths ⋅ 1663538 MLS
Tucked just steps from Pattee's Pond with beautiful water views, this truly unique property offers incredible flexibility, craftsmanship, and future potential. Currently configured as a spectacular heated retreat space with deeded water access, the structure features radiant floor heat, soaring wood interiors, a handcrafted sauna, and a dramatic upper-level loft complete with exercise area, sleeping space, bath, and panoramic pond views. A spiral staircase leads to the loft level, while the expansive main floor offers abundant open space that could easily support additional finished living area if desired. Thoughtfully designed and beautifully built, this is an ideal guest house, studio, wellness retreat, recreation space, or future residential conversion. A rare opportunity to own a one-of-a-kind property in a peaceful waterfront setting just moments from the sandy beach and dock across the way.

40 White Fish Rd, Winslow

Listing courtesy of Keller Williams Realty. nick@nickisgro.com

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

313 Cushman Rd, Winslow
$265,000
3 Beds ⋅ 2 Baths ⋅ 1670612 MLS
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.

6 Stuart St, Winslow
$190,000
2 Beds ⋅ 1 Baths ⋅ 1670350 MLS
Welcome to 6 Stuart Street in Winslow, Maine. Tucked away on a quiet dead-end street, this charming 2-bedroom, 1-bath home offers the perfect blend of comfort, convenience, and flexibility. A paved driveway leads to an attached one-bay garage, providing sheltered parking and additional storage space. Inside, you'll find a functional floor plan with two bedrooms and a flex room that could easily be converted into a third bedroom, home office, or any other space to suit your needs. The bright and inviting living areas create a warm, welcoming atmosphere that's ready for you to make your own. Enjoy the peaceful setting while being just minutes from downtown Winslow, Waterville, schools, shopping, restaurants, and other everyday amenities. Whether you're a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this home has exceptional value in a desirable location.

6 Stuart St, Winslow

Listing courtesy of Real Broker.

Selling Office: Coldwell Banker Plourde Real Estate.

17 Sam St, Winslow
$280,000
3 Beds ⋅ 2 Baths ⋅ 1669171 MLS
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.

680 Maple Ridge Rd, Winslow
$285,000
2 Beds ⋅ 1 Baths ⋅ 1664295 MLS
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.

225 Morrill Rd, Winslow
$435,000
2 Beds ⋅ 3 Baths ⋅ 1669098 MLS
Experience the perfect blend of modern comfort and private rural living at 225 Morrill Road in Winslow, Maine. This stunning 2-bedroom, 2.5-bathroom contemporary post-and-beam home is tucked away on 10 pristine, wooded acres complete with its own private backyard pond. The standout feature of this property is the brand-new, pine flooring across the entire first level, adding an unmistakable warmth and rustic elegance to the home's primary living spaces. Step into a grand open-concept floor plan illuminated by natural light pouring through massive windows. The living room boasts soaring cathedral ceilings and a cozy fireplace, perfectly complemented by the aroma and look of the newly installed first-floor pine floors. The main level features a fully-equipped kitchen, a comfortable primary bedroom layout, and seamless access to outdoor living areas. Overhead, a charming second-story loft space offers the ideal footprint for a home office, creative studio, or reading nook overlooking the main level. The finished walk-out basement expands your living footprint significantly, providing an extra bonus room, a convenient half-bath, and abundant dedicated storage space. Outside, the house is set up perfectly for multi-level decking to sit back and observe the surrounding Maine woods and local wildlife. Despite the deep sense of country privacy, you are located only one mile from the public boat access at China Lake and just a short drive from downtown Winslow amenities. Contact Shari at today for a private showing.

225 Morrill Rd, Winslow

Listing courtesy of Hoang Realty.

Selling Office: Your Home Sold Guaranteed Realty.

100 N Pond Rd, Winslow
$501,000
4 Beds ⋅ 3 Baths ⋅ 1661512 MLS
Modern cape offering 4 bedrooms, 3 baths, and 3,100 sq ft of thoughtfully designed living space set on 2.5 private acres. Completely updated in 2021, this home blends classic New England charm with modern finishes throughout. The spacious, flexible layout is ideal for both everyday living and entertaining with generous living areas and abundant natural light. The walk-out basement provides excellent additional space for recreation, storage, or future expansion Step outside to low-maintenance composite decks, perfect for relaxing and taking in the peaceful surroundings. Tucked away in a quiet rural setting, this property offers exceptional privacy while still providing access to nearby snowmobile trails, which become walking trails in the summer, making it an ideal year-round retreat for outdoor enthusiasts. A rare opportunity to enjoy comfort, space, and adventure right from your doorstep.

100 N Pond Rd, Winslow

Listing courtesy of Sprague & Curtis Real Estate.

Selling Office: Your Home Sold Guaranteed Realty.

Lot 75 Bassett, Winslow
$47,000
1638547 MLS
Beautiful 2.5-Acre Wooded Lot in Winslow, Maine - Approved for Building, Well, and Septic Welcome to your perfect piece of Maine! This stunning 2.5-acre wooded lot in Winslow offers the ideal blend of privacy and convenience. Nestled in a peaceful rural setting, yet just a short 5-minute drive from local amenities and schools, this property provides the perfect location to build your dream home. It's already approved for both building and for well and septic systems making it a great option. Surrounded by the beauty of nature, you'll enjoy the tranquility of rural life without being far from the everyday conveniences you need. Whether you're looking for a private retreat or a place to create your ideal home, this property is a rare find in Winslow. Don't miss out on this incredible opportunity to own your own slice of Maine! Lot 75-76 package available MLS# 1655417

Lot 75 Bassett, Winslow

Listing courtesy of Realty of Maine.

Selling Office: Coldwell Banker Plourde Real Estate.

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