1,218

Wooster Square Homes

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  • /35

    $740,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,262 Sq Ft

    96 Lyon St, New Haven, CT 06511

    Wooster Square - one of New Haven's most beloved neighborhoods! 96 Lyon Street delivers the space, the updates, and the lifestyle to match. Thoughtfully updated in 2004, this 2,262sf residence lives comfortably across two full floors, with high ceilings on first floor and expansion potential in the unfinished walk-up attic. The main level welcomes you with a spacious formal living room, an

    Agent Photo

    Jennifer D'Amato

    Real Broker CT, LLC

    (475) 254-7604

    96 Lyon St, New Haven, CT 06511
  • /141

    Starting at $1,208

    Total Monthly Price

    • Studio - 4 Beds

    87 Union St, New Haven, CT 06511

    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,

    Olive & Wooster

    (475) 241-7333

    87 Union St, New Haven, CT 06511
  • 190 Wooster St Unit 27, New Haven, CT 06511

    $230,000 Sold Jul 25, 2025

    190 Wooster St Unit 27, New Haven, CT 06511

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Built 1964

    Last Sold Summary

    • 8% Below List Price
    • $177/SF
    • 56 Days On Market

    Last Listing Agent Christine Maisano Berkshire Hathaway NE Prop.

    190 Wooster St Unit 27, New Haven, CT 06511
    • 329 Greene St Unit 3, New Haven, CT 06511

      Est $702,163 Not Listed For Sale

      329 Greene St Unit 3, New Haven, CT 06511

      • 3 Beds
      • 2.5 Baths
      • 1,780 Sq Ft
      • Built 2006
      329 Greene St Unit 3, New Haven, CT 06511

      Last Sold Summary

      • 3% Above List Price
      • $382/SF
      • 23 Days On Market
      • Last Sold Price $680,000
      • Apr 29, 2025

      Last Listing Agent Betsy Grauer Betsy Grauer Realty, Inc

  • /19

    $199,900 Pending

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    120 Wooster St Unit W, New Haven, CT 06511

    Where World-Class Pizza Meets Cozy City Living. Discover easy living in this beautifully updated condo, nestled in the heart of historic Wooster Square. With charming character and modern upgrades, this inviting home offers the perfect blend of comfort and convenience. Open concept living with large windows for an abundant of natural light. Modern appliances for effortless living. Steps from

    Agent Photo

    Victoria Stillings

    Coldwell Banker Realty

    (203) 408-1660

    120 Wooster St Unit W, New Haven, CT 06511
  • /6

    Starting at $2,108

    Total Monthly Price

    • Studio - 2 Beds

    20-34 Fair St, New Haven, CT 06511

    Discover Twenty Fair, New Havens 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

    Twenty Fair

    (475) 267-5056

    20-34 Fair St, New Haven, CT 06511
  • 125 Olive St Unit G4, New Haven, CT 06511

    $253,000 Sold Jun 16, 2025

    125 Olive St Unit G4, New Haven, CT 06511

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $298/SF
    • 22 Days On Market

    Current Estimated Value $245,451

    Last Listing Agent Robert Sacco Coldwell Banker Realty

    125 Olive St Unit G4, New Haven, CT 06511
    • 629 Chapel St Unit 3A, New Haven, CT 06511

      Est $400,031 Not Listed For Sale

      629 Chapel St Unit 3A, New Haven, CT 06511

      • 2 Beds
      • 2 Baths
      • 934 Sq Ft
      • Built 1900
      629 Chapel St Unit 3A, New Haven, CT 06511

      Last Sold Summary

      • $429/SF
      • 49 Days On Market
      • Last Sold Price $400,500
      • Apr 25, 2025

      Last Listing Agent Brianne Decio RE/MAX

  • /38

    $699,500 Pending

    • 6 Beds
    • 3 Baths
    • 2,930 Sq Ft

    45 Lyon St, New Haven, CT 06511

    Nestled in the heart of New Haven is this lovely Wooster Square area 2 family which has been beautifully maintained. The house has lots of updates, newer vinyl siding, Thermopane windows, gas heating units, blown-in insulation and updated electric. The first floor has five rooms and can be used as a 2- or 3-bedroom apartment. The second and third floors are combined to make a large, sunny duplex

    Betsy Grauer Betsy Grauer Realty, Inc

    45 Lyon St, New Haven, CT 06511
  • /53

    Starting at $2,245 Plus Fees

    • Studio - 2 Beds

    18 Hughes Place, New Haven, CT 06511

    Welcome to 18 High at New Haven Towers, our new luxury building Which opened in June of 2021..Located directly between Yale University and Yale-New Haven Hospital, 18 High is in the center of the action, and a haven of camaraderie, cutting edge amenities and convenience. Explore our chic spaces created with your comfort in mind - from our rooftop terrace to a state of the art fitness

