Wooster Square Homes

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  /30

  $460,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,240 Sq Ft

  299 Greene St Unit G-2, New Haven, CT 06511

  Stunning mid-century modern townhouse with the best magical views of Wooster Square Park. A spacious front porch are is at the entry and is a perfect place to relax. Tall floor to ceiling windows and an open floor plangives a feeling of space and light throughout. The first level offers a large south facing living room, a dining room, galley kitchen with excellent storage, and a laundry area. Two

  Betsy Grauer Betsy Grauer Realty, Inc

  299 Greene St Unit G-2, New Haven, CT 06511
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  Explore Wooster Square

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  /23

  $3,700 per month

  • 4 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Apartment for Rent

  90 William St Unit 2, New Haven, CT 06511

  2 story 2nd floor unit in Wooster Square, offering 4 bedrooms and 3 full bathrooms. Over 1750 sqft of living space! Beautiful hardwood floors, high ceilings, original decorative moulding and tremendous natural light. remodeled kitchen with gas stove, farm sink, built-in china cabinet and stainless appliances. brand new bathroom in primary bedroom suite w/walk-in closet. 2 bedrooms, full bathroom

  

  Jared Verrillo

  Seabury Hill REALTORS

  (203) 769-9279

  90 William St Unit 2, New Haven, CT 06511
• 

  $231,500 Sold Sep 19, 2025

  • 1,100 Sq Ft
  • $210/SF
  • 86 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1964

  190 Wooster St Unit 46, New Haven, CT 06511

  Charming Co-op in the Heart of Wooster Square - A Must-See! Discover this bright and spacious end unit co-op featuring 3 bedrooms and 1 full bath in the sought-after Wooster Square neighborhood. Perfectly situated within walking distance to downtown New Haven and Union Station, this home provides convenient access to Yale shuttles just a few blocks away. As you enter, you'll appreciate the large

  Annie Chong Coldwell Banker Calabro

  190 Wooster St Unit 46, New Haven, CT 06511
• 

  Est $476,883 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,344 Sq Ft

  817 Grand Ave Unit 403, New Haven, CT 06511

  817 Grand Ave Unit 403, New Haven, CT 06511
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  $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
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  /8

  $2,195 per month

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

  235 Wooster St Unit 4, New Haven, CT 06511

  Spacious top floor apartment with Downtown views! This 3 bedroom apartment has been completely updated with brand new kitchen granite and marble bathroom, stainless appliances, gas heat, new windows, and prime location in the heart of Wooster Square! Steps to weekly Farmers Market, Wooster Square Park, Yale Shuttle and Downtown. Pets will be considered, good credit required.

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (475) 255-7583

  235 Wooster St Unit 4, New Haven, CT 06511
• 

  $275,000 Sold Aug 14, 2025

  • 850 Sq Ft
  • $324/SF
  • 43 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1976

  125 Olive St Unit D2, New Haven, CT 06511

  Highest & Best offers are due Thursday, July 10th at 2:00 PM.Discover this exceptional Wooster Square townhouse, featuring 2 bedrooms and 1 full bath, just steps from vibrant Downtown New Haven and the picturesque Wooster Square Park. This contemporary condo boasts a sun-drenched, open living space highlighted by gleaming hardwood floors and a stylish concrete accent wall, creating a unique and

  Laura Stonoha Seabury Hill REALTORS

  125 Olive St Unit D2, New Haven, CT 06511
• 

  Est $424,807 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  817 Grand Ave Unit 203, New Haven, CT 06511

  817 Grand Ave Unit 203, New Haven, CT 06511
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  $355,000

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

  120 Wooster St Unit V, New Haven, CT 06511

  Opportunity knocks to own a freshly updated townhouse in sought after Wooster Square! This unique & desirable end unit boasts a large living room with well appointed eat-in kitchen, updated appliances, gorgeous newly installed granite countertops & real wood cabinets. Convenient half bathroom on the main level and a street facing balcony accessed by a slider. Upstairs you will find 2 well

  Adam Roy BHGRE Gaetano Marra Homes

  120 Wooster St Unit V, New Haven, CT 06511
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  $2,140 - $5,155 per month

