Wooster Square Homes under $400,000

Welcome to Wooster Square, one of New Haven's most charming and vibrant neighborhoods! Nestled in the heart of this historic city, Wooster Square is renowned for its picturesque streets, beautiful parks, and a sense of community that makes it truly special. This area is a delightful blend of classic architecture and modern amenities, making it an ideal place for families, young professionals, and retirees alike.

Wooster Square is famous for its Italian heritage, which is beautifully showcased through its local eateries, bakeries, and annual festivals. The iconic Wooster Square Park serves as the neighborhood's centerpiece, offering lush green spaces, walking paths, and a playground, perfect for leisurely strolls or enjoying a picnic with friends and family. The cherry blossom trees lining the park are a breathtaking sight in the spring, drawing residents and visitors alike to admire their beauty.

For those seeking their dream home in Wooster Square, you'll be pleased to know that there are fantastic options available under $400,000. From cozy condos to charming single-family homes, this neighborhood offers a variety of real estate choices that cater to diverse lifestyles and budgets. With its close proximity to downtown New Haven, residents enjoy easy access to shopping, dining, and cultural attractions, including theaters, museums, and universities.

Whether you’re looking to invest in a starter home or searching for a place to settle down, Wooster Square provides a welcoming atmosphere and a strong sense of community. Come explore this delightful neighborhood and discover why so many are proud to call Wooster Square home!

Newest Wooster Square Homes under $400,000

$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

$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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.