Homes for sale under $300k in Winslow, ME

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ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Step back in time with this charming 1860 property that blends historic character with modern possibilities. Featuring beautiful woodwork throughout, this unique offering includes a main home, a spacious barn, and a versatile in-law suite—perfect for multi-generational living or guest accommodations. Ideally located close to Fort Halifax, local parks, shopping, dining, and other amenities, the property provides both convenience and charm. With its layout and prime location, it also presents an excellent commercial opportunity. Whether you envision it as a residence, business venture, or a mix of both, this timeless property offers endless potential.

$299,000

5 beds2.5 baths2,066 sq ft

54 Bay St, Winslow, ME 04901

In-law suite • Spacious barn • Historic character

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Welcome to this 3-bedroom, 3-bathroom home set on a generous 1.38-acre lot, offering the perfect blend of comfort, space, and versatility. This property features an attached in-law suite, ideal for multigenerational living or guest accommodations. Step inside to find a bright and spacious layout, complete with a well-appointed kitchen and cozy living areas. Each bedroom offers ample space with a primary suite with its own private bath. The in-law suite comes equipped with its own private entrance, living area, bathroom, and kitchenette, providing added flexibility and privacy for extended family or rental potential. Enjoy the outdoors with expansive yard space, perfect for gardening, entert

$295,000

3 beds3 baths3,168 sq ft

235 S Reynolds Rd, Winslow, ME 04901

1.38 acre lot • Garage • Built 1973

FOR SALE BY OWNER

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
For Sale 1 Leland Street, Winslow, ME Discover your next home in one of Winslows most desired neighborhoods! This charming property combines comfort, style, and convenience in a peaceful setting. Highlights: Quiet neighborhood, perfect for relaxing and unwinding Spacious two-car garage for vehicles, storage, or workshop space Expansive large deckideal for entertaining, barbecues, or morning coffee Beautifully updated interior with modern touches throughout Convenient in-town location, close to schools, shopping, and local amenities This home truly blends modern updates with small-town charm, offering a move-in ready lifestyle in a location everyone wants to be. Address: 1 Lelan

$279,999

3 beds1 bath1,166 sq ft

1 Leland St, Winslow, ME 04901

Expansive large deck • 8,712 sq ft lot • Built 1964

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Attention Investors! Welcome to 88 Augusta Road in Winslow! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort, versatility, and convenience. Once a two-family residence (the garage was once a 1 bed 1 bath), this property can easily be converted back with proper town permitting and a certificate of occupancy—offering great potential for rental income or multi-generational living. Step inside to find a bright and inviting living space filled with natural light and thoughtful updates throughout. The kitchen provides ample cabinet space and opens seamlessly to the dining and living areas—ideal for both everyday living and entertaining. The first floor featur

$274,900

3 beds1.5 baths1,691 sq ft

88 Augusta Rd, Winslow, ME 04901

Bright living space • Spacious yard • Two family residence

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Charming New Englander in the Heart of Winslow. Walking distance to Winslow Jr High and High school. Welcome to 128 Benton Avenue a beautifully maintained 3-bedroom, 1.5-bath New Englander that blends timeless character with thoughtful updates. Built in 1915, this 1,380 sq ft home offers classic charm and modern convenience in a walkable, in-town location. Step into a spacious, updated kitchen featuring ample cabinetry and modern appliances, perfect for everyday cooking and entertaining. The flexible first-floor layout includes a half bath, living room, and a versatile laundry room that could serve as a formal dining room or even a fourth bedroom. Upstairs, you'll find three bedrooms with o

