Rentometer, Inc. | Data as of 10/22/2025
Winchester, Kentucky offers a welcoming blend of historic charm and modern convenience, making it an appealing destination for renters seeking both lifestyle and affordability. Nestled in the heart of the Bluegrass State, the city is known for its well‑preserved downtown district, vibrant arts scene, and easy access to outdoor recreation along the Kentucky River. Popular neighborhoods such as Old Town Winchester and the Riverfront area provide a mix of walkable streets, local boutiques, and dining options that cater to a diverse community of professionals, families, and students.
The rental market in Winchester is anchored by a variety of apartment communities that feature contemporary amenities and convenient locations near key attractions like the Kentucky Valley Railroad Museum and the historic Campbell House. Two‑bedroom apartments dominate the market, with average rents situated in the $1200‑$1300 range, reflecting the city’s reputation for cost‑effective living without sacrificing quality. Prospective renters can expect well‑maintained units, on‑site fitness centers, and pet‑friendly policies that complement the city’s family‑oriented atmosphere.
Beyond housing, Winchester’s appeal is enhanced by its strong sense of community and active local events calendar, including the annual Winchester Fall Festival and numerous farmers’ markets. Excellent schools, reliable public transportation, and proximity to larger employment hubs like Lexington further contribute to the city’s desirability. Whether you’re drawn to the historic streetscapes, the convenient downtown amenities, or the affordable rental options, Winchester provides a balanced, inviting environment for renters seeking a vibrant Kentucky lifestyle.
| Property Type | Bedrooms | Average | Median | Min - Max | 25th - 75th |
|---|---|---|---|---|---|
| Apartment | 2 Bedroom | $1,266 | $1,250 | $875 - $1,800 | $1,029 - $1,380 |
In the current period, the average rent in Winchester was
$1,267 for 2 Bedroom.
Note: This analysis includes only bedroom types with sufficient data.
Data provided by Rentometer, Inc.