Wooster Square Real Estate

Welcome to Wooster Square, a charming and historic neighborhood nestled in the heart of New Haven, Connecticut. Known for its vibrant community and picturesque tree-lined streets, Wooster Square is a delightful blend of urban convenience and small-town charm.

One of the neighborhood’s standout features is its rich Italian heritage, celebrated annually during the Wooster Square Cherry Blossom Festival. In spring, the neighborhood bursts into color as cherry trees bloom, creating a stunning backdrop for local festivities, art displays, and delicious food offerings from nearby restaurants. This event not only showcases the beauty of the area but also highlights the strong sense of community that Wooster Square is known for.

Wooster Square is also home to some of New Haven's best culinary spots, including the famous pizza establishments that have put the city on the culinary map. Residents and visitors alike flock to local pizzerias, where the aroma of fresh dough and bubbling cheese fills the air, offering a taste of authentic New Haven-style pizza.

For those who appreciate green spaces, Wooster Square Park is a central gathering place, perfect for picnics, leisurely strolls, or simply soaking in the atmosphere. The park’s historic gazebo and playground make it a favorite among families.

With its proximity to downtown New Haven, residents enjoy easy access to cultural attractions, shopping, and public transportation. Whether you’re looking for a cozy home or a vibrant community, Wooster Square offers an inviting atmosphere that captures the essence of New Haven living. Come discover the unique charm of Wooster Square, where history meets modern-day vibrancy!

Newest Listings in Wooster Square

$1,385,000

7 Beds ⋅ 7 Baths ⋅ 24193900 MLS

This remarkable Italian Villa-style home, built c.1850 and attributed to Henry Austin, is a gorgeous example of architectural finesse and what can happen when antique homes are valued and lovingly restored. Originally a 1-family home, the exterior was restored in the 1960's using best-practice historic preservation techniques and materials. The interior was converted to a 3-family home, saving lots of architectural ornament while adjusting to modern living. The work was part of Urban Redevelopment that recognized Wooster Square as a grouping of architecturally significant, grand buildings. This home is within the local Wooster Square Historic District, 1 of 3 in the City of New Haven. All 3 units have 2 levels, all centrally air-conditioned, all have washers & dryers. The lg owners' unit lower level has a renovated galley cook's kitchen, DR & LR with brick floors and walls, an extra room for exercise or office, and plenty of storage. The upper story has a dramatic 2-story entry and a beautifully restored front parlor. Units 2 & 3 are incredibly attractive, and would rent without any fuss. And where in Wooster Square will you find an in-ground pool? At 621 Chapel Street! Beautiful stone lower patio for morning coffee or dining, steps up to a stone deck surrounding the heated pool with plenty of room for chairs, chaises, dining table. The opportunity to live in an important historic building while enjoying modern conveniences doesn't come along often - it truly is a must see!

621 Chapel St, New Haven

$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

$285,000

2 Beds ⋅ 2 Baths ⋅ 24183163 MLS ⋅ Wooster Court BLDG.

Welcome home to this wonderful townhouse-style condo in the heart of New Haven's historic Wooster Square neighborhood. The main level offers a spacious living room, hardwood floor and a slider leading to a balcony. The updated kitchen features granite countertops, stainless steel appliances, and a dining area, while a convenient half bath completes the first floor. Upstairs, you'll find two generously sized bedrooms with hardwood floors and a full updated bathroom, providing comfortable living space. Additional amenities include on-site laundry, a covered carport parking space, and a storage unit. Ideally located near Yale University, Yale New Haven Hospital, Union Station, famous pizza restaurants, parks and more. Don't miss the opportunity to make this special home your own!

120 Wooster St Unit C, New Haven

$2,349,999

16 Beds ⋅ 12 Baths ⋅ 24181250 MLS

Turn-key 6-unit multifamily investment opportunity in New Haven's highly desirable Wooster Square neighborhood! Fully renovated and fully leased with long-term tenants in place, this income-producing asset offers true "collect the keys and collect the rent" ownership. Ideally located just minutes from Downtown New Haven, Yale University, Yale New Haven Hospital, Union Station, I-95, and I-91, the property benefits from strong rental demand driven by education, healthcare, biotech, and technology sectors. The approximately 6,009 SF building features updated units with modern kitchens, renovated bathrooms, contemporary finishes, and attractive layouts that appeal to today's renters. Tenants enjoy walkable access to Wooster Square Park, renowned restaurants including Frank Pepe's and Sally's Apizza, shopping, entertainment, cultural attractions, and direct rail access to New York City. With 5 off-street parking spaces, stable cash flow, and a premier location surrounded by ongoing residential and mixed-use development, this is a rare opportunity to own a fully stabilized multifamily asset in one of Connecticut's strongest rental markets.

