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Homes for Sale near Winslow High School

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  • /48

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,449 Sq Ft

    77 Halifax St, Winslow, ME 04901

    Recently renovated 3-bedroom, 1.5-bath New England-style home 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, fresh interior paint, replacement windows, a new propane furnace, and a freshly painted metal roof. This home offers a wonderful blend of classic character and

    Agent Photo

    Jill Huard

    Summit Real Estate

    77 Halifax St, Winslow, ME 04901
  • /39

    $499,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    1391 Albion Rd, Winslow, ME 04901

    1391 Albion Road, Winslow - Set on 4.97± acres in a peaceful country setting, this well-maintained home offers a practical design for everyday living. Open-concept layout that seamlessly connects the kitchen, dining, and living areas--ideal for both daily routines and entertaining. A primary suite, two additional bedrooms, and a second full bath, provide flexible space for a variety of living

    Agent Photo

    Rachel Anderson

    Coldwell Banker Plourde Real Estate

    1391 Albion Rd, Winslow, ME 04901
  • /27

    $69,900

    $30K PRICE DROP
    • Land
    • 2.02 Acres
    • $34,604 per Acre

    498 Morrill Rd, Winslow, ME 04901

    Build your dream home on this beautiful 2.02-acre lot in Winslow. With most of the groundwork already completed, including a drilled well and a leach field, you can start building right away. Enjoy the convenience of being close to town while still experiencing the tranquility of rural living. Power is readily available at the street, making this lot the perfect canvas for your future home.

    Agent Photo

    Jill Huard

    Summit Real Estate

    498 Morrill Rd, Winslow, ME 04901
  • /30

    $198,900

    • 2 Beds
    • 2 Baths
    • 1,141 Sq Ft

    75 Halifax St Unit 28, Winslow, ME 04901

    Welcome to easy, low maintenance living in this charming second floor condo in Fontaine Oaks Winslow, featuring 2 spacious bedrooms and 2 full bathrooms. Enjoy an abundance of storage space ( closet hall space & large private basement room) throughout, plus the convenience of your own garage for additional storage and parking. Relax on your private deck overlooking the beautifully landscaped side

    Kirstin McQuillan Century 21 Nason Realty

    75 Halifax St Unit 28, Winslow, ME 04901
  • /2

    $225,000

    • Land
    • 1.39 Acres
    • $161,871 per Acre

    288 China Rd, Winslow, ME 04901

    Prime development opportunity! This cleared parcel is ready for your vision and offers outstanding visibility with high daily traffic counts, making it an ideal location for a variety of uses. Conveniently located with excellent road frontage and easy access, this property provides the exposure and accessibility businesses need to thrive.

    Donald Plourde Coldwell Banker Plourde Real Estate

    288 China Rd, Winslow, ME 04901
  • /34

    $475,000

    $24K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 3,310 Sq Ft

    1300 China Rd, Winslow, ME 04901

    Beautifully landscaped private lot with large pond and expansive fenced-in back yard. All trim will be completed prior to closing. Recently renovated basement includes two bedrooms with option to complete kitchenette and bath. New wood stove and chimney liner installed in 2025 for heat supplement/backup source. Broker-owned.

    Rachel Merrill Century 21 Nason Realty

    1300 China Rd, Winslow, ME 04901
  • /6

    $100,000

    • Land
    • 5 Acres
    • $20,000 per Acre

    Lot 75-76 Bassett Rd, Winslow, ME 04901

    Two lots totaling 5 +/- wooded acres in Winslow, Maine -Lot 75 has been cleared and approved for a building site , well, and Septic Welcome to your perfect piece of Maine! This stunning 5+/- acre wooded lot in Winslow offers the ideal blend of privacy and convenience. Nestled in a peaceful rural setting, yet just a short 5-minute drive from local amenities and schools, this property provides the

    Michael Ellis Realty of Maine

    Lot 75-76 Bassett Rd, Winslow, ME 04901
  • /24

    $249,900

    $40K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    344 Benton Ave, Winslow, ME 04901

    Great home for the first time home buyer! Intown with nice backyard and updated kitchen! Easy access and a great place to start your real estate investing!

