The Winston

Starting at $2,005

301 Winchester Ave

New Haven, CT 06511 Prospect Hill Neighborhood
Studio-3 Beds
1-2 Baths
420+ Sq Ft

About The Winston

The Winston offers a lifestyle that?s equal parts refined and welcoming. Spacious studio to three-bedroom residences blend elevated design with everyday comfort?featuring 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 await?from cozy corners and rooftop views to vibrant community spaces perfect for morning coffee, remote work, or casual gatherings. And with New Haven?s energy just outside, you?re steps from caf?s, culture, and the charm of Yale?inviting 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.

Listing Provided By

Pricing and Floor Plans

The total monthly price shown includes only the required fees. Additional fees may still apply to your rent.

Studio

Studio-S2

$2,005 - $2,045 per month plus fees

Studio, 1 Bath, 420 Sq Ft

https://imagescdn.homes.com/i2/YjYj9vEKRDoYNIOiVmo_cz8NccLeg8hK01Ve4m6LMGc/116/the-winston-new-haven-ct.png?t=p&p=1
Studio-S2 Floor Plan
3 Available Units
Unit Price Sq Ft Availability
258 $2,005 420 Jan 2, 2026
458 $2,005 420 Jan 2, 2026
558 $2,045 420 Jan 2, 2026

Studio-S3

$2,015 - $2,055 per month plus fees

Studio, 1 Bath, 425 Sq Ft

https://imagescdn.homes.com/i2/rKvX5ALACQAaUMuK7l2p_AYP9eJQ6yR0rmehncmgrS4/116/the-winston-new-haven-ct-2.png?t=p&p=1
Studio-S3 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
241 $2,015 425 Jan 2, 2026
346 $2,015 425 Jan 2, 2026
541 $2,055 425 Jan 2, 2026
546 $2,055 425 Jan 2, 2026

Studio-S1

$2,080 - $2,170 per month plus fees

Studio, 1 Bath, 490 Sq Ft

https://imagescdn.homes.com/i2/TC_sU_6utDx5r77Uiyh_-fubhIYXq8haiajiWAlX0Ko/116/the-winston-new-haven-ct-3.png?t=p&p=1
Studio-S1 Floor Plan
35 Available Units
Unit Price Sq Ft Availability
204 $2,080 490 Jan 2, 2026
215 $2,080 490 Jan 2, 2026
304 $2,080 490 Jan 2, 2026
305 $2,080 490 Jan 2, 2026
315 $2,080 490 Jan 2, 2026
403 $2,080 490 Jan 2, 2026
404 $2,080 490 Jan 2, 2026
405 $2,080 490 Jan 2, 2026
503 $2,120 490 Jan 2, 2026
504 $2,120 490 Jan 2, 2026
505 $2,120 490 Jan 2, 2026
515 $2,120 490 Jan 2, 2026
217 $2,130 490 Jan 2, 2026
218 $2,130 490 Jan 2, 2026
232 $2,130 490 Jan 2, 2026
239 $2,130 490 Jan 2, 2026
240 $2,130 490 Jan 2, 2026
317 $2,130 490 Jan 2, 2026
324 $2,130 490 Jan 2, 2026
325 $2,130 490 Jan 2, 2026
332 $2,130 490 Jan 2, 2026
339 $2,130 490 Jan 2, 2026
340 $2,130 490 Jan 2, 2026
417 $2,130 490 Jan 2, 2026
418 $2,130 490 Jan 2, 2026
424 $2,130 490 Jan 2, 2026
432 $2,130 490 Jan 2, 2026
433 $2,130 490 Jan 2, 2026
439 $2,130 490 Jan 2, 2026
440 $2,130 490 Jan 2, 2026
517 $2,170 490 Jan 2, 2026
518 $2,170 490 Jan 2, 2026
525 $2,170 490 Jan 2, 2026
533 $2,170 490 Jan 2, 2026
540 $2,170 490 Jan 2, 2026

Studio-S5

$2,105 - $2,145 per month plus fees

Studio, 1 Bath, 490 Sq Ft

https://imagescdn.homes.com/i2/YqKSFI4ETo06c8X-XZZBkzC21Eq3HpGU4o4lFBzltHE/116/the-winston-new-haven-ct-4.png?p=1
Studio-S5 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
231 $2,105 490 Jan 2, 2026
331 $2,105 490 Jan 2, 2026
431 $2,105 490 Jan 2, 2026
531 $2,145 490 Jan 2, 2026

