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Olive & Wooster stands out as a strong rental option with an 8.5 expert rating, excellent scores for price, amenities, location, and trustworthiness, plus spacious closets, a modern kitchen, an open layout, a fitness center, and a swimming pool. It is also appealing for work-from-home, pet-friendly, wellness, social, and environmentally conscious lifestyles, with strong nearby transit, walkability, parks, dining, and convenient access to schools.
Things you’ll love
More spaceMiddle school nearbyHigh school nearbyGreat for
Social life
Eco living
Pet owners| S4 | Studio | 1.5 bath | 605 sqft | $1,808–$2,170 /mo | 1 unit available | The S4 studio floor plan offers 605 square feet of well-designed space with standout features throughout. This studio includes a private sleeping alcove, an extended living and dining area, and a stylish kitchen with an island—perfect for cooking, dining, or entertaining. In-unit laundry adds everyday convenience, while the open layout and modern finishes make the S4 a smart, comfortable place to call home. | |
| S1 | Studio | 1.5 bath | 501 sqft | $2,054–$2,465 /mo | 1 unit available | The S1 studio floor plan offers smart, stylish living in a compact yet comfortable 501 square feet. Designed with a cozy sleeping alcove, this layout gives you the feel of a separate bedroom while keeping an open, airy flow. Modern finishes throughout add a sleek touch, and the well-planned space makes everyday living easy and efficient. Perfect for those who want contemporary design, functionality, and a place that feels uniquely their own. | |
| A1 | 1 bed | 1.5 bath | 631 sqft | $1,864–$2,780 /mo | 11 units available | The A1 floor plan is a thoughtfully designed 1 bedroom, 1 bathroom home offering 631 square feet of stylish living space. Enjoy a private patio that extends your living area outdoors, paired with an open, modern kitchen ideal for both everyday living and entertaining. The spacious bedroom includes a walk-in closet, while in-unit laundry adds everyday convenience. Tons of natural light pour in through expansive windows, showcasing high-end finishes throughout for a bright, elevated living experience. | |
| A4 | 1 bed | 1.5 bath | 645 sqft | $1,959–$2,351 /mo | 1 unit available | The A4 floor plan offers 645 square feet of beautifully designed living space with a warm, inviting flow. The open kitchen and living area feel effortless and refined, perfect for relaxed mornings or hosting friends. A spacious bedroom with a walk-in closet adds a sense of retreat, while in-unit laundry keeps everyday living seamless. Sunlight pours in through large windows, bringing out the richness of the high-end finishes and creating a space that feels both calm and elevated. | |
| A5 | 1 bed | 1.5 bath | 616 sqft | $2,271–$2,726 /mo | 1 unit available | The A5 floor plan presents 616 square feet of elegantly designed living space with a seamless, open layout. The modern kitchen flows effortlessly into the living area, ideal for both quiet mornings and sophisticated entertaining. The spacious bedroom features a walk-in closet, while in-unit laundry adds effortless convenience. Expansive windows fill the home with natural light, highlighting the high-end finishes and creating a serene, elevated atmosphere. | |
| A3 | 1 bed | 1.5 bath | 708 sqft | $2,451–$2,942 /mo | 1 unit available | The A3 floor plan offers 708 square feet of bright, modern living with an open layout that feels easy and inviting. The open kitchen connects seamlessly to the living area, perfect for everyday moments or low-key entertaining. A spacious bedroom with a walk-in closet adds comfort and storage, while in-unit laundry keeps life simple. Large windows bring in abundant natural light, showcasing high-end finishes throughout for a fresh, elevated vibe. | |
| A2 | 1 bed | 1.5 bath | 709 sqft | $2,516–$3,032 /mo | 2 units available | The A2 floor plan offers 709 square feet of well-designed living with a modern, open layout that feels both stylish and comfortable. The open kitchen flows easily into the living space, making it great for everyday living or casual entertaining. A spacious bedroom with a walk-in closet adds plenty of storage, while in-unit laundry keeps things convenient. Large windows bring in tons of natural light, highlighting the high-end finishes throughout. | |