    Donald Plourde Coldwell Banker Plourde Real Estate

    344 Benton Ave, Winslow, ME 04901
  • /13

    $187,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    28 Meadow View Ln, Winslow, ME 04901

    Enjoy the ease of single-level living in this well-maintained 2-bedroom / 1 bathroom condo. Offering a comfortable and functional layout, this home is perfect for those looking to simplify without sacrificing convenience. Ample storage in the basement. The monthly condo fee includes both heat and hot water, making for worry-free living. Conveniently located close to shopping, dining, healthcare,

    Jamie Plourde Coldwell Banker Plourde Real Estate

    28 Meadow View Ln, Winslow, ME 04901
  • /22

    $299,900

    $30K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,775 Sq Ft

    8 Saint John St, Winslow, ME 04901

    Well-maintained 4 bedroom, 1 bath ranch located in Winslow. Conveniently situated close to in-town amenities including grocery shopping, gas stations, convenience stores, restaurants, and just a short drive to Waterville. Recent updates in 2025 include fresh paint throughout the home. The property features a full unfinished basement offering additional storage or potential for future use, as well

    Francois Rodrigue Keller Williams Realty

    8 Saint John St, Winslow, ME 04901
  • /2

    $55,000

    $10K PRICE DROP
    • Land
    • 2.27 Acres
    • $24,229 per Acre

    Lot 76 Bassett Rd, Winslow, ME 04901

    Beautiful 2.27-Acre Wooded Lot in Winslow, Maine - Approved for Building, Well, and Septic Welcome to your perfect piece of Maine! This stunning 2.27 -acre wooded lot in Winslow offers the ideal blend of privacy and convenience. Nestled in a peaceful rural setting, yet just a short 5-minute drive from local amenities and schools, this property provides the perfect location to build your dream

    Michael Ellis Realty of Maine

    Lot 76 Bassett Rd, Winslow, ME 04901
  • /21

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,530 Sq Ft

    599 China Rd, Winslow, ME 04901

    Located on a spacious 2.18-acre lot with its own pond, this charming 2-bedroom, 1-bath ranch is a must-see. It features a spacious open concept layout, which is perfect for hosting and entertaining guests. The backyard offers an expansive area, perfect for hosting summer barbecues. With ample space for gardening or outdoor activities, this property is a unique find.

    Lindsay Book The Maine Real Estate Experience

    599 China Rd, Winslow, ME 04901
  • /38

    $270,000

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 2,210 Sq Ft

    40 White Fish Rd, Winslow, ME 04901

    Tucked just steps from Pattee's Pond with beautiful water views, this truly unique property offers incredible flexibility, craftsmanship, and future potential. Currently configured as a spectacular heated retreat space with deeded water access, the structure features radiant floor heat, soaring wood interiors, a handcrafted sauna, and a dramatic upper-level loft complete with exercise area,

    Nicholas Isgro Keller Williams Realty

    40 White Fish Rd, Winslow, ME 04901
  • /41

    $329,000

    $26K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    19 Chickadee Trail Unit 19, Winslow, ME 04901

    Immaculate stand alone condo in a sought after neighborhood! This beautiful one owner home is in move-in shape! Features an open layout, attractive kitchen with all appliances and a large dining area open to the living room. Two nice sized bedrooms plus an attached garage, propane heat and even a heat pump! This condo allows pets too! There are two patios-one in front & one in back to enjoy your

    Kim Moxcey Century 21 Nason Realty

    19 Chickadee Trail Unit 19, Winslow, ME 04901
  • /29

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,505 Sq Ft

    168 Augusta Rd, Winslow, ME 04901

    Move-in ready 3-bedroom ranch with over 1,500+/- square feet of finished space and numerous updates in a convenient Winslow location. The kitchen opens to a sunny living room with wood floors, creating an inviting main living area. The partially finished lower level offers flexible bonus space ideal for a family room, home office, exercise area, hobby room, bar, or storage. Major updates include

