Winchester Kentucky homes for sale starting at Fifty Thousand Dollars

$3,175,000 - Winchester, KY

4664 Lexington Road Winchester, KY - Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot residence offers eight bedrooms and 7.5 bathrooms. Classical elements, from the refined columns to the oversized fanlight, add gravitas. Immaculately maintained, the home's warm interiors and fine millwork provide a welcoming backdrop for decor. Designer details include stylish wallpapers, tray ceilings, marble accents, & elegant fireplaces. A sunny walk-out lower level provides additional living space including a full kitchen and second laundry room. Ample storage including well-designed closets are found throughout. An attached 4-car garage accommodates vehicles. Outside, a workshop adds space for leisure and hobbies. Mature trees provide a pleasing backdrop for the large in-ground pool and outdoor living spaces. A barn and verdant fields also allow for equestrian pursuits.

$1,249,500 - Winchester, KY

700 Nick Lane Winchester, KY - 🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you can enjoy both style and comfort. This farm is ready to work with a brand-new 2,000 sqft metal pole barn—plenty of space for storage, projects, or hobbies. There's also a classic 10-bent barn at the back of the property, adding some old-school charm and functionality. With city water running throughout the farm, everything is super convenient. Whether you're looking to start a farm, expand your operations, or just enjoy wide-open spaces and fresh air, this property checks all the boxes. It's the perfect mix of practical and peaceful country living.

$1,200,000 - Winchester, KY

6237 Bybee Road Winchester, KY - Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that includes a first-floor primary suite with a fireplace, sitting area, and private wrap-around porch. The gourmet kitchen connects to a butler's pantry, prep area, breakfast room, and formal dining room, ideal for entertaining. Upstairs offers two more primary suites, 2 more spacious bedrooms, and a private study/office with a fireplace. An elevator provides easy access to all three levels. The finished walkout lower level includes an in-ground pool, outdoor bar, private bath, movie room, rec space, and 1100+ sq ft of storage. Custom moldings, built-ins, hand painted Kohler sinks and hardwood floors throughout—this is luxury living at its finest! Other notable features include a 3 car garage, finished storage space above the garage & unfinished storage in the basement.

$999,900 - Winchester, KY

2447 Clintonville Road Winchester, KY - What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been beautifully updated with gleaming, newly refinished hardwood floors, tall ceilings and lavish woodwork. The two story Entry is flanked by a formal Dining Room with a double tray ceiling. The spacious Kitchen has cream cabinetry with pull out shelving in many cabinets, granite countertops and a large island for bar stools. Stainless appliances complete this chef's Kitchen which opens to a Breakfast Area with French doors to a balcony overlooking the adjacent farm. The huge Great Room features a vaulted ceiling, lovely carved mantle fireplace and entertainment center which will remain with the house. There are two Bedrooms on the main level with a remodeled full Bathroom. The second floor has a spacious Primary Suite with vaulted ceiling. The Primary Bath offers beautiful cabinetry with double sinks and an amazing marble shower. The finished, walkout Basement features a Theatre Room, Rec Room, full Bath, large storage closet and 2 car Garage.

$995,000 - Winchester, KY

1150 Craig Crossing Winchester, KY - Stunning new construction featuring 5 bedroom. 3.5 bath nestled on roughly 2.5 serene acres, surrounded by picturesque farmland and panoramic views. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and tile throughout. Primary bathroom is gorgeous with a freestanding soaker bathtub, tile shower, custom dual vanities and granite countertops. Unwind on the covered back porch. Cozy up by the stone fireplace in the great room. Enjoy the separate laundry room also with custom cabinets, folding space and granite. This home offers and abundance of sunlight and a side entry garage. Large walk-in storage room for all your extra items! Covered entry space for all your deliveries. 4 bedrooms on the main floor. Roughly 21 minutes to Hamburg in Lexington, 20 minutes to I-75 / I-64 interchange, with multiple drive options. Roughly 5 minutes to grocery options and variety stores. Don't wait to build, this one is move in ready, just add your decor and enjoy!

$990,000 - Winchester, KY

1701 Gay Evans Road Winchester, KY - Escape to your own private retreat with this beautiful brick ranch set on 8 plus acres. This home boasts a bright and airy sunroom, perfect for enjoying morning coffee watching the sunrise or unwinding with the nature views. The fully finished basement offers extra living space, while the in-ground pool is ready for summer fun. This property offers a two-car attached garage as well as a detached garage with a loft above providing endless possibilities--workshop, guest space, or storage. This is country living at its best!

$989,000 - Winchester, KY

1110 Craig Crossing Winchester, KY - Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room features a coffered ceiling, gas fireplace with custom mantle, and custom paneling. The heart of the home is the gourmet kitchen, boasting flush inset white oak cabinetry, Taj Mahal quartz countertops with full slab splash back, and premium ZLINE appliances, including a 36' gas range, refrigerator, built-in microwave, and dishwasher. The luxurious master suite offers a vaulted, box-beamed ceiling, a spa-inspired bathroom with a freestanding soaking tub, large walk-in shower, and a generous walk-in closet. There are multiple selections remaining for buyers that include outdoor kitchen, interior paint colors, landscaping/shrubbery, and one exterior color selection. Large in-ground pool to be completed within coming week. Schedule your showing today!

$950,000 - Winchester, KY

186 Chardonnay Court Winchester, KY - Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio features stunning rock landscape with a firepit creating a perfect setting for gatherings and starlit nights. Oversized bedrooms with walk in closets provide an abundance of storage solutions throughout the home. Elegant hardwood flooring adds warmth and character to the first floor living spaces with LVP in the finished basement area. The basement offers a versatile space for entertainment, a home office or a playroom. The basement also has the extra convenience of hosting and entertaining. An oversize lot, more than 3/4 of an acre, with historical connections to the area add charm to the property. This property is well worth a visit in order to see all that the home has to offer.

$849,000 - Winchester, KY

150 Jones Nursery Road Winchester, KY - Experience the perfect blend of modern comfort and country charm in this stunning 4-bedroom, 3.5-bathroom Craftsman-style home, built in 2018. Nestled on 2.58 acres of scenic countryside, this property offers the serenity of rural living with convenient access to Lexington. Designed for both style and functionality, the spacious interior features a chef's kitchen with custom countertops, a large island, and ample space for entertaining. The light-filled living areas create an inviting ambiance, while the expansive primary suite boasts a luxurious bath and an oversized walk-in closet. Outside, take in breathtaking farmland views and enjoy the freedom of open space. Whether you're seeking privacy, modern conveniences, or the perfect setting to unwind, this exceptional home delivers.

$839,000 - Winchester, KY

Winchester, Kentucky listings for sale

End of list

There were no properties mapped for this search