$269,900

3 beds1.5 baths1,380 sq ft

128 Benton Ave, Winslow, ME 04901

5,227 sq ft lot • Parking • Built 1915

Property at 364 Cushman Rd, Winslow, ME 04901, 2 beds, 1.5 baths

$260,000

2 beds1.5 baths991 sq ft

364 Cushman Rd, Winslow, ME 04901

Property at 85 Halifax St, Winslow, ME 04901, 2 beds, 1.5 baths

$254,900

2 beds1.5 baths1,730 sq ft

85 Halifax St, Winslow, ME 04901

Property at 436 N Pond Rd, Winslow, ME 04901, 2 beds, 1 bath

$229,000

2 beds1 bath854 sq ft

436 N Pond Rd, Winslow, ME 04901

Property at 13 Poulin St, Winslow, ME 04901, 2 beds, 1 bath

$219,500

2 beds1 bath1,040 sq ft

13 Poulin St, Winslow, ME 04901

Property at 29 Halifax St, Winslow, ME 04901, 6 beds, 3 baths

$200,000

6 beds3 baths2,000 sq ft

29 Halifax St, Winslow, ME 04901

Property at 5 Mar Val Ter Unit B1, Winslow, ME 04901, 2 beds, 1 bath

$199,900

2 beds1 bath1,122 sq ft

5 Mar Val Ter Unit B1, Winslow, ME 04901

Property at 441 S Reynolds Rd Rd, Winslow, ME 04901, 2 beds, 1 bath

$179,000

2 beds1 bath720 sq ft

441 S Reynolds Rd Rd, Winslow, ME 04901

Property at 137 Heywood Rd, Winslow, ME 04901, 3 beds, 1 bath

$106,500

3 beds1 bath960 sq ft

137 Heywood Rd, Winslow, ME 04901

Property at 670 Benton Ave #8, Winslow, ME 04901, 2 beds, 1 bath

$45,000

2 beds1 bath980 sq ft

670 Benton Ave #8, Winslow, ME 04901

Property at 499 Augusta Rd #25, Winslow, ME 04901, 2 beds, 2 baths

$43,000

2 beds2 baths884 sq ft

499 Augusta Rd #25, Winslow, ME 04901

Property at 499 Augusta Rd #24, Winslow, ME 04901, 2 beds, 1 bath

$40,000

2 beds1 bath858 sq ft

499 Augusta Rd #24, Winslow, ME 04901

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ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
This recently remodeled, move-in ready home offers one-level, open-concept living with a warm and inviting feel. Conveniently located in a quiet neighborhood close to downtown amenities and the interstate, it's perfect for an easy commute. The kitchen boasts granite countertops, newer appliances, and a spacious center island, ideal for cooking and entertaining. Additional features include a first-floor laundry room, a full basement with ample storage, and a beautifully landscaped yard. Open House: Saturday, November 8, from 11-1.

$299,900

3 beds2 baths1,296 sq ft

30 Cottage St, Fairfield, ME 04937

0.34 acre lot • Parking • Built 1968

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Welcome to your perfect new investment property! The impressively spacious duplex has 2 identical sides that consists of 3 bedrooms and 2 full bathrooms and over 1200 sq ft of living space each! The property is turn key with many updates already done for you. New LVP floors, fresh paint, modern fixtures on each side. A new on-demand boiler and hot water heater have been installed and side #32 has a finished bonus space. Each side has their own basement and front porch area to entertain on. There is a cozy backyard and a park within eyeshot. This property is close to downtown for shopping, dining, farmers markets, Colby and Thomas College and the highway. This property has solid rental hist

$299,900

6 beds4 baths2,520 sq ft

30-32 Green St, Waterville, ME 04901

Fresh paint • New lvp floors • Spacious duplex

$299,000

2 beds2 baths1,608 sq ft

23 West St, Waterville, ME 04901

Former schoolhouse • Expansive yard • Updated interior

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Location meets functionality! This lovely 3+ bedroom, 2 full bath ranch sits on a prime in-town corner lot in Waterville. Previously used for multiple in-home businesses, including a daycare and a dance studio. Flexible layout with two kitchens, a main-level living room, and a lower-level family room are ideal for multigenerational living or rental potential. Two driveways and a back deck to enjoy. Close to Waterville High School, Colby College, Maine General, and all of Waterville's growing amenities. Additional photos coming soon.

$289,900

4 beds2 baths2,637 sq ft

122 Western Ave, Waterville, ME 04901

Two driveways • Two kitchens • Back deck

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Move right into this beautifully well-kept single-family style condo featuring 4 bedrooms, 2 full baths with a heat pump installed on the main floor for cooling and additional heat. Convenient direct entry 1-car garage right into the kitchen. Located in a desirable association, this home offers the perfect blend of comfort, convenience, and low-maintenance living—all in a warm and welcoming community you'll love to call home!

