5 New York Estates and Landmark Retreats from the Hamptons to the Hudson Valley

Set on a private 0.97-acre parcel in East Hampton, 15 Fieldview Lane presents a brand-new, custom-built estate where timeless Hamptons architecture is paired with modern luxury. The residence spans three expansive levels and is arranged for both daily living and effortless entertaining. On the main floor, an open-concept layout includes a junior primary suite, sun-filled living spaces, and easy indoor-outdoor flow to a rear entertaining terrace. Upstairs, the primary suite is joined by three additional ensuite bedrooms and a second-floor laundry. The fully finished lower level reads like a retreat, with a media room, gym, spa/sauna, two guest bedrooms, and a second laundry area. Outdoors, a heated 20×50 gunite pool with integrated spa anchors the grounds, alongside a separate pool house and expansive lawn. A detached three-car garage connected by a breezeway completes the setting for unhurried Hamptons seasons.

Set on 85 acres, Bald Mountain Estate unfolds as a four-building, ultra-contemporary compound overlooking the Hudson Valley and the Berkshire Hills. Floor-to-ceiling glass walls and a steel infrastructure give the architecture a crisp, modern edge, while reclaimed wood floors add warmth underfoot. The open-concept main residence is designed for indoor-outdoor living, anchored by three fireplaces and a striking maple staircase. Two custom guest houses sit nearby, along with a workshop, creating a true multi-structure retreat. Outside, meandering hiking trails cross the property toward the mountaintop, where panoramic views stretch to the Catskill, Berkshire, and Taconic Mountain Ranges. Two serene ponds and a gunite pool framed by dramatic stone walls complete the setting. Here, privacy and wide-open horizons shape an easy rhythm from morning light to sunset.

Along the water’s edge overlooking Saratoga Lake, this custom French Country château unfolds across 9.15 acres of pristine, private grounds. Classical European influence meets modern craftsmanship throughout, from the chef’s kitchen—appointed with Miele appliances, an imported Italian backsplash, a dramatic marble island, and an oversized walk-in pantry—to the grand yet welcoming Great Room designed for entertaining. For quieter evenings, a Club Room with a full bar sets a more intimate tone. A private elevator and grand staircase lead to the Primary Suite, where a spa-level white marble bath features a freestanding soaking tub, steam shower, and private sauna. Arrival is marked by an elegant porte-cochère and a heated four-car garage. Outside, a beautifully positioned pool, hot tub, and built-in barbecue frame sweeping lake views, complemented by a pool house with kitchenette, bath, and fireplace for year-round hosting.

Set on 20 private acres in Monticello, this nearly 18,000-square-foot estate is designed for life at a generous scale, balancing open, partially cleared grounds with natural surroundings. Indoors, the layout leans into gathering and unwinding, with an indoor pool, bar, pizza oven, game room, theater, and gym creating a true at-home destination. Multiple fireplaces add warmth and atmosphere, while a sauna and hot tub extend the retreat-like feel. Outside, a firepit anchors evenings under the sky. With 14+ bedrooms, the property has already proven its ability to host—having welcomed events and weddings—yet it still reads as an exceptionally private escape. Days here can move easily from recreation to rest, with room for everyone to settle in and stay awhile.

Size: 20.00 acres

Originally built as the world-renowned Friar Tuck Inn, this storied Catskill property recalls its heyday from the 1970s through the 1990s and now awaits a thoughtful restoration. Set across 170 acres, the scale is unmistakably resort-like, with 370+ guest rooms and over 300,000 square feet spread among multiple structures. The grounds include ponds that punctuate the landscape, while parking for 800+ vehicles underscores the site’s history of hosting crowds and events. Positioned along Route 32 in Catskill, NY, the setting feels made for an ambitious reimagining—whether as a revived hotel campus or a broader destination concept—where a legacy property can be brought back to life for a new era of gathering and retreat.