    Jonathan Farr Rizzo Mattson

    168 Augusta Rd, Winslow, ME 04901
  • /19

    $315,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 739 Sq Ft

    6 Blue Heron Ln, Winslow, ME 04901

    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

    MAKAYLA ARMSTRONG Coldwell Banker Realty

    6 Blue Heron Ln, Winslow, ME 04901
  • /25

    $186,000

    $9K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,122 Sq Ft

    5 Mar Val Terrace Unit B3, Winslow, ME 04901

    Welcome to 5 Mar Val Terrace, Unit B3. Here you will find a move in ready 2 bedroom 1 bath condo. The kitchen & living room have an open concept feel. Off the kitchen is the laundry room and pantry/storage area. There is an ample amount of closets in this condo for all of your personal items. Enjoy energy efficient heating and cooling year-round with the heat pump. Two nice sized bedrooms and a

    Darcy Liberty Integrity Homes Real Estate Group, PC

    5 Mar Val Terrace Unit B3, Winslow, ME 04901
  • /47

    $325,000

    $50K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,676 Sq Ft

    380 Clinton Ave, Winslow, ME 04901

    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,

    Judy Williams Coldwell Banker Plourde Real Estate

    380 Clinton Ave, Winslow, ME 04901
  • /43

    $569,000

    • 3 Beds
    • 2.5 Baths
    • 2,472 Sq Ft

    25 Frankwood Dr, Winslow, ME 04901

    Move right into this beautifully maintained 3-bedroom, 2-bath home nestled in one of Winslow's sought after neighborhoods. The updated kitchen flows seamlessly into the dining area, creating a bright and inviting space for everyday living and entertaining. The spacious primary suite features a private ensuite bath, offering a comfortable retreat at the end of the day. Outside, you'll find a

    Donald Plourde Coldwell Banker Plourde Real Estate

    25 Frankwood Dr, Winslow, ME 04901
  • /16

    $64,900

    • Land
    • 2.52 Acres
    • $25,754 per Acre

    Lot 4 Peachtree Ln, Winslow, ME 04901

    Offering the perfect space to build your dream home as part of one of the most desirable areas of Winslow, this new expanded are of Peachtree Lane offers over 2.5 acres of private, wooded acres. Enjoy the serenity of country living just minutes away from the conveniences of Winslow and downtown Waterville. This is truly a unique opportunity bring your dreams to life!

    Nicholas Isgro Keller Williams Realty

    Lot 4 Peachtree Ln, Winslow, ME 04901
  • /30

    $239,900

    • 4 Beds
    • 1 Bath
    • 1,277 Sq Ft

    45 Cushman Rd, Winslow, ME 04901

    Charming 3-4 bedroom cape in a convenient neighborhood set on a pretty lot with a welcoming backyard & back deck to enjoy! Features a new boiler & oil tank in 2022 and 2 bedrooms on the main floor (one has the laundry hook-up and access to the back deck and would make a nice office!) On the second level you will find 2 nice bedrooms that share a closet at the top of the steps. All this plus an

    Kim Moxcey Century 21 Nason Realty

    45 Cushman Rd, Winslow, ME 04901
  • /13

    $69,900

    • Land
    • 2.63 Acres
    • $26,578 per Acre

    Lot 3 Olde Heritage Place, Winslow, ME 04901

    Looking for the perfect place to build your dream home? This 2.63-acre lot may be exactly what you have been waiting for. Nestled at the end of a beautifully paved, town-accepted, tree-lined road, Olde Heritage Place offers a welcoming setting and a wonderful opportunity to put down roots. The lot has already been surveyed and soil tested, allowing you to move forward with confidence. Enjoy the

