The Winston

Property highlights

Discover The Winston, where modern design meets comfortable living in prestigious Prospect Hill. Spacious apartments with high ceilings and large windows provide a bright, airy atmosphere that residents love. The property features premium amenities, including a fitness center, pool, and rooftop views, perfect for relaxing or socializing. Steps away from Yale University and cultural attractions, this location is ideal for exploring the dynamic charm of New Haven. Consistently positive reviews highlight the friendly management and inviting community spaces. Cats and dogs are welcome, making this an ideal home for pet owners seeking a vibrant lifestyle.

100 units available: Studio • 1 Bed • 2 Beds • 3+ Beds

Location: 301 Winchester Avenue, New Haven CT 06511, Prospect Hill

Amenities: In unit laundry, Patio / balcony, Hardwood floors, Dishwasher, Pet friendly, Stainless steel + more

Price range (total price, 12 month lease): $1,812 mo - $4,610 mo

Commute

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Price and Availability

The Winston apartments start at $1,812/month. There are 100 available apartments priced from $1,812 to $4,610. Prices were last verified by The Winston 43 minutes ago. (Total price includes base rent and required monthly fees—select a unit to view full breakdown.)

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Unit 241

Avail. now

$1,884 moTotal price12-mo lease

Unit 346

Avail. now

$2,087 moTotal price12-mo lease

Connect with The Winston

(203) 902-0495

Closed, opens Today at 11:00 AM EST

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Location

The Winston is located in the Prospect Hill neighborhood at

301 Winchester Avenue, New Haven, CT 06511

.

Amenities

In Unit Laundry
Patio / Balcony
Hardwood Floors
Dishwasher
Pet Friendly
Stainless Steel

Unit Amenities

Air Conditioning
Dishwasher
Furnished
Hardwood Floors
Microwave
Patio / Balcony
Range
Refrigerator
In Unit Laundry
Bathtub
Stainless Steel

Property Amenities

Accessible
Business Center
Conference Room
Clubhouse
Courtyard
Elevator
Gym
Pool
BBQ/Grill
Bike Storage
Internet Access
Media Room
Walking Trail
Cats Allowed
Dogs Allowed
Pet Friendly
E-Payments
Fire Pit
Game Room
Online Portal
Yoga

The Winston offers a lifestyle thatâs equal parts refined and welcoming. Spacious studio to three-bedroom residences blend elevated design with everyday comfortâfeaturing open layouts, warm finishes, and thoughtful details that make it easy to settle in and make it your own. Beyond your front door, curated amenities awaitâfrom cozy corners and rooftop views to vibrant community spaces perfect for morning coffee, remote work, or casual gatherings. And with New Havenâs energy just outside, youâre steps from cafs, culture, and the charm of Yaleâinviting you to explore, linger, and love where you live. Now leasing.The price shown reflects Base Rent only. Residents are responsible for additional required fees, including but not limited to an application fee, security deposit, community amenity fee, and utility charges. These fees are assessed per applicant or per unit as applicable and may vary based on usage or lease terms. Please consult a leasing agent for a comprehensive list of all required, optional, and situational fees.

Verified reviews

We are collecting reviews from verified residents who have toured or leased from The Winston. Check back soon.

Property Details

Explore the Area

GreatSchools rating 3 out of 10.
Highville Charter School
Charter
PK-12
502 Students
0.1 mi
Highville Charter School — Charter, PK-12, 502 students, 0.1 miles away,GreatSchools rating 3 out of 10.
GreatSchools rating 4 out of 10.
Wexler/Grant Community School
Public
PK-8
425 Students
0.3 mi
Wexler/Grant Community School — Public, PK-8, 425 students, 0.3 miles away,GreatSchools rating 4 out of 10.
GreatSchools rating 3 out of 10.
Celentano School
Public
PK-8
376 Students
0.3 mi
Celentano School — Public, PK-8, 376 students, 0.3 miles away,GreatSchools rating 3 out of 10.
GreatSchools rating 1 out of 10.
James Hillhouse High School
Public
9-12
927 Students
0.6 mi
James Hillhouse High School — Public, 9-12, 927 students, 0.6 miles away,GreatSchools rating 1 out of 10.
GreatSchools rating 2 out of 10.
Lincoln-Bassett School
Public
PK-6
376 Students
0.6 mi
Lincoln-Bassett School — Public, PK-6, 376 students, 0.6 miles away,GreatSchools rating 2 out of 10.
Data provided by GreatSchools. Ratings are based on test scores and additional metrics when available.

Getting Around

Walk Score^®

Very Walkable

Transit Score^®

Good Transit

Walk & Transit Scores

Walk Score: 73 — Very Walkable, with shops and services easily within reach.Transit Score: 50 — Offers reasonable public transit options nearby.

Public Transit Access

The Prospect Hill area benefits from access to public transit options, such as 17 nearby routes: 17 bus, 0 rail, 0 other

Nearby public transit stops include:

Divinity (~0.28 mi)
Prospect/Canner (~0.34 mi)
Prospect/Edwards (~0.35 mi)
Chemistry/225 Prospect (~0.42 mi)

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Bedrooms

Amenities

Property Type

New Haven Short-term Apartments (5)

Frequently Asked Questions (FAQs)

The Winston has 100 units available starting at $1,812 per month (total price with fees when signing a 12 month lease). Check out the Price and Availability section for the most up-to-date unit information.

In New Haven, CT, the average rent is $2,134+ for a studio, $2,346+ for a 1-bedroom, $3,009+ for a 2-bedroom, and $3,786+ for a 3-bedroom.* For more information on rental trends in New Haven, CT, check out our monthly New Haven, CT Rent Report.

*Based on base prices that don’t include fees

Some of The Winston's amenities include in unit laundry, patio / balcony, and hardwood floors. To see the other amenities this property offers, check out the Amenities section.

The Winston is offering the following rent specials: For a limited time, receive 3 months free off base rent on select apartments *Restrictions May Apply

Yes, The Winston is pet-friendly.

No, The Winston does not offer parking.

Yes, The Winston offers units with in unit laundry.

Yes, The Winston has a pool.

Yes, The Winston has accessible units.

Yes, The Winston has units with dishwashers.

Property highlights

Rent Special

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Frequently Asked Questions (FAQs)

The Winston

Property highlights

Rent Special

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Price and Availability

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Amenities

Verified reviews

Property Details

Income Requirement

Furnished Details

Explore the Area

Grocery Stores

Restaurants

Public Transportation

Airports

Nearby Schools

Parks

Entertainment

Pets

Getting Around

Walk & Transit Scores

Public Transit Access

Nearby public transit stops include:

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Frequently Asked Questions (FAQs)

Does The Winston have any available units?

How much is rent in New Haven, CT?

What amenities does The Winston have?

Is The Winston currently offering any rent specials?

Is The Winston pet-friendly?

Does The Winston offer parking?

Does The Winston have units with washers and dryers?

Does The Winston have a pool?

Does The Winston have accessible units?

Does The Winston have units with dishwashers?