Winchester

Find Winchester, KY farms for sale below! The land on Winchester farms varies quite drastically, with high-quality lands in the west and lower quality acreages in the east. The western lands have such desirable soils that a few families have owned much of the land for multiple generations, as it has become too invaluable to sell for profit. Winchester land has managed to escape the development that has occurred in much of Central Kentucky, resulting in tranquil farms and sprawling lands that go on for miles. Winchester is the closest community to Lexington with the freedom to ride for hours without retracing any steps. As a result, it's a fantastic place for both recreational and professional horse people.


Horse FarmsLand For SaleLand For Sale



Sunrise over a Kentucky farm

Search Winchester Farm Real Estate Listings

Sort by:
2090 Pretty Run Road, Winchester

$5,795,000

2090 Pretty Run Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 23019893

Lexington-Bluegrass Assocation of Realtors Logo

4664 Lexington Road, Winchester

$3,500,000

4664 Lexington Road, Winchester

8 Beds 8 Baths 12,702 SqFt Land - Farm/Land MLS® # 24009605

Lexington-Bluegrass Assocation of Realtors Logo

1395 Two Mile Road, Winchester

$2,500,000

1395 Two Mile Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 23018755

Lexington-Bluegrass Assocation of Realtors Logo

275 Gentry Lane, Winchester

$1,695,000

275 Gentry Lane, Winchester

3 Beds 3 Baths 3,593 SqFt Land - Farm/Land MLS® # 24017370

Lexington-Bluegrass Assocation of Realtors Logo

5810 Van Meter Road, Winchester

$799,500

↓ $199,000

5810 Van Meter Road, Winchester

4 Beds 4 Baths 4,143 SqFt Land - Farm/Land MLS® # 24016912

Lexington-Bluegrass Assocation of Realtors Logo

1275 Old Log Lick Road, Winchester

$775,000

↓ $25,000

1275 Old Log Lick Road, Winchester

3 Beds 2 Baths 1,392 SqFt Land - Farm/Land MLS® # 23009644

Lexington-Bluegrass Assocation of Realtors Logo

1395 Two Mile Road, Winchester

$603,750

1395 Two Mile Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 23018853

Lexington-Bluegrass Assocation of Realtors Logo

1395 Two Mile Road, Winchester

$519,500

1395 Two Mile Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 23018854

Lexington-Bluegrass Assocation of Realtors Logo

4860 Schollsville Road, Winchester

$375,000

4860 Schollsville Road, Winchester

0 Beds 0 Baths 960 SqFt Land - Farm/Land MLS® # 24016371

Lexington-Bluegrass Assocation of Realtors Logo

2110 Athens Boonesboro Road, Winchester

$235,000

2110 Athens Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24004644

Lexington-Bluegrass Assocation of Realtors Logo

835 Midway Road, Winchester

$210,500

835 Midway Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24016554

Lexington-Bluegrass Assocation of Realtors Logo

4700 Boonesboro Road, Winchester

$200,000

↓ $50,000

4700 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24009984

Lexington-Bluegrass Assocation of Realtors Logo

4750 Boonesboro Road, Winchester

$200,000

↓ $50,000

4750 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24009985

Lexington-Bluegrass Assocation of Realtors Logo

4800 Boonesboro Road, Winchester

$200,000

4800 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24009986

Lexington-Bluegrass Assocation of Realtors Logo

4878 Boonesboro Road, Winchester

$200,000

4878 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24009987

Lexington-Bluegrass Assocation of Realtors Logo

990 Craig Crossing Road, Winchester

$195,000

990 Craig Crossing Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22004991

Lexington-Bluegrass Assocation of Realtors Logo

1030 Craig Crossing Road, Winchester

$180,000

1030 Craig Crossing Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22004993

Lexington-Bluegrass Assocation of Realtors Logo

115 Dixon Way, Winchester

$160,000

↓ $15,000

115 Dixon Way, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 24006770

Lexington-Bluegrass Assocation of Realtors Logo


Register Now

Create a free account for unlimited access to exclusive listings. We'll even send you properties that meet your search criteria!

Sign Up for FREE

Invest In Winchester Farms

When you decide to invest in Winchester farms, you'll be met with plenty of options. The Winchester real estate market offers the full spectrum of rural-style properties. Million dollar estates that span more than 200 acres make the perfect space for agriculture or commercial horse farming ventures. Explore expansive properties that are home to handsome heritage houses that date back to the late 1880s and feature exceptional Southern architecture and old-world charm. Find examples of more recent construction that includes every modern amenity and all the convenience of contemporary design.winchester farms

If horses are your passion, you'll find that many of the farm houses in Winchester are accompanied by stables that have space for anywhere between two and ten horses. For some home buyers, this is an exceptional convenience. It's rare to find a farm that has both your dream home and your dream barn, but in Winchester, it is possible.

Winchester homes for sale were designed to offer residents a high quality of life. Wrap-around porches provide an expansive space where homeowners can relax in the sunshine and reflect on rolling hills, brilliant blue skies, and leafy green trees. Living rooms are expansive. Many feature handsome stone fireplaces where families can gather round in the evenings. Many kitchens adopt a large, open kitchen which provides residents ample space to prepare meals in a beautiful, yet functional, space.

Amenities Near Winchester Farms For Sale

Residents of Winchester love living here for its welcoming and warm community and stunning landscapes. This city offers tremendous amounts of character and plenty to do. From a local brewery, to museums, to wineries, to shops, to hiking trails, to restaurants and everything in between, Winchester truly has something for everyone.

When it comes to community, the town of Winchester has a lot to offer. A well-developed parks and recreation sector ensures that residents are never left without things to do. Marathons, fitness classes, swimming, and kids' camps are just the tip of the iceberg when it comes to fun in Winchester. The downtown core is a charming compilation of shops that embody all the charm of a classic American small town. There, you'll find all of your basic needs can be met by a range of independent and major retailers..

Despite the premium farm lands in Winchester, the region has remained relatively void of major horse farms. Nursery Place is currently located in the city, while Bwamazon Farm was originally built in Winchester as well. Meanwhile, a number of smaller horse farms have absolutely flourished. Similar to Nicholasville and Versailles, this city is a pocket community of Lexington. And Winchester farms for sale are affordable, fruitful, and filled with endless opportunities. 

The Clark Regional Medical Center is one of the community's major draws, attracting home owners from the eastern regions of Kentucky. The center is a 79-bed hospital specializing in many areas of practice and offers a general practice clinic with very friendly staff.

Contact Hill & Regan Parker Today

Send us a message online or call us at 859-608-8039!

Login Contact Us

^Back To Winchester Farms For Sale

Beautiful field on a horse farm in Kentucky

Start searching for your dream farm now.

When it comes to convenience, our site is unparalleled. Whether you're in the comfort of your home, or on the go.
Our site works flawlessly on multiple devices so you can find the information you need.

Start Search