Wooster Square Homes

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  /39

  $575,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,380 Sq Ft

  4 Jefferson St, New Haven, CT 06511

  Located in the heart of historic Wooster Square overlooking Lenzi Park, this two-family home blends charm, flexibility, and investment potential in one of New Haven's most desirable neighborhoods. Just minutes to Yale University, Yale New Haven Hospital, Downtown New Haven, Union Station, I-91, I-95, local restaurants, coffee shops, and Wooster Street's famous pizza scene. The owner's unit

  

  Heike Severine

  Coldwell Banker Realty

  4 Jefferson St, New Haven, CT 06511
• Explore Wooster Square

• 

  

  

  /10

  $1,900 Per Month

  • 1 Bed
  • 1 Bath
  • 841 Sq Ft
  • Apartment for Rent

  182 Chestnut St Unit 1, New Haven, CT 06511

  Charming first floor, renovated one bedroom apartment one block to Wooster Square Park! Enjoy downtown views and gorgeous sunsets from your private back patio! Shaker style cabinets in kitchen, granite counters, stainless appliances including dishwasher and gas stove. Hardwood floors throughout, exposed brick, updated bathroom and lots of closet space. Free laundry in basement private to first

  

  Jennifer D'Amato

  Real Broker CT, LLC

  182 Chestnut St Unit 1, 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
• 

  Not Listed For Sale

  190 Wooster St Unit 16, New Haven, CT 06511

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Built 1964

  190 Wooster St Unit 16, New Haven, CT 06511

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /32

  $2,400,000

  • 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

  

  Arian Hoxha

  Serhant Connecticut, LLC

  177 Chestnut St, New Haven, CT 06511
• 

  

  /6

  Starting at $2,075

  Total Monthly Price

  • Studio - 2 Beds

  20-34 Fair St, New Haven, CT 06511

  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

  Twenty Fair

  

  20-34 Fair St, New Haven, CT 06511
• 

  $335,000

  Sold May 19, 2026

  120 Wooster St Unit V, New Haven, CT 06511

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1968

  Last Sold Summary

  • 4% Below List Price
  • $327/SF
  • 71 Days On Market

  Current Estimated Value $346,125

  Last Listing Agent Adam Roy BHGRE Gaetano Marra Homes

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

  Not Listed For Sale

  190 Wooster St Unit 51, New Haven, CT 06511

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

  190 Wooster St Unit 51, New Haven, CT 06511

  Last Sold Summary

  • 20 Days On Market
• 

  

  /30

  $1,500,000

  Under Contract

  • 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. Income per year is

  Susan Frew Betsy Grauer Realty, Inc

  171 Wooster St, New Haven, CT 06511
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  /8

  $1,850 Per Month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  235 Wooster St Unit 1R, New Haven, CT 06511

  Live the Wooster Square experience in this beautifully renovated one bedroom apartment on right on Wooster Street! This stylish apartment puts you minutes from the weekly Farmers Market, Wooster Square Park, Yale Shuttle, Little Italy's best restaurants, and Downtown New Haven - all from one of the city's most charming and walkable neighborhoods. Inside, you'll find high ceilings, granite

  

  Jennifer D'Amato

  Real Broker CT, LLC

  235 Wooster St Unit 1R, 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 $399,193

  Last Listing Agent Dawn D'Auria Coldwell Banker Realty

  43 Chestnut St Unit 106, New Haven, CT 06511
• 

  Est $431,740

  Not Listed For Sale

  12 Academy St Unit 3B, New Haven, CT 06511

  • 2 Beds
  • 2 Baths
  • 947 Sq Ft
  • Built 1860

  12 Academy St Unit 3B, New Haven, CT 06511

  Last Sold Summary

  • 84 Days On Market
• 

  

  /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
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  /159

  Starting at $1,029

  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

  

  87 Union 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 $1,505,533

  Last Listing Agent Betsy Grauer Betsy Grauer Realty, Inc

  560 Chapel St, New Haven, CT 06511
• 

  Est $334,282

  Not Listed For Sale

  120 Wooster St Unit H, New Haven, CT 06511

  • 2 Beds
  • 1.5 Baths
  • 1,026 Sq Ft
  • Built 1968

  120 Wooster St Unit H, New Haven, CT 06511

  Last Sold Summary

  • 82 Days On Market
• 

  

  /39

  $360,000

  $10K PRICE DROP

  • 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
• 

  

  /15

  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,262 Sq Ft
  • Townhouse for Rent

  182 Chestnut St Unit 2, New Haven, CT 06511

  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

  

  Jennifer D'Amato

  Real Broker CT, LLC

  182 Chestnut 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 $475,191

  Last Listing Agent Betsy Grauer Betsy Grauer Realty, Inc

  323 Greene St Unit 2, New Haven, CT 06511
• 

  Est $374,624

  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

  • 97 Days On Market
• 

  

  /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
• 

  

