3760 Old Boonesboro Road, Winchester, KY 40391

• 5 beds |
• 5 baths |
• 5,666 sqft

Property Description

Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end finishes, and the home offers multiple unique spaces for relaxing or entertaining. From the second floor, enjoy your own private balcony overlooking the expansive backyard and in ground pool. On the main level, a covered porch provides easy access to the pool area, along with a convenient exterior door leading directly to a small bathroom—perfect for swimmers. The basement is also a cozy retreat including a living area with a stone fireplace and a bar, another full bed and bathroom, plus a bonus space that could be used as an exercise room or a creative space. Recent updates include new tile and hardwood flooring and fresh interior paint. Outside, the fully fenced yard is beautifully landscaped with mature trees and manicured lawn. This property also includes a separate garage ideal for hobbyists, a storage building with a screened room suitable for chickens or small animals, and a full 2,000 sq ft barn—offering endless possibilities for country living.

Listing Status:

Pending

Date Added:

April 8, 2026

Data Last Updated:

May 21, 2026 at 1:39AM

Listing Office:

Freedom Realty & Property Management : 859-771-0777

MLS ID:

26006697

Interior

• General: Breakfast BarEntrance FoyerEat-in KitchenPrimary First FloorWalk-In Closet(s)Ceiling Fan(s)Soaking Tub
• Appliances: DishwasherMicrowaveRefrigeratorOvenRange
• Laundry: Electric Dryer HookupMain LevelWasher Hookup
• Basement: Exterior EntryFinishedWalk-Up Access
• Flooring: CarpetCeramic TileHardwood
• A/C: Heat PumpMulti Units
• Heating: Heat Pump
• Fireplace: BasementFamily RoomFireplaceFireplaces: 2
• Disability Feature: Accessible Common Area

Exterior

• General: Barn(s)Shed(s)
• Style: Contemporary
• Other Structures: Barn(s)Shed(s)
• Pool: In Ground
• Parking: Attached GarageDetached GarageDrivewayGarage Door OpenerOff StreetGarage Faces Rear

Construction

• Roofing: Dimensional StyleShingle
• Windows: Blinds
• General: StoneWood SidingOne and One HalfBlockConcrete Perimeter

Location

• Originating MLS: Imagine MLS (Bluegrass REALTORS®)
• School District: Clark County - 7
• County: Clark

Lot

• Zoning: 044-0000-042-00
• View: RuralFarmView
• Fencing: Other

Utilities

• Utilities: Electricity ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Imagine MLS (Bluegrass REALTORS®)