Wooster Square Homes for Sale

Welcome to Wooster Square, one of New Haven, Connecticut’s most charming and vibrant neighborhoods! Nestled just a stone’s throw from the bustling city center, Wooster Square is renowned for its rich history, picturesque parks, and a delightful blend of residential and commercial spaces. This area is a true gem, offering a perfect mix of urban convenience and suburban tranquility.

Strolling through Wooster Square, you’ll be captivated by the historic brownstones and beautifully restored homes that line the tree-shaded streets. The neighborhood is particularly famous for its stunning cherry blossom trees, which bloom spectacularly each spring, drawing visitors and locals alike to enjoy the breathtaking scenery. The park at Wooster Square is a hub of community activity, hosting farmers markets, art fairs, and seasonal events that foster a strong sense of community.

For those looking to make Wooster Square their home, there are an array of homes for sale that cater to various tastes and budgets. Whether you’re seeking a cozy condo with modern amenities or a spacious family home with character and charm, Wooster Square has something for everyone. The real estate market here is thriving, making it an excellent time to invest in a property in this enchanting neighborhood.

In addition to its beautiful homes, Wooster Square boasts a variety of local eateries, coffee shops, and boutique stores that add to its unique character. With easy access to public transportation and proximity to Yale University, this neighborhood is not only a wonderful place to live but also a strategic location for work and play. Discover the magic of Wooster Square and find your dream home in this delightful community today!

Newest Wooster Square Homes for Sale

$775,000

3 Beds ⋅ 2 Baths ⋅ 24187215 MLS

Rare historic Wooster Square compound featuring a detached carriage house and private garden retreat. Opportunities like this seldom come to market in New Haven's iconic Wooster Square Historic District. Built in 1870, this distinguished brick residence offers 3 BR, 2 full baths, and a rare blend of architectural character, flexible living space, and private outdoor living. Behind the historic brick facade, soaring ceilings, original details, and two decorative fireplaces evoke the craftsmanship & charm of a bygone era, while thoughtful updates provide modern comfort, including a remod 2nd bath. The unfinished third floor offers expansion potential and a lookout perch overlooking the neighborhood. The walk-out lower level has been transformed into a cozy cabin-inspired retreat, ideal for entertaining or relaxing, with abundant storage. Set on a fenced corner lot, the property lives like a private compound with mature landscaping, intimate garden spaces, and off-street parking-an unexpected retreat in the heart of the city. The detached carriage house has been extensively upgraded into a sophisticated home office & fitness studio, offering flexibility and potential Yale Homebuyer Program eligibility, with the option to convert back to a 2-car gar. Just moments from Wooster Square's cherry blossoms, farmers market, world-famous pizza, Union Station,Yale,Yale NH Hospital, downtown, restaurants, and major highways. Historic. Private. Flexible. Walkable.

161 Olive St, New Haven

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