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Homes for Sale near Winslow High School

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  • /16

    $237,500

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft

    13 Poulin St, Winslow, ME 04901

    Quaint and easy to maintain, this Winslow ranch features warm wood floors, vinyl windows, and an attached garage. The kitchen offers plenty of cabinets and countertop space, flowing to a sunny back porch that opens to a slate patio—perfect for morning coffee or evening grilling. Two heat pumps keep things comfortable year-round and easy to heat. Nicely sized bedrooms, a tidy bath, and a bright

    Agent Photo

    Jeffrey Jolicoeur

    EXP Realty

    (207) 618-9601

    13 Poulin St, Winslow, ME 04901
  • /29

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,303 Sq Ft

    158 Clinton Ave, Winslow, ME 04901

    Fully remodeled 2-3 bedroom, 1-bath ranch on a large, level 0.23-acre lot just minutes from Waterville. With a new propane boiler being installed in October of 2025, this 1,303 sq ft home is a clean slate waiting for you to make it your own. Updated features include new flooring throughout, fresh interior paint, an updated full bath, new interior doors and new windows in both the eat-in kitchen

    Agent Photo

    Jill Huard

    Summit Real Estate

    (207) 507-7583

    158 Clinton Ave, Winslow, ME 04901
  • /16

    $125,000

    • Land
    • 7 Acres
    • $17,857 per Acre

    360 Nowell Rd, Winslow, ME 04901

    Great 7 acre building lot in a peaceful rural setting on Winslow's outskirts. Well is already in place from an older home that was on site, demolished and removed. Bring your ideas for this beautiful spot that is ready for your dream home.

    Agent Photo

    Tim Fortin

    NextHome Northern Lights Realty

    (207) 346-5755

    360 Nowell Rd, Winslow, ME 04901
  • /27

    $74,900

    • Land
    • 2.02 Acres
    • $37,079 per Acre

    498 Morrill Rd, Benton, 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

    (207) 607-7975

    498 Morrill Rd, Benton, ME 04901
  • /27

    $139,000

    • 1 Bed
    • 1 Bath
    • 557 Sq Ft

    1 Oakhill Terrace, Winslow, ME 04901

    Discover this inviting and efficient 2-bedroom, 1-bath home offering a convenient first-floor laundry. The open layout provides a cozy yet functional space perfect for easy maintenance and comfort. Enjoy the convenience of a high efficiency modern heat pump hot water heater. Ideally located close to I-95, shopping, dining, and all local amenities—this home combines comfort, efficiency, and

    Dustin Larochelle Fontaine Family-The Real Estate Leader

    1 Oakhill Terrace, Winslow, ME 04901
  • /32

    $306,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    0 S Reynolds Road Lot 2 Rd Unit 1632273, Winslow, ME 04901

    This brand-new home offers the perfect blend of comfort, style, and convenience, all customizable to your taste! Featuring 3 bedrooms, 2 full baths, and a wide-open kitchen and living area, the layout is designed for easy, single-level living. The spacious master suite includes a walk-in closet and private bath with double sinks and a walk-in shower. Located in a desirable area of Waterville,

    Anna Boucher Summit Real Estate

    0 S Reynolds Road Lot 2 Rd Unit 1632273, Winslow, ME 04901
  • /54

    $329,000

    • 4 Beds
    • 2 Baths
    • 1,845 Sq Ft

    701 Augusta Rd, Winslow, ME 04901

    Set back from the road, this Winslow country Cape offers a peaceful place to slow down and enjoy simple Maine living. Mornings feel easy on the sun-filled three-season porch, and the large, private backyard is made for gardening, fresh air, and quiet moments on the deck, complete with raspberry bushes, rhubarb, and a chicken coop ready for your flock. Inside, the home blends character with

    Nicholas Isgro Keller Williams Realty

    701 Augusta Rd, Winslow, ME 04901
  • /50

    $369,000

    • 3 Beds
    • 3 Baths
    • 2,354 Sq Ft

    5 2nd St, Winslow, ME 04901

    Beautiful 3-Bedroom Colonial in Winslow! Nestled on a quiet dead-end street, this stunning Colonial offers 3 spacious bedrooms and 3 full baths, blending classic charm with modern comfort. Kitchen with newer appliances is perfect for entertaining, opening to a bright dining area and inviting living spaces. Step outside to your private backyard oasis featuring a sparkling saltwater in-ground

    Kirstin McQuillan Century 21 Nason Realty

    5 2nd St, Winslow, ME 04901
  • /59

    $354,900 Open Sat 9AM - 10:30AM

    • 3 Beds
    • 1.5 Baths
    • 1,512 Sq Ft

    5 Robert St, Winslow, ME 04901

    Have you been searching for easy one level living in one of Winslow's most desirable neighborhoods? This could be the one you have been waiting for. Step inside to a bright open concept kitchen and dining area, equipped with brand new KitchenAid appliances that are perfect for holiday meals and family gatherings. Off the kitchen, a spacious living room invites you to relax with a glass of wine by

