Winslow, ME Homes

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  /58

  $344,999 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,926 Sq Ft

  311 Benton Ave, Winslow, ME 04901

  New Price!! Graceful Craftsman-era home with Timeless Charm and Home Business Potential. This beautifully preserved 4-bedroom Victorian showcases original woodwork, detailed trim, and classic craftsmanship throughout. Features include formal living and dining rooms, two enclosed porches, and a cozy fireplace. The finished 3rd floor offers a versatile bonus space—ideal for a primary suite, home

  April Butler Integrity Homes Real Estate Group, PC

  

  311 Benton Ave, Winslow, ME 04901
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  /22

  $60,000 Sold Apr 30, 2025

  • 3,246 Sq Ft
  • $18/SF
  • 14 Days On Market

  • 2 Baths
  • Built 1920

  85 Benton Ave, Winslow, ME 04901

  Investors take notice! This property is in a prime location for exposure & convenience. Building is in need of extensive repair. 2 apartments & small storefront/office area. The 2 storefront rooms could easily be added to the first floor apartment to make it larger.ALL INFORMATION ON THE PROPERTY IS FROM THE TOWN OF WINSLOW. ENTER AT OWN RISK. HIGHLY SUGGESTED TO WEAR MASK & DRESS

  Dawn Gilman Century 21 Nason Realty

  

  85 Benton Ave, Winslow, ME 04901
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  /28

  Est $340,992 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,834 Sq Ft

  34 Frankwood Dr, Winslow, ME 04901

  

  34 Frankwood Dr, Winslow, ME 04901
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  /67

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 3,122 Sq Ft

  89 Benton Ave, Winslow, ME 04901

  Have you been looking for an affordable home in Central Maine? This could be the perfect opportunity for you. This home features 2 spacious bedrooms, 1 full bathroom, A big kitchen, living room, and dining room area upstairs. Downstairs is very open, and could be transformed into any envisions you may have. Located right across the bridge from the revitalized downtown Waterville area. Minutes to

  Corey Lee Real Broker

  

  89 Benton Ave, Winslow, ME 04901
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  /30

  $269,900 Sold Apr 30, 2025

  • 1,350 Sq Ft
  • $200/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  58 Meadow View Ln Unit 42, Winslow, ME 04901

  Don't miss the rare opportunity to own a spacious 3 bedroom 2 full bathroom, end unit condominium that offers easy one level living in a desirable location. This condo offers an open concept kitchen living room area. The kitchen has an ample amount of cabinets and pantry. The primary bedroom has it's own private En-Suite with a large walk-in closet. Head to the other end of the condo, and find

  Darcy Liberty Integrity Homes Real Estate Group, PC

  

  58 Meadow View Ln Unit 42, Winslow, ME 04901
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  /57

  Est $392,442 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft

  13 Frankwood Dr, Winslow, ME 04901

  

  13 Frankwood Dr, Winslow, ME 04901
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  /13

  $349,900

  • 2 Baths
  • 1,536 Sq Ft

  3 Baker St, Winslow, ME 04901

  Turn-Key Duplex with many updates since 2018. 2018 updates includes new propane boiler, new tankless hot water, all new vinyl windows, floors, kitchens (granite countertops), all new stainless appliances, bathrooms, plumbing and electric. New metal roof installed 2023. New paved driveways 2024. Unit 1 comes fully furnished. Unit has always been rented fully furnished for short-term stays

  Spenser Ouellette EXP Realty

  

  3 Baker St, Winslow, ME 04901
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  /23

  $350,000 Sold Apr 30, 2025

  • 3,000 Sq Ft
  • $117/SF
  • 6 Days On Market

  • 4 Baths
  • Built 1870

  47 Clinton Ave, Winslow, ME 04901

  Great rents in this Winslow 4 unit. there are 2 Two bedrooms and 2 One bedroom apartments. All have newer flooring and newer kitchens and baths. Laundry hook ups available and a covered porch for your tenants. Plenty of parking. 24-36 hour notice as a courtesy to these great tenants.