Studio-S7

$2,120 - $2,160 per month plus fees

Studio, 1 Bath, 510 Sq Ft

https://imagescdn.homes.com/i2/yPIEJz5tV2FWD0fnsPchPHoAPWFiXeOo-LDkerdD118/116/the-winston-new-haven-ct-5.png?t=p&p=1
Studio-S7 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
253 $2,120 510 Jan 2, 2026
353 $2,120 510 Jan 2, 2026
453 $2,120 510 Jan 2, 2026
553 $2,160 510 Jan 2, 2026

Studio-S4

$2,145 per month plus fees

Studio, 1 Bath, 510 Sq Ft

https://imagescdn.homes.com/i2/PSeX4ZWFWkjyHIR0BgMwg6wbRYDPiFQe9_EEbQmENYY/116/the-winston-new-haven-ct-6.png?p=1
Studio-S4 Floor Plan
3 Available Units
Unit Price Sq Ft Availability
126 $2,145 510 Jan 2, 2026
226 $2,145 510 Jan 2, 2026
426 $2,145 510 Jan 2, 2026

Studio-S6

$2,180 - $2,220 per month plus fees

Studio, 1 Bath, 550 Sq Ft

https://imagescdn.homes.com/i2/9J89vwVWQF_DM_NggViU4EhhqoSxed-SBjHxxwTlo-I/116/the-winston-new-haven-ct-7.png?t=p&p=1
Studio-S6 Floor Plan
5 Available Units
Unit Price Sq Ft Availability
113 $2,180 550 Jan 2, 2026
216 $2,180 550 Jan 2, 2026
316 $2,180 550 Jan 2, 2026
416 $2,180 550 Jan 2, 2026
516 $2,220 550 Jan 2, 2026

Studio-S8

$2,295 - $2,435 per month plus fees

Studio, 1 Bath, 535 Sq Ft

https://imagescdn.homes.com/i2/UdB5wjYhNNyhJvFFlMymcNpXZme2pzU5QqtVTg_ZFsY/116/the-winston-new-haven-ct-8.png?t=p&p=1
Studio-S8 Floor Plan
42 Available Units
Unit Price Sq Ft Availability
335 $2,295 535 Jan 2, 2026
336 $2,295 535 Jan 2, 2026
119 $2,345 535 Jan 2, 2026
120 $2,345 535 Jan 2, 2026
121 $2,345 535 Jan 2, 2026
122 $2,345 535 Jan 2, 2026
123 $2,345 535 Jan 2, 2026
220 $2,345 535 Jan 2, 2026
222 $2,345 535 Jan 2, 2026
318 $2,345 535 Jan 2, 2026
320 $2,345 535 Jan 2, 2026
322 $2,345 535 Jan 2, 2026
337 $2,345 535 Jan 2, 2026
420 $2,345 535 Jan 2, 2026
422 $2,345 535 Jan 2, 2026
435 $2,345 535 Jan 2, 2026
437 $2,345 535 Jan 2, 2026
520 $2,385 535 Jan 2, 2026
522 $2,385 535 Jan 2, 2026
535 $2,385 535 Jan 2, 2026
537 $2,385 535 Jan 2, 2026
219 $2,395 535 Jan 2, 2026
221 $2,395 535 Jan 2, 2026
223 $2,395 535 Jan 2, 2026
234 $2,395 535 Jan 2, 2026
319 $2,395 535 Jan 2, 2026
321 $2,395 535 Jan 2, 2026
323 $2,395 535 Jan 2, 2026
334 $2,395 535 Jan 2, 2026
338 $2,395 535 Jan 2, 2026
419 $2,395 535 Jan 2, 2026
421 $2,395 535 Jan 2, 2026
423 $2,395 535 Jan 2, 2026
434 $2,395 535 Jan 2, 2026
436 $2,395 535 Jan 2, 2026
438 $2,395 535 Jan 2, 2026
519 $2,435 535 Jan 2, 2026
521 $2,435 535 Jan 2, 2026
523 $2,435 535 Jan 2, 2026
534 $2,435 535 Jan 2, 2026
536 $2,435 535 Jan 2, 2026
538 $2,435 535 Jan 2, 2026