    Corey Lee Real Broker

    5 Robert St, Winslow, ME 04901
  • /38

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    242 China Rd, Winslow, ME 04901

    Welcome to this charming 3-bedroom, 2-bathroom single-level ranch offering comfort, space, and unbeatable convenience. Enjoy easy single-living with radiant heat, central air, and an expansive layout that includes a full basement and oversized garage for all your storage needs. The large, private yard is perfect for outdoor gatherings, gardening, or simply unwinding. Whether you're a first-time

    Jamie Plourde Coldwell Banker Plourde Real Estate

    242 China Rd, Winslow, ME 04901
  • /50

    $295,000

    • 3 Beds
    • 3 Baths
    • 3,168 Sq Ft

    235 S Reynolds Rd, Winslow, ME 04901

    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

    Alysia Berry Keller Williams Realty

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

    $190,000

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft

    24 Meadow View Ln, Winslow, ME 04901

    Move-in ready, well-maintained condo conveniently located just minutes from walking trails, shopping, restaurants, in-town amenities and 1-95. This condo features one floor living, an open floor plan, laundry, 1 car garage and a secure dry storage area in the basement! Condo fee covers the heat, hot water, mowing, plowing and maintenance.

    Tina Clifford Coldwell Banker Plourde Real Estate

    24 Meadow View Ln, Winslow, ME 04901
  • /46

    $274,900

    • 3 Beds
    • 1.5 Baths
    • 1,691 Sq Ft

    88 Augusta Rd, Winslow, ME 04901

    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

    Sandra Irish Keller Williams Realty

    88 Augusta Rd, Winslow, ME 04901
  • /65

    $369,500

    • 2 Beds
    • 2 Baths
    • 1,508 Sq Ft

    2 Whippoorwill Dr Unit 35, Winslow, ME 04901

    13029 - Why 2 Whippoorwill Drive? Experience easy living in this charming ranch-style condo offering privacy because this home is located on a favorable corner lot, along with comfort and low-maintenance lifestyle. The setting features plenty of natural sunlight, allowing this home to be inviting. There is a whole house generator for convenience, private back deck, and as a bonus there is a

    Aaron Bolster Allied Realty

    2 Whippoorwill Dr Unit 35, Winslow, ME 04901
  • /19

    $199,900

    • 2 Beds
    • 1 Bath
    • 1,122 Sq Ft

    5 Mar Val Terrace Unit B1, Winslow, ME 04901

    Welcome to 5 Mar Val Terrace, Unit B1 an inviting 2-bedroom, 1-bath ground-level condo offering comfort, convenience, and style! This move-in-ready unit features abeautifully updated kitchen with stainless steel appliances and a modern bath with fresh finishes. Enjoy energy-efficient heating and cooling year-round with the recentlyinstalled heat pump. A spacious storage and laundry room

    Alice MacKenzie Coldwell Banker Plourde Real Estate

    5 Mar Val Terrace Unit B1, Winslow, ME 04901
  • /8

    $80,000

    • Land
    • 2.4 Acres
    • $33,333 per Acre

    484 China Rd, Winslow, ME 04901

    Imagine the endless possibilities of 2.4 acres just outside of the town of Winslow with the Well, Septic, Power and Driveway already completed. This land is just waiting for someone to build their perfect home or getaway retreat.

    Sonya Porter Burrill Adams Realty

    484 China Rd, Winslow, ME 04901
  • /28

    $40,000

    • 2 Beds
    • 1 Bath
    • 858 Sq Ft

    499 Augusta Rd Unit 24, Winslow, ME 04901

    This well-maintained 2-bedroom, 1-bath single-wide offers comfortable and affordable living in a quiet park community. The home is clean, bright, and ready for new owners. Enjoy easy, low-maintenance living in a welcoming neighborhood, all at an exceptional value.

    Nicholas Isgro Keller Williams Realty

    499 Augusta Rd Unit 24, Winslow, ME 04901
  • /54

    $365,000

    • 2 Beds
    • 2 Baths
    • 1,483 Sq Ft

    5 Chickadee Trail Unit 5, Winslow, ME 04901

    Beautiful, cozy, and peaceful doesn't begin to describe this well cared for condo. Located minutes from downtown Winslow and Waterville, shopping, entertainment, and restaurants are in short driving distance. With almost 1500 sq ft of living space this sweet home is open concept with an easily accessible kitchen, dining room area, attached 4 season sunroom, and living room. One side of the home

    Kara Bickford Coldwell Banker Realty

    5 Chickadee Trail Unit 5, Winslow, ME 04901
  • /12

    $45,000

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    670 Benton Ave Unit 8, Winslow, ME 04901

