Wooster Square Homes under $1.25 million

Welcome to Wooster Square, one of New Haven’s most charming and historic neighborhoods, where tree-lined streets and vibrant community spirit create a unique living experience. Nestled in the heart of New Haven, Wooster Square is renowned for its picturesque parks, historic brownstones, and a delightful sense of community that beckons both families and young professionals alike.

One of the neighborhood's crown jewels is Wooster Square Park, a beautiful green space that serves as a gathering spot for residents and hosts seasonal events, including the famous Wooster Square Cherry Blossom Festival each spring. The area is also known for its rich Italian heritage, which is reflected in its local eateries and annual festivals. Indulge in authentic Italian cuisine at nearby restaurants and bakeries that have been cherished by locals for generations.

For those seeking a home in this vibrant neighborhood, Wooster Square offers a variety of charming properties under $1.25 million. From beautifully restored Victorian homes to modern condos with stunning city views, there's something for everyone. Whether you're looking for a cozy space to call your own or a family-friendly home with room to grow, Wooster Square has it all.

With its close proximity to downtown New Haven, top-rated schools, and cultural attractions, Wooster Square is not just a place to live; it’s a community to thrive in. Experience the warmth and charm of Wooster Square, where your dream home awaits!

Newest Wooster Square Homes under $1.25 million

$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

$449,900

2 Beds ⋅ 2 Baths ⋅ 24205542 MLS ⋅ Sage Arts BLDG.

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 details that set this home apart, including exposed brick walls, striking wood beams, acid-washed floors, and incredible natural light throughout. The spacious living room offers a beautiful gas fireplace, creating the perfect setting for relaxing or entertaining, while the formal dining room features a picturesque window that fills the space with light and character. The remodeled kitchen is both beautiful and functional, featuring stainless steel appliances, a farmhouse-style sink, granite countertops, and an abundance of cabinetry and workspace. The primary bedroom suite provides generous closet space and a beautifully remodeled private bathroom with an impressive updated shower, creating a comfortable retreat at the end of the day. A second generously sized bedroom offers excellent closet space and is complemented by an additional remodeled full bathroom. In-unit laundry, central air, natural gas heat, and off-street parking add to the convenience of this truly move-in-ready home.

43 Chestnut St Unit 201, 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

$1,200,000

5 Beds ⋅ 4 Baths ⋅ 24198627 MLS

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 brick and charming architectural details. All four units are being offered fully furnished, creating a truly turnkey opportunity. Select units have been utilized as Airbnb rentals, while the property's proximity to Yale makes it ideally positioned for strong rental demand. Whether continuing with short-term rentals, transitioning to traditional leases, or exploring a combination of both, this property offers tremendous flexibility. Enjoy the best of New Haven with world-class dining, cafes, parks, Yale University, and downtown amenities all close by. A rare opportunity to own a distinctive four-family property in one of New Haven's most sought-after neighborhoods, combining historic charm, modern updates, prime location, and multiple income-producing possibilities.

341 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

$595,000

2 Beds ⋅ 2 Baths ⋅ 24194029 MLS ⋅ On The Park BLDG.

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 cooking. A full bath with walkin shower and a flexible second bedroom-complete with Murphy bed and access to a shared back deck-round out this floor. The lower level features a spacious primary suite with a walkin closet, full bath, and inunit laundry, creating a quiet, comfortable retreat. The association offers a common patio for grilling, relaxing, and outdoor dining. Additional basement storage, updated mechanicals, and central A/C add everyday convenience. Located on a quiet block in one of New Haven's most beloved neighborhoods, you're steps from worldfamous Apizza, downtown, the Wooster Square Farmers Market, and major highways. Pets allowed (with restrictions). Onstreet parking. A rare chance to live directly on Wooster Square with character, comfort, and unbeatable walkability.

42 Academy St Unit 2, New Haven

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