Wooster Square Homes

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  $949,000

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

  8 Academy St, New Haven, CT 06511

  Attention Investors and Visionaries! The historic Samuel Wadsworth House offers a rare opportunity overlooking the beauty of Wooster Square Park. This legal four-family residence is currently arranged as three units, with the main house spanning three generous floors of living space. Once configured as two separate apartments, the main house features expansive living, dining, and family rooms,

  Cheryl Szczarba Seabury Hill REALTORS

  8 Academy St, New Haven, CT 06511
• Explore Wooster Square

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  $1,950 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,296 Sq Ft
  • Apartment for Rent

  108 William St Unit 1, New Haven, CT 06511

  Charming and spacious one-bedroom first-floor apartment located in a well-maintained three-family building. It features gleaming hardwood floors throughout, high ceilings, and large windows. The good-size bedroom offers plenty of room for a king size bed and extra furniture, the spacious kitchen is equipped with all appliances, including a dishwasher, and provides direct access to the yard. Pets

  

  Wojtek Borowski

  Pearce Real Estate

  (203) 580-6835

  108 William St Unit 1, New Haven, CT 06511
• 

  $650,000 Sold Oct 31, 2025

  • 1,263 Sq Ft
  • $515/SF
  • 27 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1843

  7 Wooster Place Unit 6, New Haven, CT 06511

  Housed in a beautifully converted former carriage house, this unique residence blends classic charm with modern design. The spacious open-concept living and dining area flows into a stylish California-style kitchen, complete with granite and butcher block countertops and stainless steel appliances (VIKING range, Fisher & Paykel dishwasher, wine fridge). High ceilings, oversized bow windows,

  Wojtek Borowski Pearce Real Estate

  7 Wooster Place Unit 6, New Haven, CT 06511
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  Est $350,223 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 921 Sq Ft

  576 Chapel St Unit 4, New Haven, CT 06511

  576 Chapel St Unit 4, New Haven, CT 06511
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  $1,477,000

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

  614 Chapel St, New Haven, CT 06511

  Nestled in the Historic heart of New Haven's Wooster Square, this 1873 charmer is elegance & sophistication at it's best! Just feet away from the legendary Wooster Street,coined most recently as the "Pizza Capital of the America", this beautifully restored French Empire style brick mansion,once the home of Daniel Goffe Phipps, offers the perfect blend of old-world charm and modern luxury.This

  Carissa Mastriano GRL & Realtors, LLC

  614 Chapel St, New Haven, CT 06511
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  /19

  $2,250 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  90 William St Unit 2, New Haven, CT 06511

  2nd floor unit in Wooster Square, offering 2 bedrooms and 2 full bathrooms. Over 1300 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. Private back deck, perfect for

  

  Jared Verrillo

  Seabury Hill REALTORS

  (203) 769-9279

  90 William St Unit 2, New Haven, CT 06511
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  $520,000 Sold Oct 10, 2025

  • 1,240 Sq Ft
  • $419/SF
  • 37 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  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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  Est $481,692 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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  $175,000

  • Land
  • 0.04 Acre
  • $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
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  $2,950 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • House for Rent

  177 Chestnut St Unit 2R, New Haven, CT 06511

  Exceptional re-design at this 6 unit building in Wooster Square! Brand new from the inside out, the apartments were fully fitted with all new white shaker style kitchen cabinets, quartz counters, stainless appliances, washer/dryer, two full bathrooms and brand new heat and central air! This versatile layout can function well as a four bedroom apartment or as a three bedroom with a larger living

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (475) 260-6852

  177 Chestnut St Unit 2R, New Haven, CT 06511
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  $441,000 Sold Oct 01, 2025

  • 2,338 Sq Ft
  • $189/SF
  • 9 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1842

  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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  Est $431,585 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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  $899,999 Pending

  • 5 Beds
  • 3 Baths
  • 2,885 Sq Ft

  99 Olive St, New Haven, CT 06511

  Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus office space, has been thoughtfully updated. The

