Winthrop Homes for Sale

Welcome to Winthrop, a hidden gem nestled in the picturesque town of Deep River, Connecticut. This charming neighborhood is renowned for its serene atmosphere, friendly community, and stunning natural beauty. If you're seeking a tranquil retreat just a stone's throw from the bustling lifestyle of larger towns, Winthrop is the perfect place to call home.

As you stroll through the tree-lined streets of Winthrop, you'll be captivated by the diverse architectural styles of the homes, ranging from classic New England colonials to modern designs. Each property reflects the unique character of the neighborhood, making it a delightful place for families, retirees, and everyone in between. With a variety of homes for sale, there’s something to suit every taste and budget, whether you're looking for a cozy starter home or a spacious residence with room to grow.

The community spirit in Winthrop is palpable, with residents often gathering at local parks and community events, fostering a sense of belonging. Nature lovers will appreciate the proximity to the Connecticut River and nearby hiking trails, offering endless opportunities for outdoor activities such as kayaking, fishing, and hiking.

Conveniently located, Winthrop provides easy access to Deep River's quaint shops, restaurants, and cultural attractions, while also being just a short drive from larger cities like Middletown and Old Saybrook.

Explore the homes for sale in Winthrop today and discover the perfect blend of tranquility, community, and natural beauty that awaits you in this enchanting neighborhood!

Newest Winthrop Homes for Sale

$999,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205606 MLS

Set on nearly six beautifully landscaped acres, this distinctive four-bedroom, three-and-a-half-bath estate blends timeless character with thoughtfully designed living spaces. A welcoming foyer with brick flooring sets the tone, with custom details throughout including wide-board floors, exposed beams, french doors, detailed millwork and four fireplaces. The kitchen is anchored by an impressive oversized fireplace spanning nearly an entire wall, fitted with a gas insert, and a large center island that creates a natural gathering place. The expansive great room features soaring ceilings, custom windows, built-ins, beautiful woodwork and a fireplace, with french doors opening to a covered rear porch overlooking the grounds. The private primary suite encompasses the entire third floor, creating a true retreat. Beyond the home, stone patios and walls create inviting spaces around the saltwater inground pool and pool house. A professionally engineered pond offers swimming and fishing in warmer months and skating in winter. A substantial barn, additional two-car barn/garage and mature landscaping complete this exceptional private estate.

141 Cedar Swamp Rd, Deep River

$579,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24202496 MLS

A private New England retreat where character, craftsmanship and nature come together. 2-3 bedroom, 1861 sq. ft. country cape set on 3.75 beautifully landscaped acres in Deep River's Winthrop area, 41 Glen Grove is a truly special property surrounded by stone walls, mature plantings and its own private pond. Inside, wide-board floors, exposed beams, built-ins, a slate entry and two fireplaces-one wood-burning and one gas-give the home warmth and authenticity, while the granite and stainless chef's kitchen brings modern function to its historic-inspired character. Currently two bedrooms, the floor plan offers excellent flexibility with a main-level den and a charming parlor/study adjoining the primary bedroom-ideal for guests, an office, nursery or additional private space. The septic system is sized for a 3-4 bedroom home, offering future possibilities. Stone patios extend the living outdoors, with a hot tub hookup already in place. The former stable barn, complete with stalls and tack room, could return to equestrian use with room for a paddock or become an incredible studio, workshop or hobby space. Two laundry areas, an attached two-car garage with generous storage, generator and two wells-including a separate irrigation well-complete the property. Private, peaceful and wonderfully distinctive, this is the kind of property that feels worlds away while still feeling completely like home.

41 Glen Grove Rd, Deep River

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