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$209,000
3 Beds ⋅ 1 Baths ⋅ 26020135 MLS
This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

32 Jackson St, Winchester
$789,000
3 Beds ⋅ 2 Baths ⋅ 26018078 MLS
**Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses, gardening, recreation, or simply taking in the scenic views, this property is ready for you to make it your own! The detached garage has a second floor office area. There are four other outbuildings for horses, hobbies, or equipment storage. Plenty of fenced areas for horses or other farm animals. The gated entrance provide privacy and security. A rare opportunity to enjoy Kentucky living at its best!

6500 Mount Sterling Rd, Winchester
$235,000
2 Beds ⋅ 2 Baths ⋅ 26018337 MLS
Country living with the convenience of being in the city! This rare find offers over an acre of land inside the Winchester city limits with beautiful views of surrounding farmland. Relax on the spacious partially covered back deck, entertain family and friends, or enjoy plenty of room for gardening, pets, and play. The home features 2 bedrooms, 1.5 baths, and approximately 1,039 square feet of living space on the main level. The finished upstairs adds approximately 385 square feet divided into two bonus rooms currently cooled with a window A/C unit. With the addition of a permanent heat source, this space could easily serve as additional bedrooms, a home office, hobby room, or flex space. Outside you'll find an impressive detached 3-car garage with plenty of room for vehicles, a workshop, or storage, plus a separate storage building for even more space. A remote-controlled gated driveway adds convenience, privacy, and security. If you've been searching for a property that offers the feel of the country while enjoying the convenience of city living, this one checks all the boxes. Potential for second home site! Schedule your private showing today!

47 Hughes Ave, Winchester
$409,500
3 Beds ⋅ 2 Baths ⋅ 26016762 MLS
215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season.

215 Delaplain Rd, Winchester
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 26016393 MLS
Welcome to a truly one-of-a-kind Kentucky estate where luxury, craftsmanship, and country living come together on 27 breathtaking acres in Clark County—just 10 minutes from the interstate for an easy commute while still enjoying complete privacy. Built with exceptional quality and thoughtfully designed by its original owner, this custom home offers over 7,000 square feet of living space with 4 spacious bedrooms, 3 full bathrooms, and two additional finished rooms in the walkout basement that provide incredible flexibility for guest space, a home gym, office, hobby rooms, or other uses. From the moment you step inside, you'll appreciate the attention to detail. Brazilian Tigerwood flooring flows throughout the main level, while engineered flooring extends through the basement. The inviting living room is anchored by a gas fireplace, creating the perfect gathering space, while the home's two full kitchens make multigenerational living, entertaining, or hosting guests effortless. The custom bar showcases beautiful copper accents, including a stunning copper backsplash that adds warmth and character. The primary suite serves as a private retreat with a luxurious soaking tub and its own sunroom—a peaceful space to enjoy your morning coffee while overlooking the surrounding countryside. Built for both comfort and efficiency, this home features geothermal heating and cooling, an in-home dehumidifier, a security system, automated gated entry, and robust 2x12 floor joists, reflecting the superior craftsmanship found throughout. Outside, the opportunities are endless. A massive 50' x 64' insulated shop and a 14-foot garage door is ideal for equipment, RV storage, business operations, or workshop space. The above-ground pool provides the perfect place to unwind during the summer months, while the fully fenced property is currently home to cattle but offers endless possibilities for horses, farming, recreation, or simply enjoying your own private slice of Kentucky. Whether you're searching for a luxury family estate, an equestrian property, a working farm, or a private retreat with room to grow, this remarkable property delivers a rare combination of quality construction, thoughtful amenities, and unmatched versatility—all within minutes of modern conveniences.

