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Homes for Sale near Winthrop High School

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  • /58

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft

    39 Turtle Run Rd Unit 8, Winthrop, ME 04364

    Lakeside Village waterfront Condo on coveted Cobbossee . Central Maine 's only year round condo situated on 7 acres in a sheltered cove with fabulous southern exposure on 700 feet of waterfrontage. Enter the reception foyer area where your mailbox is and intercom system to contact owners for axcess .Take the elevator to your second floor end unit that has 2 bedrooms and 2 full baths .Cook's

    Agent Photo

    John Blouin

    LAER

    (207) 690-6153

    39 Turtle Run Rd Unit 8, Winthrop, ME 04364
  • /54

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,308 Sq Ft

    545 Memorial Dr, Winthrop, ME 04364

    Lovely year round home with 100' Maranacook Lake frontage. Completely renovated with expansive windows to take in the sunset views. Large wrap around deck is a wonderful place to relax, entertain and over water frontage, lawns and gardens. Beautifully remodeled kitchen with stainless appliances, propane cookstove, tiled back splash, center island, granite counters all open to dining area and

    Pat Ladd Homestead Realty

    545 Memorial Dr, Winthrop, ME 04364
  • /49

    $799,900

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    160 Heritage Woods Ln, Winthrop, ME 04364

    This beautiful red home in Winthrop is a true lakeside gem, located right on the edge of the gorgeous Cobbosseeconte Lake. Spacious and full of charm, it features 2 bedrooms and 2 bathrooms, with an open-concept kitchen, dining, and living area. The main floor bathroom/laundry room includes cozy heated tile floors, and the upstairs welcomes you with a large foyer and coat closet. Both bedrooms

    Jessica Fike Brookewood Realty

    160 Heritage Woods Ln, Winthrop, ME 04364
  • /69

    $499,000

    • 4 Beds
    • 2 Baths
    • 2,344 Sq Ft

    206 Route 133, Winthrop, ME 04364

    This 1891 farmhouse is nestled on 11 acres just minutes from Maranacook Lake and downtown Winthrop. Featuring four spacious bedrooms and two full bathrooms, this home blends historic character with modern comfort. The main floor boasts an open, flowing layout ideal for both everyday living and entertaining, with versatile spaces perfect for a home office, library, or den. Natural light pours in

    Heather Allen Szala Sprague & Curtis Real Estate

    206 Route 133, Winthrop, ME 04364
  • /82

    $539,900

    • 4 Beds
    • 3 Baths
    • 2,233 Sq Ft

    72 Annabessacook Dr, Winthrop, ME 04364

    Experience the epitome of lakeside living with exclusive deeded access to 200' of Annabessacook Lake waterfront, offering all the joys of lakefront life without the higher costs of lakefront taxes. Whether you crave winter adventures like snowmobiling and ice fishing or prefer summer pastimes such as kayaking, water skiing and boating, this year-round sanctuary promises endless outdoor activities

    Michael Roddy Your Home Sold Guaranteed Realty

    72 Annabessacook Dr, Winthrop, ME 04364
  • /4

    $559,900

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    Lot #6 Fox Run Ln, Winthrop, ME 04364

    Similar to be built or bring the builder your own plans. Highly sought after town of Winthrop location. New construction 1416 SF ranch style home with farmers porch including 3 bedrooms two baths propane radiant heat an attached garage all on 1.93 acres to be constructed by B.L.Williams Const. Building also packages offered.

    Jeffrey Perkins Brookewood Realty

    Lot #6 Fox Run Ln, Winthrop, ME 04364
  • /28

    $760,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 3,360 Sq Ft

    467 Memorial Dr, Winthrop, ME 04364

    Ashley Croll NextHome Northern Lights Realty

    467 Memorial Dr, Winthrop, ME 04364
  • /29

    $212,000

    • Land
    • 12 Acres
    • $17,264 per Acre

    M3 L9 Winthrop Center Rd, Winthrop, ME 04364

    Rare opportunity to own 12.28 acres of beautiful, wooded land with an impressive 1,315 feet of waterfront on Cobbossee Lake. Nestled in peaceful Longfellow Cove, this property offers a quiet retreat surrounded by nature. Enjoy serene views, privacy, and abundant wildlife—ducks, deer, turtles, and even the occasional moose. Whether you're looking to build your dream home, create a private getaway,

    Maria Kempton LAER

    M3 L9 Winthrop Center Rd, Winthrop, ME 04364
  • /2

    $37,500

    • Land
    • 2.26 Acres
    • $16,593 per Acre

    M003L006 Winthrop Center Rd, Winthrop, ME 04364

    Here's your chance to own a beautiful 2+/-acre lot right on the corner of Winthrop Center Road and Pine Point Lane. This spot offers a great mix of privacy and convenience—just a short drive to downtown Winthrop, local schools, and several nearby lakes. Come take a walk around and see what this lot has to offer!