  Stephen Morgan Maine Real Estate Pros

  

  47 Clinton Ave, Winslow, ME 04901
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  /53

  Est $366,073 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  15 Frankwood Dr, Winslow, ME 04901

  

  15 Frankwood Dr, Winslow, ME 04901
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  /27

  $175,000

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  1 Chadwick St, Winslow, ME 04901

  Welcome to 1 Chadwick Street, a charming 2-bedroom home nestled on an oversized lot in a convenient Winslow location—close to schools, trails, and downtown. This property offers a great opportunity for buyers looking for a well-priced, functional home with room to make it their own.Recent updates include new kitchen flooring (2025), added electrical service and insulation in the garage (2023),

  Jason Erwin EXP Realty

  

  1 Chadwick St, Winslow, ME 04901
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  /25

  $299,000 Sold Apr 15, 2025

  • 1,008 Sq Ft
  • $297/SF
  • 1 Day On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  20 Smiley Ave, Winslow, ME 04901

  Welcome to 20 Smiley Avenue, Winslow! Step into the warmth of this inviting Ranch located in one of Winslow's most desirable neighborhoods. This home offers exceptional amenities inside and out. Single story living with 2 bedrooms, 1 bathroom, and a one car garage. This home features beautiful hardwood floors and a functional layout. Many upgrades such as new vinyl siding, an appealing stone

  Justine Duvall Coldwell Banker Plourde Real Estate

  

  20 Smiley Ave, Winslow, ME 04901
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  /51

  Est $433,555 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  6 Frankwood Dr, Winslow, ME 04901

  

  6 Frankwood Dr, Winslow, ME 04901
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  /44

  $275,000

  • 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, updated kitchen

  Patrick Coughlan Real Broker

  

  128 Benton Ave, Winslow, ME 04901
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  /38

  $475,000 Sold Apr 04, 2025

  • 2,444 Sq Ft
  • $194/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  16 Primrose St, Winslow, ME 04901

  Experience the epitome of modern living in this exquisite 4-bedroom Colonial home, ideally located on a beautifully landscaped corner lot in a highly coveted neighborhood. Step outside to the Winslow Community Trails, merely a stone's throw away from schools, sports fields, and a vibrant playground. The renovated kitchen features opulent granite countertops, a top-of-the-line Jenn-Air cooktop,

  Amy St Peter Your Home Sold Guaranteed Realty

  

  16 Primrose St, Winslow, ME 04901
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  /26

  Est $333,590 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,233 Sq Ft

  107 Perch Rd, Winslow, ME 04901

  

  107 Perch Rd, Winslow, ME 04901
• 

  

  /65

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft

  10 Hollingsworth St, Winslow, ME 04901

  This charming 3 bedroom 2 bath turn of the century New Englander abuts one of the numerous walking trails in the area. This home is one of the few that were built exclusively for the former executives of the Hollingsworth & Whitney Company. The character of this home is outstanding with period details including gleaming wood floors, original wood trim, stained glass & farmers porch. There are

  Tom Cole NextHome Premier Realty

  

  10 Hollingsworth St, Winslow, ME 04901
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  /34

  $197,000 Sold Apr 04, 2025

  • 1,024 Sq Ft
  • $192/SF
  • 68 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  5 Mar Val Terrace Unit A6, Winslow, ME 04901

  Move in ready- Meticulous condo in desired Winslow Community, This upper level unit is located up only a few stairs and on the back side of the building. Beautiful views of spacious, shared back yard, and flower gardens. Inside has been beautifully renovated and welcomes you as soon as you enter. Generous sized bedrooms, and in unit laundry makes this home feel even more luxurious. Association

  Michelle Casavant Summit Real Estate

  

  5 Mar Val Terrace Unit A6, Winslow, ME 04901
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  /18

  Est $245,374 Not Listed For Sale

  • 1 Bed
  • 0.5 Baths
  • 528 Sq Ft

  16 Black Raven Ln, Winslow, ME 04901

  

  16 Black Raven Ln, Winslow, ME 04901
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  /160

  $1,540,000

  • 7 Baths
  • 7,634 Sq Ft

  23 N Garand St, Winslow, ME 04901

  Welcome to 23 N. Garand Street an Amazing Investment Opportunity!! This Well Maintained Clean 7 Unit Complex Consists of 3-Duplex Style Ranch Home Buildings with Great Layouts and Design, Paved Wrap Around Driveway with Off Street Parking, Vaulted Ceilings, Full Basements, Newer Shingled Roofs in 2021, Decks, and In-Unit Washer and Dryer Hookups. Building #1 Features a Large 3 Bay Garage (Rented

  Robert Metayer Client First Realty Maine

  

