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158 Bassett Rd, Winslow
$365,000
3 Beds ⋅ 2 Baths ⋅ 1663316 MLS
Step into comfort, style and convenience, with this beautiful 3 bedroom home on the outskirts of town. Offering the perfect blend of privacy and convenience just minutes from major amenities. Featuring a clean, modern aesthetic throughout, this move-in ready home offers bright living spaces and the finished basement adds incredible versatility, ideal for a family room, home office, fitness space, or guest retreat. The bright and open living spaces make this home perfect for gatherings. The spacious and level back yard has endless potential for family fun and entertaining. The attached garage offers extensive storage and functionality. This home is blissfully off the beaten path while still being only minutes from shopping, hospitals, restaurants, quick access to I-95 and schools. If you're looking for room to grow, this home is the perfect start to new beginnings.

158 Bassett Rd, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

Selling Office: Coldwell Banker Plourde Real Estate.

22 Court St, Winslow
$530,000
4 Beds ⋅ 3 Baths ⋅ 1661843 MLS
Offered to the market for the very first time, this one-owner home in Winslow's desirable Smiley Acres neighborhood reflects years of thoughtful care and timeless design. A paved driveway leads to the attached direct-entry two-car garage with overhead storage. Inside, the tiled mudroom with closet creates the perfect transition space and connects to the first-floor laundry room complete with a wash sink. Just beyond, the home opens into warm and inviting living spaces filled with natural light and classic details. The living room features gleaming wood floors, a brick gas fireplace, French doors leading to the rear deck. The kitchen serves as the heart of the home with its center island, wall oven, cooktop, pantry cabinetry, and a charming brick archway that echoes the character of the fireplace. A formal dining room, accessed through a pocket door, features custom built-ins and storage drawers provides the perfect setting for holiday meals, entertaining, and keeping seasonal décor neatly organized. The first floor also includes a family room, welcoming foyer with closet, full bath, and a spacious bedroom convenient one-floor living. Upstairs, the primary suite was designed as a peaceful retreat, featuring multiple closets, a private study, additional storage, and an ensuite bath with a standing shower and soaking jet tub. Two additional spacious bedrooms and another full bath complete the second level. The partially finished lower level offers excellent potential for a future media room, recreation area, or hobby space, while the utility room includes a workshop area for projects and storage. This is a rare opportunity to own a home where care, quality, and memories have been built over a lifetime.

22 Court St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

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

51 N Reynolds Rd, Winslow
$305,000
2 Beds ⋅ 1 Baths ⋅ 1656449 MLS
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.

73 Halifax St, Winslow
$237,500
2 Beds ⋅ 1 Baths ⋅ 1661042 MLS
This charming New-Englander style home has been tastefully and thoughtfully updated while preserving its original character and charm. Recent improvements include a completely renovated kitchen featuring new SS appliances. The spacious 20 x 30 great room has been fully redone and offers the perfect space for entertaining family and friends, with direct access to the large backyard. A formal dining room adds to the homes appeal, along with an additional versatile room that can be used as a bedroom or home office. Relax and unwind on the enclosed front porch, perfect for enjoying your morning coffee. The first-floor bathroom has also been updated. Upstairs you will find two bedrooms. The entire home has been freshly painted, and some rooms feature new LVP flooring, creating a clean and cohesive look. With nothing left to do but move in, this home is ready for it's next owners. Schedule your showing today!

73 Halifax St, Winslow

Listing courtesy of Integrity Homes Real Estate Group, PC.

Selling Office: EXP Realty.

41 White Fish Rd, Winslow
$625,000
2 Beds ⋅ 1 Baths ⋅ 1663545 MLS
Set on the shores of Pattee's Pond with beautiful sandy frontage and sweeping water views, this exceptional year-round waterfront retreat offers a truly one-of-a-kind living experience. Thoughtfully designed with extraordinary craftsmanship throughout, the home blends rustic lodge-inspired character with high-end finishes, featuring exposed natural timber beams, warm wood interiors, granite countertops, tiled baths, and stunning architectural details rarely found in the area. The open living space is highlighted by soaring ceilings, lofted sleeping area, and a custom rope bridge leading to an additional loft space, creating a setting that feels both inviting and unforgettable. Just steps from the water, the expansive deck overlooks the pond and private dock, while the incredible wood-fired pizza oven can be accessed from both inside and outside the home, offering a centerpiece for entertaining in every season. With approximately 100 feet of waterfront, breathtaking sunrise views, and a grandfathered setting remarkably close to the water's edge, this is a rare opportunity to own one of Pattee's Pond's most distinctive and compelling properties.