Studio-S9

$2,390 - $2,430 per month plus fees

Studio, 1 Bath, 600 Sq Ft

https://imagescdn.homes.com/i2/fDGB6OWZ1kGleQ7-bvLP0-qiik-f2i0Zhm67v2VPU2M/116/the-winston-new-haven-ct-9.png?t=p&p=1
Studio-S9 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
254 $2,390 600 Jan 2, 2026
354 $2,390 600 Jan 2, 2026
454 $2,390 600 Jan 2, 2026
554 $2,430 600 Jan 2, 2026

Studio-S10

$2,470 - $2,510 per month plus fees

Studio, 1 Bath, 640 Sq Ft

https://imagescdn.homes.com/i2/XDABCrVNDw2Z86XAR2Nb7Qz2eufvPnCTW1YRdWLuyvU/116/the-winston-new-haven-ct-10.png?t=p&p=1
Studio-S10 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
257 $2,470 640 Jan 2, 2026
357 $2,470 640 Jan 2, 2026
457 $2,470 640 Jan 2, 2026
557 $2,510 640 Jan 2, 2026

Studio-S11

$2,570 per month plus fees

Studio, 1 Bath, 660 Sq Ft

https://imagescdn.homes.com/i2/50VW_Ny5ecPDFzSiHpuYWTcR9KUmnU8MpB_pj20w6k8/116/the-winston-new-haven-ct-11.png?t=p&p=1
Studio-S11 Floor Plan
1 Available Unit
Unit Price Sq Ft Availability
238 $2,570 660 Jan 2, 2026

1 Bedroom

1 Bed-1 Bath-A3

$2,560 - $2,600 per month plus fees

1 Bed, 1 Bath, 715 Sq Ft

https://imagescdn.homes.com/i2/NYaoEBw8vWeXqEqSzxcYZScDjPtbTrd0U8KnI8hw4RA/116/the-winston-new-haven-ct-12.png?t=p&p=1
1 Bed-1 Bath-A3 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
255 $2,560 715 Jan 2, 2026
355 $2,560 715 Jan 2, 2026
455 $2,560 715 Jan 2, 2026
555 $2,600 715 Jan 2, 2026

1 Bed-1 Bath-A1

$2,565 - $2,655 per month plus fees

1 Bed, 1 Bath, 725 Sq Ft

https://imagescdn.homes.com/i2/nW_U202fkFzoAWKxVTT6QLylyqmIn2bpzmiY5BepMtA/116/the-winston-new-haven-ct-13.png?t=p&p=1
1 Bed-1 Bath-A1 Floor Plan
49 Available Units
Unit Price Sq Ft Availability
104 $2,565 725 Jan 2, 2026
112 $2,565 725 Jan 2, 2026
114 $2,565 725 Jan 2, 2026
206 $2,565 725 Jan 2, 2026
207 $2,565 725 Jan 2, 2026
212 $2,565 725 Jan 2, 2026
213 $2,565 725 Jan 2, 2026
214 $2,565 725 Jan 2, 2026
250 $2,565 725 Jan 2, 2026
251 $2,565 725 Jan 2, 2026
306 $2,565 725 Jan 2, 2026
307 $2,565 725 Jan 2, 2026
312 $2,565 725 Jan 2, 2026
313 $2,565 725 Jan 2, 2026
314 $2,565 725 Jan 2, 2026
350 $2,565 725 Jan 2, 2026
351 $2,565 725 Jan 2, 2026
352 $2,565 725 Jan 2, 2026
406 $2,565 725 Jan 2, 2026
407 $2,565 725 Jan 2, 2026
413 $2,565 725 Jan 2, 2026
414 $2,565 725 Jan 2, 2026
451 $2,565 725 Jan 2, 2026
452 $2,565 725 Jan 2, 2026
259 $2,590 725 Jan 2, 2026
260 $2,590 725 Jan 2, 2026
263 $2,590 725 Jan 2, 2026
264 $2,590 725 Jan 2, 2026
359 $2,590 725 Jan 2, 2026
363 $2,590 725 Jan 2, 2026
364 $2,590 725 Jan 2, 2026
459 $2,590 725 Jan 2, 2026
460 $2,590 725 Jan 2, 2026
463 $2,590 725 Jan 2, 2026
464 $2,590 725 Jan 2, 2026
506 $2,605 725 Jan 2, 2026
507 $2,605 725 Jan 2, 2026
512 $2,605 725 Jan 2, 2026
550 $2,605 725 Jan 2, 2026
551 $2,605 725 Jan 2, 2026
552 $2,605 725 Jan 2, 2026
230 $2,615 725 Jan 2, 2026
330 $2,615 725 Jan 2, 2026
442 $2,615 725 Jan 2, 2026
450 $2,615 725 Jan 2, 2026
559 $2,630 725 Jan 2, 2026
560 $2,630 725 Jan 2, 2026
564 $2,630 725 Jan 2, 2026
542 $2,655 725 Jan 2, 2026

