Winchester, Kentucky listings for sale

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$1,479,000 - Winchester, KY
700 Nick Lane Winchester, KY - 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.
2022 | 3 | 2 | 2,400 sqft.
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$1,185,000 - 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 property features a beautiful brick home built by Michael Childers to use as his main residence. 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 covered 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, plus French doors opening to a balcony. There are two additional Bedrooms and a remodeled Bath on this floor. The finished, walkout Basement features a Theatre Room, Rec Room, full Bath, large storage closet and 2 car Garage. 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. This property has so much to offer and is move in ready!
1989 | 5 | 4 | 4,058 sqft.
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$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!
2025 | 5 | 4 | 2,842 sqft.
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$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!
2003 | 4 | 4 | 4,221 sqft.
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$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!
2025 | 4 | 2 | 2,670 sqft.
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$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.
1994 | 4 | 2 | 5,290 sqft.
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$850,000 - Winchester, KY
1183 The Ridings Winchester, KY - This beautiful 5 bedroom 3 full bath home sits on 5 acres in The Ridings at Colby. This neighborhood has horseback riding trails throughout & is a 15 minute drive to the Hamburg/Lexington area. Large eat in kitchen with island, granite countertops & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax in either your living room or large family room with beautiful exposed beams & bar area with sink. First floor primary has walk out access to the covered back porch and a primary bath with double vanity, large walk in shower & lovely stand alone soaker tub. A breezeway connecting attached garage has built in shelving & heating/cooling keeping your coats & boots warm in the winter. The attached garage, used as a home office has a PTAC unit, so it is also heated and cooled. Upstairs you will find 4 more bedrooms & 2 full bathrooms as well as a finished attic which is also heated & cooled. There is a large 36' x 28' detached garage with large level parking area as well as a greenhouse for your gardening projects. Voluntary HOA $50/year
1989 | 5 | 3 | 3,664 sqft.
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$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.
2017 | 5 | 4 | 3,384 sqft.
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$839,000 - 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.
2017 | 5 | 4 | 3,384 sqft.
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$829,900 - Winchester, KY
8129 Wades Mill Road Winchester, KY - This is what BARDOMINIUM Dreams are made of!!!! Welcome to your barndo retreat — an expansive 92' x 120' steel-framed structure situated on 4.27 partially fenced acres with breathtaking pond views and unmatched amenities for both living and working. This massive structure boasts an open-concept interior layout with endless potential! Ideal for combining luxury living with functional workspace. Designed with the enthusiast in mind, it features a 15+ car garage with a 12,000 lbs. capacity hydraulic lift, 8' thick concrete in the lift area, built to withstand heavy duty use, 6' throughout the rest of the shop. When designing this space nothing was overlooked! Climate controlled shop consist of numerous 220 outlets, concrete drain that extends through both sides of the space, paint booth with ventilation system and so much more. Perfect for collectors, mechanics, or business operations. Power outages are never a concern thanks to the Generac whole-house generator, ensuring uninterrupted comfort and security. Outdoors, enjoy serene views of the stocked pond from your private fishing dock. A fenced in area for your farm animals, with a run in shed and automatic waterer.
2017 | 2 | 3 | 12,900 sqft.