41 White Fish Rd, Winslow

Listing courtesy of Keller Williams Realty.

Selling Office: RE/MAX JARET & COHN.

5 Robert St, Winslow
$310,000
3 Beds ⋅ 2 Baths ⋅ 1654887 MLS
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.

218 S Reynolds Rd, Winslow
$675,000
4 Beds ⋅ 3 Baths ⋅ 1652856 MLS
Set privately along the South Reynolds Road, this thoughtfully updated contemporary home offers a rare balance of space, efficiency, and peaceful rural living -- all just minutes from town amenities. Positioned on 10 beautifully wooded and landscaped acres, the property provides a sense of quiet retreat while remaining conveniently accessible. Inside, 3,000± square feet of living space unfolds with an easy, comfortable flow designed for both everyday living and entertaining. Sunlight fills the open living areas, while the gas fireplace creates a warm focal point during Maine's winter months. The granite kitchen and formal dining spaces connect seamlessly, offering an inviting setting for gatherings large or small. A beautifully-appointed primary suite provides a private escape, complete with ensuite bath, soaking tub, walk-in closet, and built-in features--all designed with comfort and functionality in mind. Three additional bedrooms allow flexibility for guests, home office space, or multi-generational living. Outdoor living is equally enjoyable, with a spacious deck overlooking scenic woods and natural surroundings frequently visited by local wildlife. The property also features both an attached garage and an oversized detached garage that has roughly 2000 total square feet of floor space combined over both floors with plenty of room to work on all your vehicles and tons of storage space! The current owners have made a significant investment in long-term efficiency with a fully owned (not leased) solar energy system paired with Tesla battery storage, which has nearly eliminated their electricity bill. The system produces approximately 14.9 MWh annually, offsetting nearly all household energy use--including daily charging of a fully electric Ford F-150 Lightning. The result is an exceptionally low monthly bill along with a level of energy independence and sustainability rarely found in homes of this size.

218 S Reynolds Rd, Winslow

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

Selling Office: Meservier & Associates.

20 Court St, Winslow
$391,000
2 Beds ⋅ 2 Baths ⋅ 1659684 MLS
13088 - Welcome to 20 Court Street, nestled in Winslow's sought-after Smiley Acres neighborhood -- a home where warmth, comfort, and thoughtful design come together beautifully. Set on a quiet dead-end street, this meticulously maintained ranch invites you in from the moment you arrive, with colorful flower gardens framing the home, an inviting front porch perfect for morning coffee, and the kind of area where neighborly waves and evening conversations still exist. Step inside and feel instantly at home in the sun-filled open-concept kitchen and dining area, thoughtfully designed for everyday living and effortless entertaining. Just beyond, the spacious living room centers around a cozy built-in propane stove with rich wood mantle -- the perfect place to gather on cool Maine evenings. The first floor offers a generous primary bedroom retreat, a beautifully appointed bath with corner soaking tub, stand-up shower and double vanities, plus a second bedroom for guests or family. Down the wood staircase, the finished lower level opens a world of possibilities. Completely refinished with a full system by TC Hafford Basement Systems, including waterproof wainscoting half walls and poured concrete floors, this space is ideal for a family room, game room, or cozy den. A bonus room offers flexibility for an office, hobby room or additional bedroom, alongside a second full bath (to be completed before closing) and dedicated laundry room. Outside, enjoy an expansive two-car attached garage, paver patio, and open backyard ready for gardens, gatherings, and play -- a truly special place to call home.

20 Court St, Winslow

Listing courtesy of Allied Realty.

Selling Office: Rizzo Mattson.

