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The average rent in Winchester, as of June 2026, is up 2.05% compared to last month and up 5.3% year-over-year.
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2h ago
2 beds
1 bath
$995
Apartment for rent
2h ago
100 Boyd Pl, Winchester, KY 40391
In-unit laundry | Fitness center | Outdoor space
1–4 beds
1–2 baths
$995–$1,500
Apartment for rent
10h ago
300 Bellbrook Ln, Winchester, KY 40391
In-unit laundry | Swimming pool | Fitness center
1–2 beds
1–2 baths
$1,125–$1,350
Apartment for rent
13h ago
3 beds
2 baths
$1,690
Price drop
Apartment for rent
13h ago
1 bed
1 bath
$950
Apartment for rent
19h ago
1–2 beds
1–2 baths
$915–$1,195
Apartment for rent
22h ago
2 beds
2 baths
$1,195
Apartment for rent
23h ago
Apartment for rent in Winchester
265 S Highland St #1, Winchester, KY 40391
On-site laundry | Hardwood floor
2 beds
1 bath
$970
Apartment for rent
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23h ago
2 beds
1 bath
$1,195
Apartment for rent
23h ago
Apartment for rent in Winchester
3 beds
2 baths
$1,499
Apartment for rent
In-Unit Laundry
Dishwasher
On-Site Laundry
Outdoor Space
23h ago
House for rent in Winchester
3 beds
2 baths
$1,195
House for rent
Available May 10
2d ago
1 bed
1 bath
$1,105
Price drop
Apartment for rent
2d ago
House for rent in Winchester
3256 Irvine Rd, Winchester, KY 40391
Air conditioning | Assigned parking | Dishwasher
2 beds
1 bath
$1,200
House for rent
Available Jun 23
3d ago
House for rent in Winchester
3 beds
2 baths
$1,495
House for rent
Available Jun 23
3d ago
2 beds
2 baths
$1,225
Apartment for rent
4d ago
1 bed
1 bath
$825
Apartment for rent
4d ago
Studio
1 bath
$950
Apartment for rent
4d ago
Atrium Pl, Winchester, KY 40391
In-unit laundry | Dishwasher | Outdoor space
2 beds
1 bath
$975
Apartment for rent
4d ago
2 beds
1 bath
$1,049
Apartment for rent
4d ago
Studio–1 bed
1 bath
$814–$899
Apartment for rent
5d+ ago
Apartment for rent in Winchester
1 bed
1 bath
$875
Apartment for rent
Available Jan 7
5d+ ago
Apartment for rent in Winchester
362 S Main St #A, Winchester, KY 40391
On-site laundry | Assigned parking | Hardwood floor
1 bed
1 bath
$996
Apartment for rent
Available Jun 15
5d+ ago
House for rent in Winchester
In-unit laundry | Swimming pool | Fitness center
3 beds
2.5 baths
$1,995
House for rent
5d+ ago
Apartment for rent in Winchester
18 Calloway Street - 18 Calloway #4, Winchester, KY 40391
Air conditioning
1 bed
1 bath
$879
$829
Price drop
Apartment for rent
Available May 28
5d+ ago
Apartment for rent in Winchester
25 Hays St #E, Winchester, KY 40391
In-unit laundry | Air conditioning | On-site laundry
2 beds
2 baths
$1,300
Apartment for rent
Available May 14
5d+ ago
House for rent in Winchester
104 Colby Hills Dr, Winchester, KY 40391
Garage parking | Ceiling fan | Dishwasher
4 beds
2 baths
$2,900
House for rent
5d+ ago
Apartment for rent in Winchester
265 S Highland St #4, Winchester, KY 40391
On-site laundry | Hardwood floor
2 beds
1 bath
$970
Apartment for rent
Available Mar 10
5d+ ago
Townhouse for rent in Winchester
3 beds
2.5 baths
$1,599
House for rent
5d+ ago
House for rent in Winchester
3 beds
2 baths
$2,350
House for rent
Available Aug 14
5d+ ago
Townhouse for rent in Winchester
2 beds
2.5 baths
$1,399
House for rent
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13 rentals
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8 rentals
17 rentals
556 rentals
38 rentals
143 rentals
18 rentals
3 rentals
3 rentals
21 rentals
5 rentals
19 rentals
14 rentals
6 rentals
Locals appreciate the small-town vibe of Winchester, KY, highlighting its friendly atmosphere and accessible local amenities, including a variety of shops and restaurants. Many enjoy the slower pace of life, as well as the community events that bring residents together. However, some mention that housing options can be limited, and there's a noticeable lack of recreational facilities for families and active individuals. Parking can also be a concern in certain areas, making it a point of frustration for some renters.
Winchester's 2025 rental market shows one-bedroom apartments averaging around $880 per month, while two-bedroom units average around $1,100 monthly. These figures represent the current market rates across the city's rental inventory.
July offers the lowest rental prices in Winchester, while March sees the highest rent with approximately a 15% difference between these months. This seasonal pattern creates clear timing opportunities for renters looking to secure better rates.
Winchester accommodates pet owners with around 30% of rental listings welcoming pets. With an average of 50 listings available monthly, this provides a solid selection of pet-friendly options for animal-loving renters.
Utilities are rarely included in Winchester rental properties, with only about 7 listings or less than 1% of total inventory including utilities in the rent. This pattern remains consistent across all bedroom types, from studios to three-bedroom apartments.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
| 🔑Available apartment rentals | 41 |
|---|---|
| 💰Best rent deal | 27 E Washington St |
| ✨Popular amenities | , , |
| 🍽With dishwasher | |
| 🏠With photos |