| B1 | 2 bed | 2.5 bath | 967 sqft | $2,416–$4,002 /mo | 3 units available | The B1 floor plan offers 967 square feet of open, inviting living. The modern kitchen flows naturally into the living and dining areas, creating a seamless space for relaxing or entertaining. Two spacious bedrooms, including a primary suite with a walk-in closet, provide privacy and comfort, while in-unit laundry keeps daily life easy. Sunlight pours through expansive windows and onto your private patio, highlighting high-end finishes and giving the home a bright, airy, and effortlessly refined feel. | |
| B2 | 2 bed | 2.5 bath | 998 sqft | $3,218–$4,184 /mo | 1 unit available | The B2 floor plan offers 998 square feet of thoughtfully designed living with a seamless, open layout. The modern kitchen flows gracefully into the living and dining areas, creating a sophisticated space for both everyday life and entertaining. Two generously sized bedrooms, including a primary suite with a walk-in closet, provide comfort and privacy, while in-unit laundry adds effortless convenience. Expansive windows fill the home with natural light, highlighting high-end finishes and creating an airy, refined atmosphere throughout. | |
| C1 | 3 bed | 3.5 bath | 1,314 sqft | $4,019–$5,828 /mo | 1 unit available | The C1 floor plan offers 1,314 square feet of thoughtfully designed living, blending style, comfort, and functionality. A modern kitchen with a breakfast bar flows seamlessly into the living area, while a separate dining space creates the perfect setting for gatherings. Three spacious bedrooms, each with walk-in closets, provide privacy and ample storage, and three full bathrooms ensure convenience for everyone. In-unit laundry adds everyday ease, and a private terrace extends your living space outdoors. Expansive windows fill the home with natural light, highlighting modern finishes throughout and creating a bright, refined atmosphere. | |
| C2-A with Den | 3 bed | 3.5 bath | 1,513 sqft | $4,324–$6,054 /mo | 1 unit available | The C2-A With Den offers 1,513 square feet of modern, elevated living. A sleek, chef-inspired kitchen with a breakfast bar opens to a bright living and dining area, perfect for entertaining. Three spacious bedrooms with generous closets and three contemporary bathrooms provide comfort and style, while a versatile den creates space for work or relaxation. Expansive windows showcase luxurious finishes and flood the home with natural light, creating a sophisticated, airy atmosphere throughout. | |
| C2 with Den | 3 bed | 3.5 bath | 1,513 sqft | $4,394–$6,372 /mo | 1 unit available | The C2 With Den floor plan defines modern, elevated living across 1,513 square feet of impeccably designed space. A sleek, chef-inspired kitchen with a breakfast bar, premium countertops, and high-end appliances flows seamlessly into the open living and dining area, perfect for entertaining or relaxing in style. Three expansive bedrooms, each with spacious closets, are complemented by bathrooms featuring contemporary fixtures and refined finishes. A versatile den provides space for a home office, creative studio, or personal sanctuary. Expansive windows bathe the home in natural light, accentuating clean architectural lines, luxurious finishes, and a bright, sophisticated ambiance that elevates everyday living. | |
| C5 Townhouse | 3 bed | 2.5 bath | 1,849 sqft | $5,284–$7,662 /mo | 1 unit available | Experience the spacious elegance of the C5 Townhouse, spread across two thoughtfully designed floors with 1,849 sq. ft. of modern living space. Step into a generous foyer that leads to an open-concept main level featuring a modern kitchen with a breakfast bar, a pantry for ample storage, and a cozy fireplace for relaxing evenings. Enjoy in-unit laundry for convenience and step outside to your private patio, perfect for entertaining or unwinding. Designed for comfort, style, and functionality, the C5 Townhouse offers the perfect balance of contemporary living and welcoming charm. | |