    Corey Lee Real Broker

    Lot 3 Olde Heritage Place, Winslow, ME 04901
  • /62

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 3,715 Sq Ft

    26 S Reynolds Rd, Winslow, ME 04901

    Welcome to 26 S Reynolds Road in Winslow! This spacious 3-4 bedroom, 2.5 bath oversized Ranch style home offers over 3,500 sq ft of living space, including a fully finished basement-perfect for today's flexible lifestyle needs. Enter the home through the attached two-car garage into a convenient mudroom with laundry, providing the ideal drop zone for coats and shoes. The kitchen features an

    Darcy Liberty Integrity Homes Real Estate Group, PC

    26 S Reynolds Rd, Winslow, ME 04901
  • /27

    $125,000

    • Land
    • 6 Acres
    • $20,833 per Acre

    Lot 113-2 Cushman Rd, Winslow, ME 04901

    Welcome to Cushman Road in Winslow, Maine--Lot 113-2! This beautiful 6-acre parcel offers an impressive 636 feet of road frontage, providing both accessibility and privacy. With power and a well already in place, a soil test and much of the groundwork has been started for your future plans. The property features a driveway with access via a right-of-way, and offers a nice blend of mostly wooded

    Julie Peacock LAER

    Lot 113-2 Cushman Rd, Winslow, ME 04901
  • /8

    $179,900

    • 2 Beds
    • 1 Bath
    • 1,063 Sq Ft

    5 Mar-Val Terrace Unit D3, Winslow, ME 04901

    Move right into this comfortable and easy-to-maintain 2-bedroom, 1-bath condo in Winslow. Offering 1,063 square feet of living space, this home provides a practical layout and a lifestyle of convenience that today's buyers are looking for.Whether you're purchasing your first home, downsizing, or seeking a solid investment, this property delivers an appealing combination of comfort, value, and

    David White OwnerEntry.com

    5 Mar-Val Terrace Unit D3, Winslow, ME 04901
  • /27

    $250,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    245 China Rd, Winslow, ME 04901

    Discover comfortable, low-maintenance living at 245 China Road in Winslow. This well-maintained 2006 home offers 2 bedrooms, 2 full bathrooms, and approximately 920 square feet of thoughtfully designed living space--ideal for first-time buyers, downsizers, or anyone seeking an affordable, move-in-ready home. Inside, you'll find a bright living area, a functional kitchen with ample cabinet space,

    Ethan Jackson Drakes Real Estate LLC

    245 China Rd, Winslow, ME 04901
  • /31

    $340,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,405 Sq Ft

    15 Cushman Rd, Winslow, ME 04901

    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

    Emily Caron Coldwell Banker Plourde Real Estate

    15 Cushman Rd, Winslow, ME 04901
  • /28

    $329,900

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,441 Sq Ft

    941 Augusta Rd, Winslow, ME 04901

    Well-maintained 3 bedroom, 1.5 bath home located just outside of in-town Winslow, offering a convenient location with a short drive to Waterville and nearby local amenities. The home has seen several recent improvements, including fresh paint throughout in 2023. Exterior updates include the driveway being sealed in 2024, foundation freshly painted, and landscaping improvements with shrubs cleaned

    Francois Rodrigue Keller Williams Realty

    941 Augusta Rd, Winslow, ME 04901
  • /13

    $74,900

    • Land
    • 3.15 Acres
    • $23,778 per Acre

    Lot 2 Olde Heritage Place, Winslow, ME 04901

    Looking for the perfect place to build your dream home? This 3.15-acre lot may be exactly what you have been waiting for. Nestled at the end of a beautifully paved, town-accepted, tree-lined road, Olde Heritage Place offers a welcoming setting and a wonderful opportunity to put down roots. The lot has already been surveyed and soil tested, allowing you to move forward with confidence. Enjoy the

    Corey Lee Real Broker

    Lot 2 Olde Heritage Place, Winslow, ME 04901
  • /37

    $289,900

    $10K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,368 Sq Ft

    29 Smiley Ave, Winslow, ME 04901

    Welcome home to this 4-bedroom, 1.5-bath ranch-style property located on generous double lot, this home offers plenty of room both inside and out. Enjoy hardwood floors, a spacious layout perfect for entertaining family and friends, and a large backyard deck ideal for summer barbecues and outdoor gatherings. The full basement provides ample storage or potential for additional living space. With

