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modified
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Highlights

  • Pet Friendly
  • Smoke-free
  • Smart tvs
  • Fast wi-fi
  • Stylish furnishings

Location

275 Winchester Ave #227, New Haven, CT 06511, USA|Prospect Hill
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Tour 275 Winchester Avenue

Contact

Leasing office

(844) 394-8701 ext. 9822

Property Overview

275 Winchester Avenue is a high-scoring, verified property (overall 9.2/10) with exceptional quality and location ratings, offering strong value for the price. Smoke-free living, fast Wi‑Fi, smart TVs, and stylish furnishings complement a lively, walkable neighborhood with abundant dining, cultural venues, and nearby pet amenities. Extensive listing details, including 50 photos, and a top-tier value per square foot help provide transparency and confidence for prospective renters.

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.

Zumper Expert Rating

9.2
Excellent
275 Winchester Avenue 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 Location and Quality, which help to make this rental a great place to call home.

Things you’ll love

  • More space
  • Images Available

Great for

  • Pet owners
  • Social life

Floor plans

Landing Furnished Apartment at Winchester Lofts.227.1412525Studio1 bath515 sqft$2,625 /mo
Landing Furnished Apartment at Winchester Lofts.147.14125271 bed1 bath683 sqft$2,755 /mo
Landing Furnished Apartment at Winchester Lofts.137.14125261 bed1 bath668 sqft$2,875 /mo
Landing Furnished Apartment at Winchester Lofts.119.14125281 bed1 bath690 sqft$2,995 /mo
Landing Furnished Apartment at Winchester Lofts.410.14125292 bed2 bath1,420 sqft$4,187 /mo

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Amenities for 275 Winchester Avenue

Apartment Amenities

FurnishedUtilities Included

Building

Cats OKDogs OK
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

Utilities

Monthly. Flat rate to cover electricity, Internet etc.

$295–$325

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

Lease terms1+ month
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About 275 Winchester Avenue

HomeApartments in New HavenProspect Hill 275 Winchester Avenue

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support, our apartments have everything you need for monthly and longer stays. Landing's apartments at Winchester Lofts are designed for comfortable, easy living, with the ability to stay as long as you like. All Landing apartments include: - Fast Wi-Fi - Stylish furnishings - Fully-stocked bathroom - Smart TVs - Comfortable bed - Professionally cleaned - Guest support Stay longer for cheaper! The longer you stay, the bigger your discount. Price advertised is for a 12-month stay, including all utilities and fees, and may vary based on availability. We manage multiple units at this property. While all feature a similar style and furnishings, the layout and specific design elements may vary slightly from the photos provided. Some of the nitty-gritty: a background check and proof of income are required; we're completely smoke-free; pet-friendly options are available; parking is subject to availability.


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.
9.2
/10
Excellent
275 Winchester Avenue 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 Location and Quality, which help to make this rental a great place to call home.
How we rated 275 Winchester Avenue
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.
275 Winchester Avenue 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, 275 Winchester Avenue 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·10A score based on proximity and ease of access to shops, restaurants, schools, and public transportation while considering the desirability of the area.
275 Winchester Avenue offers residents unparalleled convenience to popular points of interest, transportation, schools, and more, which provide an elevated quality of life. Communication with management is usually quick and easy, allowing for a more expedited application and renting process, saving you time and money.
Quality·10A 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.
275 Winchester Avenue has notable characteristics that give it an edge. It is a verified property that stands out from others nearby as an exceptional choice for renters looking for a specific lifestyle. Offering a combination of prestige, modernity, and tailored living experiences, residents can expect nothing short of excellence at 275 Winchester Avenue.
Trustworthiness·9A 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.
275 Winchester Avenue has gone above and beyond to craft a useful, detailed description, demonstrating transparency and trustworthiness, and giving renters a clear picture of what to expect from the property and its management, so they can make an informed decision about whether the rental meets their needs.