| D1 Co-Living | 4 bed | 3.5 bath | 347 sqft | $1,012–$1,310 /mo | 2 units available | The D1 Co-Living offers spacious, modern living with 4 bedrooms and 3 full baths. Each bedroom measures approximately 347 sq. ft., with the entire apartment sharing 1,386 sq. ft. of thoughtfully designed space. The open kitchen features a central island, perfect for cooking, entertaining, or casual dining. Each bedroom includes ample closet space, while in-unit laundry adds convenience to daily living. Flexible leasing options make this home ideal for any lifestyle. Rent on a by-bedroom basis, with options A, B, C or D. Designed for comfort and functionality, the D1 floor plan combines modern finishes with a bright, open layout to create a home that fits your lifestyle. | |
| D2 Co-Living | 4 bed | 4.5 bath | 381 sqft | $1,057–$1,328 /mo | 3 units available | The D2 Co-Living offers spacious, modern living. Each personal space measures approximately 381 sq. ft. with a combined living area of 1,523 sq. ft., encompassing all 4 bedrooms and 4 full baths. Designed for both comfort and functionality, each bedroom includes ample closet space, while the open layout provides bright, airy living areas perfect for relaxing or entertaining. The modern kitchen is ideal for cooking and gathering, and in-unit laundry adds convenience to daily life. Rent on a by-bedroom basis, with options A, B, C or D. With thoughtful design and flexible spaces, the D2 floor plan combines contemporary style with the room and amenities you need to feel at home. | |
| D5 Co-Living | 4 bed | 4.5 bath | 405 sqft | $1,377–$1,652 /mo | 1 unit available | The D5 Co-Living floor plan offers spacious, modern living. Each private space is about 405 square feet and comes with its own full bath and plenty of closet space. The oversized shared living area connects all four bedrooms, creating the perfect space to host or relax. A sleek kitchen, in-unit laundry, and bright open layout keep things easy and comfortable. Rent by the bedroom (A, B, C, or D) and enjoy a flexible setup that feels like home—without sacrificing space or style. | |
| D1 | 4 bed | 3.5 bath | 1,386 sqft | $5,380–$6,456 /mo | 1 unit available | The D1 offers spacious, modern living with 4 bedrooms and 3 full baths across 1,386 sq. ft. of thoughtfully designed space. The open kitchen features a central island, perfect for cooking, entertaining, or casual dining. Each bedroom includes ample closet space, while in-unit laundry adds convenience to daily living. Designed for comfort and functionality, the D1 floor plan combines modern finishes with a bright, open layout to create a home that fits your lifestyle. |
Let's explore this property.
Apartment Amenities
| Air Conditioning | Balcony |
| Ensuite Bathroom | High Ceiling |
| High Ceilings | Terrace Level |
| View | Walk-in Closet |
| Wrap Around Balcony |
Tech
| Internet |
Building
| Cats OK | Dogs OK |
Grounds
| Swimming Pool |
Other
| ADA Accessible |
One-time.
One-time. Refundable.
Questions about this property’s policies and fees?
| Units | 428 |
|---|
Welcome to Olive & Wooster, the ultimate living experience nestled in the heart of Wooster Square. Oliver & Wooster offers spacious modern apartments ranging from studios to four bedrooms, featuring all the comforts you desire and lease term options built just for you. Our pet-friendly community provides tastefully designed amenities including a state-of-the-art clubhouse and bar, fitness center, swimming pool, and more. Enjoy our little "slice" of paradise conveniently located near downtown, Yale campus, and the medical district. Discover Olive & Wooster today!
Showing 8 highest rated
I chose a co-living room when I first moved in, and it was at the same day that I realized that the lifestyle of my roommate didn’t suit me. Thankfully Melissa acted quickly and helped me to resign the lease to move in to another unit within 2 days. This is the kind of efficiency that I’ve never seen in the other apartments I’ve ever lived. I am happy about my current roommates and I enjoy living here; it’s Melissa who made these all happen!!!