    Josh Plowman Plowman Realty Group

    M003L006 Winthrop Center Rd, Winthrop, ME 04364
  • /54

    $319,000

    • 4 Beds
    • 1 Bath
    • 1,498 Sq Ft

    25 Holmes Rd, Winthrop, ME 04364

    This adorable little cape is nestled in a great neighborhood on a quiet street, making it the perfect place for those seeking a peaceful and serene atmosphere. The property boasts a spacious 1.3 acres, providing plenty of room for outdoor activities and privacy from neighbors. The back yard is a private oasis, ideal for relaxing or entertaining guests. For those with multiple vehicles, the 2 car

    Tracie Pooley Pooley Realty Group

    25 Holmes Rd, Winthrop, ME 04364
  • /44

    $425,000

    • 2 Beds
    • 3 Baths
    • 1,264 Sq Ft

    27 Mace Ave, Winthrop, ME 04364

    Escape to this cozy, year-round or seasonal retreat nestled at the head of beautiful Cobbossee Lake. Perfect for those seeking relaxation or adventure, this charming home has it all! With shared Lake Access you'll can enjoy fishing, kayaking, or lounging by the water with ease. Updated from the bottom up, this home offers modern comforts while maintaining its rustic charm. Year-round lake views

    Shelley Nadeau Your Home Sold Guaranteed Realty

    27 Mace Ave, Winthrop, ME 04364
  • /87

    $464,900

    • 4 Baths
    • 4,092 Sq Ft

    98 & 100 Main St, Winthrop, ME 04364

    Located in the heart of Winthrop, just a short walk from the public beach on Maranacook Lake, this historic three-unit property offers incredible investment potential. The elegant main home, featuring four-plus bedrooms, has been tastefully renovated while preserving its period charm. It can serve as a luxurious owner's residence, a bed-and-breakfast, or a rental unit.The separate two-unit

    Joel Alexander NextHome Northern Lights Realty

    98 & 100 Main St, Winthrop, ME 04364
  • /16

    $67,500

    • Land
    • 9 Acres
    • $7,258 per Acre

    Lot 53 South Rd, Winthrop, ME 04364

    Located just off South Road in the heart of the Winthrop Lakes Region, this 9.3+/- acre parcel offers a tranquil mix of open fields and mature woods. Fully surveyed and soils-tested, the lot provides flexibility to bring your vision to life. A peaceful stream winds through the western edge, adding to the property's natural beauty and rural charm. With over 1,000 feet of road frontage and nearby

    Sophia Rosen Sierra Boler Portside Real Estate Group

    Lot 53 South Rd, Winthrop, ME 04364
  • /16

    $87,500

    • Land
    • 6 Acres
    • $14,344 per Acre

    Lot 53 South Rd, Winthrop, ME 04364

    Tucked just off South Road in the heart of the Winthrop Lakes Region, this 6.1+/- acre parcel offers a peaceful blend of open fields and woods. Whether you're envisioning a year-round home or a family compound, this surveyed and soils-tested lot gives you the flexibility to bring your plans to life. Two building sites have already been soils-tested, giving you options, and with 300+/- feet of

    Sophia Rosen Sierra Boler Portside Real Estate Group

    Lot 53 South Rd, Winthrop, ME 04364
  • /20

    $155,000

    • Land
    • 15 Acres
    • $10,065 per Acre

    Lot 53 South Rd, Winthrop, ME 04364

    Opportunity meets natural beauty on South Road in Winthrop, Maine. This surveyed and soils-tested 15.4-acre parcel offers a rare blend of space, flexibility, and serene surroundings just minutes from the shores of Cobbossee Lake. With an impressive 1,324+/- feet of road frontage, the property lends itself to a variety of possibilities, including potential division into two spacious

    Sophia Rosen Sierra Boler Portside Real Estate Group

    Lot 53 South Rd, Winthrop, ME 04364
  • /15

    $187,700

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    109 Pineland Dr, Winthrop, ME 04364

    2022 Double Wide Mobile Home

    Derek Eisenberg Continental Real Estate Group, Inc.

