Wooster Square Homes under $1.25 million

Welcome to Wooster Square, one of New Haven, Connecticut's most charming and vibrant neighborhoods! Known for its rich history and picturesque tree-lined streets, Wooster Square offers a unique blend of urban convenience and suburban tranquility. Nestled just a stone's throw from downtown New Haven, this neighborhood is a delightful haven for families, young professionals, and anyone seeking a warm community atmosphere.

One of the most enticing features of Wooster Square is its stunning array of homes, many of which can be found for under $1.25 million. Here, you’ll discover beautifully restored historic properties, cozy single-family homes, and modern townhouses, each exuding character and charm. Whether you’re drawn to the classic Italianate architecture or the contemporary designs, there’s a perfect home waiting for you in this delightful neighborhood.

Wooster Square is also renowned for its vibrant cultural scene. Each spring, the neighborhood hosts the famous Wooster Square Cherry Blossom Festival, celebrating the beauty of the blooming trees that line the park. Food lovers will appreciate the close proximity to some of New Haven's best eateries, including the iconic pizza places that have put this city on the culinary map.

With easy access to public transportation and a strong sense of community, Wooster Square is not just a place to live; it’s a place to thrive. Come explore the charm and warmth of Wooster Square, where your dream home awaits!

Newest Wooster Square Homes under $1.25 million

$825,000

7 Beds ⋅ 3 Baths ⋅ 24215853 MLS

Historic Wooster Square beautiful brick multi family for sale a must see! Make this one your home! close to downtown New Haven and local attractions. This is an Probate sale, being sold as is where is.

71 William St, New Haven

$1,250,000

6 Beds ⋅ 4 Baths ⋅ 24215546 MLS

A truly magical find in Wooster Square! Meticulously renovated with exceptional care and attention to detail, this unique three-unit compound blends historic charm with modern comfort and convenience. The freestanding brick house features 2 bedrooms and 1 full bath, a spacious eat-in kitchen, generous living and dining rooms, and a huge finished basement. High ceilings and beautiful original details add timeless character. Tucked at the rear of the property, the former carriage house has been thoughtfully converted into two additional residences. Unit #2 offers 3 bedrooms, 2 full baths, an open-concept living, dining, and kitchen area, a den, and an exceptional private terrace. Unit #3 features an inviting open living space, a well-appointed kitchen, a private bedroom, and a full bath, complemented by high ceilings. Each unit has its own washer/dryer. The charming courtyard provides off-street parking for up to five cars, and separately fenced off area for a dog run or a secure play area. Newer mechanicals; tankless water heaters; Central Air in #50 and #52; window units in #54. A rare opportunity for investors or owner-occupants seeking a distinctive property with multiple income possibilities or extended family living in one of New Haven's most beloved neighborhoods!

50-54 Lyon St, New Haven

$749,000

2 Beds ⋅ 3 Baths ⋅ 24212128 MLS ⋅ Gables At Wooster Square BLDG.

One of Wooster Square's most iconic buildings is The Gables, formerly a church and parish house, located right on Wooster Square Park. One of its most remarkable units is Number 9, with its amazing Great Room. This grand space is 23 feet square and 16 feet high, with tall windows on the north and east sides. It houses the living room, dining area, kitchen, and a balconied office overlooking the space. It's truly unique, and must be seen to be believed. Hardwood floors, a chef's kitchen with stainless steel appliances, and Italian lighting are but a few features of this sensational space. But there's much more! Off the Great Room is a study, with a balcony overlooking your own private terrace. This semi-enclosed outdoor space is perfect for relaxing and casual entertaining. There's a discreet half-bath and storage closets galore.

329 Greene St Unit 9, New Haven

$950,000

6 Beds ⋅ 6 Baths ⋅ 24212980 MLS

Rare opportunity to own a classic brick three-family directly on the park in Wooster Square, one of New Haven's most distinctive and sought-after neighborhoods. This property combines historic character, an exceptional location, and a highly desirable apartment configuration. The building features three spacious 2-bedroom, 2-bathroom apartments, providing a layout that works equally well for an investor or owner-occupant. Each residence offers the added convenience of in-unit laundry, along with generous living space and the privacy of two full bathrooms. The property's timeless brick exterior, arched entryway, and architectural details complement its prime park-front setting in the heart of Wooster Square. Enjoy immediate access to the neighborhood's tree-lined streets, historic architecture, restaurants, cafes, and the renowned Wooster Street dining district, while remaining convenient to Downtown New Haven and Yale. With three 2-bedroom/2-bath units, laundry in every apartment, and an outstanding location directly on Wooster Square Park, this is a unique opportunity to acquire a substantial multifamily property in one of New Haven's premier neighborhoods.

