Winchester In Rentals

265 S Highland St - Unit 3, Winchester, KY 40391

1 / 14

$1,095/mo

Available Now

265 S Highland St - Unit 3

2 bd1 ba— sqft

Apartment·via Rpmky002·Cats allowed, Small dogs allowed

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1 / 39

$3,800/mo

Available Now

33025 Goldie Ct.

5 bd3 ba3,133 sqft

Single Family·via Utopiamanagement·Cats allowed, Small dogs allowed

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18 W. Whitlock Avenue, Winchester, VA 22601

1 / 19

$1,800/mo

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18 W. Whitlock Avenue

4 bd2 ba— sqft

Single Family·via Olivetreeproperty·N/A

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28055- 28085 Washington Avenue - 28057 Washington Ave

1 / 25

$2,700/mo

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28057 Washington Avenue

3 bd2 ba1,200 sqft

Multi-Family·via S.D.S. Realty & Property Management DRE#02094558·N/A

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1 / 28

$1,495/mo

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200 Madison Ave

3 bd2 ba1,124 sqft

Single Family·via PURE Property Management of Kentucky·Cats not allowed, Dogs not allowed

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1 / 31

$1,195/mo

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135 Chatham Place - 5

2 bd2 ba1,058 sqft

Apartment·via Sparkles Rentals·N/A

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1 / 31

$1,195/mo

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240 Chatham Place - 5

2 bd2 ba1,056 sqft

Apartment·via Sparkles Rentals·N/A

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1 / 14

$1,095/mo

Available Now

265 S Highland St - Unit 4

2 bd1 ba— sqft

Apartment·via Rpmky002·Cats allowed, Small dogs allowed

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1 / 7

$1,200/mo

Available Now

811 S Braddock St Apt 6

2 bd1 ba— sqft

Apartment·via Olivetreeproperty·N/A

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1 / 15

$1,195/mo

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240 Chatham Place - 2

2 bd2 ba1,056 sqft

Apartment·via Sparkles Rentals·N/A

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1 / 10

$1,650/mo

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201 Molden Drive

2 bd1 ba— sqft

Single Family·via AIP Management, LLC.·N/A

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1 / 20

$1,950/mo

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504 Yorktowne Place

3 bd1 ba1,116 sqft

Townhouse·via AIP Management, LLC.·N/A

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Rental Market Analysis — Winchester, VA

Fizbo has collected 26 rental listings in Winchester, VA. Among these, monthly rents range from $900 to $4,500, with an average of $1,744/mo and a median of $1,495/mo. 26 units are available for immediate move-in.

These properties range from 1 to 5 bedrooms and 1 to 3.5 bathrooms, averaging 2.4 beds / 1.6 baths. Living space averages 1,340 sqft (range: 400–3,133 sqft). Rent scales with size: 1-bedroom units average $1,025/mo (3 listings), 2-bedroom units average $1,272/mo (10 listings), 3-bedroom units average $2,137/mo (7 listings), 4+-bedroom units average $2,800/mo (2 listings).

These listings are primarily composed of Apartments (46%), Single Familys (27%) and Townhouses (23%), with the remainder split among multi-family. Security deposits average $1,644, ranging from $100 to $4,500. Properties were built between 2007 and 2007, with an average construction year of 2007.

7 of 26 listings (27%) are pet-friendly. Properties are managed by 8 property management companies, led by Olivetreeproperty (6 listings).

Our AI photo analysis across these listing images reveals common finishes and features. The most prevalent countertop material is Laminate Countertops (found in 19% of listings, -27% vs. average rent). Hardwood Flooring is the most common flooring (27%). White Appliances appliances appear in 27% of units. The most common architectural style is Traditional (27% of listings, avg $1,248/mo).

Winchester Rentals

Avg Rent by Bedroom

Property Types

Lease Terms

Property Managers

Availability

Popular Features

AI Photo Analysis · Price by Finish

Countertops

Flooring

Cabinets

Appliances

Exterior

Outdoor

Home Style

Condition & Price

Rental Market Analysis — Winchester, VA