Last updated December 19 2025 at 11:47 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.
- 49 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
- $2,005 - $4,610 per month
- Commute
Rent Special
For a limited time, receive 2 months free off base rent on select apartments & Free Parking *Restrictions May Apply
Restrictions may apply
Price and Availability
The Winston apartments start at $2,005/month. There are 49 available apartments priced from $2,005 to $4,610. Prices were last verified by The Winston 1 hour ago.
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Unit 258
Avail. Jan 2
$2,005
Unit 241
Avail. Jan 2
$2,015
Unit 346
Avail. Jan 2
$2,015
Unit 204
Avail. Jan 2
$2,080
Unit 405
Avail. Jan 2
$2,080
Unit 240
Avail. Jan 2
$2,130
Unit 253
Avail. Jan 2
$2,120
Unit 126
Avail. Jan 2
$2,145
Unit 216
Avail. Jan 2
$2,180
Unit 336
Avail. Jan 2
$2,295
Unit 121
Avail. Jan 2
$2,345
Unit 318
Avail. Jan 2
$2,345
Unit 254
Avail. Jan 2
$2,390
Unit 257
Avail. Jan 2
$2,470
Unit 238
Avail. Jan 2
$2,570
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Location
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
Property Details
Must have 3x the rent in total household income (before taxes)
Furnished apartments often have extra fees beyond the rent listed. Please contact for more information.
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
Getting Around
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 otherNearby 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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Frequently Asked Questions (FAQs)
The Winston has 49 units available starting at $2,005 per month. Check out the Price and Availability section for the most up-to-date unit information.
In New Haven, CT, the average rent is $2,118 for a studio, $2,294 for a 1-bedroom, $3,018 for a 2-bedroom, and $3,918 for a 3-bedroom. For more information on rental trends in New Haven, CT, check out our monthly New Haven, CT Rent Report.
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 2 months free off base rent on select apartments & Free Parking *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.