$495,909Average Value$341Average Price per Sq Ft4Homes For Sale
Historic buildings, community and “Little Italy” in Wooster Square
Wooster Square is a historic district just steps from Downtown New Haven and less than a mile from Yale University. Home to the city’s “Little Italy,” it’s known for its quiet, tree-lined residential streets and sense of community, with regular events at Wooster Square Park. Its historic buildings and wide variety of housing types provide options for both homeowners and renters.
Residents enjoy a beautiful spring day on their front porches in Wooster Square.
The cherry blossom trees in Wooster Square make a beautiful background for a photo or two.
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Walking, buses and the Yale Shuttle downtown, easy highway access
Wooster Square brushes right against Downtown New Haven, so it’s an easy walk for many. Bus stops and the Yale Shuttle also make it easy to get around. Wooster Square sits at the crux of several highways, including Interstates 95 and 91, U.S. Route 1 and U.S. Route 5, which connect residents to other parts of New Haven and beyond. Residents can catch trains to New York City or Connecticut’s shore towns at Connecticut Street Station. Tweed New Haven Airport is 4 miles away, and it’s under 2 miles to Yale New Haven Hospital.
The State Street train station is just a couple of minutes away from Wooster Square.
Connecticut State Street Station has trains leaving for NYC and Connecticut's shore towns.
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Buying or renting distinct multi-family homes and condos
Most of Wooster Square’s homes are multi-family with street parking; many single-family houses have been converted into multi-family options. These homes are often Italianate houses and brownstone rowhouses built in the 1800s, with a few Colonial Revival and traditional style homes. Unique condominiums are also common. “There’s a lot of old buildings and churches that have been converted into condos,” says Jennifer D'Amato, a broker and team leader at Real Broker who used to live in Wooster Square and has been selling homes in the area for 23 years. “There have been some newer buildings popping up too, so apartment complexes with retail on the first floor.”
Prices vary greatly in this competitive market. Townhouses can start in the high $100,000 range and climb to the mid $700,000s, while condos start in the mid $200,000s and max out in the mid $500,000s. Multi-family homes occasionally drop to the low $400,000s, but most start closer to the low $600,000s and max out at around $1.4 million. Only a handful of single-family homes sell each year, but they can cost anywhere from the mid $400,000s to over $1.5 million. Many Wooster Square residents rent their homes.
Stunning Italianate homes are seen throughout Wooster Square.
Buyers explore newly built condo options in Wooster Square.
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Wooster Square is known for its quite vibe and friendly community
D’Amato says crossing into Wooster Square brings an immediate vibe shift from downtown. It’s quieter, more residential and known for its tight-knit community. “You can walk around, and people are picnicking in the park all year long, so it’s a really nice way to meet neighbors,” D’Amato says. “It’s not as generational as Westville might be, but there are some people whose families have lived there for 100 years.”
Historic homes with modern updates are a hallmark of Wooster Square.
St. Michael's Church stands as a historic landmark in Wooster Square.
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Community gathers at Wooster Square Park, pups play at the dog park
Wooster Square Park anchors the neighborhood. Its walking trails are lined with cherry trees and benches, and it’s a frequent gathering place for community events. People let their pups burn some energy at Union Street Dog Park, which has a water fountain and some shade to keep romping dogs cool during the summer. Wooster Square also has a community garden. The 425-acre East Rock Park is 2 miles north.
Neighbors can grow their own vegetables at the Wooster Square Community Garden.
Residents can spend a sunny afternoon enjoying Wooster Memorial Park's serene beauty.
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"Little Italy" on Wooster Street, more dining downtown
The Wooster Street Arch — which lights up red, white and green at night for the Italian flag — marks the entrance to “Little Italy.” “That’s where you’ll find places like Sally’s Apizza and Frank Pepe Pizzeria, which have been competing as the number one pizza place in New Haven for close to 100 years,” D’Amato says. They’re among the most well-known pizza spots in the United States; some locals insist you can’t say you’ve been to New Haven without eating there. Other Italian spots along Wooster Street include:
Zeneli Pizzeria e Cucina Napoletana
Libby's Italian Pastry Shop and Italian Ice
Consiglio's Restaurant
D’Amato says an influx of new eateries is blurring the line between Wooster Square and Downtown New Haven. Being so close to downtown also means residents can walk to its hole-in-the-wall bars like Cafe Nine and upscale eateries like Barcelona Wine Bar. For groceries, residents head to The Meat King by C-Town on Wooster Square’s east side.