Vermil J
Dec 01, 2024
I have been living at Olive and Wooster for over 6 months now and I have to say that I am so happy to be here. I mean, the neighborhood is a dream, we all can attest to that but what makes this place beyond special is Melissa and Anthony in the leasing office. They are both so kind, helpful and so fun to interact with. They both bring joy to my day when I see them and I am confident that they bring joy to a lot of other residents as well :)
Jessica Loya
Jan 23, 2025
We’re sharing just 8 of many, sorted highest to lowest. Visit the Google business profile to view all reviews.
How Olive & Wooster compares to other nearby properties.
Positives
Considerations
Studio apartments at Olive & Wooster cost about 6% less than the average rent price for studios in Downtown New Haven.
1-bedroom apartments here are priced 5% lower than 1-bedrooms in Downtown New Haven.
If you decide to upgrade your space, you can expect 2-bedrooms at Olive & Wooster to be 19% less than the average for similarly sized apartments in Downtown New Haven.
3-bedroom apartments at Olive & Wooster cost about 50% more than the average rent price for 3-bedroom apartments in Downtown New Haven.
4-bedroom apartments at Olive & Wooster cost about 17% more than the average rent price for 4-bedroom apartments in Downtown New Haven.
| Month | Median Rent |
|---|---|
| July 2024 | $1,756 |
| August 2024 | $1,614 |
| September 2024 | $1,838 |
| October 2024 | $1,879 |
| November 2024 | $1,999 |
| December 2024 | $2,051 |
| January 2025 | $2,074 |
| February 2025 | $2,003 |
| March 2025 | $1,997 |
| April 2025 | $1,992 |
| May 2025 | $1,961 |
| June 2025 | $1,810 |
| July 2025 | $1,720 |
| August 2025 | $1,730 |
| September 2025 | $1,779 |
| October 2025 | $1,747 |
| November 2025 | $1,776 |
| December 2025 | $1,804 |
| January 2026 | $1,714 |
| February 2026 | $1,780 |
| March 2026 | $1,710 |
| April 2026 | $1,724 |
| May 2026 | $1,718 |
| June 2026 | $1,698 |
| Month | Median Rent |
|---|---|
| July 2024 | $2,041 |
| August 2024 | $2,012 |
| September 2024 | $2,086 |
| October 2024 | $2,035 |
| November 2024 | $2,085 |
| December 2024 | $2,130 |
| January 2025 | $2,137 |
| February 2025 | $2,133 |
| March 2025 | $2,143 |
| April 2025 | $2,138 |
| May 2025 | $2,177 |
| June 2025 | $2,066 |
| July 2025 | $1,972 |
| August 2025 | $2,073 |
| September 2025 | $2,176 |
| October 2025 | $2,136 |
| November 2025 | $2,109 |
| December 2025 | $2,100 |
| January 2026 | $2,099 |
| February 2026 | $2,142 |
| March 2026 | $2,126 |
| April 2026 | $2,112 |
| May 2026 | $2,129 |
| June 2026 | $2,058 |
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$2,379–$3,264
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The price shown reflects a 12-month lease. Fees may apply.500 Boulder Pass
1–2 Beds
$2,385–$3,420
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Dwight • 133 Howe St
1 Bed
$1,850
The price shown reflects a 12-month lease. Fees may apply.140 Mill St
1–3 Beds
$2,379–$3,264
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.1298 Hartford Tpke
2 Beds
$2,925
The price shown reflects a 12-month lease. Fees may apply.Downtown New Haven • 56 Hillside Pl #1
4 Beds
$2,395
The price shown reflects a 12-month lease. Fees may apply.Dwight • 104 Howe St
Studio–2 Beds
$1,695–$3,145
The price shown reflects a 12-month lease. Fees may apply.East Rock • 575 Whitney Ave
1 Bed
$2,300
The price shown reflects a 12-month lease. Fees may apply.Prospect Hill • 550 Whitney Ave #14
Studio
$1,325
The price shown reflects a 12-month lease. Fees may apply.500 Boulder Pass
1–2 Beds
$2,385–$3,420
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Dwight • 133 Howe St
1 Bed
$1,850
The price shown reflects a 12-month lease. Fees may apply.
