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Apartments for Rent in Winchester, KY

Average rent

$1,185
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Fountain at the Farms - Photo 1 of 1

11h ago

8.5

Very good

Fountain at the Farms

300 Bellbrook Ln, Winchester, KY 40391

In-unit laundry | Swimming pool | Fitness center

Studio–1 bed

1 bath

$950–$1,095

Apartment for rent

Pet-Friendly Comfort with Pool & Fitness Perks

Fountain at the Farms offers a cozy one-bedroom apartment in Winchester, KY, designed for both you and your furry friends. Enjoy a dedicated dog spa and park, a state-of-the-art fitness center, and a refreshing zero-entry swimming pool. In-unit laundry keeps life convenient, while included lawn care ensures a beautiful environment. With easy access to I-75, this community provides the perfect blend of comfort and convenience for a vibrant lifestyle.

Meadow Creek Phase II - Photo 1 of 1

4d ago

8.5

Very good

Meadow Creek Phase II

110 Buffalo Trce, Winchester, KY 40391

In-unit laundry | Outdoor space

2 beds

2 baths

$1,125

Apartment for rent

Comfort and Convenience near Downtown Winchester

Residents of Meadow Creek Phase II enjoy modern living in pet-friendly, 2-bedroom apartments with in-unit laundry. This thoughtfully designed community features well-maintained lawns with included lawn care. A prime location ensures easy access to I-75 and the vibrant Downtown Main St, where dining, shopping, and entertainment options abound. Experience a seamless blend of comfort and convenience in the heart of Winchester!

Norwood Manor - Photo 1 of 1

5d+ ago

8.8

Very good

Norwood Manor

329 S Burns Ave, Winchester, KY 40391

On-site laundry | Dishwasher | Microwave

2 beds

1 bath

$1,185

Apartment for rent

Charming Apartments Steps from College Park

Norwood Manor offers delightful 2-bedroom, 1.5-bathroom apartments in Winchester, KY, complete with new appliances and a convenient pet spa and park for furry friends. Located within walking distance to College Park and downtown, it ensures easy access to local attractions and a short drive to Lexington. Enjoy your own private rear patio sitting area and hassle-free front door parking in this inviting community. Perfect for those seeking charm and convenience!

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

$1,095

Apartment for rent

Available Mar 10

Cozy Apartment with Hardwood Floors & Large Yard

This charming 2-bedroom, 1-bathroom apartment offers beautiful wood floors throughout, creating a warm inviting space. Enjoy the convenience of an in-unit laundry room and a large yard, perfect for pets and outdoor activities. Located near downtown and shopping, this apartment ensures easy access to amenities while providing a comfortable lifestyle. Experience a blend of historic charm and modern convenience in this pet-friendly home!

265 S Highland St #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

265 S Highland St #2, Winchester, KY 40391

On-site laundry | Hardwood floor

2 beds

1 bath

$1,095

Apartment for rent

Available Mar 13

Cozy Apartment with Wood Floors & Large Yard

This charming 2-bedroom, 1-bath apartment features beautiful wood floors that create a warm ambiance. Enjoy conveniences like in-unit laundry and a spacious yard, perfect for outdoor activities. Ideally located near downtown and shopping, this pet-friendly home combines comfort with accessible amenities, making it a great choice for anyone seeking a vibrant living experience in Winchester.

The Lofts at Winchester! 2 BR, 1 Bath, Off - Photo 1 of 1

5h ago

8.8

Very good

The Lofts at Winchester! 2 BR, 1 Bath, Off

508 College St, Winchester, KY 40391

Ceiling fan

3 beds

1 bath

$1,249

Apartment for rent

Stylish 2BR Living Near Downtown Vibrancy

Located in Winchester, this charming 2-bedroom, 1-bath apartment offers a perfect blend of modern updates and convenience. Featuring beautiful updated flooring and stainless steel appliances, the unit also includes off-street parking. Enjoy the comfort of central heat and AC, with the added benefit of virtual tours available. Situated near downtown and various dining and shopping options, this pet-friendly home is designed for an easy lifestyle.

Studio 28 Apartments - Photo 1 of 1

1d ago

8.8

Very good

Studio 28 Apartments

27 E Washington St, Winchester, KY 40391

Air conditioning | Central heat | Microwave

Studio–1 bed

1 bath

$749–$899

Apartment for rent

All-Inclusive Studio Living Near Downtown

Studio 28 Apartments offers a cozy studio space just 5 minutes from downtown Winchester, perfect for those seeking convenience. Enjoy all utilities included, along with essential kitchen appliances. Pet-friendly and non-smoking, this community features off-street parking and the option for virtual tours. Plus, a special September promotion of one month’s free rent makes this an opportunity not to miss! Embrace comfortable living with easy access to shopping and dining.