    109 Pineland Dr, Winthrop, ME 04364
  • /36

    $259,000

    • 2 Beds
    • 1.5 Baths
    • 2,682 Sq Ft

    19 Greenwood Park, Winthrop, ME 04364

    This unique multi purpose property with 2,682 square feet has plenty of possibilities including office space, 2 unit or single family. Located in a desirable location within walking distance to beach or in town. set up for apartment in place for rental or living space to renovate for single family includes all newer appliances. Attached finished space originally used as a barn has plenty of

    Debra DelMonaco Better Homes & Gardens Real Estate/The Masiello Group

    19 Greenwood Park, Winthrop, ME 04364
  • /39

    $290,000

    • 4 Beds
    • 1.5 Baths
    • 2,502 Sq Ft

    14 Central St, Winthrop, ME 04364

    Step into the charm and character of this historical in town home. The spacious glassed-in porch opens to the front hallway, featuring a grand staircase and a stained glassed window. This broad hallway presents handsome hardwood floors and multiple French-doors that open into the Living Rooms and Dining Room. The sunlight streams through the spacious windows highlighting the tin ceilings,

    Pat Ladd Homestead Realty

    14 Central St, Winthrop, ME 04364
  • /100

    $1,290,000

    • 5 Beds
    • 3.5 Baths
    • 3,852 Sq Ft

    1163 Memorial Dr, Winthrop, ME 04364

    Picture perfect custom built home on 20+/- acres located in the heart of central Maine. This 5 bedroom 3.5 bath dream home awaits a new owner. Imagine yourself waking up to sunshine pervading your primary bedroom and opening your double doors to a luxurious great room with open concept to dining and kitchen area. This spacious kitchen features high end appliances, quartz countertop and expansive

    Daren Hachey Homestead Realty

    1163 Memorial Dr, Winthrop, ME 04364
  • /13

    $199,500

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    795 Memorial Dr, Winthrop, ME 04364

    This property began life as a double wide mobile home but has since blossomed into a wonderful family home with many updates including a NEW ROOF STRUCTURE and furnace. A wonderful location on desirable Memorial drive in Winthrop. Right across from the Lake! There is a beautiful cherry kitchen with granite countertops, a laundry room and separate dining room. Garage underneath. Maintenance

    Lewis Benner Berkshire Hathaway HomeServices Northeast Real Estate

    795 Memorial Dr, Winthrop, ME 04364
  • /29

    $135,000

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    46 Pineland Dr, Winthrop, ME 04364

    In this 55+ Community Mobile Home Park, modern comfort meets affordable living! 2023 beautifully designed 2 bedroom, 2 full bath home offers a bright and airy living space with modern kitchen, stylish finishes and energy efficient appliances. Perfectly situated in a quiet, well-maintained location with a shed for additional storage and generator for those unanticipated power outages. Only a 10

    Khristian Potter Keller Williams Realty

    46 Pineland Dr, Winthrop, ME 04364
  • /17

    $89,900

    • Land
    • 3.11 Acres
    • $28,907 per Acre

    0 U S Highway 202, Winthrop, ME 04364

    Incredible opportunity to live or build right next to Winthrop High School and Middle School—walk to both! This former apple orchard offers 3.1 acres with two access points: one through Apple Farm Crossing and the other directly off Route 202. Zoned for commercial use, with public water and sewer available, it's a prime location with great visibility and road frontage on busy Route 202. Ideal for

    Brian Rizzo Rizzo Mattson

    0 U S Highway 202, Winthrop, ME 04364
  • /24

    $99,000

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    64 Pineland Dr, Winthrop, ME 04364

    Live the easy life in the wonderful 2 bedroom 2 bath home. Located in the heart of central Maine, this newer, well maintained home features a primary bedroom with private bath, gas range, a large shed and ample sunlight. Simple application and $25 park entry fee apply. See also MLS#1619009

    Daren Hachey Homestead Realty

    64 Pineland Dr, Winthrop, ME 04364
  • /42

    $129,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    88 Pineland Dr, Winthrop, ME 04364

