This historic 18th-century Gaylord family homestead in New Milford, Connecticut, offers a perfect blend of authentic period charm and thoughtful modern enhancements. Set on picturesque grounds at 43 Gaylord Road, this distinctive Litchfield County property features versatile living spaces including an open-concept kitchen, living room, inviting Sun Room, formal dining room, and a cozy Snuggery with brick fireplace abutting the kitchen. The upper level showcases a spacious primary bedroom with vaulted ceilings, two walk-in closets, an en-suite bathroom, and a private balcony overlooking the backyard oasis. Three additional bedrooms and a full hall bath complete the second floor, providing generous accommodation for family and guests. Outdoor living reaches its pinnacle with a heated in-ground swimming pool, adjacent cabana, and expansive entertainment areas perfect for gatherings of all sizes. The property’s amenities extend to a two-car attached garage and separate temperature-controlled barn offering versatile space for storage, workshop, or creative pursuits. Perfectly positioned with nearby hiking trails, minutes to Kent and New Milford’s charming village centers, and convenient access to Metro North, this exceptional historic estate combines architectural significance, modern comfort, and an ideal location in one of Connecticut’s most desirable communities.