Last updated November 4 2025 at 5:28 PM
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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.
- 226 units available
- Studio • 1 Bed • 2 Beds • 3+ Beds
- Location
- 301 Winchester Avenue, New Haven CT 06511, Prospect Hill
- Amenities
- In unit laundry, Pet friendly, Stainless steel, Gym, Pool, Yoga + more
- Price range (base price, 12 month lease)
- $2,005+ mo - $4,610+ mo
- Commute
Price and Availability
Verified by The Winston 5 HRS ago. 226 apartments available today. Rent starts at $2,005/month (base rent only—contact the property for full details).
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Unit 258
Avail. Jan 2
$2,005+ moBase rent12-mo lease
Unit 458
Avail. Jan 2
$2,005+ moBase rent12-mo lease
Unit 558
Avail. Jan 2
$2,045+ moBase rent12-mo lease
Unit 241
Avail. Jan 2
$2,015+ moBase rent12-mo lease
Unit 346
Avail. Jan 2
$2,015+ moBase rent12-mo lease
Unit 541
Avail. Jan 2
$2,055+ moBase rent12-mo lease
Unit 204
Avail. Jan 2
$2,080+ moBase rent12-mo lease
Unit 305
Avail. Jan 2
$2,080+ moBase rent12-mo lease
Unit 315
Avail. Jan 2
$2,080+ moBase rent12-mo lease
Unit 231
Avail. Jan 2
$2,105+ moBase rent12-mo lease
Unit 331
Avail. Jan 2
$2,105+ moBase rent12-mo lease
Unit 431
Avail. Jan 2
$2,105+ moBase rent12-mo lease
Unit 353
Avail. Jan 2
$2,120+ moBase rent12-mo lease
Unit 253
Avail. Jan 2
$2,120+ moBase rent12-mo lease
Unit 453
Avail. Jan 2
$2,120+ moBase rent12-mo lease
Unit 126
Avail. Jan 2
$2,145+ moBase rent12-mo lease
Unit 426
Avail. Jan 2
$2,145+ moBase rent12-mo lease
Unit 226
Avail. Jan 2
$2,145+ moBase rent12-mo lease
Unit 113
Avail. Jan 2
$2,180+ moBase rent12-mo lease
Unit 216
Avail. Jan 2
$2,180+ moBase rent12-mo lease
Unit 316
Avail. Jan 2
$2,180+ moBase rent12-mo lease
Unit 335
Avail. Jan 2
$2,295+ moBase rent12-mo lease
Unit 336
Avail. Jan 2
$2,295+ moBase rent12-mo lease
Unit 119
Avail. Jan 2
$2,345+ moBase rent12-mo lease
Unit 254
Avail. Jan 2
$2,390+ moBase rent12-mo lease
Unit 354
Avail. Jan 2
$2,390+ moBase rent12-mo lease
Unit 454
Avail. Jan 2
$2,390+ moBase rent12-mo lease
Unit 257
Avail. Jan 2
$2,470+ moBase rent12-mo lease
Unit 457
Avail. Jan 2
$2,470+ moBase rent12-mo lease
Unit 357
Avail. Jan 2
$2,470+ moBase rent12-mo lease
Unit 238
Avail. Jan 2
$2,570+ moBase rent12-mo lease
Find apartments similar to The Winston
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Location
Amenities
In unit laundry
Pet friendly
Stainless steel
Gym
Pool
Yoga
Unit Amenities
in unit laundry
bathtub
stainless steel
Property Amenities
accessible
business center
clubhouse
courtyard
gym
pool
bbq/grill
bike storage
internet access
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
Property Details (Fees & Lease)
Must have 3x the rent in total household income (before taxes)
Pets allowed
Cats, dogs
Explore the Area
Stop & Shop
0.8 mi
Anna's
0.8 mi
Minore's Market
0.9 mi
Edge of the Woods
0.9 mi
J&B Deli
1.0 mi
Ivy cafe
0.1 mi
Fussy Coffee
0.1 mi
Orchid Cafe
0.1 mi
H&K
0.2 mi
Tropical Caribbean Restaurant
0.4 mi
Divinity
0.3 mi
Prospect/Canner
0.3 mi
Prospect/Edwards
0.3 mi
Prospect/Canner
0.4 mi
Chemistry/225 Prospect
0.4 mi
Tweed New Haven Airport
4.7 mi
Tweed New Haven Airport
4.7 mi
North Branford Heliport
7.2 mi
Tie Communications Heliport
7.8 mi
Sikorsky Heliport
9.8 mi
3 /10
Highville Charter School
CharterPK-12
502 Students
0.1 mi
4 /10
Wexler/Grant Community School
PublicPK-8
425 Students
0.3 mi
3 /10
Celentano School
PublicPK-8
376 Students
0.3 mi
1 /10
James Hillhouse High School
Public9-12
927 Students
0.6 mi
2 /10
Lincoln-Bassett School
PublicPK-6
376 Students
0.6 mi
Data provided by GreatSchools. Ratings are based on test scores and additional metrics when available.
Munson Street Triangle
0.1 mi
Marsh Botanical Gardens
0.2 mi
Farnam Memorial Gardens
0.3 mi
Scantlebury Skate Park
0.4 mi
Elm Haven Public Housing Playground
0.4 mi
City Climb
0.2 mi
Cosgrove Marcus Messer Sports Center
0.3 mi
Dixwell Community House (Q House)
0.4 mi
New Haven Free Public Library Stetson Branch
0.4 mi
Ingalls Ice Rink
0.5 mi
Saint Ronan Dog Park
0.5 mi
Veterinary Wellness Center
1.0 mi
Pawtero
1.1 mi
Mechanic Street Dog Park
1.2 mi
Union Street Dog Park
1.4 mi
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Frequently Asked Questions (FAQs)
The Winston has 226 units available starting at $2,005 per month (base price without 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 $2,068+ for a studio, $2,219+ for a 1-bedroom, $2,889+ for a 2-bedroom, and $3,651+ 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, pet friendly, and stainless steel. To see the other amenities this property offers, check out the Amenities section.
The Winston is not currently offering any rent specials.
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.
No, The Winston does not have units with dishwashers.