    18 High

    (475) 241-0624

    18 Hughes Place, New Haven, CT 06511
  • 43 Chestnut St Unit 106, New Haven, CT 06511

    $370,000 Sold Jun 30, 2025

    43 Chestnut St Unit 106, New Haven, CT 06511

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Built 1890

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 61 Days On Market

    Current Estimated Value $378,249

    Last Listing Agent Dawn D'Auria Coldwell Banker Realty

    43 Chestnut St Unit 106, New Haven, CT 06511
    • 120 Wooster St Unit Q, New Haven, CT 06511

      Est $287,117 Not Listed For Sale

      120 Wooster St Unit Q, New Haven, CT 06511

      • 2 Beds
      • 1.5 Baths
      • 1,045 Sq Ft
      • Built 1968
      120 Wooster St Unit Q, New Haven, CT 06511

      Last Sold Summary

      • 4% Above List Price
      • $263/SF
      • 32 Days On Market
      • Last Sold Price $275,000
      • May 05, 2025

      Last Listing Agent Dallas Davis Dalvis Realty

  • /40

    $1,295,000

    • 5 Beds
    • 4 Baths
    • 4,048 Sq Ft

    562 Chapel St, New Haven, CT 06511

    This coveted iconic end unit Brownstone is part of the National Historic Places. The amazing location faces Wooster Square Park, has a side yard of Paul Russo park, water views of Long Island sound from the distinctive cupola, + easy access to Yale and the train station. The beautiful architectural details inside and out include the restored facade, renovated cornices + iron work. There are 11'

    Betsy Grauer Betsy Grauer Realty, Inc

    562 Chapel St, New Haven, CT 06511
  • /13

    Starting at $2,650 Plus Fees

    • 2 Beds

    99 Olive St, New Haven, CT 06511

    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

    (888) 270-3195

    99 Olive St, New Haven, CT 06511
  • 560 Chapel St, New Haven, CT 06511

    $1,500,000 Sold Jul 11, 2025

    560 Chapel St, New Haven, CT 06511

    • 4 Beds
    • 4 Baths
    • 3,036 Sq Ft
    • Built 1865

    Last Sold Summary

    • 8% Above List Price
    • $494/SF
    • 52 Days On Market

    Current Estimated Value $1,507,118

    Last Listing Agent Betsy Grauer Betsy Grauer Realty, Inc

    560 Chapel St, New Haven, CT 06511
    • 576 Chapel St Unit 4, New Haven, CT 06511

      Est $325,147 Not Listed For Sale

      576 Chapel St Unit 4, New Haven, CT 06511

      • 2 Beds
      • 1 Bath
      • 921 Sq Ft
      • Built 1860
      576 Chapel St Unit 4, New Haven, CT 06511

      Last Sold Summary

      • 3% Below List Price
      • $364/SF
      • 97 Days On Market
      • Last Sold Price $335,000
      • Feb 05, 2024

      Last Listing Agent Karen Floriano William Raveis Real Estate

  • /28

    $349,900

    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft

    120 Wooster St Unit V, New Haven, CT 06511

    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

    Adam Roy BHGRE Gaetano Marra Homes

    120 Wooster St Unit V, New Haven, CT 06511
  • /16

    $1,900 Plus Fees

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    40 Academy St Unit 2, New Haven, CT 06511

    Property Id: 1191038Location, location, location! Beautiful, spacious apartment directly overlooking historical Wooster Square. One large bedroom and smaller second bedroom or office. Apartment also includes a living room, full size kitchen with refrigerator and stove, and bathroom. Walking distance to Yale, farmer's market, Wooster Street restaurants, Cherry Blossom Festival and Downtown

    (475) 234-4661

    40 Academy St Unit 2, New Haven, CT 06511
  • 190 Wooster St Unit 51, New Haven, CT 06511

    $222,500 Sold Jun 25, 2025

    190 Wooster St Unit 51, New Haven, CT 06511

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $202/SF
    • 20 Days On Market

    Last Listing Agent Roseann Iuvone Coldwell Banker Realty

    190 Wooster St Unit 51, New Haven, CT 06511
    • 817 Grand Ave Unit 403, New Haven, CT 06511

      Est $396,249 Not Listed For Sale

      817 Grand Ave Unit 403, New Haven, CT 06511

      • 1 Bed
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1880
      817 Grand Ave Unit 403, New Haven, CT 06511

      Last Sold Summary

      • 7% Below List Price
      • $316/SF
      • 11 Days On Market
      • Last Sold Price $425,000
      • Nov 14, 2023

      Last Listing Agent Jack Hill Seabury Hill REALTORS

  • /30

    $1,500,000 Coming Soon

    • 8 Beds
    • 7 Baths
    • 7,014 Sq Ft

    171 Wooster St, New Haven, CT 06511

    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.

