Four bedroom, three-and-a-half bathroom restored estate residence on 3.2 acres | Originally the caretaker’s residence and carriage house of the former Filer/Guggenheim Estate | 4,697 square feet | Six-year restoration preserving original wide-plank floors, hand-hewn beams, antique windows, and stone fireplaces | Chef’s kitchen with deVOL fixtures, heated European limestone floors, soapstone island, and professional six-burner range | Heated saltwater pool | Interior courtyard | Historic ice house, smokehouse, century-old grapevine, and stone walls | One hour from NYC | Asking $1,375,000

Set on 3.2 acres within the former Filer/Guggenheim Estate in Orange County, Rockbound is a thoughtfully restored historic residence where more than a century of craftsmanship has been carefully preserved alongside contemporary updates designed for modern living. Featured recently in the New York Times, Rockbound was originally built as the estate’s caretaker’s residence and carriage house. The two buildings have been joined into a single home through a meticulous six-year renovation that honors the property’s architectural history without sacrificing comfort or function.

Throughout the home, original materials remain front and center. Wide-plank floors, hand-hewn beams, antique windows, and stone fireplaces anchor a series of living spaces that feel both intimate and generous in scale. At the center of the home, a fully renovated kitchen introduces a quieter, more contemporary palette with imported tile, deVOL fixtures, heated European limestone floors, a substantial soapstone island, and a professional six-burner range.

The heated saltwater pool opens onto gardens, mature trees, and a century-old grapevine. Photos: Phil Mansfield

The home’s layout unfolds through a collection of distinctive spaces designed for both gathering and retreat. A formal den, library, home office, media room, and wine cellar provide flexibility for everyday living, while an interior courtyard creates a natural extension of the surrounding rooms. Above, a dramatic catwalk overlooks the skylit dining room before leading to the private primary suite. The second floor of the original carriage house is among the home’s most memorable spaces, where soaring ceilings, massive hand-hewn beams, original three-over-eight windows, and an oversized stone fireplace create an extraordinary gathering room with direct access to the pool terrace.

Outside, the grounds continue the property’s story. Mature gardens surround a heated saltwater pool, while historic stone walls—built from rock found on the property—trace the landscape. The original ice house and root cellar, now repurposed as a smokehouse, remain as reminders of the estate’s early years, while a productive 120-year-old grapevine continues to bear fruit each season.

Though Rockbound feels worlds away from the city, Manhattan is just an hour south. Storm King Art Center, Harriman State Park, Bear Mountain, West Point, and the Hudson Valley’s network of restaurants, galleries, hiking trails, and river towns are all within easy reach, making the property equally suited for weekends away or full-time living.

Listed by Todd Baker and Craig Smith of the Upstate Curious Team at Compass. For showings and inquiries contact Todd at todd@upstatecurious.com, cell: 917.499.0901 or Craig at craig@upstatecurious.com, cell: 845.518.3844

The Neighborhood: In + Around Woodbury, NY

Rockbound sits at the southern gateway to the Hudson Valley, where mountain landscapes begin to replace suburban streets. Spend the afternoon wandering Storm King Art Center’s expansive sculpture fields, explore the miles of hiking and lakes within Harriman and Bear Mountain State Parks, or tour the historic grounds of West Point. Nearby Cornwall, Cold Spring, Beacon, and Newburgh offer an ever-growing collection of restaurants, galleries, antique shops, and riverfront parks, while Woodbury Common Premium Outlets is just minutes away for a day of shopping.

Why We Love This House: A Century of Craftsmanship

More than a century after it was built, Rockbound still wears many of its original materials. Wide-plank floors, hand-hewn beams, antique windows, and stone fireplaces remain throughout the house, while the original ice house, smokehouse, and stone walls continue to shape the landscape outside. Contemporary updates sit comfortably alongside the home’s original architecture, preserving the character that has defined the property for generations.