  The Whit

  Studio - 2 Beds

  630-673 Chapel St, New Haven, CT 06510

  Perched at the gateway to historic Wooster Square, an iconic neighborhood renowned for its rich history and quiet charm, these modern luxury apartments and 2-story lofts are a seamless blend of past and present. Offering elegant features, exceptional amenities, and close proximity to New Haven’s thriving urban center, The Whit delivers an unrivaled living experience. A variety of floor plan

  630-673 Chapel St, New Haven, CT 06510
• 

  $645,000 Sold Aug 13, 2025

  • 1,310 Sq Ft
  • $492/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1857

  42 Academy St Unit 3, New Haven, CT 06511

  Chic Wooster Sq Condo where elegance meets modern convenience! Welcome to this stunning 2-bed, 2-bath condo in the heart of Wooster Square, directly overlooking the park. Originally built in 1857 as the Edward Rowland House, this historic gem is a boutique 6-unit condo building-quiet, well-managed, and full of character. This 1st fl unit impresses with soaring 11' ceilings, oversized 8' windows,

  Melanie Gunn Seabury Hill REALTORS

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

  Est $692,190 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,613 Sq Ft

  44 Lyon St, New Haven, CT 06511

  44 Lyon St, New Haven, CT 06511
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  /39

  $880,000 Open Sun 1PM - 2:30PM

  • 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
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  /23

  $1,800 per month

  • 2 Beds
  • 1.5 Baths
  • 1,026 Sq Ft
  • Townhouse for Rent

  120 Wooster St Unit I, New Haven, CT 06511

  Live in the Heart of Wooster Square! This spacious 2-bedroom, 1.5-bath end unit offers comfort, convenience, and charm. Step into the extended kitchen, designed with abundant counter space and cabinetry to make cooking and storage a breeze. The generous living room features modern track lighting and sliders that open to a private balcony overlooking the peaceful courtyard-perfect for relaxing or

  Craig Bellot eXp Realty

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

  $760,000 Sold Aug 01, 2025

  • 3,315 Sq Ft
  • $229/SF
  • 43 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1865

  272 Saint John St, New Haven, CT 06511

  Fabulous Wooster Square Italianate Style Stucco 3 unit home, 2 family with garden level accessory apartment. Opportunity for owner occupant with 2nd floor coming available August 1. 1st floor leased for 1 year and available garden level unit. Very well maintained home with several improvements: new roof, replacement windows, 3rd floor space with exposed beams, lots of charm, mahogany rail,

  Gena Ruocco-Lockery GRL & Realtors, LLC

  272 Saint John St, New Haven, CT 06511
• 

  Est $677,177 Not Listed For Sale

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

  303 Saint John St, New Haven, CT 06511

  303 Saint John St, New Haven, CT 06511
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  /11

  $399,500 Pending

  • 4 Beds
  • 2 Baths
  • 2,338 Sq Ft

  216 Saint John St, New Haven, CT 06511

  Wooster Square area c.1842 Greek Revival style gem waiting to have a new owner complete the interior restoration of the house. An extraordinary renovation of the exterior of the house was completed by master restoration contractor Christopher Wuerth. The house has three fireplaces, some wide plank flooring, gracious entry with beautiful portico, leaded glass surrounding the front door, lovely

  Betsy Grauer Betsy Grauer Realty, Inc

  216 Saint John St, New Haven, CT 06511
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  $1,109 - $5,935 per month

  Olive & Wooster Apartments

  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,

  87 Union St, New Haven, CT 06511
• 

  $525,000 Sold Jul 25, 2025

  • 2,400 Sq Ft
  • $219/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1890

  43 Chestnut St Unit 60, New Haven, CT 06511

  Rare opportunity to purchase a huge 2400 sq ft 3 bedroom, 2.5 bath New York Style Loft in the charming Wooster Square's neighborhood of New Haven. Incredible open floor plan with exposed wood beams, ~10 ft ceilings, acid washed concrete floors and a gas fireplace. Formal dining room with exposed brick, wood beams and contemporary lighting fixtures. Spacious eat in kitchen with granite counters,

  Jack Hill Seabury Hill REALTORS

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

  Est $346,374 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  135 Olive St Unit 1C, New Haven, CT 06511

  135 Olive St Unit 1C, New Haven, CT 06511
• 

  

