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181 Bassett Rd, Winslow
$689,000
3 Beds ⋅ 3 Baths
A beautiful winding driveway, lined with maple trees, leads you past a stocked pond to this custom built home sitting on 14 pastoral and wooded acres. Classically styled 3 story barn on a full foundation with a lean-to off the side for animal shelter and additional bird coop. Top end 12x16 chicken coop, countless berries and fruit trees and beautiful garden rows with rich fertilized soils, this property is perfect for homesteading. Deer blind on the far end of the property near Mill Brook. This 3 bedroom home has lots of space and 2 and a half bathrooms. Generous mud room connects the garage to the home. Spacious kitchen with granite counter tops, long island and custom cabinetry. Office adjacent to the kitchen and first floor primary suite with walk-in closet make one story living possible. Open living room off the kitchen and sunroom with an energy efficient wood stove are perfect for entertaining. Upstairs features 2 additional bedrooms, full bath and a den. The walkout basement is flooded with natural light and boasts new flooring and a heat pump. In addition, you'll find a processing room and large heated workshop. Extremely energy efficient home with a heat recovery ventilator and standby generator. Properties like this are hard to find. Peaceful and private! Close to Colby College, multiple towns and abundant outdoor recreation.

181 Bassett Rd, Winslow

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

25 Frankwood Dr, Winslow
$569,000
3 Beds ⋅ 3 Baths
Move right into this beautifully maintained 3-bedroom, 2-bath home in one of Winslow's most sought-after neighborhoods. The updated kitchen flows seamlessly into the dining area, creating a bright and welcoming space that's perfect for everyday living and entertaining. The spacious primary suite offers a private retreat with an ensuite bath featuring a walk-in shower and a relaxing soaking tub. Two additional bedrooms and a second full bath provide plenty of space for family, guests, or a home office. Step outside to enjoy the beautifully landscaped backyard, complete with a sparkling pool, hot tub, and generous outdoor living space ideal for relaxing or hosting family and friends. The attached garage includes a convenient 50-amp EV charger. This home also features several energy-saving upgrades, including a GEOSPRING heat pump water heater, LED lighting, ceiling fans, and water-saving toilets, helping improve comfort and efficiency. With its desirable location, thoughtful updates, and exceptional indoor and outdoor amenities, this is a home you won't want to miss!

25 Frankwood Dr, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

9 Olde Heritage Pl, Winslow
$525,000
3 Beds ⋅ 2 Baths
Brick colonial set well back from the road at the end of a maple-lined drive, surrounded by open lawn with room for recreation, gardens, and pets. The kitchen has maple cabinetry, granite counters, stainless appliances, a wine fridge, and a skylight, and opens to a dining area with hardwood floors. The living room's wood stove insert adds warmth through Maine winters, and solar panels help lower monthly electric bills. A bright bonus room with a vaulted ceiling and arched window works as a home office, playroom, or family room. 3-4 bedrooms and 2 baths, including a primary bedroom with double closets. The attached 2-car garage has room for vehicles, tools, and toys, with a mudroom entry and a back patio under a pergola. Set on 2.54 acres with restrictive covenants to protect your investment.

9 Olde Heritage Pl, Winslow

Listing courtesy of EXP Realty.

9 Chadwick St, Winslow
$475,000
4 Beds ⋅ 2 Baths
MOVE RIGHT INTO this immaculate, extremely well-maintained, 4-bedroom home just 3 miles to Colby College, 2 miles to Thomas College and a short drive to Maine General Hospital in Augusta. ENJOY peace & privacy while you sit under the gazebo (complete with a ceiling fan!) and slip into the pristine above-ground pool with a brand-new liner (2026). The deck has a 20-amp breaker w/ 50-amp service just waiting for your new hot tub. The property is on a dead-end road with a path at the end that leads right to the High School. Small brook at the rear of the property. The front steps are a 3-year-old Shawnee product and the entire interior is freshly painted. Completely renovated kitchen with ample room and plenty of cabinet space. The comfy basement is completely finished with a full bath and a tub, raised floor with insulation & carpet and 2 BONUS rooms with closets and plenty of natural light. *** The garage has a work area, space for a vehicle PLUS the 2nd floor is finished, has electricity, is well-insulated and is currently being used as the ''ultimate play space''. Plenty of room for all your toys with the driveway paved in 2022. *** 9 Chadwick Street has it ALL and is ready for you to call her ''HOME''. Schedule a private showing today! You'll be glad you did.

9 Chadwick St, Winslow

Listing courtesy of Realty of Maine.

