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Apartments for Rent in Winchester, KY

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1018 W Lexington Ave #20 - Photo 1 of 1

3d ago

Apartment for rent in Winchester

1 bed

1 bath

$995

Apartment for rent

Frontier Crossing Apartments - Photo 1 of 1

1d ago

8.3

Very good

Frontier Crossing Apartments

100 Boyd Pl, Winchester, KY 40391

In-unit laundry | Fitness center | Outdoor space

1–2 beds

1–2 baths

$995–$1,295

Apartment for rent

1-bed apartments with dog spa near I-75 access

Located in Winchester, KY, these one-bedroom apartments include in-unit washer/dryer with water, sewer, and trash covered in rent. The community features a fitness center, dog spa, and outdoor space, plus lawn care handled for residents. Quick I-75 access and a quiet environment make it a good fit for remote workers.

202 S Maple St - Photo 1 of 1

1d ago

8.3

Very good

202 S Maple St

202 S Maple St, Winchester, KY 40391

2 beds

1 bath

$1,550

Apartment for rent

Worry-Free Living with All Utilities Covered

Nestled in a charming community, this spacious 2-bedroom upstairs unit offers a truly hassle-free lifestyle with all utilities included in the rent. Perfectly designed for convenient living, enjoy the comfort of a worry-free rental experience without the burden of extra bills. Relax and enjoy the simplicity of home!

1028 W Lexington - Photo 1 of 1

1d ago

8.1

Very good

1028 W Lexington

1028 W Lexington Ave, Winchester, KY 40391

1 bed

1 bath

$1,145

Apartment for rent

1-bed apartment near parks and restaurants

Located in Winchester, KY, this cozy 1-bedroom, 1-bathroom apartment features a spacious living area and functional kitchen with water, gas, and electricity included. The property sits near Legacy Grove Park, Harmon Park, restaurants like Engine House Pizza Pub and Abettor Brewing, plus fitness options including Planet Fitness and Anytime Fitness.

135 Winn Ave - Photo 1 of 1

1d ago

8.1

Very good

135 Winn Ave

135 Winn Ave, Winchester, KY 40391

3 beds

2 baths

$1,700

Apartment for rent

Renovated 3BR/2BA home near College Park

In Winchester, KY, this renovated 3-bedroom, 2-bathroom residence features a modern kitchen, bright open living area, and contemporary finishes throughout. The spacious layouts offer move-in ready comfort on a quiet residential street, with College Park and top-rated elementary schools within half a mile.

Norwood Manor - Photo 1 of 1

1d ago

8

Very good

Norwood Manor

329 S Burns Ave, Winchester, KY 40391

1 bed

1 bath

$950

Apartment for rent

2-bed townhomes with pet spa near College Park

Norwood Manor offers 2-bedroom, 1.5-bathroom apartments and townhomes in Winchester, KY with new appliances, private rear patios, and front door parking. The community includes a pet spa and pet park, with walkable access to College Park and downtown Winchester, plus a short drive to Lexington.

Meadow Creek Phase II - Photo 1 of 1

1d ago

8.6

Very good

Meadow Creek Phase II

110 Buffalo Trce, Winchester, KY 40391

In-unit laundry | Outdoor space

2 beds

2 baths

$1,195

Apartment for rent

2-bed apartments near I-75 with in-unit laundry

Set in Winchester, KY, these 2-bedroom, 2-bathroom apartments include in-unit washer and dryer plus lawn care service. The pet-friendly community offers easy I-75 access for commuting and sits near Downtown Main St with dining options like Engine House Pizza Pub and La Trattoria within reach.

The Reserve at Fairholme - Photo 1 of 1

1d ago

8.6

Very good

The Reserve at Fairholme

Two Mile Rd, Winchester, KY 40391

In-unit laundry | Dishwasher | Microwave

3 beds

2 baths

$1,499

Apartment for rent

Spacious Townhomes with Community Charm

The Reserve at Fairholme offers inviting 2-bedroom, 2.5-bath townhomes just minutes from downtown Winchester. Featuring fully equipped kitchens, private patios, and hard surface flooring, each unit provides comfort and style. Residents enjoy amenities like on-site washers and dryers, a community dog park, and a picnic area, all set in a peaceful environment. Dog-friendly and perfect for any lifestyle, this home is ready to welcome beloved pets with open arms.

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Meadow Creek Phase 1 - Photo 1 of 1

1d ago

8.6

Very good

Meadow Creek Phase 1

100 Buffalo Trce, Winchester, KY 40391

Package service | Outdoor space

2 beds

1 bath

$1,195

Apartment for rent

2-bed apartments near I-75 with private patios

Set in Winchester, KY, these 2-bedroom, 1-bath apartments include in-unit laundry, private patios, and outdoor space with lawn care included. The community sits minutes from I-75, shopping, and dining, with nearby access to Melbourne Park, Leeds Theatre, and local markets for convenient daily errands.