    Immaculately cared for home located in a peaceful park. This home features a well appointed kitchen, beautiful floor and decor. Enjoy the outdoors on the newly built expansive deck or sit quietly on the front porch. This 2 bedroom, 2 bath home is conveniently located to all area amenities. Simply application and $25 fee apply. See also MLS#1618998

    Daren Hachey Homestead Realty

    88 Pineland Dr, Winthrop, ME 04364
  • /4

    $59,900

    • Land
    • 1.84 Acres
    • $32,554 per Acre

    Lot #2 Fox Run Ln, Winthrop, ME 04364

    Located In a subdivision of very fine homes sits this just under 2-acre lot. Highly sought after Winthrop location. Bring us your plans. Open views, paved road & public water.Other lots also available.All building needs to be done by B.L. Williams.Taxes to be determined.

    Jeffrey Perkins Brookewood Realty

    Lot #2 Fox Run Ln, Winthrop, ME 04364
  • /40

    $225,000

    • Land
    • 1.00 Acre
    • $225,000 per Acre

    40 Winthrop Center Rd, Winthrop, ME 04364

    Great property with your storage needs in mind. Garage has 2 - 9' x 8' insulated garage doors and 1 - 10' x 8' insulated garage door. Maintenance free siding and trim. This property is a buildable lot and can accommodate the home of your dreams. Drilled well in place as well as driveway. Great for a home, storage facility or shop.

    Dylan Armstrong Sprague & Curtis Real Estate

    40 Winthrop Center Rd, Winthrop, ME 04364
  • /55

    $449,900

    • 4 Beds
    • 2 Baths
    • 2,828 Sq Ft

    229 Bearce Rd, Winthrop, ME 04364

    Welcome to 229 Bearce road in beautiful Winthrop Maine. This colonial features 4 large bedrooms, 2 1/2 bathrooms, an office, and a separate dining room with a large brick fireplace. The kitchen offers, granite countertops, lots of storage and a butcher block island with built in range. Beautiful wood and tile floors throughout. The Primary bedroom has a large walk-in closet with an unfinished

    Jeffrey Perkins Brookewood Realty

    229 Bearce Rd, Winthrop, ME 04364
  • /6

    $154,900

    • 2 Baths
    • 3,698 Sq Ft

    32 Bowdoin St, Winthrop, ME 04364

    Great investor property needs remodeling, can become a great rental 2 unit home

    DANIEL DEMERS Sell Your Home Services

    32 Bowdoin St, Winthrop, ME 04364
  • /50

    $359,900

    • 3 Beds
    • 2 Baths
    • 2,575 Sq Ft

    170 Hathaway Rd, Winthrop, ME 04364

    Where old meets new. The charm of this original 1840's Brick Cape paired with a thoughtful 2004 addition. Located on a quiet dead end road, offering 3.3 acres with trees/ fields, wildlife and ultimate privacy. The home includes three spacious bedrooms and two full baths. The open kitchen and living area, complete with a cozy wood fire stove, create a welcoming space for family and friends.

    Heidi Libby NextHome Northern Lights Realty

    170 Hathaway Rd, Winthrop, ME 04364
  • /28

    $240,000

    • 3 Baths
    • 2,114 Sq Ft

    294 Main St, Winthrop, ME 04364

    Classic Greek Revival currently used as a duplex in Winthrop. Large owners' unit with two or three bedrooms plus two baths. Full concrete basement with updated wiring and boiler. Barn would make a great workshop or current vehicle storage. Additional one bedroom unit for income or family member. Private backyard but in town conveniences. 60 days for closing, for tenants, unless tenants are able

    Wendy-Jo Mansir McAllister Real Estate

    294 Main St, Winthrop, ME 04364
  • /129

    $1,245,000

    • 6 Beds
    • 4 Baths
    • 6,493 Sq Ft

    172 Annabessacook Rd, Winthrop, ME 04364

    Now includes a 20-foot right of way to Annabessacook Lake and 20 sprawling acres!! This custom-built executive estate offers unparalleled luxury and comfort. A true one-of-a-kind haven, it blends resort-style amenities with high-end finishes for the perfect combination of elegance and functionality. Originally completed in 1997 and beautifully renovated in 2019 and 2023, the residence boasts

