Winchester Real Estate Search

Winchester Properties over $1,000,000 for Sale

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Newest Winchester Properties over $1,000,000 for Sale

2100 Irvine Rd Unit 40391, Winchester
$1,125,000
3 Beds ⋅ 4 Baths ⋅ 26026878 MLS
Tucked away behind private gates on 28 beautiful acres, this one-of-a-kind cabin offers the perfect blend of privacy, luxury, and country living. Step inside to a stunning open-concept living, dining, and kitchen area designed for gathering and entertaining. The kitchen is a showstopper with custom cabinetry, quartz countertops, a waterfall island, top-of-the-line appliances, and a spacious walk-in pantry. Off the kitchen on the right wing of the house there is a mudroom area with half bathroom, followed by the primary suite. The main-level primary suite is a true retreat, very spacious bedroom area with a private sunroom and direct access to the patio and in-ground pool, walk-in closet and laundry closet. The bathroom features a soaking tub and a tiled walk-in shower. Upstairs, you'll find an additional spacious bedroom with built-in bunk beds, a walk-in closet, and full bath. The left wing of the home provides ideal in-law or guest quarters featuring its own kitchen, open concept living and bedroom area with fireplace, walk-in closet, full bath with walk-in shower, and private exterior entrance. Outside is where this property truly sets itself apart. Enjoy your own private oasis with an in-ground pool surrounded by picturesque acreage. The backyard also includes a "she shed" currently used as a workout room, chicken coop, run-in shed, and 30x33 detached garage. This property features an AKC-inspected kennel facility with 14 indoor/outdoor runs, an office, a grooming area, a bathing area, an open work space, half bathroom and a fenced exercise area. Another 6-hole kennel with overhangs. The remaining property features 7 paddocks, 5 run-in sheds, multiple fenced pastures with run-in sheds and water. Bring the horses, cows, dogs—and even the in-laws! This is an animal lover's dream with room to live, work, play, and enjoy the peace of the countryside, all while being just minutes from I-64 and approximately 24 minutes from Downtown Lexington. The possibilities for this property are endless, and it is a truly special property that has to be experienced in person!

2100 Irvine Rd Unit 40391, Winchester

3166 Colby Rd, Winchester
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
NEW PRICE!!! 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

101 S Main, Winchester
$1,750,000
23021742 MLS
101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development.

101 S Main, Winchester

5039 Combs Ferry Rd, Winchester
$2,299,000
5 Beds ⋅ 4 Baths ⋅ 26028074 MLS
Experience exceptional craftsmanship, privacy and resort-style living on over 12 acres in the highly desired Combs Ferry area of Clark County. Quietly tucked away yet conveniently located just 15 minutes from Hamburg in Lexington, as well as Winchester and Richmond, this extraordinary custom home was built in 2022 and offers 6,284 finished square feet, plus an additional 1,545 square feet of unfinished space ready for the next owner to customize. From the moment you enter, the quality and attention to detail are unmistakable. Andersen 400 Series windows and doors, decorative ceilings, custom trim and built-ins, engineered hardwood flooring, quartz countertops and designer lighting are featured throughout. The spacious kitchen is a true centerpiece, showcasing custom cabinetry, soft-close doors and drawers, under-cabinet lighting, a hidden walk-in pantry, double ovens, built-in microwave and a 5-burner gas range with built-in Thermador appliances. The main-level primary suite is a private retreat, complete with decorative beams, a stacked-stone gas fireplace, double vanities, soaking tub, expansive walk-in closet and an oversized tiled pass-through shower featuring dual shower heads and a centered rain head. Large walk-in closets accompany every bedroom, providing exceptional storage throughout. The finished lower level expands the possibilities with a home gym, dedicated movie theater with projector and equipment, home office/bonus room, wet bar with granite countertops, wine and beverage refrigerators and dishwasher, plus an additional bedroom with egress window, full bathroom, and walk-in closet. Multiple unfinished areas and the additional 1,545 square feet provide tremendous potential for future customization. Step outside and discover your own private entertainment destination. The 45,000-gallon oversized heated chlorine pool features a tanning ledge, deep-end swim ledge, fountain, LED lighting and energy-efficient variable-speed pump. Enjoy evenings around the custom outdoor fireplace, with the convenience of a dedicated outdoor bathroom. The property also includes a basketball court, shooting range, and detached garage with concrete floors and double garage bays. Additional thoughtful features include a formal dining room with custom moldings, laundry room with built-in cabinetry, mudroom/drop zone with built-ins and cubbies, spray foam insulation, three all-electric HVAC systems, and two 60-gallon water heaters. This is far more than a home; it is a custom-built private estate designed for everyday luxury, entertaining, recreation and relaxation, with room to make it uniquely your own. The combination of acreage, exceptional construction, extensive amenities and convenient location is truly rare. Schedule your private showing today and experience this breathtaking property firsthand. Seller is a licensed Realtor in Kentucky.

