Wooster Square Homes

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  $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

  

  Arian Hoxha

  Serhant Connecticut, LLC

  177 Chestnut St, New Haven, CT 06511
• Explore Wooster Square

• 

  

  

  /28

  $3,850 Per Month

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft
  • Apartment for Rent

  109 Olive St Unit 1, New Haven, CT 06511

  NEW CONSTRUCTION IN WOOSTER SQUARE!! Luxury 2,100 sq ft 3 bedroom 2 full bath apartment. Designer kitchen and baths, hardwood floors, central air condition, laundry in unit - no expense has been spared. The apartment is located on the 1st floor and lower level on the property, and offers a private entrance and 2 off street parking spaces. Available October 1 with good credit, proof of income and

  

  John Hill

  Seabury Hill REALTORS

  109 Olive St Unit 1, 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 $339,414

  Last Listing Agent Adam Roy BHGRE Gaetano Marra Homes

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

  Est $417,882

  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

  Last Listing Agent Judith Normandin Pearce Real Estate
• 

  

  

  /39

  $775,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,945 Sq Ft

  161 Olive St, New Haven, CT 06511

  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

  

  Marc Seigel & Lauren Seigel-Gross

  RE/MAX RISE

  161 Olive St, New Haven, CT 06511
• 

  

  /159

  Starting at $950

  Total Monthly Price

  • 1 - 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 Aug 13, 2026

  171 Wooster St, New Haven, CT 06511

  • 8 Beds
  • 7 Baths
  • 7,014 Sq Ft
  • Built 1910

  Last Sold Summary

  • $214/SF
  • 89 Days On Market

  Last Listing Agent Susan Frew Betsy Grauer Realty, Inc

  171 Wooster St, New Haven, CT 06511
• 

  Est $454,643

  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

  Last Listing Agent John Hill Seabury Hill REALTORS
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  $279,000

  • 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
• 

  

  /25

  $1,700 Per Month

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

  121 Wooster St Unit 2, New Haven, CT 06511

  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).

  

  John Hill

  Seabury Hill REALTORS

  121 Wooster St Unit 2, 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 $1,483,847

  Last Listing Agent Carissa Mastriano GRL & Realtors, LLC

  614 Chapel St, New Haven, CT 06511
• 

  Est $440,332

  Not Listed For Sale

  817 Grand Ave Unit 402, New Haven, CT 06511

  • 2 Beds
  • 1 Bath
  • 1,145 Sq Ft
  • Built 1880

  817 Grand Ave Unit 402, New Haven, CT 06511

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Kelly Hill-Mihalyak Coldwell Banker Realty
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  /37

  $449,900

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft

  43 Chestnut St Unit 201, New Haven, CT 06511

  WOOSTER SQUARE LIVING AT ITS FINEST! Welcome to this exceptional 2-bedroom, 2-bathroom condo offering approximately 1,180 square feet of stylish, turnkey living in the highly sought-after Sage Arts building. Full of character and modern updates, this second-floor residence perfectly blends historic New Haven charm with contemporary comfort. Step inside and you'll immediately appreciate the unique

  Joseph Snell Luxe Realty LLC

  43 Chestnut St Unit 201, New Haven, CT 06511
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  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
• 

  $640,000

  Sold Aug 07, 2026

  6 Jefferson St, New Haven, CT 06511

  • 5 Beds
  • 3 Baths
  • 2,064 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $310/SF
  • 88 Days On Market

  Current Estimated Value $691,196

  Last Listing Agent Melanie Gunn Coldwell Banker Realty

  6 Jefferson St, New Haven, CT 06511
• 

  Est $370,848

  Not Listed For Sale

  817 Grand Ave Unit 301, New Haven, CT 06511

  • 1 Bed
  • 1 Bath
  • 1,034 Sq Ft
  • Built 1880

  817 Grand Ave Unit 301, New Haven, CT 06511

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Zachary Kampton Farnam Realty Group
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  $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
• 

  

  /15

  $2,500 Per Month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Apartment for Rent

  235 Wooster St Unit 2, New Haven, CT 06511

  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,

  

  Jennifer D'Amato

  Real Broker CT, LLC

  235 Wooster St Unit 2, New Haven, CT 06511
• 

  $265,000

  Sold Jun 30, 2026

  190 Wooster St Unit 45, New Haven, CT 06511

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1964

  Last Sold Summary

  • $166/SF
  • 85 Days On Market

  Last Listing Agent Roseann Iuvone Coldwell Banker Realty

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

  Est $429,005

  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

  Last Listing Agent John Hill Seabury Hill REALTORS
• 

  

  /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
• 

  

  /18

  $2,650

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  120 Wooster St Unit T, New Haven, CT 06511

  This apartment is a duplexTwo bedrooms upstairs with a full bathroomKitchen and a big living room and half bathroom downstairs

  120 Wooster St Unit T, 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 $206,265

  Last Listing Agent Victoria Stillings Coldwell Banker Realty

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

  Est $741,769

  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

  Last Listing Agent Nadia Martinez Ki Property Group
• 

  

