Refine Search
Sort by
218 S Reynolds Rd, Winslow
$675,000
4 Beds ⋅ 3 Baths
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.

41 White Fish Rd, Winslow
$625,000
2 Beds ⋅ 1 Baths
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.

22 Court St, Winslow
$530,000
4 Beds ⋅ 3 Baths
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.

38 Corbett Ln, Winslow
$512,000
4 Beds ⋅ 3 Baths
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.

100 N Pond Rd, Winslow
$501,000
4 Beds ⋅ 3 Baths
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.

891 Garland Rd, Winslow
$450,000
4 Beds ⋅ 3 Baths
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.

681 Maple Ridge Rd, Winslow
$440,000
3 Beds ⋅ 2 Baths
Welcome to **681 Maple Ridge Road in Winslow**, a charming **3-bedroom log home privately situated on 8 wooded acres**, offering the perfect blend of comfort, privacy, and outdoor recreation. Set back from the road, this property provides a peaceful Maine setting surrounded by nature. Inside, the home features the warmth and character only a log home can offer, creating a cozy and inviting atmosphere. A **screened-in porch** provides the ideal place to relax and enjoy the outdoors--perfect for morning coffee, listening to the rain, or escaping Maine's buggy summer evenings while still taking in the surrounding woods. Outdoor enthusiasts will appreciate the direct access to nearby trail systems, making this property ideal for ATV riding, snowmobiling, hiking, and exploring the outdoors right from your own land. Additional features include a detached two-car garage and ample space for outdoor enjoyment across the wooded acreage. Whether you're looking for a year-round residence or a peaceful retreat, this property offers privacy, recreation, and the timeless appeal of log home living. Don't miss the opportunity to own your own Maine woodland escape while still being conveniently located near local amenities, and also close to China Lake.

681 Maple Ridge Rd, Winslow

Listing courtesy of Berkshire Hathaway HomeServices Northeast Real Estate.

Selling Office: Coldwell Banker Plourde Real Estate.

225 Morrill Rd, Winslow
$435,000
2 Beds ⋅ 3 Baths
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.

20 Court St, Winslow
$391,000
2 Beds ⋅ 2 Baths
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.

158 Bassett Rd, Winslow
$365,000
3 Beds ⋅ 2 Baths
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.

19 Cardinal Way Unit 10, Winslow
$356,000
2 Beds ⋅ 2 Baths
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.

176 Garland Rd, Winslow
$355,000
2 Beds ⋅ 2 Baths
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.

593 Abbott Rd, Winslow
$345,000
3 Beds ⋅ 2 Baths
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.

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.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Privacy Policy

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.

How much is your home worth?

Get instant property value now!

Valuation data provided by Black Knight EasyValue