Reviews from the web

Showing 8 highest rated

I'm not sure I have the words to quantify how pleased I am with this community. My transition here was the most seamless I've ever experienced, & I've moved around quite a bit. As such, I have had a million questions and Emily and Paul are so kind and accommodating that they've made and continue to make everything so easy. The entire complex is just so aesthetically pleasing, but my apartment is to die for. It's spacious and bright with super high ceilings and huge windows, but most importantly I don't hear my neighbors, like at all. The hallways and common spaces are always spotless, even the trash room seems to emptied multiple times per day. The few maintenance requests I've had to put in have been resolved same day by Jose and Zilroy, both with a smile. Having a pretty apartment is all good, but a team of staff who actually want to be here and want to help is invaluable. I can't say enough good things about them. I think it's important to note that this is still New Haven, and safety will always be an issue. That said, I've never felt unsafe here. There's a patrol car here at night and the huge parking lot is always super well lit. The communication about the happenings of the community has also always been top notch. Cheers to never having to worry about missing packages! :) I literally never want to leave.

Patricia Morency

Patricia Morency

Jun 26, 2023

I did not actually live at Winchester Lofts but I did have a very positive experience with their leasing team, Paul and Emily in particular. I was planning to move to New Haven for a job when unfortunately the job offer fell through and I could no longer move. in Paul was extremely accommodating and I had positive experience being shown the unit. Highly recommend their team for being professional and genuine.

Cade

Cade

Jul 21, 2024

We’re sharing just 8 of many, sorted highest to lowest. Visit the Google business profile to view all reviews.

275 Winchester Avenue is great for:

Pet owners

  • 1 dog park within 1 mile
  • 1 pet supply store near the property

Social life

  • Areas nearby are accessible by walking
  • A bustling neighborhood
  • 168 restaurants within 1 mile of this property
  • 61 museums, art galleries, or cultural centers within 1 mile

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 275 Winchester Avenue compares to other nearby properties.

Positives

More space
The 2-bedroom is 438 sqft larger than other listings nearby
Images Available
There are at least 10 photos of this address

Considerations

Greater distance from grade schools
The nearest elementary school is farther than 0.4 mile away
Greater distance from high schools
The nearest high school is farther than 1 mile away

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Rent trends in Prospect Hill

Studio apartments at 275 Winchester Avenue cost about 50% more than the average rent price for studios in Prospect Hill.

1-bedroom apartments here are priced 34% higher than 1-bedrooms in Prospect Hill.

If you decide to upgrade your space, you can expect 2-bedrooms at 275 Winchester Avenue to be 63% more than the average for similarly sized apartments in Prospect Hill.

Median rents as of Apr 18 2026.
Prospect Hill
New Haven
A table of studio rental data trends in New Haven
MonthMedian Rent
May 2024$1,858
June 2024$1,691
July 2024$1,728
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$1,708
A table of studio rental data trends in Prospect Hill
MonthMedian Rent
May 2024$1,835
May 2025$1,746
June 2025$1,778
July 2025$1,730
August 2025$1,602
March 2026$1,850
April 2026$1,749

Affordability calculator

Can I afford to live at 275 Winchester Ave #227?

Bedrooms

Rent-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

$105,000/yr

With your selected rent-to-income ratio, you'd ideally want to make $105,000 annually to afford this studio monthly rent price of $2,625.
For more information on rent affordability, visit our rent calculator.

Schools near 275 Winchester Avenue

Wexler/Grant Community School

55 foote st

new haven, CT, 6511

K-8Public
C-

Lincoln-Bassett School

130 bassett st

new haven, CT, 6511

PK, K-6Public
C-

YLS Early Learning Center

127 wall st

new haven, CT, 6511

PKPublic

Worthington Hooker School

180 canner st

new haven, CT, 6511

K-8Public
B

Augusta Lewis Troup School

259 edgewood ave

new haven, CT, 6511

PK, K-8Public
C-
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Internet available near 275 Winchester Avenue

Getting around New Haven near 275 Winchester Ave #227

Walking

7/10
Grab your reusable bags–many shops and stores are within walking distance.

Driving

8/10
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
Frequent public transit options are within walking distance.

Points of interest for 275 Winchester Ave #227, New Haven

Groceries

8/10
At least one supermarket within a 10-minute walk

Shopping

5/10
Several shops within walking distance

Cafes

6/10
Some cafés within a few minutes’ walk

Restaurants

7/10
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

4/10
Some bars within walking distance

Explore the area around 275 Winchester Ave #227

B & K Variety Store
597 Winchester Ave
A to Z Grocery
738 Orchard St
Greg's Market
209 Shelton Ave
Stop & Shop Supermarket
150 Whalley Ave
Hong Kong Market
71 Whitney Ave

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