Diners savor delicious Italian dishes and pizza at Zeneli's in Wooster Square.
Residents find great prices on groceries at the Meat King By C-Town in Wooster Square.
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Annual Cherry Blossom Festival, a famers market and shows downtown
Every April, people flock to Wooster Square Park for its Cherry Blossom Festival, settling on picnic blankets to enjoy live music, food and community. The park hosts other events like an annual Christmas tree lighting and October pumpkin painting. On Saturday mornings, the year-round CitySeed Wooster Square Farmers Market sets up over three dozen vendors selling produce and handmade goods. Entertainment venues like the Yale University Art Gallery and Yale Repertory Theatre are only a mile away. “You'll go to a show there and be wondering, 'How did it end?' because it's very indie,” D'Amato says.
The annual Cherry Blossom Festival is a beloved community event in Wooster Square.
Locals enjoy farm fresh goods at the CitySeed Wooster Square Farmers Market every week.
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School choice and free college courses in New Haven schools
New Haven Public Schools’ school choice program allows students to apply to charter, magnet or out-of-district schools. Space is limited and seats are determined by lottery. The Metropolitan Business Academy is a magnet high school right in Wooster Square. The district’s "College Before College" program allows high schoolers to take courses at any New Haven university for free, including Yale.
Metropolitan Business High School in Wooster Square prepares students for success.
Elementary grade students can attend the Conte West Hills Magnet School in Wooster Square.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Wooster Square neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Wooster Square
US
Homicide
4
4
Sexual Assault
6
4
Assault with Weapon
4
4
Robbery
3
4
Burglary
6
4
Motor Vehicle Theft
6
4
Larceny
5
4
Crime Score
5
4
Source: WhatIsMyCrimeRisk.com
Wooster Square Demographics and Home Trends
On average, homes in Wooster Square, New Haven sell after 46 days on the market compared to the national average of 54 days. The median sale price for homes in Wooster Square, New Haven over the last 12 months is $408,250, up 10% from the median home sale price over the previous 12 months.
Welcome home to Wooster Square, a coveted neighborhood in New Haven. This stylish end-unit townhouse has been thoughtfully updated and is truly move-in ready. Flooded with natural light, the main level features a spacious living room flowing into a well-appointed eat-in kitchen complete with brand-new granite countertops, real wood cabinetry and updated appliances. Step out onto your private
Charming brick 2-bedroom, 1-bath end-unit townhouse-style condo in the heart of Wooster Square, available through the Yale Home Buyer's Program for qualified Yale employees. Set on picturesque, cherry-tree-lined Hughes Place, this 2024 beautifully remodeled home offers the perfect blend of character, comfort, and walk-to-everything convenience. Leave the car behind-stroll to Wooster Street
If you've ever dreamed of living in the heart of Wooster Square, this is your chance. Tucked inside Wooster Court Condominiums, a charming and intimate community of just 23 units, this townhouse-style home offers something rare - true neighborhood living in one of New Haven's most iconic locations. Step inside and you'll immediately feel how thoughtfully this home has been refreshed. Sunlight
Sophisticated New York-style loft offering 1,115 SQ FT of living space with 1 bedroom & 1 bath in a chic complex just steps from Wooster Square Park, Downtown NH & Yale. The open-concept floor plan has HW floors throughout and is perfect for entertaining. The generous flex living & dining area features an expansive window that overwhelms the room with natural light. The sleek, contemporary
Welcome to 6 Court Street, a 20-foot-wide brick building set on one of New Haven's most coveted and picturesque streets, in the heart of the historic Wooster Square neighborhood. Steps from all the history that makes New Haven famous and rich in character and architectural presence, this exceptional property spans four levels of living and is currently configured as a three-unit residence,