11 Rousseau St, Winslow
$415,000
3 Beds ⋅ 3 Baths
Lovingly maintained by the same family for over 50 years, this spacious 3-bedroom, 3-bath home offers first-floor living in a convenient in-town location. The primary bedroom features an ensuite bath, while skylights bring natural light throughout the home. The inviting living and dining area features a fireplace and heat pumps for year-round comfort, while the large family room with wet bar overlooks the private back patio and offers a great space for entertaining. Additional highlights include heat pumps, ample storage, a shed, and an oversized garage with extra storage and a roll-top door for easy access. The lower level features a wood stove, former hair salon, and bonus rooms offering plenty of potential for a home office, hobby space, gym, or additional living space. With generous living space and so much potential, this well-loved home is ready for its next chapter.

11 Rousseau St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

1310 China Rd, Winslow
$412,000
3 Beds ⋅ 2 Baths
Coming home should always feel this good. Welcome to a lovely 3 bed, 2 bath ranch with a walk out basement and attached 2 car garage. This property is so welcoming, with a 2.95 acre lot that is surrounded by trees, it feels secluded, yet minutes from town. You will be in awe when you see the Farm Pond with a rock border and the many, many perennial gardens. Each garden has been carefully prepped for Winter and will be a colorful delight in Spring!! The walkout basement has a wood stove and seating area and two rooms roughed out. With ceilings, walls and floor coverings you could nearly double the square footage of this home (with town approval). This is a home that is just right as it is, but also has room to grow. You can be minutes from work, shopping and restaurants and come home to peace and tranquility. You'll enjoy the 4 seasons of Maine in this beautiful setting and it is waiting for you! Please come to our Open House on Saturday, October 24th, between 11:00 am and 12:30 pm and see for yourself.

1310 China Rd, Winslow

Listing courtesy of LAER.

323 Augusta Rd, Winslow
$350,000
Set on 8.65 acres, this property blends historic character, open possibilities and a location that lends itself to more than one vision. Whether you're dreaming of a distinctive 5-bedroom home surrounded by land, creating a small homestead, or exploring commercial use, this property offers flexibility and opportunity. Come experience a classic Maine colonial home that has retained the charm of the 1800's era while also adopting more modern updates along the way. Additional features include a newer propane heating system, replacement windows, timeless wide-plank wood flooring, high ceilings and a detached 2-car garage/barn with plenty of storage. There is even a hidden gem to discover in the woods behind the house; a small log outbuilding that catches rainwater for use. With its substantial acreage, established location and potential for commercial use, this is an opportunity to breathe new life into a piece of Winslow's past while creating something uniquely your own.

323 Augusta Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

323 Augusta Rd, Winslow
$350,000
5 Beds ⋅ 2 Baths
Set on 8.65 acres, this property blends historic character, open possibilities and a location that lends itself to more than one vision. Whether you're dreaming of a distinctive 5-bedroom home surrounded by land, creating a small homestead, or exploring commercial use, this property offers flexibility and opportunity. Come experience a classic Maine colonial home that has retained the charm of the 1800's era while also adopting more modern updates along the way. Additional features include a newer propane heating system, replacement windows, timeless wide-plank wood flooring, high ceilings and a detached 2-car garage/barn with plenty of storage. There is even a hidden gem to discover in the woods behind the house; a small log outbuilding that catches rainwater for use. With its substantial acreage, established location and potential for commercial use, this is an opportunity to breathe new life into a piece of Winslow's past while creating something uniquely your own.

323 Augusta Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

121 Clinton Ave, Winslow
$349,000
2 Baths
Exceptional investment opportunity in Winslow! This well-maintained two-unit Colonial is move-in ready and currently vacant, allowing the next owner to establish their own rental rates, lease terms, and management approach from day one. Situated on a 0.24-acre lot with public water and sewer, the property offers a convenient location just minutes from the amenities, shopping, restaurants, and services of nearby Waterville and Fairfield. The first-floor apartment features a comfortable one-bedroom layout, while the second floor offers two bedrooms, a spacious great room, and an elevated deck that provides an inviting outdoor living space. A standout feature is the daylight, walk-out basement, which has previously been utilized as commercial space and may offer potential for additional income or flexible use, subject to municipal approvals and local zoning requirements. Completing the property is a spacious three-car garage, providing ample parking, storage, or workshop space. Whether you're seeking an owner-occupied property or a fully income-producing investment, this turnkey duplex offers outstanding versatility, excellent condition, and an ideal location. Call today for your private showing.

121 Clinton Ave, Winslow

Listing courtesy of Whittemore's Real Estate.

