Sally Jessy Raphael Lists Historic Hudson Valley Estate For $5 Million
Sally Jessy Raphael is seeking a buyer for her Elizabethan-style Hudson Valley estate, listing the property for $5 million.
The Emmy-winning television host, best known for her long-running daytime talk show “Sally”, purchased the estate in 1997 for $1.725 million after it had been held by the same family for nine generations.
Over nearly three decades of ownership, Raphael invested more than $1 million into improvements while carefully preserving the home’s historic character and architectural details.
Set atop Quaker Hill, the estate, known as Elmwood Farm, is more than 25 acres and ranks among the area’s most recognizable historic properties.
Property Highlights
Price: $5 Million
Location: Pawling, New York
Size: 15,000 square feet
Lot Size: 25.5 acres
Bedrooms: 8
Bathrooms: 9 full, 4 half
Notable Features: Elizabethan-style manor, 10 fireplaces, leaded glass windows, carved oak staircase, two caretaker homes, carriage house, groom’s quarters, yoga studio, greenhouse, rolling countryside views
For more information about this listing, reach out to Jake Garay at jakegaray@serhant.com.
Walking up to Raphael’s Mansion
Approached by a winding gated drive, Raphael’s Elmwood Farm occupies a prominent position atop Quaker Hill, one of the Hudson Valley’s most historic residential communities.
The estate unfolds across rolling acreage before revealing the Elizabethan-style manor that has served as a landmark in the community for generations.
The home’s architecture reflects the craftsmanship of a different era, with dramatic rooflines, carved timber details, Gothic-inspired spires, and leaded glass windows contributing to its distinctive appearance.
Stepping Inside
Inside, a hand-carved oak staircase serves as the centerpiece of the home, featuring whimsical animal carvings and artisan detailing rarely found in modern construction.
Main Living Rooms
From the staircase, the home moves into a collection of formal and informal gathering spaces that showcase the craftsmanship that defines the historic manor.
Formal Sitting Room
The first of the two main living rooms serves as a formal sitting room, centered around a wall of diamond-pane leaded glass windows that draw natural light into the richly detailed interior.
Carved wood furnishings, paneled walls, decorative millwork, and a coffered ceiling reinforce the home’s Tudor character, while views into connected rooms emphasize the home’s interconnected layout.
Fireside Living Room
A larger living room offers a more relaxed setting with a carved stone fireplace set beneath elaborate woodwork, while window-lined seating areas bring in views of the surrounding grounds.
Dining Areas
The house also has multiple dining spaces, each designed for different occasions, ranging from formal entertaining to casual everyday meals.
Casual Dining Room
The most relaxed of the three is a sun-filled dining room wrapped in walls of windows overlooking the grounds.
Positioned between indoor and outdoor living spaces, the room features a long farmhouse-style table beneath exposed ceiling beams and woven pendant lights.
Formal Dining Room
For more formal occasions, the estate offers a grand dining room rich in period detail. Paneled wood walls, built-in cabinetry, decorative columns, and an intricate geometric ceiling frame a polished dining table sized for large gatherings.
A dramatic chandelier hangs overhead, while tall windows at the far end bring natural light into one of the home’s most impressive entertaining spaces.
Breakfast Nook
Closer to the kitchen, a smaller breakfast room provides a more intimate setting for everyday meals.
Its convenient location makes it an ideal spot for morning coffee, casual breakfasts, or informal family meals away from the formality of the larger dining rooms.
Kitchen
Balancing historic character with everyday functionality, the kitchen centers around a large marble-topped island and a black custom range hood set against exposed brick.
Open shelving, built-in storage, and display cabinets showcase copper cookware and collected pieces, while the checkerboard flooring and oversized farmhouse-style sink add to the kitchen’s distinct personality.
Bedrooms
The estate’s bedrooms continue the home’s preservation of original craftsmanship, with decorative plaster ceiling details, carved woodwork, and period millwork appearing throughout.
Blue Floral Bedroom
One of the more formal guest chambers pairs blue-and-white botanical wallpaper with polished hardwood floors and oversized windows.
A decorative fireplace is framed by millwork within the same line as a dining table for four, and two twin beds with blankets that match the wallpaper.
Green Dormer Bedroom
Tucked beneath a dramatically sloped ceiling, another bedroom embraces the home’s historic character through floor-to-ceiling patterned wall coverings.
A four-poster canopy sits across from window seating beneath the arched dormer, while carved wood trim, leaded-glass windows, and decorative plaster ceiling motifs reinforce its early 20th-century craftsmanship.
Interior Amenities
Beyond its main living spaces and private quarters, the estate includes several specialized rooms that reflect the property’s long history as both a family home and creative retreat.
Billiards Lounge
The billiards lounge centers around a full-size pool table, while the rest of the room is filled with built-in bookshelves, window seats, and a carved stone fireplace.
Bar
Nearby, a compact bar is lined with illuminated display shelving, mirrored walls, and patterned wallpaper that provide storage and display space for glassware and spirits.
Chapel and Art Studio
Perhaps the most unique space in the home is a room that appears to have served both spiritual and creative purposes over the years.
A striking stained-glass window framed by intricate Gothic-inspired woodwork fills the room with colored light, while a carved wooden lectern stands at its center.
The current setup includes easels and artwork, suggesting the space now functions as an art studio, though its architectural details evoke the atmosphere of a private chapel.
Beyond the Main House
The estate extends well beyond the main residence, functioning as a true compound with multiple supporting structures.
Two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse provide flexibility for guests, staff, or creative pursuits.
Additionally, the surrounding grounds feature mature trees, rolling lawns, and sweeping countryside views that have long attracted artists, writers, and public figures to Quaker Hill.
Final Thoughts
Raphael spent nearly 30 years preserving and maintaining one of Quaker Hill’s most significant historic estates, investing in upgrades while carefully respecting the property’s heritage.
Her ownership helped safeguard many of the home’s original details, allowing Elmwood Farm to retain the character that has defined it for generations.
Now, as the longtime television host looks to pass the estate on to its next caretaker, Raphael appears ready to relinquish the responsibility that comes with owning such a large historic estate.
For a future owner, the listing offers the opportunity to acquire a landmark Hudson Valley property with over 25 acres of rolling countryside, and a collection of structures that create the scale and flexibility of a true country compound.
