$517,614Average Value$354Average 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 62 days on the market compared to the national average of 56 days. The median sale price for homes in Wooster Square, New Haven over the last 12 months is $428,000, up 17% from the median home sale price over the previous 12 months.
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
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
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
Experience modern living in the heart of historic Wooster Square. This stunning 3-bedroom, 1.1-bathroom townhome was fully renovated in 2016, taken down to the studs to ensure modern comfort and efficiency. The main level features a seamless, open-concept floor plan where the designer kitchen by Bender flows effortlessly into the living and dining areas-perfect for entertaining. Step through
Wooster Square condo living with direct park views and historic character. This twolevel, 2 bedroom, 2 bath home offers oversized windows overlooking the cherrytreelined square, 11+ ft ceilings, exposed brick, and hardwood floors. The main level includes a bright living area with dramatic 8 ft windows, an office nook ideal for remote work, and a kitchen with granite counters, an island, and gas
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
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
Enjoy the vibrant community of Wooster Square in this not to miss architecturally designed, renovated 2 bedroom, 2 bathroom apartment! Exposed brick, soaring ceilings, flooded with natural light, hardwood floors throughout. Main level has a renovated kitchen with granite counters, stainless appliances, gas stove, breakfast bar open to dining room and full bathroom. Entry way has two floor ceiling
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,
Incredible renovation on this spacious Old World style apartment in the heart of Wooster Square! The apartment features a new kitchen with stainless steel appliances and granite countertops, a beautiful marble bathroom, high ceilings, French doors, new windows, gorgeous decorative marble fireplaces, and beautiful hardwood floors throughout. There is a shared yard, on site laundry in the basement,
Discover Twenty Fair, New Haven's newest luxury residential destination where downtown sophistication meets neighborhood charm. Nestled at the coveted intersection of thriving downtown and historic Wooster Square, this 168-home community redefines modern living with floorplans that surprise and delight, alongside amenities that blend modern luxury with everyday comfort.Create your home in New
Spacious third floor 1 or 2 bedroom apartment located in charming brick brownstone on world famous Wooster St. The apartment has a spacious eat in kitchen, living room with exposed brick, high ceilings and exceptional light. Large eat in kitchen and separate pantry area with ample cabinet space. No pets, and street parking only. Tenants pay for all utilities (gas for heat, hot water & cooking).
Property Id: 2736992 2nd floor 2 bdrm in the heart of Wooster! Walk to some of the best rated pizzerias and Wooster Square Park is right around the corner. Spacious living room Eat-in kitchen Hardwood floors thruout On-site, shared laundry Street parking Lease term - 1 yr minimum Pets 35lbs and under ok - one tike pet fee of $300 (per pet) All
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
Newly Renovated 2BR Apt in Wooster SquareFirst Floor (2 Levels)** Beautiful Hardwood Floor ** Washer & Dryer** Decorative Fireplace** Lots of Natural Light** Exposed Brick Wall** Walking Distance to Wooster Sq Restaurants & Cafes** Near Yale - Students are Welcome ! Requirements:Proof of Monthly Income of 3x the Rent (Must Show Pay Stubs) 1
***ONE MONTH FREE RENT*** Bright and inviting 2bedroom unit in highly desirable Wooster Square, offering an abundance of natural light throughout. Enjoy low maintenance living with hardwood and tile flooring, a spacious eat in kitchen, and the convenience of an in-unit washer and dryer. Off-street parking adds tremendous value in this sought-after neighborhood. Just one block from historic
The Urban Team at Wareck D OstilioHoulihan Lawrence WD
Welcome to your dream home in the heart of New Haven! This charming 2-bed, 1-bath apartment on Chapel St is the perfect place for you to call home. With its stunning colonial design, you'll feel like you've stepped back in time to a more elegant era.Inside the apartment, you'll be impressed by the stunning features that await you. The living room boasts a beautiful fireplace and a
You will love the location of this condo rental. Mint 2 Bdr Townhouse in the Wooster Street area. Walk to all the infamous pizzerias & have dessert in one of the local bakeries. Relax on the front porch and enjoy the Wooster Park view. Kitchen & bath recently renovated. Laundry on 2nd level. Generously sized bedrooms. Hardwood flooring throughout. Assigned parking in locked private parking lot.
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