506 S Reynolds Rd, Winslow
$344,900
3 Beds ⋅ 2 Baths
Tucked away on a beautiful, private wooded lot in Winslow, Maine, this brand new Pine Grove G-242 home by NERTO Homes offers the perfect blend of modern style, comfort, and convenience! Featuring 3 bedrooms, 2 full bathrooms, and 1,344 square feet of thoughtfully designed living space, this home has an inviting open concept layout filled with natural light. The gorgeous kitchen features stylish cabinetry, tile backsplash, stainless steel appliances, a farmhouse sink, and a spacious peninsula perfect for entertaining. The primary suite offers a walk in closet and private bathroom with double vanities. Enjoy the peace and privacy of a wooded setting while being just minutes from shopping, dining, and amenities in Winslow, Waterville, and Augusta. The home is now onsite, and the finishing touches are underway! Updated photos and video coming very soon. Come take a look and see everything this beautiful new construction home has to offer!

506 S Reynolds Rd, Winslow

Listing courtesy of Summit Real Estate.

6 Blue Heron Ln, Winslow
$299,000
2 Beds ⋅ 1 Baths
This adorable and serene waterfront retreat on Pattee Pond is ready just in time for summer, offering the perfect blend of comfort, charm, and lakeside living. Built in 2012, the cottage features two bedrooms plus a large loft, a full bathroom with new toilet, and a generous kitchen featuring freshly painted cabinets, a new gas range and refrigerator that opens to inviting living and dining space with new flooring and a propane stove to enjoy on cool nights. A new water heater also provides peace of mind. A covered and open porch extends directly from the living area, giving you effortless indoor-outdoor flow and beautiful water views enhanced by new rustic-modern handrails. The grassy lot gently meets the shoreline, where you'll enjoy approximately 65 feet of private waterfrontage plus 16 feet shared, along with your own private dock for swimming, paddling, fishing and relaxing. A shed with electricity sits near the water for added convenience, and there's ample storage beneath the home plus plenty of space to roam. Located just minutes from Waterville's amenities, Colby & Thomas College, this peaceful property offers the ideal balance of accessibility and escape--your own lakeside retreat to enjoy all season long.

6 Blue Heron Ln, Winslow

Listing courtesy of Coldwell Banker Realty. 207-282-5988

16 Paine St, Winslow
$289,000
4 Beds ⋅ 2 Baths
Welcome to this well-maintained 1965 ranch, offering 4 bedrooms, 1 full bath, 1 half bath, about 2,184 square feet of living space, and a 2-car attached garage in a peaceful, established neighborhood. The main level features a spacious kitchen with ample cabinetry and an open connection to the living room (with hardwood flooring). The rest of upstairs includes 3 bedrooms, a full bath, and all hardwood floors. The finished basement includes a half bath, laundry room, tool room and a spacious bedroom and family room. The private, fenced in backyard includes a refurbished raised child's clubhouse with a new roof and a carpeted 7' x 7' play-and-sleeping area inside. Additional features include a paved driveway, roomy storage shed, new front steps, and a metal roof installed about 5 years ago. Included appliances and furnishings are a newer refrigerator and oven/stove, a microwave, washer, dryer, 3 portable air conditioners, a beautiful extendable kitchen table, office desk/chair, 2 comfortable couches, and a 46" Smart TV. Conveniently located within a quarter mile of shopping, restaurants, grocery, Walgreens and McDonald's. A Family-Friendly Community...Winslow High School is known locally for strong academics and high school sports. The community also offers active youth sports and recreation programs, including basketball, fall soccer, and intramurals. Winslow Public Schools provide opportunities in academics, athletics, music, performing arts, clubs, Advanced Placement, and college-credit courses. Our family has firsthand experience with Winslow Schools. All 3 of our children attended grades K-12 here and thrived at every age level under the district's academic excellence and school sports opportunities. With its character and charm, 16 Paine Street is an appealing opportunity for buyers seeking a vintage, "move-in ready" home in Winslow.

16 Paine St, Winslow

Listing courtesy of LAER.

33 Halifax St, Winslow
$269,900
4 Beds ⋅ 2 Baths
Welcome home! This well-maintained property offers plenty of space and flexibility in a convenient Winslow location. With thoughtful reconfiguration, the home could provide a comfortable 3-4 bedroom layout with room for everyone to spread out. The first floor features a formal dining room, laundry area, and enclosed porch, along with inviting living spaces. Outside, enjoy a level yard, private driveway, covered porch, and a two-car detached garage offering plenty of room for parking, storage, hobbies, or a workshop. Vinyl siding provides a low-maintenance exterior, making this a home that's easy to enjoy and maintain. A great opportunity to create a home that fits your needs in a convenient location!