  /40

  $949,000 Under Contract

  • 6 Beds
  • 4 Baths
  • 4,458 Sq Ft

  8 Academy St, New Haven, CT 06511

  Investors take note! The historic Samuel Wadsworth House sits gracefully on Wooster Square Park. A legal four-family home is currently configured as a three-family residence. The main house was once configured as two units and there are 2 units in the rear, a studio on the lower level and a 1 bedroom on the upper floor. The utilities are separate (electric and gas) and there are 3 heating/hot

  Cheryl Szczarba Seabury Hill REALTORS

  8 Academy St, New Haven, CT 06511
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  /8

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  94 William St, New Haven, CT 06511

  Charming 2 bedroom 1 bath garden level apartment with all utilities included!! This fully furnished lower level apartment boasts laminate hardwood floors, an open living room-dining room and an updated eat-in kitchen! Two generously sized bedrooms and a private in unit washer/dryer! There is a shared back yard and off street parking for an additional $50 a month. Enjoy historic Wooster Square

  Cathy Hill Conlin Seabury Hill REALTORS

  94 William St, New Haven, CT 06511
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  $230,000 Sold Jul 25, 2025

  • 1,300 Sq Ft
  • $177/SF
  • 56 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  190 Wooster St Unit 27, New Haven, CT 06511

  SELLER MOTIVATED ! Welcome to the vibrant and historic Wooster Square, a truly iconic neighborhood where charm and community come together! You've found your perfect home in this stunningly updated, impeccably maintained 2-bedroom, 1-bath townhouse, offering both character and comfort in every detail. Step inside to discover rich, hardwood floors throughout, paired with a newer, modern kitchen

  Christine Maisano Berkshire Hathaway NE Prop.

  190 Wooster St Unit 27, New Haven, CT 06511
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  Est $938,653 Not Listed For Sale

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

  257 Greene St, New Haven, CT 06511

  257 Greene St, New Haven, CT 06511
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  /53

  $2,245 - $4,795 per month

  18 High

  Studio - 2 Beds

  18 Hughes Place, New Haven, CT 06511

  Welcome to 18 High at New Haven Towers, our new luxury community, having opened just several years ago.Located directly between Yale University and Yale-New Haven Hospital, 18 High is inthe center of the action, and carefully designed to be a haven of camaraderie, cutting edge amenities and convenience. Explore our chic spaces created with your comfort in mind - from our rooftop terrace

  18 Hughes Place, New Haven, CT 06511
• 

  $1,500,000 Sold Jul 11, 2025

  • 3,036 Sq Ft
  • $494/SF
  • 52 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1865

  560 Chapel St, New Haven, CT 06511

  This exquisite Wooster Square C. 1871 French Empire style townhouse has been beautifully maintained and preserved and is one of the architectural jewels of New Haven. The combination of a glorious single family brownstone and the outstanding location with direct views of Wooster Square Park makes this property so special. There are many original details including magnificent entry doors, leaded

  Betsy Grauer Betsy Grauer Realty, Inc

  560 Chapel St, New Haven, CT 06511
• 

  Est $803,888 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 3,360 Sq Ft

  278 Saint John St, New Haven, CT 06511

  278 Saint John St, New Haven, CT 06511
• 

  

  /14

  $1,495 per month

  • 1 Bath
  • 550 Sq Ft
  • Apartment for Rent

  502 Chapel St Unit 4, New Haven, CT 06511

  AVAILABLE NOW - 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 side storage.

  Sarah Beth Luce-Del Prete Coldwell Banker Realty

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

  $750,750 Sold Jul 02, 2025

  • 1,746 Sq Ft
  • $430/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  12 Hughes Place Unit 12, New Haven, CT 06511

  Welcome to 12 Hughes Place - A Rare Gem nestled on one of New Haven's most picturesque, cherry lined streets. This beautifully remodeled, four-level townhouse offers the perfect blend of charm, comfort, and convenience. With a private entrance, attached two-car garage, hardwood floors, central air, and stunning views of cherry blossoms and Wooster Square Park, this condo truly has it all. The

  Melanie Gunn Seabury Hill REALTORS

  12 Hughes Place Unit 12, New Haven, CT 06511
• 

  Est $413,244 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,164 Sq Ft

  284 Saint John St, New Haven, CT 06511

  284 Saint John St, New Haven, CT 06511
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  /75

  $3,500 - $4,500 per month

  • 2 - 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Condo for Rent

  528 Chapel St, New Haven, CT 06511

  This apartment is recommended for a couple or a family of hard working so they can dream leaving peacefully in the best area in Connecticut not just New Haven. Famous Wooster Square Park New Haven.