5039 Combs Ferry Rd, Winchester

4664 Lexington Rd, Winchester
$2,750,000
8 Beds ⋅ 8 Baths ⋅ 26009631 MLS
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester

510 612 Quisenberry Ln, Winchester
$3,450,000
2 Beds ⋅ 3 Baths ⋅ 26018838 MLS
Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and rock walls, the farm was carefully developed for beauty and functionality. Atop a knoll at the heart of the farm is an 18th century cabin constructed from logs of the now functionally-extinct American Chestnut. Relocated and rebuilt here with modern systems, it serves as a warm and welcoming 2,275 sq. ft. main residence. Two stone fireplaces and tasteful décor contribute to the cabin's polished rustic charm. With an inviting front porch and screened side porch, as well as expansive stone patios and deck, the cabin offers many opportunities to enjoy bucolic views. An approximately 4,000 sq. ft. party barn or recreation building with restroom and custom moveable bar allows ample open space for gatherings. Two large garage doors open to the building while large windows allow abundant natural light. Nearby, a bent barn makes for an excellent workshop or storage facility. A third stock barn is perfect for equipment. The small cottage adds space for a guest or employee. The land is gently rolling, with large open fields and three ponds. Mature trees add to the landscape's verdancy. Over 440 acres adjoining the farm have been acquired by the Lower Howard's Creek Nature and Heritage Preserve, conserving the local ecosystem's many native plants and animals for perpetuity. The immense heritage and natural beauty of this farm will make it an enduring legacy for its next stewards.

510 612 Quisenberry Ln, Winchester

5825 Combs Ferry Rd, Winchester
$4,895,000
3 Beds ⋅ 4 Baths ⋅ 26028325 MLS
A Rare 77 ± acre Kentucky Estate with a new custom home & equestrian facilities offers privacy, commanding views, and the natural beauty of Kentucky's renowned horse country that truly define this exceptional recreational estate. Offering an extraordinary combination of luxury living, equestrian amenities and recreational opportunities, the property has been thoughtfully designed to provide both functionality and tranquility. The setting is simply spectacular, with Nursery Place Thoroughbreds and Harkness Edwards Winery as immediate neighbors, placing this estate in an impressive equestrian environment just minutes from Fayette County. A winding private drive passes the beautiful stocked ponds, leading to the highest point of the estate where an impressive custom stone residence and equestrian facility command panoramic views. The recently completed 5,800 ± square-foot custom 3 BR/3.5 BA stone manor home combines elegant finishes with a warm aesthetic. Features include rustic boxcar-wood flooring, a custom kitchen with granite center island and countertops, Wolf and Sub-Zero appliances and custom cabinetry. The spectacular great room provides generous space for both living and dining, highlighted by a floor-to-ceiling stone fireplace and an expansive wall of windows framing remarkable views of the surrounding countryside. Both the great room and first-floor primary suite open onto a massive covered deck featuring an outdoor fireplace and hot tub—an exceptional setting for entertaining or simply enjoying the serenity of the property. The private main floor primary suite includes its own fireplace, luxurious en suite bath, large walk-in closet, convenient laundry area, and private office. A beautiful stone entrance foyer leads to a loft overlooking the great room. The walkout lower level features 2 additional spacious bedrooms and an open family room, with direct access -through the walkout doors- to the impressive in-ground swimming pool. Adding another dimension to the estate is the remarkable barndominium which includes approx 1,000 sf of living quarters featuring 1 bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility- capable of accommodating aircraft, collector cars, RVs, and/ or other recreational vehicles. Impressive hydraulic doors and extra-tall ceilings provide easy access. Inside, rustic barnwood finishes create a warm and inviting atmosphere ideal for entertaining, gatherings, or displaying a collection. A substantial wood shop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with 4 horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the 10-acre fenced field for horse turnout. Whether envisioned as a private equestrian estate, recreational compound, luxury country residence or a combination of all three, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings- it truly must be seen to be appreciated.

