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323 Augusta Rd, Winslow
$350,000
5 Beds ⋅ 2 Baths ⋅ 1681922 MLS
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.

559 Abbott Rd, Winslow
$280,000
3 Beds ⋅ 1 Baths ⋅ 1681909 MLS
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.

33 Halifax St, Winslow
$274,900
4 Beds ⋅ 2 Baths ⋅ 1681680 MLS
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
$274,900
2 Baths ⋅ 1681676 MLS
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.

1 Fortier St, Winslow
$329,000
4 Baths ⋅ 1680348 MLS
A true side-by-side duplex in a pleasant residential neighborhood, two units, each with 2 bedrooms, 1.5 baths, and its own heating system. No one living above or below you, which is what sets these units apart from a stacked two-family and keeps it a low vacancy rate. Tenants pay their own heat, electricity, and yard maintenance. Each unit has its own laundry hookups, a feature that's hard to find in rentals at this level. Roof shingles were replaced in 2020, so the largest maintenance item is already handled. Both tenants are month to month. That leaves the door open either way: hold it as a straight investment with income in place, or move into one side and let the other side help carry the mortgage.

1 Fortier St, Winslow

Listing courtesy of EXP Realty.

9 Poulin St, Winslow
$289,900
3 Beds ⋅ 1 Baths ⋅ 1680185 MLS
If you've been looking for an in-town home with an oversized garage, fenced in back yard and a functional lay out, look no further. This 3 bed,1 bath home offers the convenience of 1 story living with the addition of 2 good size bedrooms on the 2nd story. The oversized garage is perfect for those with more than 1 car, lots of toys or looking to add a workshop to the back. From the garage you enter directly into the mudroom which than leads into the Kitchen. The open Kitchen and living room area are ideal for entertaining and the updated bathroom, laundry room and Bedroom make it so you can live on one floor while having additional bedrooms upstairs. This cute cape has been well taken care of, it is close to all amenities Winslow has to offer and under 300k, come take a look and make this move-in ready home yours today!

9 Poulin St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

2 Bizier St, Winslow
$310,000
3 Beds ⋅ 2 Baths ⋅ 1679911 MLS
This raised ranch home is waiting for you in the Sunset Heights neighborhood in Winslow. The home welcomes you as you pull down the street with window boxes, warm color palette and landscaping. When you step inside you are on the main floor kitchen and dining area, bonus living room or den, half bath, utility room and laundry room. There is a one car garage accessible on this main level as well. When you continue up the stairs to the upper level the living room has lots of natural light, a brick fireplace and sliding glass door to the back deck. Down the hall you will find the full bathroom and three bedrooms. Outside the seller has created a backyard space with upper and lower deck sitting areas and a fenced in yard for pets. There is even a storage building. The home has been lovingly taken care of and was completely gutted and re-done in 2017 prior to the current owner where electrical, insulation, plumbing and all finishes were new. More recently a heat pump was added and replacement windows installed. Come see if this home is the right move for you!

2 Bizier St, Winslow

Listing courtesy of Taylor Realty, Inc..

40 Meadow View Ln Unit 40, Winslow
$180,000
2 Beds ⋅ 2 Baths ⋅ 1679898 MLS
** Seller is offering a 5000.00 credit for flooring & Paint in the condo**Welcome to Meadow View Condominiums! This one level unit offers 2-bedrooms and 1.5 baths in a quiet setting, just minutes from downtown Winslow & Waterville. The kitchen provides ample cabinet storage and counter space, flowing easily into the living room area. Both bedrooms are generously sized with closet space. The primary has a private half bath. The full bath includes an in-unit laundry for every day convenience. Step outside on your private deck, perfect for relaxing. This unit also includes a one car garage and a designated storage space in the basement. The association handles landscaping, snow removal, and general exterior upkeep, while the monthly HOA fee covers heat & hot water, making this a cost effective and low-maintenance lifestyle. Bring your style and taste, and make it home.

40 Meadow View Ln Unit 40, Winslow

Listing courtesy of Integrity Homes Real Estate Group, PC.

979 Augusta Rd, Winslow
$250,000
3 Beds ⋅ 1 Baths ⋅ 1679136 MLS
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.

593 Abbott Rd, Winslow
$349,900
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

16 Paine St, Winslow
$289,000
4 Beds ⋅ 2 Baths ⋅ 1676955 MLS
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.

950 China Rd, Winslow
$239,900
2 Beds ⋅ 2 Baths ⋅ 1675871 MLS
Impeccable Property on 3+ Private Acres! Nothing but the best awaits you at this beautifully maintained and remodeled property, offering the perfect blend of quality, privacy, and modern comfort. The remodeled mobile home features high-end finishes and appliances throughout, a 50 year transferable new roof installed this year, heat pump and pellet stove, creating n a truly move-in-ready home with a level of quality rarely found. The impressive heated, finished two-car garage provides exceptional space for vehicles, hobbies, storage, or a workshop. 2nd floor of garage could lend itself as a fantastic in law apartment! Step outside and enjoy two beautiful decks, including a large composite back deck perfect for entertaining or relaxing while taking in the peaceful private setting. Gorgeous, thoughtfully designed landscaping surrounds the property, adding to its exceptional appeal. Set on over 3 acres, this property offers privacy and serenity. Every detail has been thoughtfully considered and meticulously maintained. A TRULY special property where quality is evident at every turn! HUGE PRICE REDUCTION!

950 China Rd, Winslow

Listing courtesy of Century 21 Nason Realty.

380 Clinton Ave, Winslow
$299,000
3 Beds ⋅ 1 Baths ⋅ 1672018 MLS
Classic early 1800's farmhouse on 22 acres of fields and woods awaits your arrival. Interior in need of renovations, but many of the pricier items have already been addressed such as vinyl siding and replacement windows, metal roofs on house and barn, foundation repair, basement insulated and concrete floor installed. Outside, you'll find a huge post and beam barn ideal for storage, hobbies, livestock, or workshop space. Set in a picturesque location close to town, this property offers the perfect balance of country charm and everyday convenience. Whether you're looking for a potential Bed and Breakfast, a peaceful place to call home, a hobby farm, or a home with room to grow, this property is ready for your personal touches. All firewood in house and barn will remain. SELLER WILL CONSIDER ALL REASONABLE OFFERS

380 Clinton Ave, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

121 Clinton Ave, Winslow
$349,000
2 Baths ⋅ 1669867 MLS
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.

77 Halifax St, Winslow
$259,900
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. Listing Broker is a family member.

77 Halifax St, Winslow

Listing courtesy of Summit Real Estate.

6 Blue Heron Ln, Winslow
$299,000
2 Beds ⋅ 1 Baths ⋅ 1665008 MLS
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

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