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Apartments for Rent in Winchester, KY

Average rent

$1,185
increased by5%

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Barrett Manor - Photo 1 of 1

2h ago

8.4

Very good

Barrett Manor

300 Moundale Ct, Winchester, KY 40391

2 beds

1 bath

$995

Apartment for rent

2-bedroom apartment with screened porch near parks

Located in Winchester, KY, this spacious 2-bedroom apartment features a screened-in porch and sits across from Moundale Manor. The location provides access to top-rated schools within a mile, plus nearby College Park, Wiseman Park, and local dining options like Boone House Grill and Engine House Pizza Pub.

Frontier Crossing Apartments - Photo 1 of 1

2h ago

8.3

Very good

Frontier Crossing Apartments

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

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.

Fountain at the Farms - Photo 1 of 1

10h 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.

135 Winn Ave - Photo 1 of 1

13h ago

8.3

Very good

135 Winn Ave

135 Winn Ave, Winchester, KY 40391

3 beds

2 baths

$1,690

Price drop

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

13h ago

8.3

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

19h ago

8.6

Very good

Meadow Creek Phase II

110 Buffalo Trce, Winchester, KY 40391

In-unit laundry | Outdoor space

1–2 beds

1–2 baths

$915–$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.

135 Chatham Place - Photo 1 of 1

22h ago

8.4

Very good

135 Chatham Place

135 Chatham Pl, Winchester, KY 40391

2 beds

2 baths

$1,195

Apartment for rent

Updated 2-bed townhome with private yard

Set in Winchester, KY, this recently updated 2-bedroom townhome includes fresh paint, new vinyl flooring, and 2.5 bathrooms with no shared walls above or below. The property comes with lawn care included and allows up to 2 pets with approval. No fee listing with 15 photos available.

265 S Highland St #1 - Photo 1 of 1

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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Meadow Creek Phase 1 - Photo 1 of 1

23h ago

8.5

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
The Reserve at Fairholme - Photo 1 of 1

23h ago

Apartment for rent in Winchester

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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In-Unit Laundry

Dishwasher

On-Site Laundry

Outdoor Space

14 A St - Photo 1 of 1

23h ago

House for rent in Winchester

14 A Street

14 A St, Winchester, KY 40391

In-unit laundry | Air conditioning | On-site laundry

3 beds

2 baths

$1,195

House for rent

Available May 10

1028 W Lexington - Photo 1 of 1

2d ago

8

Very good

1028 W Lexington

1028 W Lexington Ave, Winchester, KY 40391

1 bed

1 bath

$1,105

Price drop

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.

3256 Irvine Rd - Photo 1 of 1

2d ago

House for rent in Winchester

Escape to the Quiet! ​Looking to swap city noise for peaceful county living

3256 Irvine Rd, Winchester, KY 40391

Air conditioning | Assigned parking | Dishwasher

2 beds

1 bath

$1,200

House for rent

Available Jun 23

222 Buffalo Trce - Photo 1 of 1

3d ago

House for rent in Winchester

222 Buffalo Trce, Winchester, KY 40391

In-unit laundry | On-site laundry | Hardwood floor

3 beds

2 baths

$1,495

House for rent

Available Jun 23

Bright and Accessible Home with Vaulted Ceilings

This charming 3-bedroom home features luxury vinyl plank flooring, soaring vaulted ceilings, and fresh neutral paint, creating a welcoming atmosphere. The spacious kitchen flows into the dining area, and one bedroom includes an accessible bathroom with a walk-in shower. Enjoy the semi-private patio and included storage shed for outdoor relaxation. Pet-friendly with modern conveniences throughout, this residence is perfect for comfort and accessibility in downtown Winchester.

401/403 Noble King Ct - Photo 1 of 1

3d ago

8

Very good

401/403 Noble King Ct

401 Noble King Ct, Winchester, KY 40391

2 beds

2 baths

$1,225

Apartment for rent

543 N. Maple Street - Photo 1 of 1

4d ago

8.3

Very good

543 N. Maple Street

543 N Maple St, Winchester, KY 40391

1 bed

1 bath

$825

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.