  /53

  Starting at $2,345 Plus Fees

  • Studio - 2 Beds

  18 Hughes Place, New Haven, CT 06511

  SOLD OUT for 2026 Occupancy -- Thank you to all of our new renters!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

  18 High

  18 Hughes Place, 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 $1,417,547

  Last Listing Agent Carissa Mastriano GRL & Realtors, LLC

  614 Chapel St, New Haven, CT 06511
• 

  Est $427,767

  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

  • 11 Days On Market
• 

  /2

  $175,000

  Pending

  • Land
  • 1,742 Sq Ft
  • $4,375,000 per Acre

  329 Saint John St, New Haven, CT 06511

  Lot for sale at 329 Saint Johns St offering approximately 1,742 sq ft of usable space. The lot is open, level, and easily accessible directly from the street. It currently accommodates multiple vehicles with a paved surface. The space sits between two established buildings and has clear visibility from the road. Suitable for private parking, tenant/employee parking, storage, or future

  Naftali Caplan Caplan Realty Corp.

  329 Saint John St, New Haven, CT 06511
• 

  /2

  $2,400 Plus Fees

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Condo for Rent

  106 William St Unit 2, New Haven, CT 06511

  Property Id: 2618859Charming and spacious 2br apartment located on 2nd floor wooster square area. Conveniently located within minutes of walk to downtown, State st train station, grocery store, restaurants and coffee shops. Amazing view from front windows of downtown and apartment is full of natural light. Apartment features hardwood floor, high ceiling, washer dryer hook up and street

  106 William St Unit 2, 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 $644,560

  Last Listing Agent Melanie Gunn Coldwell Banker Realty

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

  Est $403,572

  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

  • 81 Days On Market
• 

  

  /18

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  120 Wooster St Unit C, New Haven, CT 06511

  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

  Abby Chow Berkshire Hathaway NE Prop.

  120 Wooster St Unit C, New Haven, CT 06511
• 

  

  /19

  $2,650 Plus Fees

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Condo for Rent

  23 Brown St Unit 3, New Haven, CT 06511

  Discover this beautifully renovated 3-bedroom, 1-bath apartment offering the perfect combination of space, comfort, and modern updates. Featuring generously sized rooms, abundant natural light, and a functional layout, this home provides plenty of room to relax and enjoy everyday living. Fresh finishes throughout create a clean, welcoming atmosphere that's ready for you to move right

  23 Brown St Unit 3, New Haven, CT 06511
• 

  $200,000

  Sold May 19, 2026

  120 Wooster St Unit W, New Haven, CT 06511

  • 1 Bed
  • 1 Bath
  • 496 Sq Ft
  • Built 1968

  Last Sold Summary

  • $403/SF
  • 65 Days On Market

  Current Estimated Value $196,677

  Last Listing Agent Victoria Stillings Coldwell Banker Realty

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

  Est $713,358

  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

  • 40 Days On Market
• 

  

  /25

  $325,000

  $14K PRICE DROP Under Contract

  • 1 Bed
  • 1 Bath
  • 1,115 Sq Ft

  817 Grand Ave Unit 202, New Haven, CT 06511

  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

  Jack Hill Seabury Hill REALTORS

  817 Grand Ave Unit 202, New Haven, CT 06511
• 

  

  /7

  $2,000 Plus Fees

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

  46 Warren St Unit BSMT, New Haven, CT 06511

  Recently renovated and move-in ready, this charming 1-bedroom, 1-bath apartment offers bright living spaces, generously sized rooms, and modern updates throughout. The inviting layout provides a comfortable setting for relaxing, working from home, or enjoying everyday living, while natural light and fresh finishes create a warm and welcoming atmosphere.Conveniently located in New Haven,

  46 Warren St Unit BSMT, 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 $558,627

  Last Listing Agent Jack Hill Seabury Hill REALTORS

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

  Est $681,636

  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

  • 6 Days On Market
• 

  

  /37

  $2,250,000

  Under Contract

  • 18 Beds
  • 10 Baths
  • 6,771 Sq Ft

  334 Saint John St, New Haven, CT 06511

  Turnkey & fully occupied 6 unit investment property in the heart of the Wooster Square neighborhood steps to Downtown New Haven & Yale! The building offers the best of both worlds: its historic brick facade and original details complement its modern, sparkling interior. The building features fantastic apartment layouts, including two four-bedroom, two-bath townhouse units on the first floor and

  Jack Hill Seabury Hill REALTORS

  334 Saint John St, New Haven, CT 06511
• 

  

  /10

  $1,695 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  197 Wooster St Unit 2B, New Haven, CT 06511

  Property Id: 2704974Very nice 1 bdrm on 2nd floor.Hardwood floors thruoutShared laundryMicrowave and dishwasher includedStreet parkingSmall pets ok - monthly pet fee required (Does not apply to ES/Service animals)LANDLORD REQUIREMENTS BELOW-Stable employment history -Household income, after taxes, must be at least 2.5 times the rent, NO

  197 Wooster St Unit 2B, 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
• 

  Est $720,255

  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

  • 106 Days On Market

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