Horses or Hosting
Redefining 59 South Shore Road
This high-angle aerial photograph captures the expansive estate at 59 South Shore Road at the center of a neighborhood dispute. The primary residence is shown with its multiple outdoor amenities, which neighbors allege have functioned as part of a high-traffic event venue, now tethered to the property behind it by a newly recorded service easement (Jamie Feeley, inset)
A recorded easement and plans for a private stable complex highlight a shifting landscape on the South Shore, while the developer insists the future is about horses, not hospitality
Dominick Costanzo • April 19, 2026
Nantucket is no stranger to the evolution of the island estate, those sprawling, multi-structure properties often shielded by towering privet and shielded titles. But as a high-profile zoning dispute at 59 South Shore Road grinds through the town’s regulatory machinery, a more aggressive dimension of land-use planning is coming into focus. It's a story of physical expansion and legal craftsmanship, where a developer’s private vision is now moving in opposition to the neighborhood’s sense of place.
​
While public scrutiny has largely remained fixed on the front gates of 59 South Shore, the broader story is unfolding across the acreage behind it. Newly surfaced records reveal that the property has formally reached out to absorb the functionality of 14 Tripp Drive, forging a combined seven-acre contiguous footprint. It is a unification that neighbors fear provides the tactical infrastructure for a commercial-scale event venue, but which owner-occupant Jamie Feeley insists is a high-minded return to island tradition: the private equestrian estate.
A Recorded Connection
The technical link was forged in August 2024. A recorded easement, executed between the 59 South Shore Road Nominee Trust and the Tripp Stable Nominee Trust, formally tethered the two parcels. This wasn't a minor utility agreement, it was a non-exclusive, perpetual right of access for motor vehicles, pedestrians, and equestrian use.
The easement provides 59 South Shore access to a Proprietors Road, creating a permanent route through 14 Tripp Drive. For neighbors, the weight of this document is immense, as it effectively creates a new artery into the South Shore property from a quiet residential cul-de-sac.
However, Feeley, the principal of Cottage + Castle and the owner-occupant of 59 South Shore Road, argues that the linkage is not about shifting traffic, but about stewarding the land. Feeley has been categorical about the plan, and has said that he has “zero intention” of it being an event space. Instead, he describes a vision centered on horses and equine therapy.
Equestrian Enclave: This architectural rendering details the proposed redevelopment of the two-acre parcel at 14 Tripp Drive. The plan, featuring a six-stall stable, a carriage house, and expansive paddocks with a riding arena, has been linked via easement to the neighboring estate at 59 South Shore Road, fueling concerns about the "functional compound" being built within a residential cul-de-sac
A Vision in Blueprints
The legal foundation provided by the easement supports a substantial redevelopment planned for 14 Tripp Drive. Architectural plans dated April 3, 2025, reveal a complex consisting of a six-stall stable, a carriage house, and associated outbuildings.
To a skeptical observer, the plans, which include a bunk room, kitchenette, multiple shower baths, and a lounge area, resemble the infrastructure for a large-scale hosting operation. Feeley counters that these amenities are standard requirements for a modern, professional stable. He notes the spaces are designed for grooms, barn managers, and riding instructors who require on-site facilities to care for the animals.
Feeley intends for the finished product to be a singular sanctuary. The plan includes a riding arena and irrigated paddocks stretching across the combined acreage, seeking to restore a sense of Nantucket’s agricultural heritage to this corner of the South Shore.
The Historic Context of the Horse
Feeley’s incentive taps into a recently diminished history of equestrian life on Nantucket. Historically, the island’s moors and open spaces were home to hardy ‘Nantucket Ponies’ and extensive grazing lands. While much of that character has been lost to residential density, the South Shore remains one of the few areas where the scale of the lots can still support equine activity.
By repositioning 14 Tripp and 59 South Shore as a unified equestrian estate, Feeley wants to revive a specific type of island ‘gentleman’s farm.’ It’s a move that, on paper, aligns with the island’s historic preservation goals, even as it creates a footprint that dwarfs its residential neighbors.
The Housing Paradox
The redevelopment of 14 Tripp Drive does, however, require a significant removal. Public Historic District Commission (HDC) records show the property has entered a "move-off" review process for the existing five-bedroom house on the site.
"Of course that would be our preference to move it," Feeley says regarding the house, adding that he's spoken to a neighbor who has expressed interest in taking a portion of the house at 14 Tripp.
At a time when Nantucket is desperate for year-round housing, the loss of a functional five-bedroom home is a point of friction. Critics note the irony: Feeley is also the co-developer behind Surfside Crossing, the controversial 156-bedroom affordable housing project. While he fights to build density in Surfside, he is clearing a residential footprint on Tripp Drive to make way for a stable.
The Dispute That Brought the Light
The scrutiny of the Tripp Drive project is fueled by the ongoing battle over the current use of 59 South Shore Road. Neighbors have documented a pattern of large-scale events, including high-profile weddings and fundraisers that have drawn global icons like Beyoncé and Jay-Z. They point to current rental listings that offer the estate for up to $75,000 per week.
In a Zoning Board of Appeals (ZBA) hearing in February 2025, Feeley defended the property’s use as purely residential. “The house is used as a residence. It is rented as a residence," he said, maintaining that the private gatherings held there do not constitute a commercial event venue.
The ZBA found itself at a stalemate. A 3-2 majority actually supported overturning the Building Commissioner’s ruling. Because Nantucket requires a four-vote supermajority to reverse such a decision, the appeal failed. The developer’s victory was secured by the narrowest of procedural margins.
Exit Strategy
The ultimate resolution of the South Shore dispute may not come from a courtroom or a town board, but from the open market.
Feeley confirmed to Below Deck that he intends to bring the combined estate back to the market in May. The listing will debut as a fully realized vision: a primary residence at 59 South Shore Road paired with a 14 Tripp Drive parcel already cleared and permitted for its luxury stable complex. By securing the HDC approvals in advance, Feeley is not just selling land, he’s selling a pre-packaged turnkey compound.
"I’m creating the opportunity for this to be stewarded in the vision I had hoped to create for the property," Feeley says. For him, the May listing is the culmination of a multi-year effort to define what a modern Nantucket estate can, and should, be.
A Neighborhood in Limbo
For the neighbors, however, the news of the upcoming sale adds a new layer of uncertainty. They see a system where property boundaries are fluid for those with the resources to redefine them, and where a 3-2 loss at the ZBA can be leveraged into a high-value market offering.
While the hammers have not yet started at 14 Tripp Drive, the legal and architectural framework is now firmly in place for whoever holds the keys next. Whether the property becomes a quiet sanctuary for equine therapy or the event-hosting machine the neighbors have long feared will ultimately depend on the next steward who buys into Feeley’s seven-acre vision.
The question of how a residence functions on a changing Nantucket remains unsettled. With the property set to hit the market in the coming weeks, the answer may hinge less on zoning boards than on the priorities of whoever ultimately buys into the vision.