1 Day Ago
Location
99 Olive St, New Haven, CT 06511, USA|Wooster Square - Mill River
Hi! Let’s figure out if this property is right for you.
Powered by Zumper AI
Nearby rentals
Renter hub
Property management
Apartments for rent HartfordApartments for rent New HavenApartments for rent Barry SquareApartments for rent West HavenApartments for rent South GreenApartments for rent StamfordApartments for rent Clay ArsenalApartments for rent BridgeportApartments for rent NorwalkApartments for rent West HartfordApartments for rent DanburyApartments for rent DwightApartments for rent East Garden CityApartments for rent East Garden CityApartments for rent Downtown New HavenApartments Near Me
Houses for rent StamfordHouses for rent NorwalkHouses for rent Newfield - Westover - Turn of RiverHouses for rent HamdenHouses for rent GlastonburyHouses for rent EssexHouses for rent West HartfordHouses for rent Westhampton BeachHouses for rent New HavenHouses for rent BridgeportHouses for rent GlenbrookHouses for rent WaterburyHouses for rent DanburyHouses for rent SouthamptonHouses for rent BristolHouses for rent near me
Property Overview
99 Olive St is a highly rated rental option with an overall expert score of 8.1/10, excellent value for price, strong amenities, and an especially convenient location near quality schools. Large windows, multiple coworking spots, and strong connectivity make it supportive of working from home, while abundant parks, fitness options, and walkable access to restaurants, events, and transit support sustainability, wellness, and an active social life.
This summary uses Zumper’s proprietary data. “Zumper Expert Ratings,” “Things you’ll love,” and “Great for” are based on our internal analyses of market trends and renter insights.
Things you’ll love
Middle school nearby- High school nearby
Great for
Work-from-home
Social life
Eco living
Floor plans
| 2BR/2.0BA | 2 bed | 2 bath | $2,750 /mo | 1 unit available | This stunning 3rd-floor residence offers a unique blend of modern sophistication and cozy architectural character. Nestled in prime Wooster Square, this massive 1-bedroom apartment features beautiful sloped ceilings, rich hardwood floors, and high-end finishes that create an inviting, one-of-a-kind urban retreat. 2 Bedroom 2 Bathroom Massive Living/Kitchen area Unit Features: - Ample natural light - Fully updated bathroom & kitchen - Charming architectural details - Hardwood flooring Neighborhood Features: - Prime Wooster Square location, just steps from the historic park and weekly Farmer’s Market. - Highly walkable neighborhood with easy access to Downtown New Haven and Yale University. - Excellent commuter access to I-95, I-91, and the State Street Train Station. Application screening fee is $50/adult. Security deposit and first month's rent due up front. We support Equal housing opportunities - Anyone can apply! Application approval contingent on credit score and financial background. |
Let's explore this property.
Amenities for 99 Olive St
Other
| Cold Water & Sewer |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
Building details
Property details
| Units | 2 |
|---|
Advertisement
About 99 Olive St
This stunning 3rd-floor residence offers a unique blend of modern sophistication and cozy architectural character. Nestled in prime Wooster Square, this massive 1-bedroom apartment features beautiful sloped ceilings, rich hardwood floors, and high-end finishes that create an inviting, one-of-a-kind urban retreat. 2 Bedroom 2 Bathroom Massive Living/Kitchen area Unit Features: - Ample natural light - Fully updated bathroom & kitchen - Charming architectural details - Hardwood flooring Neighborhood Features: - Prime Wooster Square location, just steps from the historic park and weekly Farmer’s Market. - Highly walkable neighborhood with easy access to Downtown New Haven and Yale University. - Excellent commuter access to I-95, I-91, and the State Street Train Station. Application screening fee is $50/adult. Security deposit and first month's rent due up front. We support Equal housing opportunities - Anyone can apply! Application approval contingent on credit score and financial background.
Zumper Expert Rating
Our expert rating is based on a weighted average score of property attributes that renters care about most: price, amenities, location, quality, and trust.
8.1
/10
Very GoodWith a solid 8.1 out of 10 overall, 99 Olive St is a great option for renters. While some aspects, like Quality, might not be as distinguished as other properties nearby, 99 Olive St has a number of attractive features—namely its Price— so you can be assured your rent will come with a high standard of living.
Price·9A score that weighs the cost and location of the property, which we calculate by comparing rent prices of recent units to the median price of nearby rentals, adjusting for overall quality and features.
99 Olive St stands out with a remarkable rating of 9/10 for its cost per bedroom compared to other rentals in the area. Considering the excellent balance between price, convenience, and comfort that it provides, residents enjoy a high-quality living experience.
