11 Trolley Crossing, Old Saybrook, CT 06475

Discover the best of Connecticut shoreline living at 11 Trolley Crossing in Old Saybrook-a private 3+ acre compound blending classic Colonial architecture with modern luxury. Designed for those who value space, comfort, and connection, this 3,600 sq ft residence invites you to experience an exceptional lifestyle surrounded by nature and minutes from the coast. A covered front porch opens to expansive, light-filled rooms where timeless craftsmanship meets everyday convenience. The kitchen fireplace creates a welcoming centerpiece for gatherings, while a second fireplace in the living room adds warmth and style. The first-floor primary suite allows for true one-level living, complemented by four additional bedrooms upstairs. The walk-out lower level features a third fireplace, half bath, and flexible space ideal for an in-law, recreation room, guest suite, or studio. Step outside to your own resort-style oasis an in-ground pool, pool house with full bathroom, and extensive stone patio designed for entertaining and relaxation. A heated, oversized 30x20 outbuilding offers additional garage or workshop space, joined by a detached three-car garage. The fenced yard and stone wall surround enhance privacy in a serene natural setting close to beaches, marinas, golf, and Old Saybrook's vibrant Main Street.Luxury, space, and versatility combine at 11 Trolley Crossing a property that invites you to visit, explore, and stay. Easy commute on Amtrak to New York City. Only 2hrs door - door Introducing 11 Trolley Crossing - an exceptional Connecticut shoreline estate offering the rare combination of compound-style living, privacy, and timeless elegance. Set on 3.1 private acres in the heart of Old Saybrook, this 3,600 sq ft Colonial masterpiece blends classic architecture with resort-caliber amenities, creating a private retreat just minutes from beaches, marinas, golf, and Main Street's fine shops and dining. Enclosed by stone walls and mature trees, the approach sets a tone of understated grandeur. A stately covered front porch opens to expansive, light-filled interiors that showcase hardwood floors, refined millwork, and exceptional craftsmanship throughout. The chef's kitchen serves as the centerpiece of the home, complete with a fireplace, oversized island, and custom cabinetry, flowing seamlessly into elegant dining and living spaces designed for effortless entertaining. The living room, warmed by a second fireplace, exudes comfort and style with sunlit views of the landscaped grounds. The first-floor primary suite provides a serene escape with private bath and garden views, ideal for one-level living. Upstairs, four additional bedrooms offer flexible space for family, guests, or dual home offices. The walk-out lower level adds another dimension of luxury, featuring a third fireplace, half bath, and open layout perfect for an in-law suite, guest quarters, or recreation area-tailored for multi-generational or compound-style living. Outdoors, the estate transforms into a private resort. The heated in-ground pool, pool house with full bath, and expansive stone patio create an unparalleled setting for entertaining or relaxation. A heated 30x20 outbuilding provides additional space for a gym, studio, or car collection, while the detached three-car garage enhances both form and function. Set in a peaceful, natural landscape yet close to Old Saybrook's coastal attractions, Fenwick, Essex Village, and commuter routes to New Haven and Hartford, this property redefines Connecticut shoreline luxury. At 11 Trolley Crossing, every element-from the architecture to the acreage-has been thoughtfully curated for those who value space, privacy, and refined coastal living. This is more than a home; it's a private Connecticut compound designed for generations to enjoy. Can you work remote? Easy commute on Amtrak from Old Saybrook Station to New York City.