Winthrop Real Estate

Winthrop Real Estate

Welcome to Winthrop, Maine – a hidden gem nestled in the heart of Kennebec County! This charming town, with its picturesque landscapes and tight-knit community, offers a perfect blend of rural tranquility and modern convenience. Known for its stunning lakes and vibrant outdoor activities, Winthrop is an ideal destination for nature lovers and families alike.

With a population of just over 6,000 residents, Winthrop exudes a warm, welcoming atmosphere. The town is surrounded by beautiful natural scenery, including the sparkling waters of Maranacook Lake and the serene banks of the Cobbosseecontee Stream. Whether you enjoy boating, fishing, hiking, or simply soaking in the breathtaking views, Winthrop provides endless opportunities for outdoor adventures.

In addition to its natural beauty, Winthrop boasts a rich history and a strong sense of community. The town features a charming downtown area filled with local shops, cafes, and eateries, where you can experience the warm hospitality of its residents. Throughout the year, Winthrop hosts various events and festivals, fostering a spirit of togetherness and celebrating the unique culture of the region.

Families will appreciate the excellent educational opportunities available in Winthrop, with well-regarded schools that prioritize student success. The town’s safe neighborhoods and friendly atmosphere make it a wonderful place to raise children.

If you’re looking for a peaceful retreat with a vibrant community spirit, Winthrop, Maine, is the place to call home. Explore the beauty and charm of this delightful town, and discover why so many have chosen to make Winthrop their forever home!

Newest Listings in Winthrop

5 Union St, Winthrop
$199,000
Some buildings offer square footage. Others offer possibilities. And a select few offer more than 160 years of history, character, and the opportunity to become part of a community's next chapter. Welcome to 5 Union Street, a circa-1860 commercial property in the heart of Winthrop's historic downtown. Offering approximately 9,165 square feet across multiple levels, this distinctive building presents an opportunity for entrepreneurs, investors, and visionaries looking for something beyond the ordinary. For generations, this location has been woven into Winthrop's history. Most notably, the address was home to the Gull Theatre, a 430-seat movie theater that opened in 1945 and entertained audiences into the early 1960s. The property later became Winthrop Lanes, bringing the community together for candlepin bowling. From the silver screen to the bowling lanes, this address has a history of bringing people together. Today, the building offers versatile spaces ready for reinvention. Approximately 1,833 square feet of front commercial space welcomes visitors from Union Street, while the rear features an expansive 3,080-square-foot open area. Additional offices, unfinished upper-level post-and-beam space, mezzanine storage, and a daylight basement with an overhead door provide further flexibility. Imagine a destination retail establishment, antique marketplace, creative studios, professional offices, entertainment venue, or a combination of complementary businesses. The layout also invites exploration of residential apartments or mixed-use redevelopment, subject to municipal approvals. Located just off Main Street, the property offers convenient access to Augusta, Lewiston, and surrounding communities. Whether your vision is to preserve its legacy, introduce something new, or blend the best of both, 5 Union Street offers an opportunity to write the next chapter of a Winthrop landmark. The history is already here. The next chapter is yours to create!

5 Union St, Winthrop

Listing courtesy of McAllister Real Estate.

202 Readfield Rd, Winthrop
$547,000
3 Beds ⋅ 2 Baths
Experience the ease of brand-new, single--level living in this newly constructed 3-bedroom, 2-bath ranch, perfectly situated on 3 peaceful country acres. Designed w/ both comfort and functionality in mind, this home offers a modern open concept layout ideal for everyday living and entertaining. The inviting kitchen features a spacious dining area a center island, abundant cabinetry, and seamless sightlines to the bright and welcoming living area. Natural light fills the space, highlighting the attractive hardwood flooring and creating a warm and comfortable atmosphere throughout the main living areas. A well-designed mudroom provides outstanding everyday convenience with durable tile flooring, triple closets, and direct access to the main living space, making organization effortless. Privately located, the spacious master suite serves as a relaxing retreat and includes a walk in closet, double vanity, and separate shower area. Two additional bedrooms offer generous closet space and flexibility for family, guests, or a home office. Step outside onto the rear deck and enjoy views of the surrounding acreage, the perfect setting for morning coffee, evening relaxation, or simply taking in the quiet rural surroundings. A two-car garage provides secure parking and additional storage. Featuring efficient systems, quality construction, and modern finishes throughout, this thoughtfully designed ranch combines comfort, practicality, and low maintenance living. The single level layout offers a mobility-friendly design, adding versatility for a variety of lifestyles and future needs. Enjoy the tranquility of country living while benefiting from a layout tailored to today's lifestyle.