Amenities·8A score based on the amenities offered at this property compared to other rentals in the area. We consider the quantity, quality, and popularity of features both on site and within the units.
With multiple in-demand amenities, 99 Olive St is committed to enhancing the renting experience. And while it may have fewer total conveniences and features than similar rentals nearby, it remains a top choice for renters wanting an specific standard of living.
Location·9A score based on proximity and ease of access to shops, restaurants, schools, and public transportation while considering the desirability of the area.
99 Olive St is exceptional when it comes to location and conveniences. Communication with management or leasing staff is usually quick and easy and they often use advanced scheduling and communication tools to streamline the process. The location of this property offers easy access to popular points of interest in the area and options for getting around.
Quality·6A score based on what makes the property stand out, such as luxury features, unique offerings, age of the building, and our ability to verify the accuracy of these details.
While 99 Olive St does not have many hallmark characteristics to highlight, it has some qualities and features that will resonate with a broad range of renters.
Trustworthiness·8A score based on the accuracy, completeness, recency, and usefulness of the information provided by this property, so you can trust that what you see is what you get.
The level of transparency this property provides distinguishes it as a great rental. With a high attention to detail and desirable features, renters can be sure they will get an accurate picture of their potential new home.
99 Olive St is great for:
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 99 Olive St compares to other nearby properties.
Positives
- Middle school nearby
- There is a middle school 1 mile away
- High school nearby
- There is a high school 0.3 mile away
Considerations
- Greater distance from grade schools
- The nearest elementary school is farther than 0.3 mile away
Get the latest listings anytime, anywhere
Receive similar listings in the area, download our app, and more.
Rent trends in Wooster Square - Mill River
2-bedroom apartments at 99 Olive St cost about 20% more than the average rent price for 2-bedroom apartments in Wooster Square - Mill River.
Median rents as of Apr 25 2026.
Wooster Square - Mill River
New Haven
| Month | Median Rent |
|---|---|
| May 2024 | $1,904 |
| June 2024 | $1,836 |
| July 2024 | $1,928 |
| August 2024 | $2,147 |
| September 2024 | $2,157 |
| October 2024 | $2,110 |
| November 2024 | $2,266 |
| December 2024 | $2,242 |
| January 2025 | $2,377 |
| February 2025 | $2,172 |
| March 2025 | $2,131 |
| April 2025 | $2,113 |
| May 2025 | $2,147 |
| June 2025 | $1,949 |
| July 2025 | $1,862 |
| August 2025 | $1,798 |
| September 2025 | $1,800 |
| October 2025 | $1,776 |
| November 2025 | $1,728 |
| December 2025 | $1,799 |
| January 2026 | $1,784 |
| February 2026 | $1,796 |
| March 2026 | $1,848 |
| April 2026 | $1,836 |
| Month | Median Rent |
|---|---|
| May 2024 | $1,795 |
| June 2024 | $1,820 |
| July 2024 | $1,672 |
| September 2024 | $1,675 |
| October 2024 | $1,675 |
| November 2024 | $1,850 |
| December 2024 | $1,850 |
| January 2025 | $1,968 |
| February 2025 | $1,897 |
| March 2025 | $1,850 |
| April 2025 | $1,898 |
| May 2025 | $1,863 |
| June 2025 | $1,850 |
| July 2025 | $1,850 |
| August 2025 | $1,750 |
| September 2025 | $1,730 |
| October 2025 | $1,728 |
| November 2025 | $1,840 |
| December 2025 | $1,962 |
| January 2026 | $1,927 |
| February 2026 | $1,907 |
| March 2026 | $1,884 |
| April 2026 | $1,905 |
Affordability calculator
Can I afford to live at 99 Olive St?
Bedrooms
2 bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$110,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $110,000 annually to afford this 2-bedrooms monthly rent price of $2,750.
For more information on rent affordability, visit our rent calculator.
Schools near 99 Olive St
YLS Early Learning Center
127 wall st
new haven, CT, 6511
PKPublic
Roberto Clemente Leadership Academy for Global Awareness
360 columbus ave
new haven, CT, 6519
K-8Public
C
Hill Central Music Academy
140 dewitt st
new haven, CT, 6519
PK, K-8Public
C-
Family Academy of Multilingual Exploration
255 blatchley ave
new haven, CT, 6513
PK, K-8Public
C-
Wexler/Grant Community School
55 foote st
new haven, CT, 6511
K-8Public
C-
Advertisement
Internet available near 99 Olive St
Getting around New Haven near 99 Olive St
Walking
8/10
Grab your reusable bags–many shops and stores are within walking distance.