891 Garland Rd, Winslow
$450,000
4 Beds ⋅ 3 Baths ⋅ 1659824 MLS
This well-maintained 4-bed, 3-bath Colonial is set on a sweeping 4-acre open lot and offers an attractive combination of space and flexibility. The first floor is designed for both everyday living and easy entertaining, with a welcoming open-concept layout that connects the kitchen, dining, and living areas. A full bath with laundry adds convenience, while a generously sized office with double closets provides excellent flexibility-- ideal for remote working, guests, or even a first-floor bedroom option. Upstairs, you'll find a comfortable primary suite with a walk-in closet and private full bath. Three additional bedrooms and another full bath offer ample space for family or visitors without feeling crowded. The full daylight walkout basement offers a variety of potential uses. Currently, as a fitness and informal family recreation area and warmed by a pellet stove, opportunities abound to finish this space further fully and as desired. Outdoors, relax on the charming farmer's porch, or gather with family and friends on the back deck overlooking the above-ground pool + hot tub and expansive yard beyond. Attached two-car garage and recent updates, including: Brand new roof and fresh interior paint throughout + newer appliances and pool liner. Conveniently located minutes from Colby and Thomas Colleges and downtown Waterville, with nearby access to local trails, parks, and the Sebasticook River, and an easy drive to Augusta, this home offers an ideal blend of comfort, flexibility, privacy, and accessibility. Do not miss this wonderful opportunity!

891 Garland Rd, Winslow

Listing courtesy of Keller Williams Realty. 207-553-2662

Selling Office: Coldwell Banker Plourde Real Estate.

6 Victor Ter, Winslow
$290,000
3 Beds ⋅ 1 Baths ⋅ 1657399 MLS
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.

14 Paine St, Winslow
$305,000
2 Beds ⋅ 1 Baths ⋅ 1657125 MLS
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.

137 Heywood Rd, Winslow
$63,000
3 Beds ⋅ 1 Baths ⋅ 1641590 MLS
Situated on 1.72 acres along quiet Heywood Road in Winslow, this property offers a peaceful rural setting with open, level land and easy access to town. The lot already has power, a drilled well, and a private septic system installed in 2013, making it an ideal build-ready site. A detached one-car garage provides storage or workspace, while the existing home experienced significant water damage from burst pipes and has not been repaired. The structure could be removed or fully renovated depending on your plans. This is a great opportunity for someone looking to start fresh with new construction or redevelop a property that already has the major infrastructure in place. Located just minutes from Waterville's shopping, restaurants, and hospital, and only a short drive to I-95, this property combines quiet country living with unbeatable convenience.

137 Heywood Rd, Winslow

Listing courtesy of United Country Lifestyle Properties of Maine. 207-794-6164

Selling Office: United Country Lifestyle Properties of Maine.

38 White Fish Rd, Winslow
$185,000
2 Beds ⋅ 1 Baths ⋅ 1657599 MLS
Escape to Pattee Pond with this rare waterfront opportunity! This charming seasonal camp sits close to the water and includes shared waterfront access with your own dock just steps away, making it easy to enjoy swimming, boating, and true lake life. Wake to loon calls, relax on the screened porch, and enjoy evenings by the firepit or out on the water. Inside features a bright, open layout with rustic pine, a cozy propane heater, a main-level bedroom, and a spacious loft for extra sleeping. The oversized family room offers beautiful pond views, and the yard is perfect for gatherings and outdoor fun. Located just minutes from Waterville's restaurants and nightlife, this property blends peaceful retreat with water access convenience--an ideal spot to create your perfect Maine summer escape.

38 White Fish Rd, Winslow

Listing courtesy of Your Home Sold Guaranteed Realty.

Selling Office: Listings Direct.

38 Corbett Ln, Winslow
$512,000
4 Beds ⋅ 3 Baths ⋅ 1655266 MLS
You have to see this beautiful, spacious, Colonial in Winslow to realize what you will have when you buy it. In addition to the regular rooms you would expect, this lovingly maintained home has a laundry room, a sunroom/office, a fireplaced formal living room with a wood stove insert, a separate dining room and an eat in kitchen. It also has a large, newly finished room in the basement (which can be accessed from inside the house and directly from the garage) that could be a home gym, game room, crafting space, or family room. All this and a new Standby generator. Located at the end of a dead-end street in a really nice, quiet neighborhood, you really need to come look at it to appreciate it.

38 Corbett Ln, Winslow

Listing courtesy of Adams Realty.

Selling Office: Keller Williams Realty.

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