66 High Street 4 Just steps from Guilford's historic town green, vibrant boutiques, and gourmet dining-and a short stroll to the town marina and train station-The Residences at 66 High Street offers an extraordinary blend of historic character & cosmopolitan luxury in the award-winning complex. Step inside this stunning two-bedroom unit, once honored as the coveted HOBI (Home Building Industry) Project of the Year. The open-concept main level showcases original exposed brick, seamlessly connecting a living area anchored by a sleek gas fireplace to a gourmet kitchen outfitted with a Wolf range, Sub-Zero refrigerator, quartz countertops, and an entertaining island w seating. Designed for effortless living, the first floor features a convenient guest suite w a connecting full bath, first-floor laundry, & heated bathroom floors. A dramatic wood-and-metal staircase leads to a second-floor loft w a built-in workspace & custom shelving. Retreat to the private primary suite, boasting dramatic 12-foot ceilings, a generous walk-in closet, & a spa-inspired bath. The crown jewel of the home is your very own secret rooftop deck crafted from teak & shaded by a pergola-an outdoor sanctuary offering expansive town views. This unit includes a detached oversized private garage w storage plus an assigned parking space just steps from your door. Residents enjoy an exceptional lifestyle enriched by community amenities, including an in-ground pool, gas fire pit lounge, garden beds, state of the art fitness center and a dedicated dog park, all complemented by an easy commute to New Haven and a convenient two-hour trip to New York City.