    Susan Frew Betsy Grauer Realty, Inc

    171 Wooster St, New Haven, CT 06511
  • /11

    $2,150 Plus Fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    533 Chapel St Unit 7, New Haven, CT 06511

    Property Id: 2508846GORGEOUS unit!Entire 4th floor unitcathedral like ceilingskitchen islanddishwasher and microwave 2 good sized bedroomsopen floor planliving and dining areagood closet spaceShared washing machine and dryer on basementBeautiful view of Wooster Square ParkRIGHT IN WOOSTER SQUARE!Small pets ok - One time pet fee required.

    (475) 267-1356

    533 Chapel St Unit 7, New Haven, CT 06511
  • 323 Greene St Unit 2, New Haven, CT 06511

    $480,000 Sold Jun 30, 2025

    323 Greene St Unit 2, New Haven, CT 06511

    • 2 Beds
    • 2.5 Baths
    • 1,208 Sq Ft
    • Built 1870

    Last Sold Summary

    • 1% Above List Price
    • $397/SF
    • 18 Days On Market

    Current Estimated Value $439,152

    Last Listing Agent Betsy Grauer Betsy Grauer Realty, Inc

    323 Greene St Unit 2, New Haven, CT 06511
    • 817 Grand Ave Unit 203, New Haven, CT 06511

      Est $369,092 Not Listed For Sale

      817 Grand Ave Unit 203, New Haven, CT 06511

      • 2 Beds
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1880
      817 Grand Ave Unit 203, New Haven, CT 06511

      Last Sold Summary

      • 9% Below List Price
      • $301/SF
      • 81 Days On Market
      • Last Sold Price $405,000
      • Jun 01, 2024

      Last Listing Agent Jack Hill Seabury Hill REALTORS

  • /40

    $699,900

    • 5 Beds
    • 3 Baths
    • 2,064 Sq Ft

    6 Jefferson St, New Haven, CT 06511

    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,

    Melanie Gunn Coldwell Banker Realty

    6 Jefferson St, New Haven, CT 06511
  • /14

    $1,650 Per Month

    • 1 Bath
    • 1,548 Sq Ft
    • Apartment for Rent

    502 Chapel St Unit 4, New Haven, CT 06511

    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

    Sarah Beth Luce-Del Prete Coldwell Banker Realty

    502 Chapel St Unit 4, New Haven, CT 06511
  • 614 Chapel St, New Haven, CT 06511

    $1,384,000 Sold Mar 13, 2026

    614 Chapel St, New Haven, CT 06511

    • 6 Beds
    • 4.5 Baths
    • 4,874 Sq Ft
    • Built 1873

    Last Sold Summary

    • 6% Below List Price
    • $284/SF
    • 118 Days On Market

    Current Estimated Value $1,455,999

    Last Listing Agent Carissa Mastriano GRL & Realtors, LLC

    614 Chapel St, New Haven, CT 06511
    • 30 Lyon St, New Haven, CT 06511

      Est $690,327 Not Listed For Sale

      30 Lyon St, New Haven, CT 06511

      • 3 Beds
      • 3 Baths
      • 2,880 Sq Ft
      • Built 1880
      30 Lyon St, New Haven, CT 06511

      Last Sold Summary

      • 1% Below List Price
      • $243/SF
      • 40 Days On Market
      • Last Sold Price $700,000
      • Mar 19, 2025

      Last Listing Agent Nadia Martinez Ki Property Group

  • /39

    $369,900

    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    120 Wooster St Unit L, New Haven, CT 06511

    Are you ready to live on the MOST famous street in New Haven? Welcome to 120 WOOSTER Unit L, in the heart of Little Italy! This little SLICE of New Haven overlooks Wooster Street and all it's charm and history. Less than a minute from your front door to the most award winning Apizza & restaurants in the nation, this updated townhouse style unit boasts newer appliances and cabinets, great natural

    Carissa Mastriano GRL & Realtors, LLC

    120 Wooster St Unit L, New Haven, CT 06511
  • /26

    $2,395

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft
    • Condo for Rent

    516 Chapel St Unit 2, New Haven, CT 06511

    Gorgeous Sunny 2-Bedroom Apartment in New Haven / Wooster SquareThis bright and spacious 2-bedroom apartment is ideally located in the desirable Wooster Square neighborhood, just minutes from Yale campus and conveniently situated on the Yale shuttle route. It is approximately one mile from Union Station, offering easy access to Metro-North and Amtrak.Enjoy the convenience of being within

