Winchester Land

View Winchester, KY land for sale below! Winchester is a gorgeous city in the Lexington-Fayette, KY Metropolitan area. Similar to other areas in Kentucky, this charming community was named after an important city in Virginia. Winchester has tremendous amounts of character, and this lively area honors its rich history with preservation of historic buildings and development that celebrates and protects the natural beauty that runs through it.

Sun rising over trees and a fence on farm land typical of Winchester, Kentucky

Winchester Land Real Estate Statistics

Average Price $142K
Lowest Price $10K
Highest Price $2M
Total Listings 87
Avg. Days On Market 247
Avg. Price/SQFT $100K

Property Types (active listings)

Learn more about the family-friendly and community-minded city of Winchester.

Search Winchester Property Listings in Kentucky

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1509 Boonesboro Road, Winchester

$2,000,000

1509 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 20101924

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2527&2439 Grimes Mill Road, Winchester

$575,000

↓ $60,000

2527&2439 Grimes Mill Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22008183

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East Broadway Street, Winchester

$450,000

↓ $54,000

East Broadway Street, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 1607828

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2990 Pretty Run Road Lot #1, Winchester

$325,000

2990 Pretty Run Road Lot #1, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 20111823

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4700 Boonesboro Road, Winchester

$299,000

4700 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024790

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4750 Boonesboro Road, Winchester

$299,000

4750 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024791

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4878 Boonesboro Road, Winchester

$249,000

4878 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024789

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4800 Boonesboro Road, Winchester

$249,000

4800 Boonesboro Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024793

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2620 Pretty Run Road Lot #8, Winchester

$199,000

2620 Pretty Run Road Lot #8, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 20111815

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990 Craig Crossing Road, Winchester

$195,000

990 Craig Crossing Road, Winchester

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

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1030 Craig Crossing Road, Winchester

$180,000

1030 Craig Crossing Road, Winchester

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

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2350 Pretty Run Road Lot #12, Winchester

$175,000

2350 Pretty Run Road Lot #12, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 20111813

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7440 Bybee Road, Winchester

$160,000

7440 Bybee Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22022868

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1280 Craig Crossing Road, Winchester

$150,000

1280 Craig Crossing Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22005002

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120 Knox Court, Winchester

$150,000

120 Knox Court, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024088

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125 Knox Court, Winchester

$150,000

125 Knox Court, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024090

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115 Knox Court, Winchester

$150,000

115 Knox Court, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22024091

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280 Wells Road, Winchester

$132,000

280 Wells Road, Winchester

0 Beds 0 Baths 0 SqFt Land - Farm/Land MLS® # 22019896

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More About Winchester Properties For Sale

When it comes to real estate opportunities, Winchester land for sale is the perfect mixture of lush, rolling landscapes, and historic charm. Those who are interested in owning a rural property will find that land in Winchester offers buyers a wealth of opportunity. Whether you're interested in a hobby farm where you can keep a few horses, or you're on a search for dozens of acres where you can dive into a commercial agriculture venture, you will find what you're looking for.

Winchester properties for sale are the perfect place to enjoy country living. With excellent forages for cattle, an abundance of tillable land for farming, and plenty of shade for livestock, these acreages will provide you with a healthy and productive farm. Land for sale in Winchester, KY is extremely affordable, promising something for every type of budget.Winchester KY Land For Sale

Strike the perfect balance between modern convenience and privacy, and invest in a six-acre lot where you can build your dream home in view of rolling hills, lush deciduous trees, and blue skies, yet enjoy manageable yard upkeep. There's a pleasing selection of level and rolling hill lots, so whether you prefer to be perched on a hilltop or at the bottom, you'll have the pick of the lot in this city.

On the low end of the market, find properties valued under $100,000. These can be perfect for a first-time buyer interested in building their own home. If you're good with your hands and have a vision in mind of the perfect Kentucky house, land can be an incredible opportunity to invest in an affordable plot and transform it into the home of your dreams. If you love to cook, create an expansive kitchen with lots of space to host friends and family for a meal. If you've always dreamed of having a living room with a handsome brick fireplace, building your own home is the perfect opportunity to do just that.

The most expensive properties for sale in Winchester can be purchased for $500,000 or more. These 40-acre properties can be transformed into a commercial horse farming venture, an agriculture opportunity, or can even be divided up into smaller lots by those interested in developing large parcels of land. The only limit on what is possible is imagination.

Living In Winchester, KY

Winchester is the ideal place to call home for both growing and established families. Residents of Winchester real estate will find that there's plenty to keep them busy. The Red River Gorge Geographical area spans nearly 30,000 acres and contains a complex system of canyons. The area is popular among climbers, and the series of natural bridges, waterfalls, and vistas of the Red River offer hikers and nature enthusiasts an incredible afternoon in the woods.

Those interested in caving will find that Daniel Boone National Forest has one of the world's largest concentrations of caves. Numerous lakes, rivers, and waterfalls make this an exceptional place to enjoy a swim. Other activities that can be done in Daniel Boone National Forest include:

  • Camping
  • Fishing
  • Hunting
  • Horseback riding
  • Hiking
  • Picnicking
  • ATVing

There's also the Bluegrass Heritage Museum and Historic Downtown Winchester to explore. Winchester has something for everyone. Or if you prefer a bustling city, you can simply head to Lexington, which is only 23 miles away. Additionally, Winchester is home to the Bluegrass Community and Technical College as well as recently renovated and athletically inclined, George Rogers Clark High School.

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