33 Halifax St, Winslow

Listing courtesy of Summit Real Estate.

33 Halifax St, Winslow
$269,900
2 Baths
So many possibilities! This well-maintained two-unit property in a convenient Winslow location offers flexibility for an investor, owner-occupant, or buyer looking for a spacious single-family home. The first-floor unit features a large kitchen and a formal dining room which could be converted to a second bedroom. This unit also includes 1st floor laundry, a small pantry and an enclosed porch. With some minor changes, the second floor unit could be converted to bedrooms and the building could easily become a comfortable 3-4 bedroom home. Outside, enjoy a level yard, private driveway, covered porch, and a two-car detached garage with plenty of room for parking, storage, or hobbies. Vinyl siding keeps exterior maintenance to a minimum. Whether you're looking for rental income or a home you can make your own, this property is worth a look!

33 Halifax St, Winslow

Listing courtesy of Summit Real Estate.

559 Abbott Rd, Winslow
$250,000
3 Beds ⋅ 1 Baths
Character, natural light, and room to make it your own—welcome to 559 Abbott Road in Winslow. Offering approximately 2,185 square feet on approximately 2 acres, this 3-bedroom Cape is surrounded by mature trees and abundant established landscaping ready to be reclaimed and enjoyed. There's room for gardens, outdoor gathering spaces, or simply enjoying the privacy and beauty of the setting. Step in from the covered front porch to a home filled with possibility. The sunroom addition is a standout, with vaulted ceilings, walls of windows, and direct access to the yard. The spacious eat-in kitchen gives you room to redesign and remodel around your own style, while the walk-in pantry adds valuable everyday storage. The main level also includes a living room with wood stove, first-floor primary bedroom, separate office or flex space, and a full bath with laundry hookups. Upstairs, two additional bedrooms feature charming built-in dresser drawers and useful storage. A metal roof and Generac standby generator are already in place, and the detached 2-car garage offers additional storage above for tools, hobbies, or seasonal gear. This is a home for someone who can see the possibilities. Restore the gardens, refresh the interiors, and make the spaces your own. At the end of the day, can you picture yourself settling into a rocking chair on the covered porch and watching the sunset over the property? Bring your vision and come see what you can create here.

559 Abbott Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

979 Augusta Rd, Winslow
$250,000
3 Beds ⋅ 1 Baths
Lots of opportunity and potential with this classic farmhouse situated on 6 acres with water frontage! Offering approximately 1,400 square feet of finished living space, this property also features an incredible amount of additional space, with more than 6,000 square feet under roof. Beyond the main living area, you'll find multiple bonus and storage areas, including a large barn, spacious entryway, mudroom, tool rooms and additional storage areas. The second floor features four additional rooms that need some attention, offering the opportunity to bring this classic farmhouse back to its full potential. Continue to the third floor where you'll find even more space in need of repair, but with possibilities for attic storage or potential additional living space. With MU zoning and its unique, expansive layout, the property offers possibilities for use as a spacious single-family home or conversion to a multi-unit property. Outside, enjoy 6 acres of land and water frontage with a partially established trail leading toward the river. Conveniently located near the interstate, Thomas College and Colby College while still offering plenty of space and privacy. A truly unique property with character, history and room to make it your own.

979 Augusta Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

75 Halifax St Unit D32, Winslow
$209,000
2 Beds ⋅ 1 Baths
Welcome home to this pristine, move-in ready condominium in the well-established community of Fontaine Oaks Association. The building's secured entrance leads to clean and quiet common areas, and this unit's entry foyer offers a coat closet, a pantry closet and an adjacent laundry room. In the main living area, a bank of windows and a full light patio door make this south-facing condo warm and sunny. The open concept kitchen, dining area, and living room have been updated with laminate flooring, new handsome light fixtures and hardware, and newer appliances. The primary bedroom offers a wall-mounted smart TV that will convey as well as a large closet and private bath with shower and luxury vinyl flooring. The spacious main bathroom near the second bedroom features a tub/shower. Since this lovely condo is located at the back corner of the development, it abuts the property's wooded buffer, offering scenic views on both sides of the unit and giving it a treehouse feel. The seller has enjoyed watching for wildlife from the comforts of the covered porch, equipped with removable screens. The building's basement is bone dry with an association-owned commercial-grade dehumidifier, and each owner has a private locked 500 sf room for storage. This unit's storage room features an elevated walk-in cedar closet. Finally, you'll enjoy the convenience of having a private garage with an auto door opener. Act now to make this wonderful condominium your new affordable home for carefree living.

75 Halifax St Unit D32, Winslow

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

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