177 Chestnut St, New Haven

$1,900,000

13 Beds ⋅ 9 Baths ⋅ 24175325 MLS

Fully stabilized Investment Property's. Multifamily Properties (9 units total and 6 garages) plenty of off street parking. 66 William is a 6 Family & 70 William is a 3 family. This property has been professionally managed and well taken care of. 7 out of the 9 units have been renovated in the past couple years. 8 of the 9 have washer and dryer in unit, and coin op in the basement. 2 of the units have mini splits for AC installed. Upgrades that have been done include 3 New Hot Water Heaters (2019), Exterior Paint & New Trim (2019), Common Area Renovations ( 2020), Upgrade All Electrical to 100w (2019), Partial Roof (2019), Driveway Repair and Striped (2019), and Paint Garages and some New Doors (2019). Schedule your tour today before this one is gone!

66-70 William St, New Haven

$575,000

4 Beds ⋅ 2 Baths ⋅ 24173215 MLS

**Eligible Yale University employees may qualify for up to $30,000 through the Yale Homebuyer Program**. Located in historic Wooster Square overlooking Lenzi Park, this two-family home offers charm, flexibility, and an exceptional location in one of New Haven's most desirable neighborhoods. Just minutes from Yale University, Yale New Haven Hospital, Downtown New Haven, Union Station, I-91, I-95, local restaurants, coffee shops, and Wooster Street's famous pizza scene, this property combines the convenience of city living with the character of a historic neighborhood. The owner's unit features tandem bedrooms, offering the perfect opportunity for a home office, nursery, or dressing room, along with hardwood floors, abundant natural light, a fireplace, and an updated eat-in kitchen with restored cabinetry and quartz countertops and a dishwasher. The second-floor apartment offers updated flooring, a functional layout, and its own laundry. Both units include newer boilers, updated hot water heaters, and separate utilities. Outside, enjoy a private patio surrounded by perennial gardens, plus a detached garage with an oversized studio/workshop ideal for a home office, fitness room, artist's studio, or additional storage. Additional highlights include a newer roof, windows, walk-up attic, full basement, natural gas heat, public utilities, and off-street parking. Whether you're looking for a home with room for extended family, space for guests, or the flexibility that a t

4 Jefferson St, New Haven

$1,500,000

8 Beds ⋅ 7 Baths ⋅ 24170960 MLS

Mixed Use Building in BA Zone, on FAMOUS - WOOSTER STREET, Once in a life-time opportunity. This building has been owned by one family for 35 years. Its for Sale. 3 residential units and one commercial unit. Total of 7,014 net square feet. Its amazing. The owners unit is approximately 3,000 square feet on ground floor, living room is a two storey height, 3 bedrooms en suite. Income per year is 124,500, Expenses $20,000. Net $104,500.

171 Wooster St, New Haven

$680,000

2 Beds ⋅ 2 Baths ⋅ 24170900 MLS ⋅ The Priory BLDG.

This luxury one-level loft condo in Wooster Square in a converted 1890's brick building is truly exciting. It's the best combination of old-world charm combined with an exciting modern spirit. The huge open spaces have lots of style and flair and offer the best of in-town living. Soaring ceilings, exposed brick and oversized windows provide incredible light and gives a wonderful bright and airy feeling. The open plan living space has spacious living and dining areas plus a dream kitchen which lends itself to a place when everyone will want to congregate in. It offers high-end appliances, a massive island with room for seating and outstanding work and storage space. You'll love to cook in this space! The primary suite has a wall of closets, a sitting area and a huge luxurious spa-like bathroom with a Jacuzzi tub plus a walk-in shower. The second bedroom is good size and is immediately next to another attractive full bath. The separate laundry room is a real plus. There is gas heat and central air conditioning, private basement storage and off-street parking. The condo is steps from Wooster Square Park and is close to Yale, the train station, YNHH, downtown New Haven and the weekly neighborhood farmer's market and is eligible for the Yale Homebuyer program. A person with good taste and a sense of adventure will love this condo!