Review from the web

I live here. Great place to live.

- Christine Ross on Jun 9, 2016
121 Bellbrook Lane - Photo 1 of 1

2d ago

8.4

Very good

121 Bellbrook Lane

121 Bellbrook Ln, Winchester, KY 40391

2 beds

2 baths

$1,620

Apartment for rent

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Outdoor Space

Fitness Center

Dishwasher

In-Unit Laundry

Pepperwood Ct - Photo 1 of 1

2d ago

8.4

Very good

Pepperwood Ct

202 Pepperwood Ct, Winchester, KY 40391

3 beds

2 baths

$1,625

Apartment for rent

Fountain at the Farms - Photo 1 of 1

2d ago

8.5

Very good

Fountain at the Farms

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

Dog-friendly 1BR with spa & pool near I-75

Located in Winchester, KY, this one-bedroom apartment includes in-unit washer and dryer, serene wooded views, and lawn care. The community features a zero-entry pool, fitness center, dedicated dog spa, and dog park with water, sewer, and trash included - a good fit for pet owners with nearby grooming services and pet supply stores.

341 Burns Ave - Photo 1 of 1

2d ago

7.9

Very good

341 Burns Ave

341 S Burns Ave, Winchester, KY 40391

Balcony | Outdoor space

2 beds

1 bath

$925

Apartment for rent

Cozy Apartment Living with Outdoor Serenity

Welcome to a charming 2-bedroom, 1-bathroom apartment designed for comfort and convenience. Enjoy a relaxing patio, pet-friendly policy, and included lawn care. With essential appliances like a stove and refrigerator, this space is perfect for cozy living. Plus, 24-hour maintenance ensures peace of mind. A wonderful opportunity awaits!

The Lofts at Winchester - Photo 1 of 1

2d ago

8.3

Very good

The Lofts at Winchester

508 College St, Winchester, KY 40391

2–3 beds

1 bath

$1,049–$1,250

Apartment for rent

2-bedroom apartments near Winchester parks & dining

Located in Winchester, KY, these 2-bedroom apartments include water, stove, and refrigerator with convenient access to shopping, dining, and interstate travel. The location sits near top-rated schools including a middle school under a mile away, plus Wiseman Park, Legacy Grove Park, and local dining like Engine House Pizza Pub and Lucky Dog Cafe.

115 Pinnacle Place - Photo 1 of 1

4d ago

8.5

Very good

115 Pinnacle Place

Winchester Rd, Winchester, KY 40391

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,425–$1,475

Apartment for rent

230 Prescott Ln - Photo 1 of 1

4d ago

House for rent in Winchester

230 Prescott Ln, Winchester, KY 40391

Garage parking | Deck | Dishwasher

3 beds

2.5 baths

$1,850

House for rent

Average rent

The average rent in Winchester, as of August 2026, is up 4.41% compared to last month and up 10.01% year-over-year.
$1,195
increased by10%

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543 N. Maple Street - Photo 1 of 1

5d+ ago

8.3

Very good

543 N. Maple Street

543 N Maple St, Winchester, KY 40391

1 bed

1 bath

$799

Apartment for rent

Move-in ready apartment with utilities included

Located in Winchester, KY, this move-in ready apartment includes electric, water, sewer, and trash with no utility deposits required. Rent is $825/month with a $75 electric allowance, making budgeting simple and predictable. Near top-rated elementary schools within a third of a mile and close to local dining like Engine House Pizza Pub and La Trattoria.

7 Calloway St - Photo 1 of 1

5d+ ago

8.3

Very good

7 Calloway St

7 Calloway St, Winchester, KY 40391

1 bed

1 bath

$799

Apartment for rent

All-Inclusive Cozy Retreat Minutes from Downtown

7 Calloway St offers a charming 1-bedroom, 1-bathroom apartment designed for stress-free living. With all utilities included at just $799/month, budgeting is a breeze. Inside, sleek hard surface flooring complements a cozy layout featuring a spacious walk-in closet. Located just minutes from downtown Winchester, enjoy easy access to shopping, dining, and local attractions while having a comfortable retreat to unwind after the hustle and bustle.

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Studio 28 - Photo 1 of 1

5d+ ago

7.7

Very good

Studio 28

27 E Washington St, Winchester, KY 40391

Microwave

Studio

1 bath

$814

Apartment for rent

Studio & 1-BR with all utilities included

Located in Winchester, KY, these studio and 1-bedroom apartments include all utilities and sit within walking distance of downtown and Depot Street. Units come with shopping, dining, and interstate access minutes away, plus a top-rated elementary school just 0.3 miles from the property.