This wonderful three family is on a quiet one-way street in the Wooster Square area. The house has been lovingly maintained by a long term owner. The first floor unit has five rooms. The living room has a high ceiling, fantastic cast iron moldings and pocket doors. There is a spacious dining room, updated kitchen with good work and storage space, two bedrooms and a bath. The apartment has gas
Exceptional re-design at this 6 unit building in Wooster Square! Brand new from the inside out, the apartments were fully fitted with all new white shaker style kitchen cabinets, quartz counters, stainless appliances, washer/dryer, two full bathrooms and brand new heat and central air! This versatile layout can function well as a three bedroom apartment or as a two bedroom with a larger living
Welcome to 18 High at New Haven Towers, our new luxury community Which opened in June of 2021..Located directly between Yale University and Yale-New Haven Hospital, 18 High is inthe center of the action, and carefully designed to be a haven of camaraderie, cutting edge amenities and convenience. Explore our chic spaces created with your comfort in mind - from our rooftop terrace with
Great 1 bedroom apartment on charming street in the Wooster Square neighborhood of New Haven. The apartment is located on the third floor of a renovated 1880's multi family home. The property has beautiful hardwood floors, skylights and modern updates throughout and an amazing shared backyard! This great apartment features a spacious living/dining area with wonderful light and modern stainless
Welcome to Olive & Wooster, the ultimate living experience nestled in the heart of Wooster Square. Oliver & Wooster offers spacious modern apartments ranging from studios to four bedrooms, featuring all the comforts you desire and lease term options built just for you. Our pet-friendly community provides tastefully designed amenities including a state-of-the-art clubhouse and bar, fitness center,
AVAILABLE JUNE 1 or JUNE 15 - WOOSTER SQUARE! Fabulous newly redesigned and renovated two-room studio with tons of light and great space. Fully appointed, completely remodeled kitchen has brand new cabinets, and all new stainless steel appliances with a built-in microwave and dishwasher. Spacious new bathroom with tub/shower combo. New hardwood flooring throughout. There is also a Murphy bed with
Live in the heart of historic Wooster Square in this beautifully renovated 2-bedroom, 1-bath apartment that blends modern comfort with classic New Haven charm. Located in one of the city's most desirable neighborhoods, this spacious unit offers exceptional natural light, original architectural details, and thoughtful updates throughout. Immediate Move-In!Key Features: Two generous
Stunning two bedroom apartment on the second floor of of a signature Wooster Square brownstone. Stylish living room with high ceilings, huge windows with amazing views of Wooster Square Park, and fireplace Cozy, but updated top of the line kitchen with quartz countertops, high end appliances, stylish backsplash, and high end fixtures. Hardwood floors throughout. Master bedroom has built in
This is a large and bright, first floor apartment, with direct access to the small back garden. Located in the very desirable Wooster Square neighborhood, you will be just five blocks from downtown and Yale University. Walk this park side neighborhood to local coffee shops, grocery stores and the best pizza in New England. There is safe, free street parking out front. The entire floor retains
*** WOOSTER SQUARE! *** Fabulous loft with tons of light and space. Just steps from Wooster Square Park - a MUST SEE! Fully appointed kitchen has granite counters and ample counter space, built-in microwave and dishwasher. Bath has granite tile floor, tub/shower combo and a pedestal sink. Open living and dining rooms have beautiful oak floors! Grand oak staircase leads to loft bedroom with
Great condition, very clean, very quiet, public transportation, near of the Wooster Square park, and lots of restaurants.If you look for a good safe historic town this is the place to live Thank you
Beautiful 3rd floor apartment in a classic brownstone overlooking Wooster Square Park. Heat, Hot Water, Laundry,WiFi Included. Comes fully furnished. Stylishly remodeled with an open-concept layout that blends modern amenities with timeless architectural details. Features include a newer kitchen, hardwood floors, high ceilings, arched windows, and a fireplace. Enjoy unparalleled views of the park
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