8 Hughes Pl Unit 1N, New Haven

$699,900

5 Beds ⋅ 3 Baths ⋅ 24169666 MLS

Located in heart of beloved Historic Wooster Square; where timeless charm, vibrant city living, and smart investment potential beautifully align. This tastefully renovated two-family offers both lifestyle and opportunity. Set on a picturesque tree lined street just around the corner from WSQ Park, world-famous Wooster Street pizza, eateries & Farmer's Market, and just minutes to Yale University, Downtown New Haven and more. Thoughtfully updated with modern finishes while preserving its classic character, this special home features new kitchens, beautiful hardwood floors, and bright, inviting living spaces designed for both comfort and style. The first-floor unit offers a warm open layout perfect for owner occupancy or rental income with 2 spacious bedrooms, a dedicated office (or dressing room!), 1 full tile bath with tub, and private laundry. The second-floor unit creates excellent flexibility for investors or multi-generational living with 3 bedrooms, 2 full baths, living room and a sunny eat in tile kitchen. This special home also features a rare find, a spacious & private backyard with a fetching brick wall, plenty of parking parking, and Lenzi Park right out your front door! Whether you're seeking a soulful place to come home, an income-producing investment, or the perfect blend of both, this Wooster Square gem offers more than real estate, it offers possibility, connection, and to be part of one of New Haven's most iconic neighborhoods.

6 Jefferson St, New Haven

$2,300,000

7 Baths ⋅ 24166782 MLS

Fantastic Opportunity to own a well maintained Retail & Office Building in a walkable neighborhood in Wooster Square/Mill River. Every space has Central Air, many upgrades throughout the years. There is retail space for rent, see MLS #24142729. Perfect opportunity for a business owner occupant to make passive income and run a storefront business at the same time

900 Grand Ave, New Haven

$3,725,000

8 Beds ⋅ 8 Baths ⋅ 24158335 MLS

Welcome to The Orange Street Collection, a mixed-use hospitality and residential investment opportunity located in the heart of Downtown New Haven. Positioned steps from Yale University, this asset combines immediate income with meaningful long-term upside in one of the city's most active corridors. The property features over 5,000 square feet of restaurant space across the main and lower levels, including two full kitchens and a flexible layout suited for a flagship dining concept, dual operators, or a hospitality-driven reposition. The lower level offers additional potential for lounge, speakeasy, or private event use. Above, eight residential units provide stabilized income and consistent cash flow, creating built-in diversification and downside protection. This is a rare opportunity to acquire a true mixed-use downtown asset with lease-up potential, strategic location advantages, and strong fundamentals driven by proximity to Yale University, surrounding retail, and vibrant nightlife. Ideal for investors, 1031 exchange buyers, or owner-operators seeking both income and long-term positioning in a growing urban corridor.

99 Orange St, New Haven

$769,000

1 Baths ⋅ 24140533 MLS

A Legacy Address Ready for Its Next Visionary. Rising with quiet confidence along the historic Grand Avenue commercial spine, 922 Grand Avenue stands as one of the city's most architecturally honest and socially resonant commercial buildings. A mid-century civic structure that has outlived trends and weathered cycles, it now emerges as a rare canvas for the next chapter of neighborhood innovation. Built in 1963 during a wave of community-minded construction across the Elm City, the 4,500-square-foot masonry building is an enduring example of New Haven's post-industrial commercial architecture: solid, straightforward, purpose-built. Constructed of concrete, cinder block, and brick, with a flat rubber roof, 12-foot wall heights, and a full 4,500-square-foot basement, the property was engineered for longevity, adaptability, and public use - traits that have allowed it to remain structurally intact for more than six decades. Its original use classification - Clubs/Lodges with a modern STORE/SHOP (MDL-94) designation - reflects its history as a gathering place, a service hub, and a point of local connectivity. The unfinished basement offers expansion potential. The property invites reinvention - fitness and wellness programs, neighborhood brewery, grocery store, performance spaces, coworking studios, nonprofit headquarters, boutique commercial concepts, retail and more possibility subject to city approval. Seize this rare opportunity now.

922 Grand Ave, New Haven

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