515 Wellington Way - Photo 1 of 1

4d ago

7

Very good

515 Wellington Way

515 Wellington Way, Winchester, KY 40391

Package service | Outdoor space

Studio

1 bath

$950

Apartment for rent

Atrium Property Investments LLC - Photo 1 of 1

4d ago

8.5

Very good

Atrium Property Investments LLC

Atrium Pl, Winchester, KY 40391

In-unit laundry | Dishwasher | Outdoor space

2 beds

1 bath

$975

Apartment for rent

Spacious 2-bed townhomes with W/D hookups

In Winchester, KY, these spacious 2-bedroom townhomes feature comfortable layouts with washer/dryer hookups, full appliances including stove, refrigerator, and dishwasher, plus patios and outdoor space. The community includes lawn care service, near Legacy Grove Park and local dining options.

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The Lofts at Winchester - Photo 1 of 1

4d ago

8.3

Very good

The Lofts at Winchester

508 College St, Winchester, KY 40391

2 beds

1 bath

$1,049

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.

Studio 28 - Photo 1 of 1

4d ago

7.4

Very good

Studio 28

27 E Washington St, Winchester, KY 40391

Studio–1 bed

1 bath

$814–$899

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
127 S Highland St #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

1 bed

1 bath

$875

Apartment for rent

Available Jan 7

1-bed Winchester apartment with convenient location

This 912 square-foot apartment in Winchester, KY includes 1-bed, 1-bath layout designed for comfortable, low-maintenance living. The space works well for relaxing or working from home, with everything you need just a short drive away for easy errands and getting around town. A top-rated elementary school sits within a third of a mile, making this a practical choice for affordable, no-fuss living.

362 S Main St #A - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

$996- weekly flex pay plan

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

102 Bellbrook Ln - Photo 1 of 1

5d+ ago

House for rent in Winchester

In-unit laundry | Swimming pool | Fitness center

3 beds

2.5 baths

$1,995

House for rent

New 3-bed house with garage and fitness center

Quietly set in Winchester, KY, this brand-new 3-bed, 2.5-bath house offers 1,830 sqft of two-story living with an attached two-car garage. The pet-friendly community includes a fitness center, zero-entry pool, dog park with spa, and on-site management. In-unit laundry and lawn care included.

18 Calloway Street - 18 Calloway #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

1-Bed/1-Bath | Winchester Apartment for Rent | 18 Calloway Street #4, Winchester, KY 40391

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

Updated 1-bed Winchester apartment with utilities

Located in Winchester, KY, this recently renovated 1-bed, 1-bath apartment offers 850 sqft with central A/C and included appliances. The $922 monthly rate covers water, sewer, and trash, with pet-friendly policies available. Positioned near Lexington Avenue and Bypass Road for easy access to shopping, dining, and downtown Winchester within minutes.

25 Hays St #E - Photo 1 of 1

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

Renovated 2-bed apartment with new appliances

Quietly set in Winchester, KY, this fully renovated 2-bed, 2-bath upstairs apartment features 1,250 sqft of updated living space with new paint, kitchen, and all new appliances including dishwasher and in-unit laundry. Located minutes from downtown Winchester and Lexington Hamburg area with convenient I-64 access. Pet-friendly with up to two pets allowed.

104 Colby Hills Dr - Photo 1 of 1

5d+ ago

House for rent in Winchester

SINGLE_FAMILY - Ranch - Winchester, KY

104 Colby Hills Dr, Winchester, KY 40391

Garage parking | Ceiling fan | Dishwasher

4 beds

2 baths

$2,900

House for rent

Ranch-style 4-bed house with garage parking

4-bed house in Winchester, KY, featuring a ranch-style design with stone and vinyl siding exterior. This 1,950 sqft layout includes 2 bathrooms, forced air heating, ceiling fans, and a dishwasher. Eleven total rooms provide ample space, with garage parking adding convenience for residents.

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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

$970

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.

Fairfield Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winchester

3 beds

2.5 baths

$1,599

House for rent

New 3-bed townhouse with garage near I-64

Quietly set in Winchester, KY, this brand-new 3-bed, 2.5-bath townhouse offers 1,500 sqft of open-concept living with a modern kitchen featuring granite counters and stainless appliances. The layout includes a primary suite with walk-in closet, second-floor laundry hookups, and an attached garage plus driveway parking. Pet-friendly with quick I-64 access to downtown Winchester and Lexington.

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 - 30 of 30 results
Home > Apartments in Winchester
Updated: June 27, 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?

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.

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

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.

Are there pet-friendly apartments in Winchester, KY?

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.

Are utilities usually included in rent in Winchester, KY?

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.

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 deal27 E Washington St
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