96 Kings Highway North Now with brand-new central air conditioning! Historic Luxury Meets Modern Living in Old Hill, Westport. Stroll to downtown Westport from this award-winning historic gem in coveted Old Hill. The David Judah House, c. 1760-honored with the 2016 Helen Muller Award for outstanding restoration-seamlessly blends timeless character with modern sophistication. Meticulously updated, the home features a chef's kitchen with Carrara marble countertops, premium appliances, and generous storage, opening to an entertainer's lounge with wet bar, beverage fridge and TV - ideal for movie nights or cocktail gatherings. French doors lead to an expansive deck and manicured backyard, perfect for al fresco dining and summer soirees. The vaulted family room and beamed living room, each with a fireplace, provide refined spaces for relaxation. The first-floor primary suite offers privacy, two fireplaces, a dressing room, and a luxurious updated bath. Upstairs are more three bedrooms and two more full baths, while a lower-level suite with full bath and walkout is perfect 5th bedroom to use as a guest room, gym, or office. Additional features include a 3-car garage with EV charger, lush landscaping, and included snow removal. With sidewalks to vibrant downtown Westport, this rare rental delivers a luxury lifestyle in a truly exceptional setting.