661 Middle Road, Bayport, NY 11705 - Suffolk County

Towering Pines – A Rare South Bayport Estate

Step beyond the wrought-iron gates and into Towering Pines, a remarkable 1860 Queen Anne Victorian where timeless architecture meets a storybook setting. Perfectly situated in South Bayport, this distinguished residence unfolds across lush, professionally landscaped grounds reminiscent of a private arboretum, where mature specimen trees, vibrant gardens, and curated pathways create an atmosphere of serenity and grace. The property’s exterior is a sanctuary of outdoor living—featuring a tranquil koi pond with waterfall, an in ground pool surrounded by flowering gardens, a pergola-covered fire pit area, a child’s play space, a covered hot tub, and a dedicated dog run. A circular driveway with a central fountain, porte-cochere, and motor court lead to a detached three-car garage crowned by an inviting bonus loft, ideal for studio use, or private retreat. The home’s wraparound porch—one of its most defining features—welcomes you to a residence where craftsmanship and character reign supreme. Through double doors, the grand oak-paneled foyer sets the tone for what’s within: hand-carved woodwork, coffered ceilings, crystal sconces, and built-in seating that speaks to the home’s heritage and grace. Flanked by a formal living room and dining room, each with its own fireplace, this level showcases extraordinary architectural detail. The living room’s curved windows open fully to the porch, while the dining room’s raised panel walls and French doors connect seamlessly to the solarium and garden beyond. The handsome study, with its built-in granite-topped desk and intricate millwork, offers the perfect space for working from home in style. The kitchen is a blend of form and function, offering custom cabinetry, granite surfaces, and chef-caliber appliances, flowing effortlessly into an impressive lounge with wine bar and window seating, plus dining area, creating a seamless space for entertaining and everyday living. A cathedral-ceilinged great room with skylights invites gatherings both grand and intimate. Two powder rooms, a laundry room, and a heated enclosed porch complete the first level. Ascend the grand staircase—or the charming butler’s stairs—to discover the second floor, where framed original blueprints line the walls beneath stained glass windows said to be authentic Tiffany. The primary suite features a marble-clad bathroom with soaking tub and walk-in shower, as well as a bespoke dressing room with custom closets. A junior suite, currently enjoyed as a library, includes built-in shelving, a fireplace, and access to a private balcony and full bath with original soaking tub. Two additional bedrooms each offer their own distinctive whimsical personality and comfort. The third level continues the home’s story with three additional bedrooms—one presently used as a sitting room, another as an office—and a full bath with charming tub. Every inch of Whispering Pines reflects enduring craftsmanship: curved glass windows, custom millwork, porches and balconies that invite quiet moments, and modern amenities including central air, gas heat, and an interior/exterior sound system.

Towering Pines is more than a home—it’s a living piece of South Bayport’s history, gracefully blending old-world artistry with modern comfort. A rare opportunity to own one of the area’s most enchanting and storied estates.

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