  23 N Garand St, Winslow, ME 04901
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  /47

  $445,000 Sold Mar 31, 2025

  • 2,514 Sq Ft
  • $177/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1978

  1 Newcomb Dr, Winslow, ME 04901

  Welcome to 1 Newcomb Drive, a beautifully maintained 4-bedroom, 2.5-bathroom home in a sought-after Winslow neighborhood. This bright and airy home features a modern kitchen with updated appliances, a spacious living room with a built-in brick propane fireplace, and a convenient first-floor bedroom. Upstairs, you'll find a large master suite and two additional bedrooms. Step outside to a private

  Emily Caron Coldwell Banker Plourde Real Estate

  

  1 Newcomb Dr, Winslow, ME 04901
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  /30

  Est $225,482 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,122 Sq Ft

  2 White Fish Rd, Winslow, ME 04901

  

  2 White Fish Rd, Winslow, ME 04901
• 

  

  /25

  $80,000

  • Land
  • 2.02 Acres
  • $39,604 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.

  Jill Huard Summit Real Estate

  

  498 Morrill Rd, Benton, ME 04901
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  /43

  $350,000 Sold Mar 24, 2025

  • 1,820 Sq Ft
  • $192/SF
  • 4 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1900

  61 W Palmer Rd, Winslow, ME 04901

  Welcome to 61 West Palmer Road, Winslow, ME! This Farmhouse sits on 18 acres of open and wooded land that is perfect for the gentleman farmer, homesteader or outdoorsman. Plenty of wood on the land to heat your home for years to come, enjoy nature and the ITS 85 snowmobile trail that runs through this lot. Relax in the hot tub on the back deck after a long day of work! The first floor offers

  Lucas Adams Adams Realty

  

  61 W Palmer Rd, Winslow, ME 04901
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  /26

  Est $263,448 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  5 Donna St, Winslow, ME 04901

  

  5 Donna St, Winslow, ME 04901
• 

  

  /24

  $199,900

  • Land
  • 2.96 Acres
  • $67,534 per Acre

  0 China Rd, Winslow, ME 04901

  Have you been looking for an ideal location for your business? If so, this could be the perfect location! This 2.96 acre lot has 200' of prime commercial frontage on China Road in busy downtown Winslow. This lot is located in the mixed use district so it is approved for Commercial, Education, Municipal, or Residential. Land here does not come up often! Priced below tax assessed value. Come scoop

  Corey Lee Real Broker

  

  0 China Rd, Winslow, ME 04901
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  /30

  $208,000 Sold Mar 24, 2025

  • 1,223 Sq Ft
  • $170/SF
  • 20 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1850

  255 Clinton Ave, Winslow, ME 04901

  Discover quiet country living situated just minutes from Waterville's thriving downtown for dining, shopping, and the historic opera house. The remodeled kitchen offers plenty of cabinet space for all your storage needs. This home features a large full bath upstairs and a convenient commode on the first floor. A spacious barn provides excellent storage for vehicles or other uses. Enjoy the peace

  Kimberly Hawkes OWN REAL ESTATE

  

  255 Clinton Ave, Winslow, ME 04901
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  /48

  Est $270,956 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,060 Sq Ft

  11 Donna St, Winslow, ME 04901

  

  11 Donna St, Winslow, ME 04901
• 

  

  /23

  $329,000

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

  10 Private Dr, Winslow, ME 04901

  Desirable location for your new one level condo in a sought after neighborhood! Features an open floor plan, living room with propane fireplace and a cozy sunroom which leads to the deck with a privacy fence between the two units. Primary bedroom with full bath, separate dining area and kitchen with all appliances. All this plus an attached garage & a full private basement. Pet friendly too!

  Kim Moxcey Century 21 Nason Realty

  

  10 Private Dr, Winslow, ME 04901
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  /15

  $375,000 Sold Mar 21, 2025

  • 4,410 Sq Ft
  • $85/SF
  • 7 Days On Market

  • 5 Baths
  • Built 1900

  2 Bellevue St, Winslow, ME 04901

  Very profitable 4-unit in a convenient location. Many updates have been done over the years including new roofing shingles, insulation, and vinyl siding. This special property should appeal to both investors and buyers who are looking for an affordable multi-family building to call home and to build wealth. (Also could be purchased with 3 Monument St)

  Jeffrey Jolicoeur EXP Realty

  

  2 Bellevue St, Winslow, ME 04901
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  /16

  Est $274,039 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  6 Harry St, Winslow, ME 04901

  

  6 Harry St, Winslow, ME 04901
• 

  

