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Gracious Country Living Meets Modern Luxury at Aquinnah. Welcome to this extraordinary 1860 estate nestled in the heart of Orange County Hunt territory minutes from both Middleburg and route 66 access. Thoughtfully restored and seamlessly expanded, this 7-bedroom, 8 full and 2 half-bathroom residence is a rare blend of historic charm and sophisticated amenities. Spectacular views all the way from Ashby Gap to Cobbler Mountain! From the heated indoor lap pool and hot tub to the tennis courts with a fully equipped tennis house, this home is designed for both relaxation and recreation. The chef’s kitchen features double islands, a butler’s pantry, heated floors, and a built-in wine fridge—ideal for both intimate gatherings and grand entertaining. A Sonos sound system graces the main level, while five fireplaces offer cozy elegance throughout. An attached private suite with separate entrance, a charming guest space/home offices with one full bathroom, kitchen, and multiple upstairs rooms (also with high speed internet). For the equestrian lovers, a professional barn with a heated and air-conditioned 2-bedroom apartment create generous guest accommodations. The barn is also equipped with run-ins equipped with fans, automatic waterers in all paddocks and stalls, plus a tack room, feed room, laundry room, and outdoor arena. The grounds are a horticultural dream: stroll through the boxwood garden, butterfly garden, mature parterre garden, and an avenue of serviceberry trees. Cultivate your own blooms in the greenhouse and cutting garden. Entertain al fresco on two patios and ensure your furry friends are safe and happy by utilizing the dog run with access through a dog door to an air conditioned laundry room. Additional highlights include a full bathroom off the pool/gym, oversized equipment shed with automatic door, gym, high-speed hardwired internet with whole-house Wi-Fi, EV outlet in garage, extensive security system, and a 60KW emergency generator. The entire property is protected by a conservation easement, ensuring timeless privacy and scenic beauty. A rare opportunity to own a truly one-of-a-kind estate where history, elegance, and modern comfort live in perfect harmony. Agent related to seller.