Winthrop Homes for Sale

Welcome to the charming neighborhood of Winthrop in Deep River, Connecticut! Nestled in Middlesex County, Winthrop is a picturesque community known for its peaceful surroundings and friendly atmosphere.

For those looking to make Winthrop their home, there are a variety of beautiful homes for sale in the area. From cozy single-family houses to spacious townhomes, there is something to suit every lifestyle and preference. Whether you are a first-time homebuyer, a growing family, or someone looking to downsize, Winthrop has the perfect home waiting for you.

Living in Winthrop offers residents a tranquil suburban feel while still being conveniently located near all the amenities and attractions that Deep River has to offer. With tree-lined streets, well-maintained parks, and a strong sense of community, Winthrop is the ideal place to put down roots and create lasting memories.

If you are searching for a place to call home that combines small-town charm with modern conveniences, look no further than Winthrop in Deep River. Explore the homes for sale in this lovely neighborhood and discover the perfect place to start the next chapter of your life.

Newest Winthrop Homes for Sale

$475,000

3 Beds ⋅ 2 Baths ⋅ 24189405 MLS

Welcome to 365 Winthrop Road in Deep River, where historic charm meets thoughtful updates. This beautifully maintained 3-bedroom, 2-bathroom home offers timeless character alongside the conveniences of modern living. The spacious main level features a large kitchen, formal dining room, inviting living room, cozy den, and a stunning great room with French doors leading to the backyard, perfect for entertaining or everyday living. Upstairs, you'll find a convenient laundry room, two bedrooms and a generous primary suite filled with natural light, featuring cathedral ceilings, exposed post-and-beam construction, ample closet space, and an en suite bathroom. Step outside to enjoy a picturesque setting with beautiful stonework, mature gardens, and a charming gazebo. A storage shed and a separate workshop with electricity and heating/cooling provide endless possibilities for hobbies, projects, or additional workspace. Recent improvements include hot water heater (December 2025) a new roof and well pump (April 2026). Don't miss this unique opportunity to own a home that seamlessly blends historic character and exceptional outdoor living in Deep River.

365 Winthrop Rd, Deep River

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