Luxury homes for sale & real estate in Winchester, KY

Luxury Home for sale in Winchester, KY:

Royal Oak farm is a well located 283 acre working Horse Farm between Lexington and Paris KY, just 1.8 miles off famed Paris Pike. The current owners have created and designed an efficient and pleasing property on which to raise the best equine athletes in the world. Amenities include a lovely 2 story brick main residence and pool, built in 2005 with over 5,500 sqft of living space that include 5 bedrooms 4 full baths, the 1st floor contains a large kitchen, expansive great/family room, formal living and dining rooms, lovely fireplaces, all with 10ft ceilings and antique hardwood floors. Farm improvements include 70 stalls in 6 barns, over 20 paddocks and 8 large fields, a maintenance and ha

Luxury Home for sale in Winchester, KY:

Welcome to unparalleled space and sophistication in this fully remodeled, custom 5-bedroom, 5-bathroom estate, perfectly situated on just over an acre. This is the definition of a move-in-ready dream home, meticulously designed for today's lifestyle, including seamless multi-generational living. Enjoy grand scale Living with 5 bedrooms and 5 bathrooms, every resident enjoys privacy and comfort. The generous floor plan offers expansive common areas perfect for large family gatherings and entertaining. Step into your gourmet showcase kitchen in the heart of the home with brand-new, high-end stainless steel appliances, gleaming granite countertops, and custom cabinetry. The fully finished base

Luxury Home for sale in Winchester, KY:

Welcome to your dream estate, nestled at the back of highly sought after Shiloh Pointe neighborhood. If you are looking for the perfect blend of luxury, privacy, and practicality, this property checks every box. This gorgeous custom built home is set well back from the street and surrounded by mature trees providing total privacy on 4.2 acres of natural beauty, but only minutes from the convenience of town. The main residence provides a generous 9100 sqft of space with soaring ceilings and expansive windows ushering in natural light and views of the woods beyond. 7 bedrooms and 9 full baths spread across multiple living areas make this home perfect for a large family or multiple generations

Luxury Home for sale in Winchester, KY:

A truly rare opportunity in Warriors Trace! Discover true artisan quality in this owner-built, custom-crafted residence. Home has a 3 car attached and 4 car detached building. This home combines exceptional workmanship with expansive, family-ready space. Before you enter the home there is a gorgeous arch barrel ceiling and upon entering the home you are greeted by a large den with beautifully detailed coffered ceilings. The mantle is handmade with marble and there is a beautiful book shelf for showcasing anything your heart desires. The formal dining room and seating area has six foot wide and eight foot tall windows. These rooms have 12' tall ceilings with stunning chandeliers that have ha

Luxury Home for sale in Winchester, KY:

This +/- 155 acres standardbred horse farm in Bourbon County is a proposed subdivision of a main tract located at 351 Spears Mill Rd in Paris, Kentucky, with a 5/8 mile oval standardbred track, and approximately 1,200 feet of road frontage. The property includes a 3-bedroom, 1-bath house sold "as-is" for renovation, a converted 18-stall tobacco barn (120 x 60 feet) with stalls measuring 11 x 13 feet, a wash stall, and a storage room. An attached open-side shed provides additional equipment and storage space. The farm also features 18 paddocks (ranging from +/- ½ acre to acre), with 16 turn out paddocks with small run-in sheds and automatic waterers, as well as 3 pastures

Luxury Home for sale in Winchester, KY:

Welcome to this remarkable 94-acre estate ideally situated on highly sought-after Paris Road in Mt. Sterling, Kentucky. This property offers the rare combination of peaceful country living with convenient access to town amenities and I-64, making it a perfect fit for those seeking space, functionality, and timeless charm. Rolling pastures, fenced fields, multiple ponds, and well-maintained barns create a setting ideal for horses, cattle, or recreational use — all surrounded by scenic countryside views that capture the beauty of Kentucky farm life. The main residence is a beautifully revived farmhouse encompassing over 3,900 sq. ft showcasing a thoughtful balance between character and