    Jessica Fike Brookewood Realty

    29 Smiley Ave, Winslow, ME 04901
  • /13

    $73,900

    • Land
    • 2.35 Acres
    • $31,447 per Acre

    Lot 4 Olde Heritage Place, Winslow, ME 04901

    Looking for the perfect place to build your dream home? This 2.35-acre lot may be exactly what you have been waiting for. Nestled at the end of a beautifully paved, town-accepted, tree-lined road, Olde Heritage Place offers a welcoming setting and a wonderful opportunity to put down roots. The lot has already been surveyed and soil tested, allowing you to move forward with confidence. Enjoy the

    Corey Lee Real Broker

    Lot 4 Olde Heritage Place, Winslow, ME 04901
  • /21

    $349,000

    • 2 Baths
    • 2,352 Sq Ft

    121 Clinton Ave, Winslow, ME 04901

    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

    Garrett Quinn Whittemore's Real Estate

    121 Clinton Ave, Winslow, ME 04901
  • /49

    $299,900

    • 2 Beds
    • 2 Baths
    • 1,328 Sq Ft

    56 Heywood Rd, Winslow, ME 04901

    13120 - Heywood Road single family ranch style home with several garages available for sale. The large commercial garage located on the lower section of the property with it's own driveway is 32' X 50' insulated with 16' ceilings that has previously been used as a repair shop for heavy equipment. According to the Town of Winslow, the zoning is MU (Mixed Use). There is a recent septic inspection

    Aaron Bolster Allied Realty

    56 Heywood Rd, Winslow, ME 04901
  • /19

    $380,000

    • 4 Beds
    • 1 Bath
    • 2,080 Sq Ft

    1700 Albion Rd, Winslow, ME 04901

    Welcome to this well maintained home set on over 3 peaceful acres in Winslow. Enjoy the perfect balance of privacy and convenience with a rural setting just minutes from town, shopping and local amenities. Beautiful landscaping enhances the property's curb appeal, while the spacious two car garage provides plenty of room for vehicles and storage. A wonderful opportunity to enjoy country living

    Nathan Natole Coldwell Banker Plourde Real Estate

    1700 Albion Rd, Winslow, ME 04901
  • /2

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    14 Court St, Winslow, ME 04901

    Located in a quiet, centrally located cul-de-sac, 14 Court St in Winslow is a single-story home offering a spacious and practical layout. Set in a welcoming community of similar homes where neighbors are frequently out walking, the property is conveniently positioned just minutes from local schools and a quick trip across the bridge to downtown Waterville.The interior features an open-concept

    Heather Caron Coldwell Banker Realty

    14 Court St, Winslow, ME 04901
  • /13

    $179,500

    $8K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,122 Sq Ft

    5 Mar-Val Terrace Unit C3, Winslow, ME 04901

    Move-in ready in-town condo with many recent updates! This well-maintained condo offers convenient in-town living close to shopping, dining, schools, and local amenities. All appliances convey, including washer and dryer, stove, refrigerator, and dishwasher. The kitchen features newer appliances and a range hood installed last year. Additional updates include windows, a walk-in shower, new carpet

    Trisha Ware Coldwell Banker Plourde Real Estate

    5 Mar-Val Terrace Unit C3, Winslow, ME 04901
  • /49

    $235,000

    $25K PRICE DROP
    • 2 Baths
    • 1,632 Sq Ft

    118 Halifax St, Winslow, ME 04901

    Nice 2 unit multi-family home in the heart of Winslow! Each unit has 2 bedrooms & 1 bath, plus an enclosed porch. Nice basement with storage & laundry hookups. Many updates throughout, Including a newer roof in 2016 and furnace replaced in 2023. Don't miss this one! Call today for your private showing.

    Matthew Sivret Real Broker

    118 Halifax St, Winslow, ME 04901
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