1 Bed-1 Bath-A2

$2,590 - $2,630 per month plus fees

1 Bed, 1 Bath, 725 Sq Ft

https://imagescdn.homes.com/i2/EHNZoyxNTRmEODNAhs2NJuiEM1yLdXY3nB6mGVaQG-8/116/the-winston-new-haven-ct-14.png?t=p&p=1
1 Bed-1 Bath-A2 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
265 $2,590 725 Jan 2, 2026
365 $2,590 725 Jan 2, 2026
465 $2,590 725 Jan 2, 2026
565 $2,630 725 Jan 2, 2026

1 Bed-1 Bath-A4

$2,690 - $2,730 per month plus fees

1 Bed, 1 Bath, 825 Sq Ft

https://imagescdn.homes.com/i2/GHbkPzJnv3QRzv2n0N2PVzZDSlZ7PYIn61nHRyAYPOY/116/the-winston-new-haven-ct-15.png?p=1
1 Bed-1 Bath-A4 Floor Plan
5 Available Units
Unit Price Sq Ft Availability
102 $2,690 825 Jan 2, 2026
202 $2,690 825 Jan 2, 2026
302 $2,690 825 Jan 2, 2026
402 $2,690 825 Jan 2, 2026
502 $2,730 825 Jan 2, 2026

1 Bed-1 Bath Den-A5

$2,780 - $2,820 per month plus fees

1 Bed, 1 Bath, 850 Sq Ft

https://imagescdn.homes.com/i2/cRqz9nZL87vqZWCm5-qmzntE-YsId9Da1yUVe3T3Hyw/116/the-winston-new-haven-ct-16.png?p=1
1 Bed-1 Bath Den-A5 Floor Plan
5 Available Units
Unit Price Sq Ft Availability
127 $2,780 850 Jan 2, 2026
227 $2,780 850 Jan 2, 2026
327 $2,780 850 Jan 2, 2026
427 $2,780 850 Jan 2, 2026
527 $2,820 850 Jan 2, 2026

1 Bed-1 Bath Den-A6

$2,800 - $2,890 per month plus fees

1 Bed, 1 Bath, 915 Sq Ft

https://imagescdn.homes.com/i2/t6-5gsRCV0cN9pFeRHUIGl7ncedZDMNIn9q52GrGEI4/116/the-winston-new-haven-ct-17.png?p=1
1 Bed-1 Bath Den-A6 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
445 $2,800 915 Jan 2, 2026
245 $2,850 915 Jan 2, 2026
345 $2,850 915 Jan 2, 2026
545 $2,890 915 Jan 2, 2026

2 Bedrooms

2 Bed-2 Bath-B2

$3,340 - $3,380 per month plus fees

2 Beds, 2 Baths, 1,035 Sq Ft

https://imagescdn.homes.com/i2/hutG9WBp1AxnJSEK-FRxJ0a3PS4cPoGc0WcL8-oiqHo/116/the-winston-new-haven-ct-18.png?p=1
2 Bed-2 Bath-B2 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
247 $3,340 1,035 Jan 2, 2026
347 $3,340 1,035 Jan 2, 2026
447 $3,340 1,035 Jan 2, 2026
547 $3,380 1,035 Jan 2, 2026