    Rather your looking for your first home, smaller home or one with easy 1 floor living and low maintenance, look no further as this move in ready mobile home is nowavailable. Located in a clean and quite mobile home park in Winslow, ideally located close to town and an easy commute to Fairfield, Waterville, or Benton. The homefeatures a metal roof, new appliances, big outdoor storage shed

    Victoria Helma Coldwell Banker Plourde Real Estate

    670 Benton Ave Unit 8, Winslow, ME 04901
  • /19

    $106,500

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    137 Heywood Rd, Winslow, ME 04901

    Situated on 1.72 acres along quiet Heywood Road in Winslow, this property offers a peaceful rural setting with open, level land and easy access to town. The lot already has power, a drilled well, and a private septic system installed in 2013, making it an ideal build-ready site. A detached one-car garage provides storage or workspace, while the existing home experienced significant water damage

    Spencer Wood United Country Lifestyle Properties of Maine

    137 Heywood Rd, Winslow, ME 04901
  • /7

    $48,000

    • Land
    • 2.2 Acres
    • $21,818 per Acre

    M2, L48B S Reynolds Rd, Benton, ME 04901

    Rural, wooded 2.2+/- acre lot but close to most amenities! Convenient to Winslow and Vassalboro. Great spot for you new home!

    Bart Stevens Century 21 Nason Realty

    M2, L48B S Reynolds Rd, Benton, ME 04901
  • /33

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,375 Sq Ft

    1 S Reynolds Rd, Winslow, ME 04901

    Welcome home to the Pleasant Valley Harding Model. A beautifully designed 3-bedroom, 2-bath ranch offering comfort, efficiency, and modern style. Set on a spacious 2.04-acre lot, this home provides the perfect blend of privacy and convenience. Tucked away on a quiet country road, yet just minutes from town, schools, and local amenities. Step inside to an open, airy layout where the kitchen takes

    Anna Boucher Summit Real Estate

    1 S Reynolds Rd, Winslow, ME 04901
  • /37

    $299,000

    • 2.5 Baths
    • 2,066 Sq Ft

    54 Bay St, Winslow, ME 04901

    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

    Kimberly Bard Coldwell Banker Plourde Real Estate

    54 Bay St, Winslow, ME 04901
  • /37

    $549,000

    • 4 Beds
    • 3 Baths
    • 3,210 Sq Ft

    105 S Pond Rd, Winslow, ME 04901

    Discover the charm and character of this beautifully unique home set on more than 10 peaceful acres in Winslow. This is not your typical cookie-cutter house, thoughtfully designed with comfort, function, and natural beauty in mind. Step inside to find four spacious bedrooms, a sun-filled interior thanks to large windows and kitchen skylights, and a layout that blends cozy charm with modern

    Pam Natole Coldwell Banker Plourde Real Estate

    105 S Pond Rd, Winslow, ME 04901
  • /28

    $369,500

    • 2 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21 Cardinal Way, Winslow, ME 04901

    One level living at its finest! This first floor, 2 bedroom, 2 full bath condo is located at the end of the street in a desirable, sought-after neighborhood. Features an open floor plan, modern kitchen with all appliances, separate dining area, large living room with a propane fireplace that opens to a lovely four-season sunroom! Primary bedroom has a modern, updated bath with walk-in shower.

    Kim Moxcey Century 21 Nason Realty

    21 Cardinal Way, Winslow, ME 04901
  • /2

    $65,000

    • Land
    • 2.27 Acres
    • $28,634 per Acre

    Lot 76 Bassett Rd, Winslow, ME 04901

    Beautiful 2.5-Acre Wooded Lot in Winslow, Maine - Approved for Building, Well, and Septic Welcome to your perfect piece of Maine! This stunning 2.5-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 perfect location to build your dream home.

    Michael Ellis Realty of Maine

    Lot 76 Bassett Rd, Winslow, ME 04901
  • /6

    $65,000

    • Land
    • 2.5 Acres
    • $26,000 per Acre

    lot 75 Bassett Rd, Winslow, ME 04901

    Beautiful 2.5-Acre Wooded Lot in Winslow, Maine - Approved for Building, Well, and SepticWelcome to your perfect piece of Maine! This stunning 2.5-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 perfect location to build your dream

    Michael Ellis Realty of Maine

    lot 75 Bassett Rd, Winslow, ME 04901
  • /25

    $179,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    441 S Reynolds Rd, Winslow, ME 04901

    Investor & Handyman Special - Prime Opportunity in Winslow!Attention savvy buyers! This charming older home is brimming with potential and ready for your finishing touches. Located in a desirable country neighborhood in the heart of Winslow, this property offers both immediate value and long-term possibilities.Recent Upgrades Include:•Brand new windows