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
223 Boone Avenue - Photo 1 of 1

1d ago

Apartment for rent in Winchester

223 Boone Avenue

223 Boone Ave, Winchester, KY 40391

Air conditioning

3 beds

1 bath

$950

Apartment for rent

Spacious 3-Bedroom Retreat in Winchester

This charming 3-bedroom, 1-bath apartment offers ample space and character on the 2nd floor of Boone Avenue, right in Winchester’s heart. The rent is $950 plus utilities, with off-street parking and shared yard access. Features include window AC units, a stackable washer & dryer, and a pet-friendly policy for small pets. Perfect for those seeking comfort and convenience—don’t miss out on this welcoming space!

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200 Madison Ave - Photo 1 of 1

1d ago

House for rent in Winchester

200 Madison Ave, Winchester, KY 40391

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

3 beds

2 baths

$1,425

House for rent

Available Jan 29

Newly Updated Downtown Haven with Modern Decor

Experience comfort and convenience in this updated 3-bedroom, 2-bath home in downtown Winchester. Fresh luxury vinyl plank flooring and neutral paint create a bright atmosphere. The spacious living room transitions seamlessly to the eat-in kitchen and dining area. Enjoy the new deck overlooking a partially fenced yard with a storage shed. The primary suite features an ensuite bathroom while two additional bedrooms share a beautifully updated bath, making this move-in ready home a perfect urban retreat.

Atrium Property Investments LLC - Photo 1 of 1

1d ago

8.5

Very good

Atrium Property Investments LLC

Atrium Pl, Winchester, KY 40391

In-unit laundry | Dishwasher

2 beds

1 bath

$975

Apartment for rent

Spacious Townhome with Comfort & Convenience

Located in charming Winchester, KY, this 2-bedroom townhome features an open floor plan and 1.5 bathrooms for easy living. The well-equipped kitchen includes essential appliances while the patio offers a cozy outdoor space. Benefit from in-unit laundry hookups and 24/7 maintenance for peace of mind. Lawn care is included, making it effortless to enjoy your home. This pet-friendly townhome ensures your furry friends are welcome too—all wrapped up in perfect comfort and convenience.

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Outdoor Space

Dishwasher

In-Unit Laundry

On-Site Laundry

114 Georgia St - Photo 1 of 1

1d ago

Apartment for rent in Winchester

114 Georgia St, Winchester, KY 40391

1 bed

1 bath

$850

Apartment for rent

Frontier Crossing Apartments - Photo 1 of 1

1d ago

8.8

Very good

Frontier Crossing Apartments

100 Boyd Pl, Winchester, KY 40391

Package service | Outdoor space

4 beds

2 baths

$1,500

Apartment for rent

Pet-Friendly Living with Modern Comforts

Residents of Frontier Crossing Apartments enjoy a stunning 2-bedroom space in Winchester, KY, designed for modern living. The community features a fitness center, on-site dog spa, and includes water, sewer, and trash services in the rent. Conveniently located with easy access to I-75, this pet-friendly apartment also offers an in-unit washer and dryer, making life a breeze. Lawn care is included, ensuring the outdoors are beautiful year-round.

16 Central Ave - Photo 1 of 1

2d ago

8

Very good

16 Central Ave

16 Central Ave, Winchester, KY 40391

4 beds

3 baths

$1,750

Apartment for rent

Bright & Modern Family Home Designed for Comfort

Residents of 16 Central Ave enjoy a spacious 4-bedroom, 3-bathroom layout that exudes modern elegance. The open design features a contemporary kitchen perfect for entertaining and comfortable living spaces ideal for families. With stylish finishes and ample storage, this home is a perfect blend of style and convenience, tailored for everyday life.

135 Winn Ave - Photo 1 of 1

2d ago

8.3

Very good

135 Winn Ave

135 Winn Ave, Winchester, KY 40391

3 beds

2 baths

$1,600

Apartment for rent

Bright & Modern Living in a Renovated Retreat

Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area complemented by a modern kitchen. Designed for comfort and style, this residence boasts contemporary finishes and spacious layouts, providing all the essentials for modern living. Ideal for families or anyone looking for a move-in ready home with a fresh, modern ambiance.

