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The average monthly rent in Winchester is up 3.88% compared to last month and up 1.11% year-over-year.
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All rentals
5d+ ago
2 beds
1 bath
$1,150–$1,185
Apartment 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
$995
Apartment for rent
Available Mar 10
11h ago
House for rent in Winchester
3 beds
1 bath
$1,185
House for rent
13h ago
1–2 beds
1–2 baths
$850–$1,195
Apartment for rent
13h ago
3 beds
2 baths
$1,800
Apartment for rent
1d ago
2 beds
2 baths
$1,195
Apartment for rent
1d ago
100 Boyd Pl, Winchester, KY 40391
In-unit laundry | Fitness center | Outdoor space
2–4 beds
2 baths
$1,295–$1,500
Apartment for rent
1d ago
2 beds
1 bath
$975
Apartment for rent
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1d ago
House for rent in Winchester
In-unit laundry
3 beds
1.5 baths
$975
House for rent
1d ago
2 beds
2 baths
$1,015
Apartment for rent
Fitness Center
In-Unit Laundry
Outdoor Space
Dishwasher
4d ago
Studio
1 bath
$795
Apartment for rent
4d ago
2 beds
1 bath
$1,195
Apartment for rent
5d+ ago
Studio
1 bath
$950
Apartment for rent
5d+ ago
2 beds
1 bath
$1,370
Apartment for rent
5d+ ago
1 bed
1 bath
$1,100
Apartment for rent
5d+ ago
300 Bellbrook Ln, Winchester, KY 40391
In-unit laundry | Swimming pool | Fitness center
1 bed
1 bath
$1,095
Apartment for rent
5d+ ago
Apartment for rent in Winchester
502 Evans St #3, Winchester, KY 40391
In-unit laundry | Air conditioning | Assigned parking
3 beds
1 bath
$1,400
Apartment for rent
Available May 11
5d+ ago
Apartment for rent in Winchester
2 beds
2.5 baths
$1,125
Apartment for rent
5d+ ago
House for rent in Winchester
2 beds
1.5 baths
$1,400
House for rent
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
$1,400
Apartment for rent
Available Apr 25
5d+ ago
Apartment for rent in Winchester
1 bed
1 bath
$950
Apartment for rent
Available Jan 5
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
1d ago
2 beds
2 baths
$945
Apartment for rent
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573 rentals
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46 rentals
142 rentals
10 rentals
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3 rentals
26 rentals
15 rentals
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2 rentals
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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 2024 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 | 36 |
|---|---|
| 💰Best rent deal | 200 Hubbard Rd |
| ✨Popular amenities | , , |
| 🍽With dishwasher | |
| 🏠With photos |