2 Bed-2 Bath-B1

$3,385 - $3,525 per month plus fees

2 Beds, 2 Baths, 1,080 Sq Ft

https://imagescdn.homes.com/i2/xfjfGNtdu-0i0ogoEyjMNxdXlzFC5OF8fvlSP5eeN7I/116/the-winston-new-haven-ct-19.png?p=1
2 Bed-2 Bath-B1 Floor Plan
27 Available Units
Unit Price Sq Ft Availability
110 $3,385 1,080 Jan 2, 2026
210 $3,385 1,080 Jan 2, 2026
310 $3,385 1,080 Jan 2, 2026
349 $3,385 1,080 Jan 2, 2026
408 $3,385 1,080 Jan 2, 2026
410 $3,385 1,080 Jan 2, 2026
411 $3,385 1,080 Jan 2, 2026
449 $3,385 1,080 Jan 2, 2026
261 $3,410 1,080 Jan 2, 2026
262 $3,410 1,080 Jan 2, 2026
361 $3,410 1,080 Jan 2, 2026
362 $3,410 1,080 Jan 2, 2026
461 $3,410 1,080 Jan 2, 2026
508 $3,425 1,080 Jan 2, 2026
511 $3,425 1,080 Jan 2, 2026
549 $3,425 1,080 Jan 2, 2026
128 $3,435 1,080 Jan 2, 2026
249 $3,435 1,080 Jan 2, 2026
561 $3,450 1,080 Jan 2, 2026
562 $3,450 1,080 Jan 2, 2026
228 $3,485 1,080 Jan 2, 2026
243 $3,485 1,080 Jan 2, 2026
344 $3,485 1,080 Jan 2, 2026
428 $3,485 1,080 Jan 2, 2026
443 $3,485 1,080 Jan 2, 2026
528 $3,525 1,080 Jan 2, 2026
543 $3,525 1,080 Jan 2, 2026

2 Bed-2 Bath-B3

$3,420 - $3,510 per month plus fees

2 Beds, 2 Baths, 1,070 Sq Ft

https://imagescdn.homes.com/i2/j4Y-XzPbvmIr9CPFy2uVvVky31qG61e2iNaFHB5j93g/116/the-winston-new-haven-ct-20.png?p=1
2 Bed-2 Bath-B3 Floor Plan
4 Available Units
Unit Price Sq Ft Availability
129 $3,420 1,070 Jan 2, 2026
229 $3,470 1,070 Jan 2, 2026
329 $3,470 1,070 Jan 2, 2026
529 $3,510 1,070 Jan 2, 2026

3 Bedrooms

3 Bed-2 Bath-C2

$4,500 per month plus fees

3 Beds, 2 Baths, 1,330 Sq Ft

https://imagescdn.homes.com/i2/3NJFUBze2L6YaXMTsIj2F0Dsudlz4FF9bNwC9Mdnckw/116/the-winston-new-haven-ct-21.png?t=p&p=1
3 Bed-2 Bath-C2 Floor Plan
1 Available Unit
Unit Price Sq Ft Availability
556 $4,500 1,330 Jan 2, 2026

3 Bed-2 Bath-C1

$4,545 - $4,610 per month plus fees

3 Beds, 2 Baths, 1,360 Sq Ft

https://imagescdn.homes.com/i2/1mzQrb-0DzKuJIK9G6-ty8gcqX5kNH-OUKnY5XO39Kk/116/the-winston-new-haven-ct-22.png?t=p&p=1
3 Bed-2 Bath-C1 Floor Plan
8 Available Units
Unit Price Sq Ft Availability
248 $4,545 1,360 Jan 2, 2026
348 $4,545 1,360 Jan 2, 2026
448 $4,545 1,360 Jan 2, 2026
201 $4,570 1,360 Jan 2, 2026
301 $4,570 1,360 Jan 2, 2026
401 $4,570 1,360 Jan 2, 2026
548 $4,585 1,360 Jan 2, 2026
501 $4,610 1,360 Jan 2, 2026

3 Bed-2 Bath-C3

$4,560 per month plus fees

3 Beds, 2 Baths, 1,375 Sq Ft

https://imagescdn.homes.com/i2/gkxiW2O29ULWXOWM1KwkEklKwgO-S-6rzJR8tW5EsLg/116/the-winston-new-haven-ct-23.png?p=1
3 Bed-2 Bath-C3 Floor Plan
1 Available Unit
Unit Price Sq Ft Availability
101 $4,560 1,375 Jan 2, 2026

3 Bed-2 Bath-C4

$4,610 per month plus fees

3 Beds, 2 Baths, 1,420 Sq Ft

https://imagescdn.homes.com/i2/x9EfBW5zUWMB5sp8b4uiilCbFgOsJOkR6Ekhd0aT3lM/116/the-winston-new-haven-ct-24.png?t=p&p=1
3 Bed-2 Bath-C4 Floor Plan
1 Available Unit
Unit Price Sq Ft Availability
309 $4,610 1,420 Jan 2, 2026

Map

Connecticut New Haven County New Haven 06511 Prospect Hill

301 Winchester Ave, New Haven, CT

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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