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Space to Spread Out
Whether you choose to spend your day floating in the spa-inspired pool capped off with drinks by the bar or curled up with work in the lounge followed by evening yoga, your choices—and spaces—are abundant.
With two decked out courtyards and ample interior amenities, you may never want to leave home.
Union Street Entrance
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!
Resident Entrance on Union Street
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.
Townhomes & Walk-Up Units
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.
Apartment-Amenities
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.
Neighborhood Cafe
Restaurants and good times are just steps from your new home.
Union Street Lobby & Management Office
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.
Union Street Lobby & Management Office
Make yourself at home in our extremely comfortable lobby area. Interested in a tour just ask!
Union Street Lobby
Beautiful open space with luxury furniture and a welcoming atmosphere.
Community Life
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!
Yale University Library
Want a different place to study? The Library is just a few blocks away.
Wooster Square Park
New Haven’s historical Wooster Square Park.
For Your Furry Friends
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!
Spa Inspired Pool Deck
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!
Outdoor Lounges
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.
Pool Deck & Lounge
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!
There’s Always Time for a Cocktail
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!
A Little Something for Everyone
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.
Sports Courtyard
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.
Sports Courtyard
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 Little Something for Everyone
The courtyard will be complete with furniture very soon. In the meantime enjoy the fresh air and good times.
Resident Lobby from Fair Street
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.
Collaborative Work Space
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.
Work & Play
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.
Fit In Some Work Time Too
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.
A Cozy Spot for Cool Nights
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.
State-of-the-Art Fitness Center
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.
Fitness Center
Get active in our Fitness Center, from running to weight lifting, the fitness center has everything you need for your active lifestyle.
State-of-the-art Fitness Center
Taking "Home-Gym" to an entire new level. We take pride in providing you with the best possible fitness equipment to fit your lifestyle.
3 Bedroom Sleep Space
Embrace your dreams and follow your heart, you miss 100% of the naps you don't take!
Kitchen Island & Storage Space
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.
3 Bedroom Kitchen & Cabinetry
High-end appliances, large counter spaces, and food prep zones are expertly arranged in your very own kitchen workspace.
3 Bedroom Spacious Living Area
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!
3 Bedroom Living Space With a View
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.
4 Bedroom Living Space
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.
4 Bedroom Kitchen
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.
Spacious 4 Bedroom Sleep Space
Beautiful open windows with a view and luxury finishes make this one of our favorite spaces.
4 Bedroom Sleep Space
Furnished and Unfurnished packages available. Beautiful open windows with a view and luxury finishes make this one of our favorite spaces.
4 Bedroom Bathroom Features
Beautiful white spaces and luxury furniture make this one of the best features of your new place.
Studio Kitchen Space
Having privacy can be a game-changer, our studios come with beautiful finishes and a great view.
Studio Kitchen
Our studio features hardwood floors and a fantastic view of downtown New Haven.
Studio Views
6 Beautiful windows with an open outdoor view of the sports courtyard.
Studio Bedroom
A fusion of style and New Haven views gives your bedroom a cozy vibe.
Studio Living
Our studio features hardwood floors and a fantastic view.
Studio Living Room
Modern furniture and beautiful views of New Haven give your living room a super at-home feel.
1 Bedroom Balcony View
Our 1 Bedroom features modern furniture and beautiful balcony with a spectacular view of New Haven.
1 Bedroom Kitchen
Featuring beautiful furniture and modern finishes, the 1 bedroom kitchen will be your new favorite spot.
1 Bedroom Bed
Imagine waking up each morning in an extra cozy bed with a spectacular view of New Haven.
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Blue State Coffee
Blue State Coffee and Yorkside Pizza along York Street near Yale University.
Arethusa Farm Dairy
Arethusa Farm Dairy and Union League Café in downtown New Haven along Chapel Street.
Sally’s Apizza
Sally’s Apizza is located just across the street, at our namesake corner of Olive & Wooster.
Pepe’s
Dare to compare Sally’s and Pepe’s pizza? Take a short stroll down Wooster Street and choose your favorite pizza parlor.
Libby’s Italian Pastry Shop
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.
Somos
Settle your cravings at the intersection of Orange Street and Center Street. When the arepas cravings hit, enjoy Somos any day of the week.



























































Resident Offerings & Community Amenities
RESIDENT SERVICES
- Professional onsite management & maintenance team
- Indoor garage parking and bicycle storage
- Mobile app rent payments & work order requests
- Package lockers & refrigerated grocery storage
- Fob entry to residential units & amenity spaces
Indoor Amenities
- Resident lounge and bar overlooking the pool deck
- Fitness center with private studio space
- Co-working space and business center
- Dog grooming room for furry friends
- On-site retail options
Outdoor Amenities
- Spa-inspired pool deck with lounge
- Sports courtyard with outdoor fitness and gaming
- Grill areas adjacent to the Resident Lounge
- Outdoor dining areas with fire pits & lounge seating
- Union Street entrance adjacent to Union Street Dog Park