351 Benton Road Mt, Mt Sterling
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester
$1,149,000
3 Beds ⋅ 4 Baths ⋅ 25018600 MLS
Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs, separate very large kennel, puppy paradise, office, has all the upgrades for shelter & housing, grooming, dog run, this home is must see, call today! Selling ''AS IS'', inspections welcome, 48 hours notice to show this property is 30 minutes to Lexington and close to I-64 , Please do not pet dogs,

2100 Irvine Rd Unit 40391, Winchester
$221,500
2 Beds ⋅ 1 Baths ⋅ 26013551 MLS
MOTIVATED SELLER!! Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of room to add another bedroom and full bath if desired. Current owner has a formal dining room, the area could be used for a 3rd bedroom in the main living area. In addition to all the potential this property has it also offers lots of updates: New Roof, New Heating & Cooling system, New Windows, and all New Plumbing. If you're looking for a place to call home this one is loaded with charm and busting with potential!! Schedule your showing today!!

2 Western Ave, Winchester
$225,000
3 Beds ⋅ 2 Baths ⋅ 26011961 MLS
Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester
$515,000
5 Beds ⋅ 3 Baths ⋅ 26007022 MLS
Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

110 White Conkwright Rd, Winchester
$899,000
3 Beds ⋅ 3 Baths ⋅ 26013217 MLS
MIDNIGHT ON THREE - Luxury Living Meets Convenience in Clark County KY Nestled on 3.054 beautifully maintained acres, this stunning home was thoughtfully designed with quality and elegance in every detail. Just 2 minutes from Exit 10 on the Mountain Parkway, this extraordinary custom-built estate offers a rare combination of privacy, craftsmanship, and accessibility. From the moment you arrive, the striking exterior, expansive covered porches, and picturesque setting create an unforgettable first impression. Inside, soaring ceilings, walls of windows, and abundant natural light showcase the home's exceptional design and create a warm, inviting atmosphere. The open-concept living space is anchored by a floor-to-ceiling stone fireplace and flows seamlessly into a designer kitchen featuring custom cabinetry, premium countertops, upscale fixtures, and a large gathering island perfect for entertaining. The luxurious primary suite offers a private retreat with a spa-inspired bath, oversized walk-in shower, soaking tub, and custom finishes throughout. Every room reflects the superior craftsmanship and attention to detail that set this home apart from ordinary construction. Whether you're enjoying morning coffee on the screened porch, hosting guests in the expansive living areas, or simply taking in the peaceful surroundings, this property delivers a lifestyle of comfort and sophistication. The versatile upper-level loft provides additional living space ideal for a media room, office, or guest retreat. Situated close to one of Eastern Kentucky's most desirable areas, this property offers quick access to Lexington, Winchester, and the Red River Gorge region while maintaining the privacy and serenity of a luxury country estate. Exquisite custom construction. Premium finishes. Exceptional location. For buyers seeking a truly remarkable home where quality, style, and convenience come together, this Clark County masterpiece is a rare opportunity. Luxury, privacy, and craftsmanship—without compromise.

330 Spencer Ln, Winchester
$429,900
4 Beds ⋅ 3 Baths ⋅ 26004512 MLS
Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your own peaceful getaway Whether you're looking for steady income, a smart investment, or a quiet escape, this riverfront property delivers.

240 Athens Boonesboro Rd, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ 26012820 MLS
Beautifully updated and truly move-in ready, this 3-bedroom, 2-bath home blends timeless charm with modern convenience. Step inside to a spacious living room and an updated kitchen featuring abundant cabinetry, while original hardwood flooring, luxury vinyl plank, and stylish finishes create a warm and inviting atmosphere throughout. The versatile utility room provides the perfect space for a home office, playroom, hobby area, or additional storage. An unfinished basement offers endless potential for future expansion or extra storage. Outside, enjoy a fully fenced backyard, patio, covered front porch, and a detached two-car garage ideal for relaxing or entertaining. Major updates provide peace of mind and include the HVAC system, furnace, roof shingles, windows, vinyl siding, flooring, kitchen cabinetry, bathroom vanities, light fixtures, doors, and hardware. With all the hard work already completed, this home is ready for you to move in and make it your own.

20 Jackson St, Winchester
$290,000
3 Beds ⋅ 3 Baths ⋅ 26011097 MLS
Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

209 Boone Ave, Winchester