HAD222 - Photo 1 of 1

2d ago

8.8

Very good

HAD222

222 Mutual Ave, Winchester, KY 40391

2 beds

1 bath

$1,075

Apartment for rent

Fairfield Way - Photo 1 of 1

2d ago

Townhouse for rent in Winchester

3 beds

2.5 baths

$1,599

House for rent

155 Chatham Place - Photo 1 of 1

2d ago

8

Very good

155 Chatham Place

155 Chatham Pl, Winchester, KY 40391

2 beds

2 baths

$1,195

Apartment for rent

Meadow Creek Phase 1 - Photo 1 of 1

4d ago

8.5

Very good

Meadow Creek Phase 1

100 Buffalo Trce, Winchester, KY 40391

In-unit laundry | Outdoor space

2 beds

1 bath

$1,125

Apartment for rent

Charming 2-Bedroom Retreat with Private Patio

Residents of Meadow Creek Phase 1 enjoy a bright and inviting living space in a peaceful community. This lovely 2-bedroom, 1-bath apartment features a practical kitchen and spacious bedrooms, perfect for daily living. Step outside to unwind on the private patio or take advantage of the convenient location just minutes from shopping and dining, with easy access to I-75. Experience comfort and convenience wrapped in one delightful package!

Review from the web

I live here. Great place to live.

- Christine Ross on Jun 9, 2016
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200 Hubbard Studios - Photo 1 of 1

4d ago

8.3

Very good

200 Hubbard Studios

200 Hubbard Rd, Winchester, KY 40391

In-unit laundry | Outdoor space

Studio

1 bath

$795

Apartment for rent

Modern Studio Living in a Prime Location

200 Hubbard Studios offers a stylish, open-concept living space with a full bathroom, perfect for comfort and convenience. This pet-friendly studio features in-unit laundry, making chores a breeze. Enjoy the hassle-free lifestyle with water, sewer, and trash services included in the rent while being just steps away from shopping, dining, and entertainment options. Experience beautifully maintained surroundings with lawn care provided—step into your new home today!

17 W. Lexington Avenue - Photo 1 of 1

4d ago

8.5

Very good

17 W. Lexington Avenue

17 W Lexington Ave, Winchester, KY 40391

Studio

1 bath

$750

Apartment for rent

Bright Studio Living in Downtown Convenience

Located in downtown Winchester, this spacious studio boasts newer flooring and paint with huge windows that flood the space with natural light. Enjoy the convenience of all utilities included, making budgeting a breeze. Walking distance to local shops, restaurants, and entertainment ensures vibrant city living. This first-floor apartment promises comfort and accessibility—schedule a visit to experience your new home today!

213 W. Hickman St - Photo 1 of 1

4d ago

7.9

Very good

213 W. Hickman St

213 W Hickman St, Winchester, KY 40391

2 beds

1 bath

$875

Apartment for rent

Cozy Space with All Utilities Included!

This charming one-bedroom, one-bath unit is packed with appeal and space, featuring all utilities included for hassle-free living. Conveniently located near schools and shopping, it offers the perfect balance of comfort and accessibility. With a monthly rent of $875 and an equal deposit, this unit is available for those ready to make it their own. Applications are required before viewing—don’t miss the chance to snag this delightful home!

321 S. Maple St - Photo 1 of 1

5d+ ago

8.6

Very good

321 S. Maple St

321 S Maple St, Winchester, KY 40391

In-unit laundry | Dishwasher

1 bed

1 bath

$875

Apartment for rent

Charming Renovated Apartment with Modern Flair

321 S. Maple St offers a fully renovated 1-bedroom, 1-bath apartment in Winchester with adorable modern updates. Enjoy new appliances, unique features, and the convenience of in-unit laundry. With its cozy ambiance and charming details, this unit promises to be a delightful retreat. Don't miss the chance to make it yours—get your application in today!

204-206  S Maple - Photo 1 of 1

5d+ ago

8

Very good

204-206 S Maple

204 S Maple St, Winchester, KY 40391

2 beds

1 bath

$1,300

Apartment for rent

117 Linden Ave - Photo 1 of 1

5d+ ago

8.1

Very good

117 Linden Ave

117 Linden Ave, Winchester, KY 40391

3 beds

2 baths

$1,700

Apartment for rent

Tranquil Family Retreat with Modern Comforts

117 Linden Ave offers a welcoming 3-bedroom, 2-bathroom sanctuary featuring 1300 square feet of stylish living space. Bright interiors and a spacious layout enhance comfort, while the tranquil backyard provides an ideal spot for relaxation or entertaining. This pet-friendly home promises a warm atmosphere, ensuring everyone feels at ease. Conveniently located near shopping, it strikes the perfect balance between functionality and style.