4 Academy St, New Haven

$462,000

2 Beds ⋅ 2 Baths ⋅ 24210805 MLS ⋅ Russell Hotchkiss House BLDG.

You'll love living on Wooster Square Park in this beautifully remodeled 2-bedroom condo in the historic Russell Hotchkiss House. The large eat-in kitchen is filled with natural southern light, creating a bright and welcoming space. The living room features floor-to-ceiling windows and a lovely built-in hutch. The primary bedroom includes a full en-suite bath. Additional features include exposed brick, hardwood floors, central air, in-unit laundry, and a large private storage room in the basement. One off-street parking space is included. Enjoy the quiet location of this unit, complete with its own private entrance. The house also features a charming side porch with beautiful views of Wooster Square Park. Conveniently located near downtown New Haven and the renowned restaurants of Wooster Street. Up to three pets are permitted with association approval. This is a rare opportunity to enjoy historic charm, modern updates, and one of New Haven's most sought-after locations. In the Yale Homebuyers Program for qualified university employees.

7 Wooster Pl Unit 2, New Haven

$275,900

2 Beds ⋅ 2 Baths ⋅ 24210063 MLS ⋅ Wooster Square BLDG.

Welcome to your next chapter in New Haven's iconic and historic Wooster Square! This 2-bedroom, 11/2-bath End-unit Townhome offers a wonderful opportunity to create a home that is truly your own. Inside, you'll find an Eat-in Kitchen ready for your vision, along with a Formal Living room featuring sliders to a Private Balcony-a great spot for morning coffee, evening unwinding, or enjoying the neighborhood atmosphere. As an end unit, the home offers a little extra sense of privacy, while its location puts you in the heart of one of New Haven's most beloved neighborhoods, surrounded by the character, charm, restaurants, cafes, and energy that make Wooster Square so special. A fantastic opportunity to live in one of New Haven's most distinctive neighborhoods and create a home that reflects you!

120 Wooster St Unit I, New Haven

$308,000

1 Beds ⋅ 1 Baths ⋅ 24209030 MLS ⋅ Olive Court BLDG.

Adorable ranch-style condo set within a charming historic building in the heart of the Wooster Square neighborhood. A large entry foyer opens seamlessly into a spacious living room featuring a decorative fireplace and ample space for a dining table, creating an inviting setting for everyday living and entertaining. The kitchen blends character and function with retro GE appliances, butcher block countertops, and a convenient pantry closet. The bedroom offers warmth and charm with an exposed brick wall and peaceful views of the rear courtyard. Additional highlights include an in unit washer and dryer, a gated street-level front patio perfect for relaxing outdoors, and shared basement storage accessed via hatch. This pet-friendly, self-managed six-unit complex has low HOA and a true sense of community. Ideally located just steps from Wooster Square's renowned restaurants, nearby theater, downtown New Haven, and easy highway access for commuters.

85 Olive St Unit 85, New Haven

$680,000

4 Beds ⋅ 2 Baths ⋅ 24197946 MLS

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 University, downtown New Haven, and a variety of dining, shopping and cultural attractions. Public transportation is easily accessible, making it convenient for tenants. Potential for increased revenue. Don't miss out on this rare opportunity to own a two-family home in one of Connecticut's most sought-after area. Walking distance to New Haven's Best! And let's not forget to mention the BEAUTIFUL back yard! You will never see another with such awesome plantings designed to cater to a multifamily residence with lush greenery and thoughtfully arranged spaces that invite both relaxation and community bonding. A true city oasis! This is a must-see property!

100 William St, New Haven

$849,500

8 Beds ⋅ 4 Baths ⋅ 24199790 MLS

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 ideal location close to Yale, YNHH, the train station and downtown New Haven.

191 Saint John St, New Haven

$278,000

2 Beds ⋅ 2 Baths ⋅ 24198228 MLS ⋅ Wooster Court BLDG.

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 inviting open living and dining area, ideal for everyday comfort and entertaining. Upstairs, both bedrooms are generously sized, and the full bath plus main level half bath add convenience for residents and guests. A garage located underneath provides secure parking and protection from the elements, while an additional private storage unit offers valuable extra space for seasonal items and belongings. Live steps from world famous Wooster Street eateries - Pepe's, Sally's, and a lineup of neighborhood favorites - while enjoying easy access to downtown, Yale, parks, and transit. Whether you're grabbing a slice, commuting, or exploring the city, everything is right at your fingertips. Commuters will appreciate the easy access to major highways, including I-95 and I-91. This home is also eligible for the Yale Homebuyer Program for Yale employees. Ask for details!

120 Wooster St Unit Q, New Haven

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Wooster Square Homes under $1.25 million

Newest Wooster Square Homes under $1.25 million

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