$285,000

4 beds2 baths1,404 sq ft

111 Evergreen Dr #111, Waterville, ME 04901

$250 HOA • Garage • Built 1988

ABOUT THIS HOME
Homes for sale under $300k in Winslow, ME
Located in one of Waterville's more sought-after neighborhoods, this charming 3-bedroom ranch is a rare find. Warm and inviting, the open family room, complete with wood stove and the designated dining area all contribute to making this a place to call home. The home has been well attended to over the years, including a newly remodeled walk-in shower with tile finish, newly shingled roof on the house and garage (April 2024), a spacious stone patio and Dry-locked basement floor and walls for peace of mind. Outdoors, you'll enjoy a large, private backyard with plenty of room for gardening, unwinding or even entertaining. The attached one-car garage offers direct entry to the home, additional

$282,500

3 beds1 bath1,500 sq ft

11 Averill Ter, Waterville, ME 04901

Newly shingled roof • Spacious stone patio • Direct entry to home

Property at 23 Western Ave, Waterville, ME 04901, 6 beds, 2 baths

$269,900

6 beds2 baths2,913 sq ft

23 Western Ave, Waterville, ME 04901

Property at 10 Edgewood St, Waterville, ME 04901, 4 beds, 1.5 baths

$265,000

4 beds1.5 baths1,438 sq ft

10 Edgewood St, Waterville, ME 04901

Property at 55 Western Ave, Waterville, ME 04901, 6 beds, 2 baths

$259,900

6 beds2 baths2,346 sq ft

55 Western Ave, Waterville, ME 04901

Property at 13 Lincoln Woods Ln #13, Waterville, ME 04901, 2 beds, 1.5 baths

$249,900

2 beds1.5 baths1,688 sq ft

13 Lincoln Woods Ln #13, Waterville, ME 04901

Property at 59 Drummond Ave, Waterville, ME 04901, 4 beds, 2 baths

$249,900

4 beds2 baths1,664 sq ft

59 Drummond Ave, Waterville, ME 04901

Property at 59 Summer St, Waterville, ME 04901, 4 beds, 2 baths

$249,900

4 beds2 baths1,942 sq ft

59 Summer St, Waterville, ME 04901

Property at 3 Bunker Ave, Fairfield, ME 04937, 3 beds, 1 bath

$249,900

3 beds1 bath1,124 sq ft

3 Bunker Ave, Fairfield, ME 04937

Property at 11 College Ave, Waterville, ME 04901, 7 beds, 3 baths

$249,900

7 beds3 baths3,414 sq ft

11 College Ave, Waterville, ME 04901

Property at 199 Neck Rd, Benton, ME 04901, 3 beds, 2 baths

$249,000

3 beds2 baths1,493 sq ft

199 Neck Rd, Benton, ME 04901

Property at 1 Bowie Ln #1, Waterville, ME 04901, 2 beds, 1 bath

$249,000

2 beds1 bath1,240 sq ft

1 Bowie Ln #1, Waterville, ME 04901

Property at 13 Junipers Ln #6, Oakland, ME 04963, 2 beds, 2 baths

$240,000

2 beds2 baths1,064 sq ft

13 Junipers Ln #6, Oakland, ME 04963

Property at 36 Central Ave, Waterville, ME 04901, 2 beds, 1 bath

$235,000

2 beds1 bath840 sq ft

36 Central Ave, Waterville, ME 04901

Property at 6 Linden St, Waterville, ME 04901, 3 beds, 2 baths

$229,999

3 beds2 baths1,418 sq ft

6 Linden St, Waterville, ME 04901

Property at 10 Leighton St, Waterville, ME 04901, 4 beds, 2 baths

$229,000

4 beds2 baths1,620 sq ft

10 Leighton St, Waterville, ME 04901

Homes for sale under $300k in Winslow

There are currently 16 homes for sale under $300k in Winslow. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winslow stay on the market for 34 days. This map is refreshed with the newest listings in Winslow every 15 minutes.

In the past month, 11 homes have been sold in Winslow. In addition to houses in Winslow, there were also 5 condos, 0 townhouses, and 4 multi-family units for sale in Winslow last month. Find your dream home in Winslow using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winslow are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winslow. Our Winslow real estate stats and trends will give you more information about home buying and selling trends in Winslow. If you're looking to sell your home in the Winslow area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winslow with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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