Driving
7/10
This area is close to freeways and has adequate parking options.
Cycling
8/10
Peddling isn’t a problem with cyclist-friendly streets and bikeable destinations.
Transit
9/10
Getting around is a breeze; rapid transit and bus lines are a few blocks away.
Points of interest for 99 Olive St, New Haven
Groceries
9/10
At least one supermarket within a 10-minute walk
Shopping
6/10
Several shops within walking distance
Cafes
6/10
Some cafés within a few minutes’ walk
Restaurants
8/10
Variety of restaurants within a few minutes' walk
Primary schools
9/10
At least one elementary school within a 10-minute walk
High schools
9/10
At least one high school within a 10-minute walk
Nightlife
6/10
Some bars within a few minutes’ walk
Explore the area around 99 Olive St
Elm City Market
274 S Orange St
The Meat King By Ctown
664 Grand Ave
Marketa
180 Temple St
Hong Kong Market
71 Whitney Ave
Oriental Pantry Cafe Grocery & Gifts
486 Orange St
Adolf Viennese Couturier in Furs
105 Court St
Greg's Tailor Shop
113 Court St
Valentino Tailors
817 Grand Ave
V Ferrucci Ltd
53 Elm St
Del Monico Hatters
47 Elm St
Kaiyden's Coffee
595 Chapel St
Cafe Java
59 Elm St
Life Bowls
97 Orange St
Cedarhurst Cafe
44 Crown St
Dunkin'
81 Church St
Regal Beagle
418 State St
O'Tooles Irish Pub
157 Orange St
Trinity Bar & Restaurant
157 Orange St
Hachiroku Shokudo & Sake Bar
261 Orange St
Firehouse 12
45 Crown St
Lucibello's Italian Pastry
935 Grand Ave
Libby's Italian Pastry Shop
139 Wooster St
Cityseed
817 Grand Ave
Mediterranea Cafe
140 Orange St
Adv Inc
779 Grand Ave
Park
Park
Park
Park
West Rock Ridge State Park
Sally's Apizza
237 Wooster St
Consiglio's Restaurant
165 Wooster St
Frank Pepe Pizzeria Napoletana
157 Wooster St
Regal Beagle
418 State St
Project Pasta
516 Chapel St
Chapel St / Academy St
East Chapel Street, New Haven / East Haven
Chapel St @ Academy St
NEW HAVEN/EAST HAVEN, EAST CHAPEL STREET, NEW HAVEN/EAST HAVEN, EAST CHAPEL STREET
Chapel St / Olive St
East Chapel Street, New Haven / East Haven
Chapel St @ Olive St
NEW HAVEN/EAST HAVEN, EAST CHAPEL STREET, NEW HAVEN/EAST HAVEN, EAST CHAPEL STREET
Chapel St / Olive St
East Chapel Street, New Haven / East Haven
State Street Station
Hartford Line
State Street Station
Hartford Line, Hartford Line
New Haven-State St
New Haven
New Haven State Street Station
Shore Line East Train
New Haven Union Station
Shore Line East Train
Compare similar properties nearby
Summit at Mill Ridge
Our team has verified this company140 Mill St
1–3 Beds
$2,224–$2,574
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.- dogs ok
- dishwasher
- fitness center
400 Boulder Pass
2 Beds
$3,125
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.- dogs ok
- dishwasher
- fitness center
East Rock • 575 Whitney Ave
1 Bed
$2,575
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
835 Mix Ave
1–2 Beds
$1,900–$2,545
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
East Rock • 431 Whitney Ave
2 Beds
$2,375–$2,825
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
Downtown New Haven • 56 Hillside Pl #1
4 Beds
$2,795
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
219 S Orchard St
3 Beds
$2,300
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
Dwight • 104 Howe St
1–2 Beds
$1,945–$3,300
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
Summit at Mill Ridge
Our team has verified this company140 Mill St
1–3 Beds
$2,224–$2,574
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.- dogs ok
- dishwasher
- fitness center
400 Boulder Pass
2 Beds
$3,125
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.- dogs ok
- dishwasher
- fitness center
East Rock • 575 Whitney Ave
1 Bed
$2,575
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
835 Mix Ave
1–2 Beds
$1,900–$2,545
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
East Rock • 431 Whitney Ave
2 Beds
$2,375–$2,825
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
Downtown New Haven • 56 Hillside Pl #1
4 Beds
$2,795
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
219 S Orchard St
3 Beds
$2,300
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center
Dwight • 104 Howe St
1–2 Beds
$1,945–$3,300
The price shown reflects a 12-month lease. Fees may apply.- dogs ok
- dishwasher
- fitness center