About Winchester

Set amid a spectacularly scenic Bluegrass landscape, the charming Kentucky town of Winchester is the proud seat of Clark County. Winchester homes come in all styles, sizes and ages, and whether home seekers choose to settle in the alluring rural outskirts or the historical downtown area, they will soon feel at home in this friendly city.

Real Estate Statistics
Total Listings 5,430
Average Price $311,133
Highest Price $17,250,000
Lowest Price $0

Serach Winchester, KY Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000

Serach Winchester, KY Real Estate Listings

153 Properties Found. Page 1 of 13.
Photo of Listing #20122439

4274 Colby Road, Winchester

$3,999,000 - 84,763 Sf

MLS® # 20122439

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Photo of Listing #20122437

4274 Colby Road Road, Winchester

$3,999,000 - 84,573 Sf

MLS® # 20122437

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Photo of Listing #1822360

7850 Veterans Memorial, Winchester


MLS® # 1822360

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Photo of Listing #1806899

2070 Boonesboro Road, Winchester


MLS® # 1806899

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Photo of Listing #20101924

1509 Boonesboro Road, Winchester


MLS® # 20101924

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Photo of Listing #20118322

321 Venable Road, Winchester

$1,850,000 - 16,857 Sf

MLS® # 20118322

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Photo of Listing #20104634

3 Shoppers Drive B, Winchester


MLS® # 20104634

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Photo of Listing #20106412

1305 Irvine Road, Winchester

$1,400,000 - 4 Beds, 3 Baths, 2,664 Sf

MLS® # 20106412

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Photo of Listing #20110358

490 Oil Springs Road, Winchester

$1,200,000 - 4 Beds, 3 Baths, 2,736 Sf

MLS® # 20110358

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Photo of Listing #20110329

490 Oil Springs Rd, Winchester

$1,200,000 - 4 Beds, 3 Baths, 2,736 Sf

MLS® # 20110329

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Photo of Listing #20104630

2 Shoppers Drive D, Winchester


MLS® # 20104630

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Photo of Listing #20119501

7100 Wades Mill Road, Winchester

$1,100,000 - 3 Beds, 3 Baths, 1,960 Sf

MLS® # 20119501

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Discover Winchester's Charming Homes for Sale

As befits this attractive Kentucky city, with its many renovated historic buildings, the variety of Winchester houses for sale is sure to satisfy any eager home buyer. Those with a desire for country life may choose beautifully restored heritage homes, or spectacular newer properties, set in expansive and tranquil surroundings. A good selection of fine family houses, located in highly popular neighborhoods, can be found close to the town's scenic core and Clark County schools.

Winchester homes for sale are often found on acreages and farmland. Farmland in this area is highly sought after for its fertile soil. The earth is nourished by limestone, giving the land all the nutrients it needs to produce top-quality crops. Land in this area is quite flat, which is an ideal farming terrain.

There are tons of open lots ready to be made into farmland in Winchester real estate. These acreages offer buyers the amazing opportunity to start their own farms and build the home of their dreams.

It’s common to find properties with fantastic barns built for housing plenty of livestock and horses. Some of the largest properties will even have equipment barns, so you can store everything with ease.

Winchester are some of the most charming homes for sale in the area. At the end of gated, tree-lined driveways you’ll find gorgeous historic homes with timeless brick facades. These homes keep their original charm with crown mouldings and wood-burning fireplaces. Oftentimes, historic properties have had modern renovations where kitchens and bathrooms have been upgraded.

Homes on acreages are made for growing families. They typically have four or more bedrooms, so there’s plenty of space for everyone. Some of the most luxurious properties in Winchester have private swimming pools, perfect for hot summer days and outdoor entertainment.

Amenities & Attractions in Winchester, Kentucky

Winchester is located in the desirable Clark County where the Appalachians meet the Bluegrass. The city is only 20 minutes away from Lexington, making it a prime location for those wanting to live a small-town lifestyle with the amenities of a big city.

Winchester is close to tons of great outdoor attractions like parks and hiking trails. Natural Bridge State Park is a local favorite, with countless amenities and activities right in the park. This is an excellent place to go for a hike through the wooded landscape and camp over the weekend. Swim in the public pool or canoe and kayak in the Middle Fork Red River.

Lower Howard’s Creek is another fantastic spot to get out and learn more about nature. You can walk the trails along the creek’s edge and traverse walking bridges over the water. The preservation program at the creek is intended to provide visitors with education about the landscape, and is meant to protect endangered and threatened species in the area.

Pilot Knob State Nature Preserve is a wonderful 4-mile hiking trail that will take you to see breathtaking waterfalls and astounding forests. You don’t want to miss this hike!

Winchester, Kentucky was founded in 1973 and has an incredibly rich history. You can learn more about this history at the Bluegrass Heritage Museum located downtown Winchester. This museum displays exhibits that teach visitors about the city’s history, from the Eskippakithiki Indian Village to the present town of Winchester.

A large part of Kentucky’s history is Ale-8-One. Kentucky has proudly called this soft drink their own since 1926, and the plant is located right in the heart of Winchester. You can tour the facility and learn about how they make the drink and how the company has evolved over the years.

Downtown Winchester is an exceptional area for its wide array of antique shops. Visit these funky shops for eclectic finds:

  • Bentley and Murray
  • Mason on Main
  • Eklektic Alchemy

The downtown core is also packed with locally owned restaurants that serve homemade, American cuisine. Try out these highly-rated eateries for splendid dinners out:

  • DJ's Bar and Grill
  • Graze Market and Cafe
  • Blue Isle Home-Style Restaurant and Bar

There are a number of recognized schools in Winchester that serve the many educational needs of the residents of the town, so those taking their children to school don’t have to commute outside of the city.

The peaceful and easy-going lifestyle of Winchester, KY will have you living in a dream. This small-town is perfect for buyers looking for large properties with tons of room for growing families.

Please contact Turftown Properties online or call (859) 268-4663 or (888) 268-4664 and we'll be happy to assist you in any way we can, from providing local real estate advice, to neighborhood tours to finding real estate in Winchester that meets your individualized needs.

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Lexington-Bluegrass Assocation of Realtors LogoThe data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Lexington-Bluegrass Association of Realtors Multiple Listing Service. Real estate listings held by IDX Brokerage firms other than Turf Town properties, inc. are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX Brokers.Information Deemed Reliable but Not Guaranteed©2021 LBAR Multiple Listing Service. All rights reserved.