Updated 5+ Days Ago
Highlights
Pet Friendly
Location
555 Winchester Ave, New Haven, CT 06511, USA|Prospect Hill
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Property Overview
555 Winchester Ave has a strong overall rating, with standout scores for price, amenities, location, and quality, suggesting excellent value and a high standard of living. It is also noted for washer/dryer in unit and is marked great for pet friendliness, with tile, vinyl or hardwood floors and a nearby dog park.
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
Laundry available on site
Great for
Pet owners
Floor plans
| 3rd fl 4 bed 2 ba left | 4 bed | 2 bath | 1,124 sqft | $1,995 /mo | 1 unit available | * 4 Bedrooms * 2 Full Baths * Hardwood floors * Updated ceramic tiled bathrooms * Updated Kitchen with granite countertops * New energy efficient stainless steel appliances, dishwasher included!!! * Exposed brick * Doorbell * Office/Study space * Washer/Dryer in unit * New high-efficiency furnace * Pets allowed!! Yay!!!! Location, Location, Location!!! * Close proximity to both West Rock Park and East Rock Park * Convenient location to Yale, Southern and Albertus Magnus * Great shops and restaurants within walking distance |
Let's explore this property.
Amenities for 555 Winchester Ave
Apartment Amenities
| Air Conditioning | Central Air Conditioning |
| Dryer |
Appliances
| Dishwasher | In-Unit Laundry |
| Range | Refrigerator |
| Stove |
Building
| Cats OK | Dogs OK |
| Onsite Laundry | Sewer |
Grounds
| Off-Street Parking |
Other
| Cold Water |
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
Dog Policy
Allowed
Cat Policy
Allowed
Contact for more information on pet policy.
Questions about this property’s policies and fees?
Building details
Property details
| Units | 8 |
|---|
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About 555 Winchester Ave
* 4 Bedrooms * 2 Full Baths * Hardwood floors * Updated ceramic tiled bathrooms * Updated Kitchen with granite countertops * New energy efficient stainless steel appliances, dishwasher included!!! * Exposed brick * Doorbell * Office/Study space * Washer/Dryer in unit * New high-efficiency furnace * Pets allowed!! Yay!!!! Location, Location, Location!!! * Close proximity to both West Rock Park and East Rock Park * Convenient location to Yale, Southern and Albertus Magnus * Great shops and restaurants within walking distance
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.
9.4
/10
Excellent555 Winchester Ave is an excellent find, offering residents a superior living experience with a wide range of desirable features. Residents will particularly enjoy knowing that this property rated highest in Price and Amenities, which help to make this rental a great place to call home.
Price·10A 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.
555 Winchester Ave offers an excellent balance between price and value. It's priced competitively for its amenities, location, and other key features. Compared to the median price per bedroom in the area, this property is less than, or about the same as, nearby rentals, so residents can expect great value without too many compromises on their desired standard of living.
Amenities·10A 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.
555 Winchester Ave stands out as a premier property with an impressive array of amenities and an excellent standard of living. Residents here have access to many of the most popular and desired perks—pets allowed—making this one of the top choices for renters seeking unparalleled comfort and convenience.
Location·9A score based on proximity and ease of access to shops, restaurants, schools, and public transportation while considering the desirability of the area.
555 Winchester Ave 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·9A 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.
555 Winchester Ave has a few standout characteristics that set it apart from similar properties nearby. Having both verified status and features that cater to discerning renters, this is a great option for renters looking for a specific and exceptional lifestyle.
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.
555 Winchester Ave 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 555 Winchester Ave compares to other nearby properties.
Positives
- Laundry available on site
- Washers and dryers are available in-building or in-unit
Considerations
- Greater distance from high schools
- The nearest high school is farther than 1 mile away
- Greater distance from middle schools
- The nearest middle school is farther than 3 miles away
- Greater distance from grade schools
- The nearest elementary school is farther than 0.3 mile away
- Lacks images
- Fewer than 10 photos available for this location
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Rent trends in Prospect Hill
4-bedroom apartments at 555 Winchester Ave cost about 33% less than the average rent price for 4-bedroom apartments in Prospect Hill.
Median rents as of Aug 22 2026.
Prospect Hill
New Haven
| Month | Median Rent |
|---|---|
| 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 |
| July 2026 | $1,698 |
| August 2026 | $1,658 |
| Month | Median Rent |
|---|---|
| May 2025 | $1,746 |
| June 2025 | $1,778 |
| July 2025 | $1,730 |
| August 2025 | $1,602 |
| March 2026 | $1,850 |
| April 2026 | $1,749 |
| May 2026 | $1,774 |
| June 2026 | $1,666 |
| August 2026 | $1,150 |
Affordability calculator
Can I afford to live at 555 Winchester Ave?
Bedrooms
4+ 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
$79,800/yr
With your selected rent-to-income ratio, you'd ideally want to make $79,800 annually to afford this 4-bedrooms monthly rent price of $1,995.
For more information on rent affordability, visit our rent calculator.
Schools near 555 Winchester Ave
Lincoln-Bassett School
130 bassett st
new haven, CT, 6511
PK, K-6Public
C-
Wexler/Grant Community School
55 foote st
new haven, CT, 6511
K-8Public
C-
Worthington Hooker School
180 canner st
new haven, CT, 6511
K-8Public
B
YLS Early Learning Center
127 wall st
new haven, CT, 6511
PKPublic
Augusta Lewis Troup School
259 edgewood ave
new haven, CT, 6511
PK, K-8Public
C-
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Internet available near 555 Winchester Ave
Neighborhood
Prospect Hill | New Haven, CT
Getting around New Haven near 555 Winchester Ave
Walking
7/10
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
7/10
Peddling isn’t a problem with cyclist-friendly streets and bikeable destinations.
Transit
6/10
Popular public transit options are just a short walk from this location.
Points of interest for 555 Winchester Ave, New Haven
Groceries
9/10
At least one supermarket within a 10-minute walk
Shopping
5/10
Several shops within walking distance
Cafes
5/10
Some cafés within a few minutes’ walk
Restaurants
6/10
Variety of restaurants within a few minutes' walk
Primary schools
9/10
At least one elementary school within a 10-minute walk
High schools
8/10
At least one high school within a 10-minute walk
Nightlife
3/10
Some bars within walking distance
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