  John Daikus eXp Realty

  99 Olive St, New Haven, CT 06511
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  $2,650 total monthly price

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • House for Rent

  177 Chestnut St Unit 1L, New Haven, CT 06511

  Exceptional re-design at this 6 unit building in Wooster Square! Brand new from the inside out, the apartments were fully fitted with all new white shaker style kitchen cabinets, quartz counters, stainless appliances, washer/dryer, two full bathrooms and brand new heat and central air! This versatile layout can function well as a three bedroom apartment or as a two bedroom with a larger living

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (475) 264-5751

  177 Chestnut St Unit 1L, New Haven, CT 06511
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  $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
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  Est $751,773 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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  $355,000 Under Contract

  • 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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  $2,650 total monthly price

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • House for Rent

  177 Chestnut St Unit 1R, New Haven, CT 06511

  Exceptional re-design at this 6 unit building in Wooster Square! Brand new from the inside out, the apartments were fully fitted with all new white shaker style kitchen cabinets, quartz counters, stainless appliances, washer/dryer, two full bathrooms and brand new heat and central air! This versatile layout can function well as a three bedroom apartment or as a two bedroom with a larger living

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (475) 264-5014

  177 Chestnut St Unit 1R, New Haven, CT 06511
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  $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
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  Est $729,356 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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  $2,105 - $4,255 total monthly price

  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
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  $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
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  Est $319,348 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
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  $2,595 total monthly price

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

  597 Chapel St Unit 2, New Haven, CT 06511

  This stunning and unique light-filled two bedroom/two full bathroom remodeled apartment is located in a small quiet building and includes off street parking in a secure parking lot in back. This space has everything on your wishlist and is two buildings away from the majestic Wooster Square Park and two blocks to Yale and Downtown New Haven. Your new fabulous rental boasts soaring cathedral

  Wendy Cohen Wendy Cohen Realty

  597 Chapel St Unit 2, New Haven, CT 06511
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  $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
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  Est $994,939 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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  $2,245 - $4,795 per month plus fees

  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
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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 $822,791 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
• 

  

  /5

  $1,900 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  73 Lyon St Unit 3, New Haven, CT 06511

  Charming one bedroom, third floor apartment in the Wooster Square neighborhood of New Haven. Spacious rooms with high ceilings and beautiful pine wood floors throughout. Updated kitchen with granite countertops, white cabinets and a private washer/dryer! There is off street parking in the driveway directly behind the house for one car. Tenant is responsible for all utilities. Walking distance to

  Cathy Hill Conlin Seabury Hill REALTORS

  73 Lyon St Unit 3, New Haven, CT 06511
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  $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
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  Est $420,588 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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  $1,079 - $5,935 per month plus fees

  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
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  $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
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  Est $276,643 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,054 Sq Ft

  15 Hughes Place, New Haven, CT 06511

  15 Hughes Place, New Haven, CT 06511
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  $3,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • Apartment for Rent

  234 Greene St Unit 204, New Haven, CT 06511

  Luxury Penthouse - Wooster Square Rarely available, this stunning penthouse is located in the heart of historic Wooster Square, offering the perfect blend of charm, culture, and walkable convenience. Enjoy tree-lined streets, acclaimed restaurants, cafes, and the iconic cherry blossoms just steps from your door. Inside, the residence features an open layout with premium finishes, high ceilings,

  Katelin Rosello Social & Co Realty

  234 Greene St Unit 204, New Haven, CT 06511
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  $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
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  Est $761,076 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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  $1,200 - $3,605 per month plus fees

  250 Greene St

  1 - 3 Beds

  250 Greene St, New Haven, CT 06511

  At 250Greene Loft styled living marries sophistication in 23 modern, luxe residences in the Wooster Square neighborhood! Limited pre-construction luxury rental apartment homes open now ! Introducing the hottest new construction historical renovation in the Wooster Square neighborhood .These stunning new apartments offer 1-3 bedrooms, with open floor plan living, lofts, custom kitchens with

  250 Greene St, New Haven, CT 06511
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  $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

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