Winthrop, ME Homes for Sale

MOTIVATED SELLERS - RECENT EXTERIOR PAINT - Step back in time and experience the character of early New England in this beautifully preserved 1790s home, nestled in the heart of Winthrop. This rare gem offers four spacious bedrooms and 1.5 baths, blending historic charm with modern comfort. Features include: four generously sized bedrooms, perfect for family or guests with an additional large

Heather Perrault Your Home Sold Guaranteed Realty

Cranberry Rock Farm, built in 1815, is a colonial-style farmhouse nestled on 32 private, picturesque acres. This certified-organic farm provides endless possibilities as a private retreat, wedding venue, equestrian property, or more. Perched atop a hillside with southwesterly exposure, it boasts panoramic views of the Presidential Range & Mt. Washington. Enjoy easy entertaining in the open

Rick Bisson Keller Williams Realty

Stunning Cape Cod - style home that has been meticulously maintained by the original owners. This dormered cape cod is immaculate and tastefully decorated. Updated applianced kitchen with granite counters and adjoining dining room. Living room with cathedral ceilings, sunroom also with cathedral ceilings and skylights is flooded with light and opens onto a backyard deck. Main floor bedroom and

Earle Kenney Sprague & Curtis Real Estate

Beautiful cape cod style home on a pretty country lot, just 5 minutes to downtown Winthrop and 15 minutes to I-95. Very spacious. Offering an eat in kitchen that opens to the massive backyard deck. Front living room, dining room, den, full bath and primary suite bedroom with full bath -- all on the first floor. Second floor offers 4 rooms -- 2 bedrooms, full bath and family room and den. Private

Earle Kenney Sprague & Curtis Real Estate

Rare opportunity to own 9 acres on an island in the middle of Cobbosseecontee Lake! This two bedroom, one bathroom home has been meticulously cared for and in the same family since its construction in the 90's . Tucked away with incredible privacy of maintained tree growth at the front, allows for viewing of the lake without recreational lake life viewing up at the cottage. The home has its own

Spencer Hazzard Rizzo Mattson

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

Spacious and versatile, this 2,200 sq. ft. Cape offers up to 5 bedrooms and 2 full baths, perfect for a growing household or those in need of flexible living space. Set on 1.1 acres, the home features a 2-car attached garage with a convenient mudroom/breezeway. Inside, you'll find fresh updates including new vinyl plank flooring, updated paint, and freshly cleaned carpets. The full finished

Shawna Cotter Maine Real Estate Pros

On the market for the first time since its construction in 1961 this well maintained home offers a little bit of everything. The large three car garage contains room for vehicles, workshops or storage galore. Even more space can be found in the full, dry, sunny basement. The five bedrooms offer space and flexibility. Whether you want to relax on the deck, in the level yard or in the spacious open

Bennett Wade Keller Williams Realty

Winthrop - Contemporary ChaletThis inviting chalet-style home features 3 bedrooms and a bright, open-concept kitchen, living, and dining area with soaring ceilings and abundant natural light. The spacious primary suite is located upstairs, offering a walk-in closet and private bathroom. A convenient mudroom enhances everyday functionality, while the newly finished bonus/playroom over the

Jessica Fike Brookewood Realty

Looking for a one of a kind Gem with an open Contemporary Design, then come take a look! Experience the Geodesic Dome style home. plus the allure of a mid 70's style home nestled in a very private hillside location. Home boasts 3 bedroom 2 baths plus a 3 season sun room, nostalgia galore! Very private yard with mature gardens plus 2 car garage with storage above. 2 separate driveways for

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

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

168 Main Street and 18 Hanson Street are being sold together. 168 Main Street has 4,244 SF +/- and 18 Hanson Street has 2,958 SF +/-. Here is a great investment property in the heart of Winthrop's downtown. Main St building has two apartments plus 3 office rental units. Hanson Street is a well maintained two family with two 2 bedroom apartments. Total of 7 rental units in the buildings - 3

Earle Kenney Sprague & Curtis Real Estate

Here is your opportunity to own this large parcel of land located just outside of Monmouth in the quaint town of Winthrop. This 22.55 acre lot offers so many possibilities, located just minutes away from Wilson Pond, Mount Pisgah Conservation Trails and much more. Use it as your private oasis for hunting, fishing, hiking, four wheeling and snowmobiling or bring your building plans and make it

Cathy Fifield Keller Williams Realty

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

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

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 residential use, with public water and sewer available, it's a prime location with great visibility and road frontage on Route 202. Ideal for a

Brian Rizzo Rizzo Mattson

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

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

Solid multi-family investment property in convenient Downtown Winthrop location. 5-unit building consisting of three 2-bedrooms and two 1-bedroom units. Strong 8.5% cap rate with further upside potential!

Jon Leahy J T Leahy Real Estate

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

Discover the perfect blend of privacy, nature, and convenience with this charming 2-bedroom, 1-bath cabin set on a spacious, wooded lot. Just minutes from both Cobbosseecontee Lake and Annabessacook Lake, this property offers an ideal base for outdoor adventures—boating, fishing, hiking, or simply unwinding in the beauty of Maine.Inside, the home features a warm and inviting layout with

Emma Bryan LAER