  528 Chapel St, New Haven, CT 06511
• 

  $370,000 Sold Jun 30, 2025

  • 1,367 Sq Ft
  • $271/SF
  • 61 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1890

  43 Chestnut St Unit 106, New Haven, CT 06511

  Experience modern loft-style living in the heart of New Haven's highly sought-after Wooster Square neighborhood. This spacious 2-bedroom, 2-bath condo offering industrial character blended with contemporary comfort. Open-concept layout features soaring ceilings, exposed brick walls, original wood beams, acid-washed concrete floors, and oversized windows that bring in natural light. The living

  Dawn D'Auria Coldwell Banker Realty

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

  Est $736,419 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  329 Greene St Unit 8, New Haven, CT 06511

  329 Greene St Unit 8, New Haven, CT 06511
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  /21

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 1,443 Sq Ft
  • Townhouse for Rent

  500 Chapel St, New Haven, CT 06511

  WOOSTER SQUARE! *** 8 month lease *** Fabulous loft with tons of light and space. Just steps from Wooster Square Park - a MUST SEE! Fully appointed kitchen has granite counters and ample counter space, built-in microwave and dishwasher. Bath has granite tile floor, tub/shower combo and a pedestal sink. Open living and dining rooms have beautiful oak floors! Grand oak staircase leads to loft

  Sarah Beth Luce-Del Prete Coldwell Banker Realty

  500 Chapel St, New Haven, CT 06511
• 

  $480,000 Sold Jun 30, 2025

  • 1,208 Sq Ft
  • $397/SF
  • 18 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1870

  323 Greene St Unit 2, New Haven, CT 06511

  Perfect views of Wooster Square from this gracious, charming 2-bedroom condo in restored historic home. Light and airy with south and east exposures, tall ceilings, bay window, decorative fireplace, hardwood floors, wonderful kitchen and baths. Outstanding combination of historic charm and modern conveniences. Washer and dryer in unit. Off street parking and private storage. Great location close

  Betsy Grauer Betsy Grauer Realty, Inc

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

  Est $728,630 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  329 Greene St Unit 6, New Haven, CT 06511

  329 Greene St Unit 6, New Haven, CT 06511
• 

  

  /75

  $3,500 - $4,500 per month

  • 2 - 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Condo for Rent

  528 Chapel St, New Haven, CT 06511

  This apartment is recommended for a couple or a family of hard working so they can dream leaving peacefully in the best area in Connecticut not just New Haven. Famous Wooster Square Park New Haven.

  528 Chapel St, New Haven, CT 06511
• 

  $416,000 Sold Jun 27, 2025

  • 947 Sq Ft
  • $439/SF
  • 84 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1860

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

  Meticulously maintained condo with 2 bedrooms & 2 full baths directly across from Wooster Square Park. Located in a historic home built 1810, this first floor condo combines old world charm with modern updates. There is a formal living with a decorative marble fireplace, original wood floors, wood trim and oversized windows. The spacious dining room has newer wood floors, and direct access to a

  Jack Hill Seabury Hill REALTORS

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

  Est $445,933 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  311 Greene St Unit A3, New Haven, CT 06511

  311 Greene St Unit A3, New Haven, CT 06511
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  /13

  $2,350 per month

  • 2 Beds
  • 1 Bath
  • 1,640 Sq Ft
  • Apartment for Rent

  95 Olive St, New Haven, CT 06511

  Wooster Square Brownstone available in the middle of August! This 1st floor apartment has over 1600 SF with 2 bedrooms, 1 bathroom and lots of closet space! There is off street parking and in a shared driveway. Shared washer/dryer in basement. This apartment is located on the yale shuttle and is close to Restaurants, Hospitals, Universities and highways.

  Kristy Agli Kelsey & Co. Real Estate

  95 Olive St, New Haven, CT 06511

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