5825 Combs Ferry Rd, Winchester

5825 Combs Ferry Rd, Winchester
$4,895,000
3 Beds ⋅ 4 Baths ⋅ 26028327 MLS
A Rare 77 ± acre Kentucky Estate with a new custom home & equestrian facilities offers privacy, commanding views, and the natural beauty of Kentucky's renowned horse country that truly define this exceptional recreational estate. Offering an extraordinary combination of luxury living, equestrian amenities and recreational opportunities, the property has been thoughtfully designed to provide both functionality and tranquility. The setting is simply spectacular, with Nursery Place Thoroughbreds and Harkness Edwards Winery as immediate neighbors, placing this estate in an impressive equestrian environment just minutes from Fayette County. A winding private drive passes the beautiful stocked ponds, leading to the highest point of the estate where an impressive custom stone residence and equestrian facility command panoramic views. The recently completed 5,800 ± square-foot custom 3 BR/3.5 BA stone manor home combines elegant finishes with a warm aesthetic. Features include rustic boxcar-wood flooring, a custom kitchen with granite center island and countertops, Wolf and Sub-Zero appliances and custom cabinetry. The spectacular great room provides generous space for both living and dining, highlighted by a floor-to-ceiling stone fireplace and an expansive wall of windows framing remarkable views of the surrounding countryside. Both the great room and first-floor primary suite open onto a massive covered deck featuring an outdoor fireplace and hot tub—an exceptional setting for entertaining or simply enjoying the serenity of the property. The private main floor primary suite includes its own fireplace, luxurious en suite bath, large walk-in closet, convenient laundry area, and private office. A beautiful stone entrance foyer leads to a loft overlooking the great room. The walkout lower level features 2 additional spacious bedrooms and an open family room, with direct access -through the walkout doors- to the impressive in-ground swimming pool. Adding another dimension to the estate is the remarkable barndominium which includes approx 1,000 sf of living quarters featuring 1 bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility- capable of accommodating aircraft, collector cars, RVs, and/ or other recreational vehicles. Impressive hydraulic doors and extra-tall ceilings provide easy access. Inside, rustic barnwood finishes create a warm and inviting atmosphere ideal for entertaining, gatherings, or displaying a collection. A substantial wood shop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with 4 horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the 10-acre fenced field for horse turnout. Whether envisioned as a private equestrian estate, recreational compound, luxury country residence or a combination of all three, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings- it truly must be seen to be appreciated.

5825 Combs Ferry Rd, Winchester

2395 Paris Rd, Winchester
$14,100,000
26011485 MLS
Welcome to Deerlawn, Winchester's newest approved residential development and a major new-construction opportunity in Clark County. Located at 2395 Paris Road, Deerlawn is a 274-acre master-planned community designed to deliver 438 single-family homes, along with additional duplex and townhome opportunities, creating long-term scale for builders and more choices for buyers looking to build in Central Kentucky. The first five stages will provide 65 buildable homesites by year-end 2026, with Stage 1 complete and build-ready now, Stages 2 and 3 anticipated for completion in October, and Stages 4 and 5 expected by year-end. The community is served by city water and sewer, KU Electric, and Columbia Gas, with a mix of traditional and larger estate-style lots planned throughout the development. Deerlawn offers a rare opportunity to purchase individual lots or build within a growing residential community just minutes from Downtown Winchester and approximately 10 miles from Lexington's Hamburg area, with convenient access to I-64, I-75, Paris, Richmond, Georgetown, shopping, dining, and major employment centers. Whether you are a builder seeking a pipeline of buildable lots, an investor looking for new-construction opportunity, or a buyer ready to build a custom Kentucky home, Deerlawn offers flexibility, location, and long-term growth potential. See individual lot listings in Stage One, (229 -241 Plantation Drive) for current lot availability, stage-specific pricing, plats, and individual homesite details.

2395 Paris Rd, Winchester

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