    516 Chapel St Unit 2, New Haven, CT 06511
  • 42 Academy St Unit 3, New Haven, CT 06511

    $645,000 Sold Aug 13, 2025

    42 Academy St Unit 3, New Haven, CT 06511

    • 2 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • Built 1857

    Last Sold Summary

    • 18% Above List Price
    • $492/SF
    • 12 Days On Market

    Current Estimated Value $608,485

    Last Listing Agent Melanie Gunn Coldwell Banker Realty

    42 Academy St Unit 3, New Haven, CT 06511
    • 44 Lyon St, New Haven, CT 06511

      Est $653,234 Not Listed For Sale

      44 Lyon St, New Haven, CT 06511

      • 5 Beds
      • 2 Baths
      • 2,613 Sq Ft
      • Built 1900
      44 Lyon St, New Haven, CT 06511

      Last Sold Summary

      • 15% Above List Price
      • $218/SF
      • 6 Days On Market
      • Last Sold Price $570,000
      • Jun 22, 2023

      Last Listing Agent Lisa Bernard Coldwell Banker Realty

  • /28

    $265,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    190 Wooster St Unit 45, New Haven, CT 06511

    Spacious three-bedroom, 1.5-bath cooperative offering more space than is typically found in a condo, along with abundant natural light and a flexible layout rarely available at this price point. The main level features a bright living room with sliding doors to a private, fenced patio, an eat-in kitchen with breakfast bar, and an open dining area ideal for everyday living and entertaining.

    Roseann Iuvone Coldwell Banker Realty

    190 Wooster St Unit 45, New Haven, CT 06511
  • /14

    $1,850 Per Month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    191 Saint John St Unit 2 B, New Haven, CT 06511

    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 Wooster Square Park and walking

    The Urban Team at Wareck D Ostilio Houlihan Lawrence WD

    191 Saint John St Unit 2 B, New Haven, CT 06511
  • 43 Chestnut St Unit 60, New Haven, CT 06511

    $525,000 Sold Jul 25, 2025

    43 Chestnut St Unit 60, New Haven, CT 06511

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Above List Price
    • $219/SF
    • 51 Days On Market

    Current Estimated Value $483,757

    Last Listing Agent Jack Hill Seabury Hill REALTORS

    43 Chestnut St Unit 60, New Haven, CT 06511
    • 48 Lyon St, New Haven, CT 06511

      Est $699,742 Not Listed For Sale

      48 Lyon St, New Haven, CT 06511

      • 6 Beds
      • 3 Baths
      • 3,100 Sq Ft
      • Built 1850
      48 Lyon St, New Haven, CT 06511

      Last Sold Summary

      • 4% Above List Price
      • $218/SF
      • 106 Days On Market
      • Last Sold Price $675,000
      • Feb 05, 2025

      Last Listing Agent Jack Hill Seabury Hill REALTORS

  • /37

    $329,900 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,010 Sq Ft

    15 Hughes Place, New Haven, CT 06511

    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

    Karin Stocknoff Century 21 AllPoints Realty

    15 Hughes Place, New Haven, CT 06511
  • /9

    $1,725

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    40 Franklin St Unit 2R, New Haven, CT 06511

    LOCATION LOCATION LOCATION! This charming one bedroom/one bathroom with historical features is a GEM! Smell the scents of the infamous Wooster Street each day as you find your way around the corner to only the best pizza in the USA! Owner pays for electricity, hot water, cold water, sewer, trash and snow removal.Tenant pays for telephone, WIFI and cable. Pets possible per owner discretion.

    40 Franklin St Unit 2R, New Haven, CT 06511
  • 12 Hughes Place Unit 12, New Haven, CT 06511

    $750,750 Sold Jul 02, 2025

    12 Hughes Place Unit 12, New Haven, CT 06511

    • 3 Beds
    • 2.5 Baths
    • 1,746 Sq Ft
    • Built 1990

    Last Sold Summary

    • 11% Above List Price
    • $430/SF
    • 5 Days On Market

    Last Listing Agent Melanie Gunn Coldwell Banker Realty

    12 Hughes Place Unit 12, New Haven, CT 06511
    • 88 Lyon St, New Haven, CT 06511

      Est $438,262 Not Listed For Sale

      88 Lyon St, New Haven, CT 06511

      • 4 Beds
      • 2 Baths
      • 2,010 Sq Ft
      • Built 1890
      88 Lyon St, New Haven, CT 06511

      Last Sold Summary

      • 10% Above List Price
      • $199/SF
      • 61 Days On Market
      • Last Sold Price $400,000
      • Jan 17, 2025

      Last Listing Agent Joe Scarpellino Coldwell Banker Realty

Showing Results 1 - 40, Page 1 of 18

Home Trends in Wooster Square, CT

Housing Trends

Median Sale Price
$416,000
Median Single Family Sale Price
$899,900
Median Townhouse Sale Price
$327,500
Median 2 Bedroom Sale Price
$416,000
Median 1 Bedroom Sale Price
$339,000
Average Price Per Sq Ft
$346
Number of Homes for Sale
8
Last 12 months Home Sales
21
Months of Supply
4.60
Median List Price
$399,500
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
8%
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