luxury farmhouse with panoramic view for sale Winchester, United States

What an opportunity as few properties in the Bluegrass carry Castleton Farm's pedigree. Established in 1793, this storied land has been shaped by generations of Kentucky's great horsemen — from a U.S. Senator's original breeding operation to the Castleman family's 1840 Greek Revival mansion, which still stands as a landmark of the farm today. Over two centuries, Castleton bred and stood champions across three breeds — Thoroughbreds, Standardbreds, and Saddlebreds — cementing its place among the Bluegrass's most storied nurseries. Today, the farm spans 951 acres and offers an unmatched scale of infrastructure: 16 barns ranging from intimate 4-stall setups to a substantial 30-stall facility, totaling 268 stalls. Ten homes across the property — including several managers' houses — provide ample accommodation for staff, making Castleton as functional as it is historic. This is more than a horse farm; it's a self-sufficient equine operation with two centuries of pedigree behind it, offered for the first time in 25 years to a new steward.

The premier Broodmare & Stallion complex of Shadwell Farm, including 90 world-class stalls. Opportunities to acquire a farm of this caliber, with this provenance, come once in a lifetime. If you've ever dreamed of owning a true diamond in the Bluegrass, now is your chance. Established in the heart of the Bluegrass more than four decades ago, Shadwell Farm quickly rose to become one of the most respected breeding and racing operations in the world. From its iconic teal-and-white silks to the countless champions that have called these rolling Central Kentucky pastures home, Shadwell has left an indelible mark on the Thoroughbred industry. Notable highlights from Shadwell Farm's extraordinary legacy include: Home to two-time Horse of the Year and leading sire Invasor (Argentine Triple Crown winner and Breeders' Cup Classic victor). Broodmare band that produced international superstars such as Nashwan (English Derby & King George VI and Queen Elizabeth Stakes), Sakhee, Haafhd, Ghanaati, Muhaarar, and Baaeed. Multiple Eclipse Award winners and champions raised and developed on the property. Consistently ranked among North America's leading breeders by earnings and stakes winners. A state-of-the-art facility that has set the standard for stallion stations, foaling barns, and yearling preparation in the region. For over 40 years, Shadwell Farm has been far more than a commercial operation--it has been a cornerstone of Lexington's equine community, a place where tradition meets excellence, and where generations of horsemen and women have walked the same lanes as some of the greatest Thoroughbreds of our time. My goal is simple: to find the next steward who understands and cherishes what Shadwell represents -- not just as one of the finest horse farms in Kentucky, but as a living piece of Thoroughbred nostalgia that deserves to be preserved, respected, and carried forward into its next chapter.

Located in Danville, KY The Farm Inn is a unique hospitality and event property offering rustic charm, scenic countryside views, and endless potential. Ideal for a boutique inn, wedding venue, retreat, or private estate, this established property combines peaceful surroundings with convenient access. A rare opportunity to own a one-of-a-kind destination in Central Kentucky. Beautiful 26-acre property offers a versatile blend of productive tillable ground and fenced pasture, perfectly suited for horses, cattle, hay production, or crops. The gently rolling terrain provides scenic countryside views and excellent usability, creating a peaceful setting ideal for both agricultural and recreational use. Guests of the inn can enjoy walking trails, open green space, and the quiet charm of the surrounding landscape. With ample room for farming, livestock, outdoor events, or future expansion. Main House-This stunning 7,348 sq. ft. Colonial-style home blends timeless character with extensive modern renovations and additions throughout. Featuring 10 bedrooms, 8 bathrooms, 2 full kitchens, multiple dining and living spaces, and several beautiful fireplaces, the property is perfectly suited for a bed & breakfast, boutique inn, or short-term room rentals. Thoughtfully updated while preserving its historic charm, this spacious estate offers exceptional flexibility for hospitality, events, or private residential use. Guest House- A charming 1,200 sq. ft. guest house offers flexible living space with a studio-style layout, full kitchen, and full bath. Ideal for long-term tenants, short-term rentals, guest accommodations, or an event prep building. Cabin 1 and Cabin 2- A pair of beautiful 1,400 sq. ft. guest cabins combines rustic warmth with comfortable living, featuring beautiful pine interior finishes, 2 bedrooms, 1 full bath, a cozy loft, full kitchen, and inviting living area. A spacious back deck offers the perfect place to relax and enjoy the peaceful countryside setting. Ideal for short-term rentals, private guest accommodations, or elegant bride and groom suites, this cabin provides both character and income-producing potential. Outbuildings/Barns-The property also features two classic barns and three silos that add incredible character and visual appeal to the grounds. Beyond their charming farmhouse aesthetic, the barns provide excellent storage and functional space for event supplies, equipment, décor, or agricultural use, further enhancing the property's versatility for hospitality, weddings, and special events. This picturesque property offers endless recreational opportunities in a peaceful countryside setting. The gently rolling 26 acres are ideal for walking trails, horseback riding, outdoor gatherings, gardening, and enjoying the scenic beauty of Central Kentucky. With open green space, charming barns, and quiet surroundings, the property creates the perfect retreat for relaxation, weekend escapes, weddings, events, or agritourism experiences just minutes from town, golfing, and the Bourbon Trail. This property is well suited for a variety of agricultural uses, featuring a combination of productive tillable ground and fenced pasture ideal for crops, cattle, horses, or a hobby farm operation. The gently rolling landscape provides excellent usability for grazing, hay production, gardening, or recreational farming, while also offering scenic open space that complements the property's peaceful rural setting. Previously operated as a successful inn from 2010-2019, the property offered guests a true Kentucky experience - waking up to breakfast before being chauffeured in a sprinter van for tours along the famous Bourbon Trail. Today, the property continues to generate income through a combination of long-term and short-term rentals, offering excellent flexibility and proven hospitality potential for future owners. Seller incentives- The sellers are amenable to including up toa $25,000 courtesy sellercredit to buyer at the time of closing. Further, recognizing the uniqueness of the Property and its many uses, the sellers will also consider offers that contemplate partial seller financing.Parties may contact the listing agent to initiate a conversation about the terms and conditions of any such dynamic financing. Kentucky enjoys a moderate four-season climate with warm summers, mild springs and falls, and generally moderate winters. The region is known for its lush green landscapes, rolling countryside, and long growing seasons that are ideal for agriculture, horse farms, and outdoor recreation. Seasonal changes bring colorful autumn foliage, blooming spring scenery, and comfortable conditions for year-round tourism and events. Danville, founded in 1787, is known as the 'Birthplace of Kentucky' because it hosted the conventions that led to Kentucky becoming the 15th state in 1792. Rich in history and preserved architecture, Danville features a vibrant downtown filled with historic buildings, locally owned shops, restaurants, and cultural attractions. The city is also home to Centre College, one of the nation's top liberal arts colleges, and is centrally located near Kentucky's famous Bourbon Trail and scenic countryside. Located in Danville, this property offers the perfect balance of peaceful countryside living and convenient access to local amenities. Known for its historic charm, vibrant downtown, and rich Kentucky heritage, Danville is home to unique shops, restaurants, entertainment, and the renowned Bourbon Trail. Centrally positioned in Central Kentucky, the area provides easy access to Lexington, outdoor recreation, and regional attractions while maintaining the quiet appeal of small-town living.