240 Chatham Place - Photo 1 of 1

5d+ ago

8.1

Very good

240 Chatham Place

240 Chatham Pl, Winchester, KY 40391

2 beds

2 baths

$1,195

Apartment for rent

Spacious Townhome with Convenient Layout

Residents of 240 Chatham Place enjoy a thoughtfully designed townhome featuring two bedrooms, a full bath, and convenient half baths, including an attached bath to the master suite. The inviting living area, kitchen, and laundry facilities are conveniently located downstairs. With lawn care included and two dedicated parking spots, this home combines comfort and practicality. Move-in ready for a seamless living experience!

48 Jackson St #1 - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

48 Jackson St #1, Winchester, KY 40391

In-unit laundry | Air conditioning | Assigned parking

2 beds

1 bath

$1,100

Apartment for rent

Available Mar 14

Modern & Cozy Apartment with Pet-Friendly Perks

Enjoy comfortable living in this fully renovated 2-bedroom, 1-bath apartment featuring granite countertops and a modern kitchen equipped with essential appliances. The unit boasts durable tile and luxury vinyl plank flooring, along with convenient in-unit washer and dryer hookups. With assigned parking and predictable utility costs, this move-in ready space is perfect for tenants looking for an updated, pet-friendly home.

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365 Colby Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Winchester

2BR/2.5BA

365 Colby Rd, Winchester, KY 40391

Garage parking | Dishwasher

2 beds

2.5 baths

$1,175

Apartment for rent

Modern 2-Bed Apartment with Garage Parking

Enjoy living in this stylish 2-bedroom, 2.5-bath apartment featuring a spacious 1,100 sq ft layout. The home includes essential appliances like a dishwasher, range, and refrigerator, plus convenient washer/dryer hookups. Additionally, residents will benefit from garage parking. This modern space is perfect for those looking for comfort and convenience in a contemporary setting.

4971 Old Boonesboro Rd - Photo 1 of 1

5d+ ago

House for rent in Winchester

Charming 3 Bed/2 Bath Home in Winchester, KY

4971 Old Boonesboro Rd, Winchester, KY 40391

In-unit laundry | Carpet | Dishwasher

3 beds

2 baths

$1,400

House for rent

Available Mar 1

Modern 3-Bed Manufactured Home on Scenic Farm

This beautifully designed 3-bedroom, 2-bathroom manufactured home offers modern living since its 2019 placement on a picturesque farm. With 1,050 sq ft of cozy space, it features essential amenities like a dishwasher, microwave, and in-unit laundry. Enjoy the convenience of select utilities included and a dog-friendly policy, perfect for small pets. This inviting home combines comfort and practicality in a tranquil setting.

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

Spacious 3-Bed Home with Cozy Backyard Oasis

This inviting 3-bedroom, 2-bath home boasts 1,780 sqft of comfortable living space and a nice size backyard, perfect for family gatherings or relaxation. Convenient access to the interstate and local amenities adds to its appeal. Enjoy modern comforts with air conditioning and a dishwasher, making everyday living a breeze. Dog-friendly property inviting those looking for a home with ample outdoor space in a prime location.

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 Townhome with Private Patio & Dog Park

This stylish 2-bedroom, 2.5-bathroom townhome features modern finishes and abundant natural light throughout its 1,100 sq ft. Enjoy the fully equipped kitchen with stainless appliances, an in-unit washer/dryer, and a private patio with storage. Located in a peaceful area with an on-site dog park and picnic spot, it's just minutes from the heart of Winchester. This pet-friendly home is perfect for comfortable living in a welcoming community.

Showing 1 - 30 of 30 results
Home > Apartments in Winchester
Updated: March 25, 2026

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Learn more about renting in Winchester, KY

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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?

The average rent for a 1-bedroom apartment in Winchester, KY is $882, while a 2-bedroom apartment averages $1,154.

Are there pet-friendly apartments in Winchester, KY?

Yes, there are pet-friendly apartments in Winchester, KY. Approximately 27.93% of the listings are pet-friendly, with 13 such listings available.

Are utilities usually included in rent in Winchester, KY?

About 11% of the apartment listings in Winchester, KY include utilities in the rent.

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 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.

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