Space to Spread Out

Olive & Wooster’s Union Street entrance is located at the intersection of Fair Street and Union Street. This entrance is where our on-site management team offices are located, and it is just a short walk to downtown or the New Haven-State Street Shore Line East CT Rail station. Across the street from this entrance is the Union Street Dog Park!

Olive and Wooster’s Studio to 4-bedroom apartment homes feature all the creature comforts you desire. Conveniently located within walking distance of downtown New Haven, the Yale New Haven Hospitals, Wooster Square, Yale University, and the New Haven-State Street Shore Line CT Rail station, Olive & Wooster is your sanctuary in the middle of it all.

Olive & Wooster’s limited 3-bedroom townhouses and ground-floor Fair Street units offer walk-up access from Fair Street for a true neighborhood experience. Opting to walk to work or class rather than drive? Just walk out your front door and your day has started. All units also have access from the interior residential hallways for easy access to the mail room, package room, fitness center, or amenity spaces.

2 way entry makes this townhome optimal for everything that we have to offer. All units have access from the interior residential hallways for easy access to the mail room, package room, fitness center, or amenity spaces.

Restaurants and good times are just steps from your new home.

Olive & Wooster offers an onsite management and maintenance team to assist residents and ensure you are enjoying your home as much as we enjoy having you.

Make yourself at home in our extremely comfortable lobby area. Interested in a tour just ask!

Beautiful open space with luxury furniture and a welcoming atmosphere.

We are living for this refreshing #NewHaven air, while enjoying the surrounding parks near our luxury homes. We cannot wait for you to know the true meaning of “being on cloud nine” while living at Olive & Wooster!

Want a different place to study? The Library is just a few blocks away.

New Haven’s historical Wooster Square Park.

The dog park is just across the street from the Union Street entrance. Take your furry friend on fun leisurely walk, and breath-in that New Haven air!

Resident Pool deck with lounge chairs and cabana-esque shades when you need a break from the sun. The pool deck is surrounded by well-appointed landscaping to provide a spa-like escape for Olive & Wooster residents. Townhouses have the luxury of direct access to the pool area right out your back door!

When you’re ready to take a break from the pool, residents can relax by the fire-pit or enjoy outdoor dining and grilling in the outdoor lounge spaces.

Your New Haven oasis awaits! Select units offer pool views to help make your future home at Olive & Wooster a resort-like escape. During the winter months, come down and enjoy our resident grills under the pergola or a glass of wine by the fire pit. Townhouses have the luxury of direct access to the pool area right out your back door!

The Olive & Wooster Club Room is perfectly located in-between the Pool Deck and Sports Courtyard and serves as a convenient social gathering space for residents to enjoy. Join us for a pint while we cheer on the Bulldogs over the Crimson in The Game!

Olive & Wooster’s Sports Courtyard offers a little something for everyone. The Sports Courtyard will feature a large central lawn for throwing around a football or relaxing with a blanket and a book. There are also areas for dining, outdoor fitness, table games, lounge areas, and gathering spaces for our residents & guests to enjoy.

A mix of active resident spaces and relaxing areas to sip, snack, work, or workout, the sports courtyard offers a mix of spaces for Olive & Wooster’s residents and their guests.

A mix of active resident spaces and relaxing areas to sip, snack, work, or workout, the sports courtyard offers a mix of spaces for Olive & Wooster’s residents and their guests.

The courtyard will be complete with furniture very soon. In the meantime enjoy the fresh air and good times.

The Resident Lobby off of the Fair Street entrance is where Olive & Wooster’s residents can check their mailbox, pick up any packages that have been delivered (including groceries from the delivery refrigerators), or do some work in the lobby-area coworking space. The stairwell off the Fair Street Lobby leads to the 2nd floor Club Room and adjacent Fitness Center, Pool Deck, and Sports Courtyard.