  /9

  $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, washers 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
• 

  

  /21

  $1,725

  Total Monthly Price

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

  49 Warren St Unit C, New Haven, CT 06511

  Beautiful 2BR Apt - Wooster Square** Beautiful Hardwood Flooring** Ceramic Tiled Bathroom** Laundry Room On Site ** Conveniently Located Near Shopping, Restaurants & Public Transportation ** Off Street Parking** Walking Distance to YALE - Students are Welcome !Requirements:Proof of Monthly Income of 3x the Rent (Must Show Pay Stubs) 1 Month Security

  49 Warren St Unit C, New Haven, CT 06511
• 

  $150,000

  Sold Sep 02, 2026

  329 Saint John St, New Haven, CT 06511

  • Land
  • 1,742 Sq Ft
  • $3,750,000 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 84 Days On Market

  Last Listing Agent Naftali Caplan Caplan Realty Corp.

  329 Saint John St, New Haven, CT 06511
• 

  Est $753,060

  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

  Last Listing Agent John Hill Seabury Hill REALTORS
• 

  

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  $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
• 

  

  /25

  $1,950 Per Month

  • 1 Bed
  • 1 Bath
  • 670 Sq Ft
  • House for Rent

  38 Academy St, New Haven, CT 06511

  .

  Deborah Rowe William Raveis Real Estate

  38 Academy St, New Haven, CT 06511
• 

  $335,000

  Sold Jun 12, 2026

  15 Hughes Place, New Haven, CT 06511

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft
  • Built 1901

  Last Sold Summary

  • 13% Below List Price
  • $332/SF
  • 97 Days On Market

  Current Estimated Value $350,411

  Last Listing Agent Karin Stocknoff Century 21 AllPoints Realty

  15 Hughes Place, New Haven, CT 06511
• 

  Est $593,433

  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

  • 61 Days On Market

  Last Listing Agent Joe Scarpellino Coldwell Banker Realty
• 

  

  /23

  $1,200,000

  Under Contract

  • 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
• 

  /2

  $2,200 Plus Fees

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

  106 William St Unit 2, New Haven, CT 06511

  Property Id: 2618859 Charming and spacious 2br apartment located on 2nd floor wooster square area. Conveniently located within minutes of walk to downtown, State st train station, grocery stores, 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
• 

  $285,000

  Sold Sep 10, 2026

  120 Wooster St Unit C, New Haven, CT 06511

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $266/SF
  • 82 Days On Market

  Current Estimated Value $288,840

  Last Listing Agent Abby Chow Berkshire Hathaway NE Prop.

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

  Est $770,642

  Not Listed For Sale

  303 Saint John St, New Haven, CT 06511

  • 3 Beds
  • 2 Baths
  • 2,420 Sq Ft
  • Built 1870

  303 Saint John St, New Haven, CT 06511

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Tracy Daye Coldwell Banker Realty
• 

  

  /21

  $3,899,999

  • 24 Beds
  • 16 Baths
  • 14,692 Sq Ft

  527 Chapel St, New Haven, CT 06511

  Exceptional opportunity to acquire a 16-unit multifamily property in the heart of Wooster Square. This approximately 14,692 SF brick building features a desirable unit mix of eight 1-bedroom and eight 2-bedroom apartments. The property currently generates $29,750 per month in in-place rental income, excluding two vacant units that provide immediate lease-up potential. At projected rents of $1,900

  Joseph Tracey Social & Co Realty

  527 Chapel St, New Haven, CT 06511
• 

  

  /13

  $2,095 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  597 Chapel St Unit 2, New Haven, CT 06511

  Wooster Square! This stunning and unique light-filled two bedroom/one bathroom newly remodeled apartment is located in a small quiet building and includes off street parking in a secure parking lot in back. This space is two buildings away from the majestic Wooster Square park and two blocks to Yale and Downtown New Haven. Exposed brick, recessed lighting, hardwood floors, central air, gas heat

  Wendy Cohen Wendy Cohen Realty

  597 Chapel St Unit 2, New Haven, CT 06511
• 

  $650,000

  Sold Oct 31, 2025

  7 Wooster Place Unit 6, New Haven, CT 06511

  • 2 Beds
  • 1.5 Baths
  • 1,263 Sq Ft
  • Built 1843

  Last Sold Summary

  • 20% Above List Price
  • $515/SF
  • 27 Days On Market

  Current Estimated Value $677,365

  Last Listing Agent Wojtek Borowski Pearce Real Estate

  7 Wooster Place Unit 6, New Haven, CT 06511
• 

  Est $1,017,198

  Not Listed For Sale

  257 Greene St, New Haven, CT 06511

  • 4 Beds
  • 3 Baths
  • 3,315 Sq Ft
  • Built 1850

  257 Greene St, New Haven, CT 06511

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Mark Poole Kazantzis Real Estate, LLC

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