  /10

  $69,900

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

  0 Olde Heritage Map 10 Lot 77-3 Place Unit 1618641, Winslow, ME 04901

  Tucked away at the end of a long, tree-lined drive, this beautiful cul-de-sac lot offers the perfect blend of privacy, space, and convenience. Nestled at the back of a wide open field, the lot is surrounded by mature trees that provide a peaceful natural buffer and a true sense of seclusion.As you approach, expansive views of the surrounding countryside unfold before you, hinting at the

  Matt Pouliot Pouliot Real Estate

  

  0 Olde Heritage Map 10 Lot 77-3 Place Unit 1618641, Winslow, ME 04901
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  /11

  $272,000 Sold Mar 21, 2025

  • 3,481 Sq Ft
  • $78/SF
  • 7 Days On Market

  • 3 Baths
  • Built 1870

  3 Monument St, Winslow, ME 04901

  Conveniently located within walking distance to downtown Waterville, this three-family building features a spacious 1700+ sq ft, 3-bedroom unit that would make an ideal owner-occupied space. Each unit has it's own laundry hookup which is sure to attract tenants. There is also a two-car garage that could either provide additional rental income or could be used for vehicle of other storage.

  Jeffrey Jolicoeur EXP Realty

  

  3 Monument St, Winslow, ME 04901
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  /44

  Est $325,785 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,865 Sq Ft

  101 Halifax St, Winslow, ME 04901

  

  101 Halifax St, Winslow, ME 04901
• 

  

  /87

  $829,000

  • 3 Beds
  • 2.5 Baths
  • 4,490 Sq Ft

  181 Bassett Rd, Winslow, ME 04901

  A beautiful winding driveway leads you past a lovely pond to this custom built home sitting on 14 pastoral acres. Classically styled 3 story barn on a full foundation with a lean-to off the side for even more storage. 12x16 chicken coop, screen building with a wood stove, and beautiful garden rows with rich fertilized soils, this property is perfect for homesteading and food production. Deer

  Tyler Gaudet Sprague & Curtis Real Estate

  

  181 Bassett Rd, Winslow, ME 04901
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  /14

  $41,000 Sold Mar 20, 2025

  • 924 Sq Ft
  • $44/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1984

  670 Benton Ave Unit 8, Winslow, ME 04901

  This is a must-see property. Located in a very well-maintained mobile home park in Winslow, this Oxford Mobile Home is in excellent condition and is move-in ready. This home features a spacious eat-in kitchen with ample counter space, plenty of storage, and updated appliances. This home boasts two bedrooms, one bathroom with a double vanity, and a roomy living area to entertain your guests.

  Garrett Quinn Whittemore's Real Estate

  

  670 Benton Ave Unit 8, Winslow, ME 04901
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  /4

  Est $290,748 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,585 Sq Ft

  2 Marcoux St, Winslow, ME 04901

  

  2 Marcoux St, Winslow, ME 04901
• 

  

  /45

  $388,000

  • 3 Baths
  • 2,656 Sq Ft

  16 S Garand St, Winslow, ME 04901

  Great Investment Opportunity! This charming multi-unit features two spacious apartments, each offering excellent value. The first unit boasts 3 bedrooms and 2 baths, while the second unit offers 3 bedrooms and 1 bath - perfect for families or tenants seeking extra space. Both units are well-maintained and include a bright, welcoming sun porch that adds a touch of warmth and character to the home.

  Kristen Nutter Summit Real Estate

  

  16 S Garand St, Winslow, ME 04901
• 

  

  /25

  $258,000 Sold Mar 19, 2025

  • 1,953 Sq Ft
  • $132/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  8 Lee St, Winslow, ME 04901

  Welcome to 8 Lee Street, Winslow! Upon entering this charming cape you will see a large mudroom, attached to the mudroom is a large bonus room that can be utilized for many different reasons. After that you will see a cozy dining room, kitchen combination, a large living room perfect for entertaining as well as private relaxing, 3 spacious bedrooms and 2 updated full baths. Don't forget about the

  Lucas Wheeler Coldwell Banker Plourde Real Estate

  

  8 Lee St, Winslow, ME 04901
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  /32

  Est $288,798 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,059 Sq Ft

  163 Clinton Ave, Winslow, ME 04901

  

  163 Clinton Ave, Winslow, ME 04901
• 

  /2

  $150,000

  • Land
  • 20 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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