When you need a little more focus, residents can office from the collaborative work space in the Fair Street Lobby, which offers focus desk areas and a collaborative desk space when you need to spread out a little. And when it’s time for a break you’re just a short walk from some fresh air out the Fair Street entrance or 2nd floor courtyards.

Take a break from your WFH office and bring your laptop down to the clubroom to get some work done in the company of your fellow Olive & Wooster residents.

Take a break from your WFH office and bring your laptop down to the clubroom to get some work done in the company of your fellow Olive & Wooster residents. When the weather is nice, setup in one of the lounge spaces on the Pool Deck or Sports Courtyard and be the envy of your Zoom colleagues.

When it’s a little too chilly to use the outdoor fire pits join us inside in the Club Room lounge for a spot by the fire. Outdoor views abound to help bring the outside in, but with a little more temperature control.

Our state-of-the-art fitness center features weight-lifting and cardio equipment. Multiple squat racks, barbells, and cardio equipment mean that you can get in the best workout for your lifestyle.

Get active in our Fitness Center, from running to weight lifting, the fitness center has everything you need for your active lifestyle.

Taking "Home-Gym" to an entire new level. We take pride in providing you with the best possible fitness equipment to fit your lifestyle.

Embrace your dreams and follow your heart, you miss 100% of the naps you don't take!

Homes today are only as luxurious as the kitchens they contain, so be prepared for your kitchen to portray just that. Luxury kitchens at Olive & Wooster call for extraordinary details, plenty of cabinet space, with the use of crisp materials and color combinations. With cabinet and island space for days, plan to fall in love with your luxury kitchen area.

High-end appliances, large counter spaces, and food prep zones are expertly arranged in your very own kitchen workspace.

Nothing captures the cozy feelings of family, friends, and food like an inviting kitchen design. For professional and aspiring chefs alike, and for all who desire luxury cooking environments with friends and family, you have come to the right place!

A spacious living room is what sets a tone for the rest of a home. The Olive & Wooster living room options are a great place to experiment with cool color patterns, fine designs, and a variety of illuminating artwork. Trickle in some of your favorite posters and people and experience bliss in New Haven.

Furnished and Unfurnished packages available. The perfect space for you and 3 friends. Our 4 Bedroom apartments have so much room for you and friends.

Furnished and Unfurnished packages available. A kitchen should be inviting and at Olive & Wooster we created a unique space that will do just that! From dinner parties to friends-giving your new kitchen will take meals to the next level.

Beautiful open windows with a view and luxury finishes make this one of our favorite spaces.

Furnished and Unfurnished packages available. Beautiful open windows with a view and luxury finishes make this one of our favorite spaces.

Beautiful white spaces and luxury furniture make this one of the best features of your new place.

Having privacy can be a game-changer, our studios come with beautiful finishes and a great view.

Our studio features hardwood floors and a fantastic view of downtown New Haven.

6 Beautiful windows with an open outdoor view of the sports courtyard.

A fusion of style and New Haven views gives your bedroom a cozy vibe.

Our studio features hardwood floors and a fantastic view.

Modern furniture and beautiful views of New Haven give your living room a super at-home feel.

Our 1 Bedroom features modern furniture and beautiful balcony with a spectacular view of New Haven.

Featuring beautiful furniture and modern finishes, the 1 bedroom kitchen will be your new favorite spot.

Imagine waking up each morning in an extra cozy bed with a spectacular view of New Haven.

Blue State Coffee and Yorkside Pizza along York Street near Yale University.

Arethusa Farm Dairy and Union League Café in downtown New Haven along Chapel Street.

Sally’s Apizza is located just across the street, at our namesake corner of Olive & Wooster.

Dare to compare Sally’s and Pepe’s pizza? Take a short stroll down Wooster Street and choose your favorite pizza parlor.

If you thought Olive & Wooster could not get any sweeter, try Libby’s Italian Pastry Shop which is a short stroll from New Haven’s newest humble abode.

Settle your cravings at the intersection of Orange Street and Center Street. When the arepas cravings hit, enjoy Somos any day of the week.