Review from the web

Friendly staff. Trust worthy. However the ppl that live in the building are sketchy. I'd keep to myself.

- Christine Helms on Jan 24, 2021
101 E Lexington Ave - Photo 1 of 1

5d+ ago

House for rent in Winchester

3 beds

1 bath

$1,475

$1,300

Price drop

House for rent

721 Wayland Dr - Photo 1 of 1

5d+ ago

House for rent in Winchester

SINGLE_FAMILY - Winchester, KY

721 Wayland Dr, Winchester, KY 40391

Garage parking | Swimming pool | Hardwood floor

4 beds

3 baths

$2,595

House for rent

101 Bellbrook Ln - Photo 1 of 1

5d+ ago

House for rent in Winchester

Package service | Outdoor space

3 beds

2 baths

$1,995

House for rent

136 Georgia St - Photo 1 of 1

5d+ ago

House for rent in Winchester

3 beds

1 bath

$1,375

$1,300

Price drop

House for rent

356 Oxford Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winchester

356 Oxford Dr, Winchester, KY 40391

Ceiling fan | Dishwasher

2 beds

1.5 baths

$1,125

House for rent

265 S Highland St #3 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

265 S Highland St #3, Winchester, KY 40391

On-site laundry | Hardwood floor

2 beds

1 bath

$955

Apartment for rent

Available May 1

Cozy Apartment with Wood Floors & Large Yard

This charming 2-bedroom apartment features beautiful wood floors throughout, enhancing its inviting atmosphere. Enjoy the convenience of an in-unit laundry room and a spacious yard, perfect for relaxing or entertaining. Located near downtown and shopping, this pet-friendly home offers easy access to local amenities, making it an ideal choice for comfortable living in Winchester.

265 S Highland St #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

265 S Highland St #4, Winchester, KY 40391

On-site laundry | Hardwood floor

2 beds

1 bath

$955

Apartment for rent

Available Mar 10

2-bed Winchester apartment with wood floors

Right in Winchester, KY, this 2-bed, 1-bath apartment features beautiful hardwood floors throughout and in-unit laundry. The unit includes a large yard and ample storage space, with close proximity to downtown, schools, and shopping areas. Rent is $995 with tenants responsible for utilities, and the property offers deposit-free living options through Obligo for qualified renters.

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15 Kittison Dr #15KIT - Photo 1 of 1

5d+ ago

House for rent in Winchester

15 Kittison Dr #15KIT, Winchester, KY 40391

Air conditioning | Garage parking | Dishwasher

3 beds

2 baths

$2,350

House for rent

Available Aug 14

3-bed Winchester house with backyard & garage

This dog-friendly 3-bed, 2-bath house in Winchester offers 1,780 sqft with a nice-size backyard and garage parking. The layout includes air conditioning and dishwasher, making it a fit for pet owners with 3 grooming services nearby and a dog park within a mile. Convenient interstate access connects to all local amenities.

Sam Winston Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winchester

Sam Winston Way, Winchester, KY 40391

In-unit laundry | Dishwasher | Microwave

2 beds

2.5 baths

$1,399

House for rent

Modern 2-bed townhouse with dog park & patio

Set in Winchester, KY, this pet-friendly 2-bed, 2.5-bath townhouse features modern finishes and stainless appliances throughout its 1,100 sqft layout. In-unit laundry, a private patio with storage, and a quiet location minutes from Main Street add convenience. The community includes an on-site dog park and picnic area.

Showing 1 - 28 of 28 results
Home > Apartments in Winchester
Updated: August 9, 2026

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Learn more about renting in Winchester, KY

Local insights: What it's like to live in Winchester, KY

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.

How much is the average rent in Winchester, KY for 1-bedroom and 2-bedroom apartments?

Based on Zumper's July 2026 data, one-bedroom apartments in Winchester average around $900/month and two-bedrooms approximately $1,140/month.

When is the best time to look for an apartment in Winchester, KY?

July offers the lowest rents in Winchester, running about 15% below March prices, which sees the highest rents of the year.

Are there pet-friendly apartments in Winchester, KY?

Based on our current listings, roughly 21% of Winchester rentals welcome pets, which works out to about 11 pet-friendly apartments each month across the city's average of 53 available units.

Are utilities usually included in rent in Winchester, KY?

In our current listings, utilities-included rentals are rare in Winchester, showing up in under 1% of units, with studios leading at 0.51% of available listings.

Methodology: How we got this data

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.

Looking for apartments in Winchester, KY near you?

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💰Best rent deal7 Calloway St
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