    Kim Larrabee Berkshire Hathaway HomeServices Northeast Real Estate

    441 S Reynolds Rd, Winslow, ME 04901
  • /16

    $69,000

    • Land
    • 2.52 Acres
    • $27,381 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
  • /10

    $43,000

    • 2 Beds
    • 2 Baths
    • 884 Sq Ft

    499 Augusta Rd Unit 25, Winslow, ME 04901

    Affordable place to call home!! 2004 Astro single wide mobile home located in Spruce Ridge Mobile Home Park. This home set up offers 2 bedrooms,1 on each end of the home, the primary bedroom consists of a large walk-in closet, & full bathroom, 2nd bedroom offers a large closet, 2nd full bathroom with tub/shower combination, large living room opens to the eat-in kitchen, separate laundry room off

    Lisa Webb-Kalloch Rizzo Mattson

    499 Augusta Rd Unit 25, Winslow, ME 04901
  • /42

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,982 Sq Ft

    2 and 3 Blue Heron Ln, Winslow, ME 04901

    Amazing 2 for 1 special! The waterside cabin is seasonal with a main living area and bedroom on the first floor, loft overhead and panoramic views from the sunroom. The hillside cabin is year round with 2 bedrooms on the second level. Located on a triple lot with 2 sheds and shared well and septic. These adorable camps are turn key and ready to become your family compound or rental investment

    Jennifer Cammack EXP Realty

    2 and 3 Blue Heron Ln, Winslow, ME 04901
  • /3

    $200,000

    • 3 Baths
    • 2,000 Sq Ft

    29 Halifax St, Winslow, ME 04901

    Duplex located in-town Winslow featuring two spacious units — one with 4 bedrooms and 1 bathroom, the other with 2 bedrooms with potential for a third and 1 bathroom. Some updates include a new concrete driveway, metal roofing on the back, exterior paint, and some new flooring. Great opportunity for investment or owner-occupancy.

    Francois Rodrigue Keller Williams Realty

    29 Halifax St, Winslow, ME 04901
  • /35

    $229,000

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft

    436 N Pond Rd, Winslow, ME 04901

    Discover the perfect blend of country living and convenience with this charming mobile home nestled on 5.2 peaceful acres. Enjoy the privacy and space of a rural setting while being just minutes from town and all local amenities. A standout feature is the oversized garage—ideal for extra storage, a workshop, or even hobby space. Whether you're looking for room to roam, a place to garden, or

    Kacie Tillson Coldwell Banker Realty

    436 N Pond Rd, Winslow, ME 04901
  • /17

    $254,900

    • 2 Beds
    • 1.5 Baths
    • 1,730 Sq Ft

    85 Halifax St, Winslow, ME 04901

    Custom-Built 2-Bedroom Home with Character: This 2-bedroom, 1.5-bath custom-built home features beautiful woodwork and a double-sided working fireplace. While the home could use some updates, it offers solid craftsmanship and plenty of charm. Centrally located for easy access to shops, dining, and local amenities.

    Michael Bard Coldwell Banker Plourde Real Estate

    85 Halifax St, Winslow, ME 04901
  • /53

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,913 Sq Ft

    1 S Ridge Dr, Winslow, ME 04901

    Let's talk....This is a spacious and beautifully crafted, 3-bedroom, 2.5-bathroom contemporary ranch. Located in the very desirable South Ridge Estates neighborhood of Winslow ME, this home is surrounded by a veil of woods and sits proudly upon its own plateau. A spacious and bright floor plan opens to an oversized living room with cathedral ceilings, with a gas fireplace insert. From there flows

    Robbin Eusebio Coldwell Banker Plourde Real Estate

    1 S Ridge Dr, Winslow, ME 04901
  • /14

    $69,900

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

    0 Olde Heritage Map 10 Lot 77-3 Place Unit 1628289, Winslow, ME 04901

    Looking for the perfect place to build your dream home? This 2.63-acre lot might be just what you've been waiting for. Tucked at the end of a beautifully paved and tree-lined road, Olde Heritage Place offers a welcoming and attractive setting that makes for a great place to put down roots.The lot is already surveyed and soil tested, with underground power in place, so you can start

    Corey Lee Real Broker

    0 Olde Heritage Map 10 Lot 77-3 Place Unit 1628289, Winslow, ME 04901
  • /41

    $269,900

    • 3 Beds
    • 1.5 Baths
    • 1,380 Sq Ft

    128 Benton Ave, Winslow, ME 04901

    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,

    Patrick Coughlan Real Broker

    128 Benton Ave, Winslow, ME 04901
  • /2

    $150,000

    • Land
    • 19.59 Acres
    • $7,657 per Acre

    Lot 063 N Pond Rd, Winslow, ME 04901

    Come and see the potential of this recently surveyed 19+ acres.

    Michael Lee Century 21 Venture Ltd.

    Lot 063 N Pond Rd, Winslow, ME 04901
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