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Wooster Square Homes for Sale

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  • /32

    $2,199,999

    $200K PRICE DROP
    • 16 Beds
    • 12 Baths
    • 6,009 Sq Ft

    177 Chestnut St, New Haven, CT 06511

    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

    Agent Photo

    Arian Hoxha

    Serhant Connecticut, LLC

    177 Chestnut St, New Haven, CT 06511
  • /33

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft

    100 William St, New Haven, CT 06511

    Discover a prime investment opportunity with this exceptional multi-family property located in the heart of New Haven, CT. This well-maintained building offers a total of 2 spacious units, each designed for comfort and convenience. Amenities include off-street parking, on-site laundry, beautifully landscaped yard. Situated in a vibrant neighborhood, this property is just minutes away from Yale

    Maryrose Field Ellison Homes Real Estate

    100 William St, New Haven, CT 06511
  • /29

    $285,000

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,045 Sq Ft

    120 Wooster St Unit Q, New Haven, CT 06511

    Your chance to experience modern townhouse living in New Haven's most iconic and legendary neighborhood awaits! Welcome to this open and sun filled 2 bedroom, 1.5 bath townhouse located on sought after Wooster Street. This move in ready home with new windows features a bright, flowing layout with freshly painted interiors that create a clean, modern feel throughout. The main level offers an

    Sherri Schwartz Coldwell Banker Realty

    120 Wooster St Unit Q, New Haven, CT 06511
  • /32

    $285,000

    $64K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    190 Wooster St Unit 63, New Haven, CT 06511

    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

    Lisa Grywalski-Bailey William Pitt Sotheby's Int'l

    190 Wooster St Unit 63, New Haven, CT 06511
  • /2

    $875,000

    • 8 Beds
    • 4 Baths
    • 3,888 Sq Ft

    191 Saint John St, New Haven, CT 06511

    This Wooster Square brick and frame 4 family is an amazing opportunity. Good size apartments, separate utilities with gas heat and hot water heaters, replacement windows, washes and dryers in each unit and off-street parking for 6 cars. The building has been well maintained. The current rents are under market value, but some updates will bring this building to its' full potential. Located in an

    Betsy Grauer Betsy Grauer Realty, Inc

    191 Saint John St, New Haven, CT 06511
  • /38

    $595,000

    • 2 Beds
    • 2 Baths
    • 1,524 Sq Ft

    42 Academy St Unit 2, New Haven, CT 06511

    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

    Cheryl Szczarba Seabury Hill REALTORS

    42 Academy St Unit 2, New Haven, CT 06511
  • /23

    $1,200,000

    • 5 Beds
    • 4 Baths
    • 2,396 Sq Ft

    341 Saint John St, New Haven, CT 06511

    Prime Wooster Square 4-Unit Investment Opportunity! Ideally located just steps from Wooster Square and minutes from Yale University, this beautifully updated four-unit property offers an exceptional opportunity for investors, owner-occupants, or those seeking flexible rental options. The property has been tastefully renovated while thoughtfully preserving its original character, including exposed

    Andrew Roach KD Realty

    341 Saint John St, New Haven, CT 06511
  • /16

    $1,900,000

    $150K PRICE DROP
    • 13 Beds
    • 9 Baths
    • 6,852 Sq Ft

    66 William St, New Haven, CT 06511

    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

    James Huffman Farnam Realty Group

    66 William 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-style 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. Local schools include Conte West Hills Magnet School and Metropolitan Business Academy. Wooster Square is near Interstate 91, Interstate 95, and U.S. State Route 1, with CT Transit 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.

Wooster Square Home Prices vs. Nearby New Haven, CT Neighborhoods

Wooster Square The Hill Fair Haven Heights Edgewood
Median Home Price
$392,200
$280,000
$340,000
$504,500
Median Sale Price
$415,000
+15% YoY
$250,000
-23% YoY
$357,500
+43% YoY
$379,000
-24% YoY
Median Single Family Price
$767,500
$246,000
$380,000
$499,500
Median Townhouse Price
$335,000
$345,000
$460,750
$569,900
Median Condo Price
$332,500
$385,000
$199,950
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Total Active Listings
3 listings
9 listings
3 listings
3 listings
Market Conditions
2 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
1 Month of Supply
Seller's Market
12 Months of Supply
Buyer's Market

Frequently Asked Questions

Is Wooster Square a good place to live?
Wooster Square is a good place to live. Wooster Square is considered fairly walkable and very bikeable with excellent transit options. Wooster Square has 6 parks for recreational activities. It is somewhat dense in population with 8.0 people per acre and a median age of 36. The average household income is $98,754 which is below the national average. College graduates make up 72.6% of residents. A majority of residents in Wooster Square are renters, with 80% of residents renting and 20% 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 5 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 $392,200. If you put a 20% down payment of $78,400 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $2,010 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $86K a year to afford the median home price in Wooster Square. Learn how much home you can afford with our Home Affordability Calculator. 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 3.7.
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 06511, 06460, 06510, 06513 and 06519.
What are the most popular neighborhoods near Wooster Square, New Haven, CT?
The most popular neighborhoods near Wooster Square, New Haven, CT are Downtown New Haven, East Rock, Fair Haven, Dwight and The Hill.
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