Winslow Homes under $500,000

Welcome to Winslow, Maine—a charming town nestled in the heart of Kennebec County that beautifully blends small-town charm with modern conveniences. Known for its picturesque landscapes and vibrant community spirit, Winslow is an ideal place for families, retirees, and anyone looking to enjoy a serene lifestyle while still being close to urban amenities.

As you explore Winslow, you’ll find a variety of recreational opportunities, from scenic parks to the tranquil waters of the Kennebec River. The town is perfect for outdoor enthusiasts, offering hiking trails, fishing spots, and picnic areas that invite you to immerse yourself in nature. Winslow’s rich history is reflected in its well-preserved architecture and friendly neighborhoods, where community events foster a strong sense of belonging.

For those considering a move to this delightful town, you’ll be pleased to discover a range of homes available for under $500,000. Whether you’re seeking a cozy single-family home with a spacious yard or a charming bungalow with modern updates, Winslow’s real estate market offers something for everyone. With competitive pricing and a variety of options, homeownership in Winslow is not only attainable but also a smart investment in your future.

With its blend of affordability, community warmth, and natural beauty, Winslow, Maine, is a place where you can truly feel at home. Come explore the possibilities and discover why so many are choosing to make Winslow their forever home!

Newest Winslow Homes under $500,000

$284,000

4 Beds ⋅ 1 Baths ⋅ 1683121 MLS

This nice cape-style home features four bedrooms and an expansive yard. The layout includes two bedrooms on the second floor and two on the first—with one currently serving as a dining room. The interior boasts an eat-in kitchen updated with a new sink and countertop, plus a remodeled bathroom with a tub. Additional highlights include a full, unfinished basement, rewired outlets throughout, a new heating zone on the second floor, basement waterproofing and paint, fresh interior paint, and a new 24x26 two-car garage with 9' ceilings. It's all here, it just needs you!

26 Cushman Rd, Winslow

Listing courtesy of EXP Realty.

$249,900

3 Beds ⋅ 2 Baths ⋅ 1682569 MLS

If you've been looking for an intown house in a popular neighborhood, look no further. This 3 bed 2 bath home has been in the same family since 1973 and is now available for its next family to call it home. The house has a new metal roof installed in 2025 on the house, garage and shed. A new electric water heater was installed in 2025 as well. 2 heat sources and a large fenced in back yard are just a few of the reasons to not let the house go. Come take a look today and become the newest members of the neighborhood!

1 Robert St, Winslow

Listing courtesy of Coldwell Banker Plourde Real Estate.

$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.

$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.

$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.

$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.

$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.

$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.

$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..

$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.

$489,000

4 Beds ⋅ 2 Baths ⋅ 1679356 MLS

Beautiful 4-Bedroom Home with Solar, Pool & open spaces! Discover the perfect blend of comfort, space, and energy efficient living in this large 4-bedroom, 2-bath home, ideally situated on beautiful, level green acreage along Taylor Road in Winslow. Recent updates include an updated kitchen, improved insulation, deck with auto awning and solar panels designed to help keep electric costs remarkably low. Enjoy the convenience of a large 2-car attached garage plus additional outbuildings offering plenty of room for storage, hobbies, or workspace. Outside, the property truly shines with mature fruit trees, established gardens, a refreshing pool, and plenty of open lawn for entertaining, gardening, recreation, or simply enjoying the peaceful setting. With its combination of recent improvements, solar efficiency, generous living space, and exceptional outdoor amenities, this property offers a rare opportunity to enjoy country-style living with modern conveniences, all in a beautiful Winslow location.

87 Taylor Rd, Winslow

Listing courtesy of Century 21 Nason Realty.

$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.

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Winslow Homes under $500,000

Newest Winslow Homes under $500,000

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