    Tim Dunham Tim Dunham Realty

    172 Annabessacook Rd, Winthrop, ME 04364
  • /2

    $32,000

    • Land
    • 2.06 Acres
    • $15,534 per Acre

    333 Metcalf Rd, Winthrop, ME 04364

    Nice 2 acre building lot in desirable Winthrop. 159' of road frontage, slightly slopes downwards. Property has been surveyed, partially cleared, and a soils test has been completed. A culvert has also been cut for the driveway. GREAT spot to build a spec house or your dream house

    Chris Vallee LAER

    333 Metcalf Rd, Winthrop, ME 04364
  • /53

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 2,126 Sq Ft

    162 Main St, Winthrop, ME 04364

    Fantastic home in the heart of downtown Winthrop. Three bedrooms and 2.5 baths. Very energy efficient w/ propane heat. New sewer line and water supply from the street. New flooring. Spacious rooms.

    Tyler Gaudet Sprague & Curtis Real Estate

    162 Main St, Winthrop, ME 04364
  • /4

    $230,000

    • Land
    • 65 Acres
    • $3,549 per Acre

    616 Stanley Rd, Winthrop, ME 04364

    64.81 acres with electric, drilled well and septic in place. If you are interested in homesteading, this could be a good starting point. 1.8 acres has been cleared for farming and living, the remaining are currently in Tree Farm status. Septic is for a 2 bedroom and Mobile and Modular Homes are allowed.

    Ashley Lutko Donna Galluzzo Signature Homes Real Estate Group, LLC

    616 Stanley Rd, Winthrop, ME 04364
  • /11

    $46,900

    • Land
    • 3.70 Acres
    • $12,676 per Acre

    Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364

    Wooded 3.7 acre building lot for sale in the Mountain View Subdivision- Winthrop. 230' of road frontage and deeded covenants to protect your investment. Power nearby, public road, no association. Situated near deep-water Maranacook Lake. Winthrop residents can enjoy the sandy beach and boat slip rentals. This small town of Winthrop offers a grocery store, shops & restaurants on Main Street. Easy

    Ann Castonguay Sprague & Curtis Real Estate

    Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364
  • /16

    $69,900

    • Land
    • 5 Acres
    • $13,340 per Acre

    22 Community Dr, Monmouth, ME 04265

    Embrace the chance to build your dream home on this remarkable 5.24-acre brookside property. Located alongside Tannery Brook, this lot is perfect for outdoor enthusiasts, offering endless opportunities for recreation. You'll also find Wilson Pond and Cochnewagon Lake just a short distance away, ideal for a variety of water activities.Conveniently situated halfway between Lewiston/Auburn

    Zach Blair PinePoint Realty

    22 Community Dr, Monmouth, ME 04265
  • /40

    $1,499,999

    • 3 Beds
    • 3 Baths
    • 2,256 Sq Ft

    42 Mace Ave, Winthrop, ME 04364

    This is a rare opportunity to own a year round home or seasonal retreat at the head of Lake Cobbossee only 1/8 of a mile from the Augusta Country Club. Relax and enjoy as the work has been done. This gorgeous cape 2019 build is turn key with a paved private road. The view is amazing and all the area has to offer awaits.Detail through out with a walk out basement for easy access to the lake

    Ralph Ingraham JR. LAER

    42 Mace Ave, Winthrop, ME 04364
  • /2

    $65,000

    • Land
    • 27 Acres
    • $2,448 per Acre

    90 Bearce Rd, Winthrop, ME 04364

    Land and privacy!! Build your dream home and belong to Maple Ridge Owners Association and have the buffer of the green space making your home even more private. This is a great building lot. Lot #23.

    Pat Ladd Homestead Realty

    90 Bearce Rd, Winthrop, ME 04364
  • /5

    $449,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft

    Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364

    Welcome to this modern ranch style home- to be built in the Mountain View Subdivision in Winthrop. Open floor plan in the kitchen, dining & living room area. French doors open to the large back yard and 3.7 acres of wooded land. Three spacious bedrooms- primary bedroom suite, two more bedrooms and second full bath. Separte first floor laundry. Attached garage, nice front porch, full basement,

    Ann Castonguay Sprague & Curtis Real Estate

    Lot #5 Sturtevant Hill Rd, Winthrop, ME 04364
  • /2

    $159,900 Open Sat 10AM - 1PM

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft

    374 Stanley Rd, Winthrop, ME 04364

    Holly Mooney Coldwell Banker Realty

    374 Stanley Rd, Winthrop, ME 04364
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