A Complete Lifestyle, By Design

At the end of a quiet stretch south of the highway, 73 Wainscott Stone Road is the kind of residence that’s come to define the upper tier of the Hamptons market. More than just a luxury home, it’s a complete lifestyle property.

Newly constructed and designed by NJ Caine Architecture, the estate sold for $12.5 million in 2025, setting a new record for Wainscott Stone Road and becoming the third-highest on-market residential trade of the year in Wainscott. The property was represented by Nathan Grome of Compass. The sale was a stark contrast to the hamlet’s broader market, which saw a median sales price of $2.805 million in the first quarter of 2026, according to Jonathan Miller’s Housing Notes.

For designer Cindy Montgomery, whose work spans projects in New York City, the Hamptons and across the country to California, it was an opportunity to flex her well-honed expertise.

Montgomery was brought into the fold by the home’s current owner prior to closing, which she said allowed her to orchestrate an unusually seamless installation process.

“My approach was to go beyond functionality and create a strong visual impact,” Montgomery says. “In any project, design is what sells — it directly contributes to a higher return on investment.”

Over the course of her career, Montgomery has worked with large-scale companies, builders, investors and private residential clients, while also taking projects internationally in Germany, Barbados, Switzerland, London, Fiji, Singapore and Australia. Her work has been featured on shows on HGTV and the former DIY Network (now Magnolia Network), and she’s developed a line of custom furniture, including pieces for seniors and children.

Once the purchase of 73 Wainscott Stone Road was finalized, furnishings for both the interior and exterior were curated and installed rapidly, resulting in a residence that felt fully realized from day one. “Throughout the process, I worked closely with the owner, presenting mood boards for each space to clearly communicate the vision and ensure alignment,” Montgomery says. “We prioritized quality at every step, sourcing from a range of manufacturers across the United States and Canada, and spared no expense in achieving a refined, cohesive result.”

The family room ultimately became the emotional center of the home, Montgomery notes. Her floor plan included custom sofas sized precisely for the room, a sculptural cocktail table and tactile materials to soften the space. “I then layered in beautiful artwork and a cast stone tic-tac-toe piece to add a playful touch, which helped make the room feel especially warm and inviting,” she says. “Two beautiful leather chairs flank the entrance, creating a natural and welcoming spot for entertaining and gathering.”

While Montgomery shaped the interiors, the home’s architecture was led by Neal James Stufano, principal of NJ Caine Architecture, who spent approximately 18 months bringing the project to completion. From the outset, the vision centered on creating a property that fully embraced the Hamptons’ defining asset: the outdoors.

“For me, engaging the backyard was a defining feature of this home,” Stufano says. 

“The rear facade opens onto the pool, spa and surrounding landscape, creating a seamless indoor-outdoor experience that’s essential to Hamptons living.”

That fluidity became one of the home’s signature gestures. Expansive living spaces open onto multiple outdoor lounges and dining areas, while a separate pool house serves as almost a second entertainment nucleus.  “It’s private, layered and incredibly well-composed,” Stufano explains. “Everything is intentional without feeling overdesigned.” 

For NJ Caine Architecture, 73 Wainscott Road reflects the firm’s growing footprint in the national luxury market. Stufano points to a portfolio that ranges from Hamptons estates to sky-high Manhattan penthouses and West Coast contemporary residences. Among the firm’s notable recent projects was the renovation of Billy Joel’s former MiddleSea estate on Centre Island, a sprawling waterfront compound overlooking Oyster Bay Harbor.

The finished product offered the perfect blend of traits needed to break records in the area, notes Compass agent Nathan Grome, who brokered the sale of 73 Wainscott Stone Road. “The home offered a rare combination of location in Wainscott, thoughtful design and a level of finish that felt cohesive throughout,” Grome says. “There was a strong alignment between the design, the setting and what today’s high-end buyer is seeking, which ultimately made it stand out.”

The buyer was drawn precisely to that combination of sophistication and ease, he adds. “The home was acquired by a private investor seeking a refined Hamptons residence that balances luxury, comfort and usability as part of a broader luxury portfolio,” Grome says. “The property aligned with what today’s high-end buyer is looking for — clean architectural design, strong indoor-outdoor flow and a fully turnkey experience.”

Cindy Montgomery