Winthrop Real Estate

Welcome to Winthrop, a charming neighborhood nestled within the picturesque town of Deep River, Connecticut. This hidden gem in Middlesex County offers a unique blend of small-town charm and natural beauty, making it an ideal place to call home.

Winthrop is characterized by its welcoming community, where friendly neighbors greet you with a smile and local businesses thrive. The area boasts a rich historical background, with beautifully preserved architecture that tells the story of its past. Strolling through the tree-lined streets, you’ll discover quaint shops, delightful cafes, and inviting parks that provide the perfect backdrop for family outings or leisurely walks.

Nature lovers will find plenty to enjoy in Winthrop, as it is surrounded by stunning landscapes and outdoor recreational opportunities. The nearby Connecticut River offers a variety of water activities, from kayaking to fishing, while the lush trails in the area are perfect for hiking and biking enthusiasts. In the fall, the foliage transforms the landscape into a breathtaking tapestry of colors, drawing residents and visitors alike to explore the great outdoors.

Education is a priority in Winthrop, with access to highly-rated schools that foster a nurturing learning environment for children. The community is also conveniently located near major highways, making commuting to nearby cities a breeze.

Whether you’re looking for a peaceful retreat or a vibrant community, Winthrop in Deep River is a place where you can truly feel at home. Discover the charm and beauty of this enchanting neighborhood, where every day feels like a breath of fresh air.

Newest Listings in Winthrop

$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

$1,270,000

10 Baths ⋅ 24156775 MLS

100% occupied industrial warehouse building in the Deep River Industrial Park. Building is on a ground lease with 64 years remaining on the lease. Propane heating, central air, paved parking lot. Great rental history. One owner building

900 Industrial Park Rd, Deep River

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