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Wooster Square Homes for Sale

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  • /40

    $899,999 Open Sat 11AM - 1PM

    • 6 Beds
    • 4 Baths
    • 2,885 Sq Ft

    99 Olive St, New Haven, CT 06511

    Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus owners unit/office space, has been thoughtfully

    John Daikus eXp Realty

    99 Olive St, New Haven, CT 06511
  • /4

    $749,500

    • 4 Beds
    • 3 Baths
    • 2,728 Sq Ft

    257 Saint John St, New Haven, CT 06511

    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

    Betsy Grauer Betsy Grauer Realty, Inc

    257 Saint John St, New Haven, CT 06511
  • /39

    $880,000

    • 4 Beds
    • 3 Baths
    • 2,386 Sq Ft

    335 Saint John St, New Haven, CT 06511

    Located in the heart of New Haven's vibrant Wooster Square neighborhood, this beautifully maintained brick 3-unit multifamily building is a prime investment opportunity. This property features three fully occupied apartments. Includes two spacious 2-bedroom, 1-bathroom units rented at $2,300 and $2,200 per month, and a studio unit rented at $1,750 per month, generating a total monthly income of

    Naftali Caplan Caplan Realty Corp.

    335 Saint John St, New Haven, CT 06511

Why Live in Wooster Square

Wooster Square in New Haven is a historic neighborhood established in 1820, known for its walkability and vibrant community. The area features a mix of architectural styles, including Colonial, Italianate, and Victorian multi-family homes, alongside modern condos and century-old brick churches. The neighborhood's centerpiece is Wooster Square Park, a popular gathering spot that hosts the annual Cherry Blossom Festival. Nearby, Wooster Memorial Park offers a shaded playground, bocci court, and memorials, while Jocelyn Square Park provides a large field, playground, basketball court, and summer splash pad. Wooster Square is renowned for its pizza, with local favorites like Sally's Apizza, Frank Pepe Pizzeria Napolentana, and Zeneli's Pizza. Residents also enjoy fresh produce from The Meat King by C-Town, the Winter Market, and the Wooster Square Farmers Market, which operates year-round. The neighborhood has two community gardens for those interested in gardening. While the local schools, Conte West Hills Magnet School and Metropolitan Business Academy, have average ratings, they offer unique educational models and specialized study paths. Wooster Square is conveniently located near Interstate 91, Interstate 95, and U.S. State Route 1, with CTtransit bus stops along Grand Avenue and Chapel Street. The State Street train station, less than a mile away, provides CTrail and Amtrak services, and Tweed New Haven Airport is just 3.5 miles away.

Frequently Asked Questions

Is Wooster Square a good place to live?
Wooster Square is a good place to live. Wooster Square is considered very walkable and a biker's paradise with great transit options. Wooster Square has 6 parks for recreational activities. It is somewhat dense in population with 7.2 people per acre and a median age of 36. The average household income is $98,754 which is above the national average. College graduates make up 72.6% of residents. A majority of residents in Wooster Square are renters, with 80.4% of residents renting and 19.6% of residents owning their home. A local real estate agent serving Wooster Square can help you decide if this neighborhood is the right one for you. Learn more on our Wooster Square neighborhood guide.
Is Wooster Square, CT a safe neighborhood?
Wooster Square, CT is less safe than the average neighborhood in the United States. It received a crime score of 6 out of 10.
How much do you need to make to afford a house in Wooster Square?
The median home price in Wooster Square is $375,000. If you put a 20% down payment of $75,000 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $1,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $78K a year to afford the median home price in Wooster Square. The average household income in Wooster Square is $99K.
What are the best public schools in Wooster Square?
The best public schools that serve Wooster Square are:
What are the best private schools in Wooster Square?
The best private schools that serve Wooster Square are:
  • St. Thomas's Day School has an A+ Niche grade, a student teacher ratio of 5:1 and an average review score of 5.0.
  • Cold Spring School has an A+ Niche grade, a student teacher ratio of 6:1 and an average review score of 5.0.
  • The Foote School has an A Niche grade, a student teacher ratio of 8:1 and an average review score of 4.2.
What are the most popular zip codes in Wooster Square, New Haven, CT?
The most popular zip codes in Wooster Square, New Haven, CT include 06460, 06510, 06511, 06519 and 06513.
What are the most popular neighborhoods near Wooster Square, New Haven, CT?
The most popular neighborhoods near Wooster Square, New Haven, CT are Wooster Square, East Rock, Dwight, Dixwell and The Hill.

Home Trends in Wooster Square, CT

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$970,500
Median Townhouse Sale Price
$275,000
Median 2 Bedroom Sale Price
$408,250
Median 1 Bedroom Sale Price
$328,750
Average Price Per Sq Ft
$340
Number of Homes for Sale
0
Last 12 months Home Sales
29
Months of Supply
0.00
Median List Price
$375,000
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
-8%
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