Wooster Square Real Estate

Welcome to Wooster Square, a charming neighborhood nestled in the heart of New Haven, Connecticut. Known for its rich history and vibrant community, Wooster Square offers a delightful blend of urban convenience and suburban tranquility. This picturesque area is most famous for its stunning cherry blossom trees, which transform the streets into a breathtaking spectacle each spring, drawing both locals and visitors to enjoy the annual festival celebrating this natural beauty.

The neighborhood is characterized by its historic brownstones and quaint brick homes, showcasing architectural styles that reflect its storied past. Strolling through Wooster Square, you’ll find tree-lined streets that invite leisurely walks and friendly conversations with neighbors. The local parks, including the beloved Wooster Square Park, provide a perfect backdrop for picnics, sports, and community gatherings, fostering a welcoming atmosphere for families and individuals alike.

Culinary enthusiasts will appreciate the neighborhood’s diverse dining options. From traditional Italian eateries to trendy cafes, Wooster Square offers a culinary adventure for every palate. Don’t miss the chance to indulge in the area’s renowned pizza, often hailed as some of the best in New Haven.

With its proximity to downtown New Haven, residents enjoy easy access to cultural attractions, shopping, and entertainment. The vibrant arts scene, including theaters and galleries, complements the neighborhood’s charm, making it an ideal place for those seeking a dynamic lifestyle.

Whether you’re looking to settle down or simply explore, Wooster Square is a neighborhood that captures the essence of community, culture, and comfort. Come discover what makes this hidden gem a beloved part of New Haven!

Newest Listings in Wooster Square

$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

$1,310,000

6 Beds ⋅ 6 Baths ⋅ 24213108 MLS

Stunning six-unit building in coveted Wooster Square. Rare opportunity to own a meticulously maintained, turnkey property on a quiet, one-way, tree-lined street. Featuring six one-bedroom apartments, each one on its own floor, most with spacious living and dining rooms. Stunning kitchens and baths, soaring 10 foot ceilings, exposed brick throughout, majestic historic decorative fireplaces, many light-filled windows, and a rare private backyard add to the charm. Five units are occupied by excellent tenants, with one furnished apartment just vacated perfect for owner occupancy. Current monthly rent roll of $9,800 including the vacant unit. Rents are very below market, offering tremendous upside potential! Tenants pay their own utilities, gas and electric. Roof is approximately 10 years old. Additional potential exists to convert the attic into another apartment, subject to buyer due diligence, approvals, and applicable requirements. Walk to Yale, train station, Yale shuttle, and New Haven's famous Pizza on Wooster Street. A truly special investment opportunity in one of New Haven's most desirable neighborhoods. This one won't last.

14-16 Lyon St, New Haven

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 24213068 MLS

Professional photos to be loaded soon. Wonderful income property right on Wooster Square. The Frederick Brown House Historic Wooster Square A rare opportunity to own a remarkable piece of New Haven history in the heart of Historic Wooster Square, one of the city's most desirable high-rent districts. Dating to circa 1800, the Frederick Brown House is an extraordinary Italianate-style residence originally built for Frederick Brown, head of the Brown and Durham Furniture Company. Filled with natural light, timeless architectural character, and ornate period details, this distinctive property showcases beautiful floors, intricate ceilings and moldings, elegant windows, and six fireplaces. Offering exceptional flexibility and significant income potential, this unique three-family property presents endless possibilities for investors, owner-occupants, or those seeking a one-of-a-kind historic residence. The expansive layout spans four levels plus a loft, including a garden-level apartment. The main portion of the home features three additional levels and a loft not included in the reported square footage. Each level offers a kitchen and full bathroom, creating versatile living arrangements and multiple opportunities for rental income or multi-generational living. Additional highlights include generous ceiling heights, spacious open rooms, central air conditioning, central vacuum, an intercom system, gas fireplaces, decks, and a balcony.

38 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

$3,899,999

24 Beds ⋅ 16 Baths ⋅ 24206633 MLS

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 and $2,250 for the vacant units, total potential rental income is approximately $33,900 per month / $406,800 annually. The property offers additional value-add potential through continued unit improvements, rent optimization as leases turn over, and expansion of in-unit laundry. Nine of the sixteen units currently feature in-unit laundry. Separate utilities and natural gas heat help minimize owner-paid expenses. Parking is available nearby through the St. Andrew's Society for an additional fee, subject to availability and separate arrangement, providing tenants with a convenient parking in this highly walkable neighborhood. Ideally situated near Wooster Square Park, Downtown New Haven, Yale University, restaurants, public transportation, and major highways, 527 Chapel Street offers investors a compelling combination of strong in-place income, immediate lease-up opportunity, and long-term value-add potential. 16 Units * 8 One-Bedrooms * 8 Two-Bedrooms * 14,692 SF * 9 Units with In-Unit Laundry * $29,750/Month In-Place Rent * $33,900/Month Potential. Agent/Owner.

527 Chapel St, New Haven

$769,000

1 Baths ⋅ 24203165 MLS

A Legacy Address Ready for Its Next Visionary. Rising with quiet confidence along the historic Grand Avenue commercial spine, 922 Grand Avenue stands as one of the city's most architecturally honest and socially resonant commercial buildings. A mid-century civic structure that has outlived trends and weathered cycles, it now emerges as a rare canvas for the next chapter of neighborhood innovation. Built in 1963 during a wave of community-minded construction across the Elm City, the 4,500-square-foot masonry building is an enduring example of New Haven's post-industrial commercial architecture: solid, straightforward, purpose-built. Constructed of concrete, cinder block, and brick, with a flat rubber roof, 12-foot wall heights, and a full 4,500-square-foot basement, the property was engineered for longevity, adaptability, and public use - traits that have allowed it to remain structurally intact for more than six decades. Its original use classification - Clubs/Lodges with a modern STORE/SHOP (MDL-94) designation - reflects its history as a gathering place, a service hub, and a point of local connectivity. The unfinished basement offers expansion potential. The property invites reinvention - fitness and wellness programs, neighborhood brewery, grocery store, performance spaces, coworking studios, nonprofit headquarters, boutique commercial concepts, retail and more possibility subject to city approval. Seize this rare opportunity now.

922 Grand Ave, 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

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Wooster Square Real Estate

Newest Listings in Wooster Square

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