202 Readfield Rd, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

12 High St, Winthrop
$315,000
3 Beds ⋅ 2 Baths
Classic New England Charm Meets Modern Updates in Winthrop! Enjoy the best of both worlds at 12 High Street in Winthrop! This charming antique home blends timeless character with thoughtful updates, offering the warmth and appeal of an older home with modern touches. Featuring 3 bedrooms, 1.5 bathrooms, and approximately 1,763 square feet of living space, this property sits on an oversized 0.64-acre in-town lot. Inside, you'll find updated flooring, an updated kitchen with granite countertops, and a versatile first-floor office/flex space perfect for working from home, pursuing hobbies, or creating a space tailored to your needs. The home offers a wonderful opportunity to enjoy its historic charm while benefiting from important modern improvements. Outside, the impressive two-story barn is a standout feature, offering abundant space, nearly 1,600 sqft, for storage, a workshop, hobbies, or a variety of other possibilities. The oversized lot provides plenty of room for gardening, outdoor entertaining, and enjoying your own private outdoor retreat. Conveniently located near Maranacook Lake, local restaurants, shopping, and schools, this property combines small-town charm with everyday convenience. Augusta is just 15 minutes away, making commuting and access to additional amenities easy. With its blend of antique character, thoughtful updates, flexible living space, and an exceptional barn, 12 High Street offers a unique opportunity to own a home with personality, space, and versatility in the heart of Winthrop!

12 High St, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. TaylorTarbox@masiello.com

337 Rte 133, Winthrop
$639,000
5 Beds ⋅ 2 Baths
A custom cherry-and-granite kitchen, beautifully updated baths, Douglas fir floors, and a fully outfitted private theater bring modern comfort to this 1788 Cape, while hand-hewn beams, heart pine trim, and a restored beveled-glass front door preserve its historic character. Nearly every room has been thoughtfully renewed, blending the warmth of an old Maine home with the convenience and style buyers want today. The kitchen is a standout, with custom cherry cabinetry, granite countertops, a thin-brick backsplash, exposed axe-hewn ceiling beams, a gas range with air fryer, and recessed, track, and under-cabinet lighting. The main-level bath offers a walk-in shower with teak seating; upstairs, find a soaking tub, custom vanity, subway tile, and Carrera marble. Recent updates include new windows, doors, decks, siding over a Tyvek membrane, flooring, lighting, plumbing, and a 2026 water heater. Known as Old Sears Farm, this five-bedroom, 4.2-acre property is in Winthrop, minutes from Maranacook Lake and Augusta, with a local story connected to early settler Paul Sears. The home is extensively insulated and equipped with eight independently controlled heat pumps for efficient heating and cooling, complemented by wood-stove warmth. The private theater is an experience of its own, with Dolby Atmos 5.1.4 surround sound, illuminated tiered seating, electric recliners with charging ports, blackout curtains, and projector connectivity. Two first-floor rooms offer flexible options for bedrooms, a home office, or other uses; one connects directly to a full bath, making first-floor living a convenient option. Outside, enjoy mature trees, gardens, grapevine trellises, landscaped paths, and two fire-pit areas within an eight-foot double-planked privacy fence. A separate chain-link enclosure offers a convenient play space for pets or children. Enjoy the privacy of your own 4.2-acre retreat, with Augusta and Lewiston within easy reach for dining, shopping, and everyday conveniences

337 Rte 133, Winthrop

Listing courtesy of McAllister Real Estate.

57 Annabessacook Rd, Winthrop
$306,000
3 Beds ⋅ 2 Baths
Welcome to this 1950s 1.5-story Cape-style home offers a comfortable layout, plenty of storage, and room to make it your own. Enter through the mudroom/laundry area, which flows into the dining room and kitchen, then into the spacious living room featuring a pellet stove for added warmth and efficiency on those cold Maine nights. A first-floor bedroom offers convenient one-level living options, while upstairs you'll find two additional bedrooms with a half bath in between. The unfinished basement offers even more versatility with multiple rooms ready to serve a variety of uses. One unique space was previously used as a photography darkroom, while another provides a dedicated workshop area ready for home projects, hobbies, and additional storage. Outside, you'll appreciate the paved driveway, front deck, perfect for sitting back and relaxing. Enjoy the large open side yard with plenty of room to play, garden, or simply enjoy the outdoors. One of the standout features is the detached three-bay barn-style garage offering generous storage, along with an additional detached one-bay garage for even more space. Move-in ready with an opportunity to add your own personal touches and updates over time. Set just outside of town while still convenient to local amenities, with an easy commute toward Augusta or Lewiston-Auburn. Come take a look, could be just what you've been looking for!

57 Annabessacook Rd, Winthrop

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. 2073956063

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