29525 Main Road · Orient

A rare estate of two building lots and 11.9 agricultural acres.

Set back roughly 250 feet from Main Road in the coveted hamlet of Orient, this 17.4-acre estate offers what almost nothing on the North Fork still does: scale. Three contiguous parcels, twenty horse stalls, a former indoor riding arena with thirty-foot ceilings, and a recently renovated 4,578-square-foot multi-use building with architectural plans already in place to convert it to a residence.

The estate combines the rare combination of two buildable residential lots — a 2.5-acre parcel at the entrance and an elevated 3-acre lot at the rear with panoramic views of the Long Island Sound — with 11.9 acres of fully fenced equestrian land in between. A blank canvas for a private compound, a working farm, a vineyard, or a multi-residence estate.

Drag the Line

Same estate. Two futures.

Every frame below pairs real photography of the property today with a rendering of what it becomes — the barns, the arena, the open land. Grab any divider and pull it across.

Watch it happen — then drag the line yourself below

The kitchen space as it stands today — framed construction — Kitchen

Rendering of the finished kitchen — Kitchen

The living room space as it stands today — framed construction — Living Room

Rendering of the finished living room — Living Room

The hallway as it stands today — framed construction — Hallway

Rendering of the finished hallway — Hallway

The office space as it stands today — framed construction — Office

Rendering of the finished office — Office

The main barn exterior as it stands today — Main Barn · Exterior

Rendering of the finished main barn exterior — Main Barn · Exterior

The arena interior as it stands today — empty span — Indoor Tennis Barn

Rendering of the arena as an indoor tennis court — Indoor Tennis Barn

The woodworking shop as it stands today — Woodworking Shop

Rendering of the finished woodworking shop — Woodworking Shop

The second woodworking shop as it stands today — Second Woodworking Shop

Rendering of the finished second woodworking shop — Second Woodworking Shop

The open paddock and fields as they stand today — The Land · Agricultural Vision

Rendering of the land planted as vineyard, orchard and market rows — The Land · Agricultural Vision

Renderings are conceptual and provided for illustration only. They depict one possible finished vision and do not represent the current condition of the buildings, which are offered as-is.

Represented By

Alexander Aquino

Licensed Real Estate Salesperson · Douglas Elliman · North Fork

Alexander Aquino represents buyers and sellers across Long Island's North Fork — Orient, Greenport, Southold and Mattituck. He is known for an unusually thorough approach to marketing: commissioning professional and drone photography, researching each property's history and potential, and building dedicated websites — like this one — so a listing is understood for what it can become, not merely what it measures.

29525 Main Road is his exclusive listing. Private showings and inquiries are handled by Alexander directly.

631.902.7351 alexander.aquino@elliman.com

Straight Answers

What buyers ask.

Can I build a home here?

Yes. Two of the three parcels are single-and-separate buildable residential lots — the 2.5-acre parcel at the entrance and the elevated 3-acre lot at the rear with Long Island Sound views. The 4,578 sq ft multi-use building also comes with architectural plans already drawn to convert it into a single-family residence. See the plans →

What does “development rights sold” actually mean for me?

It applies only to the 11.9 agricultural acres in the middle of the estate: the Town of Southold purchased the right to ever subdivide that land, which is why it stays open in perpetuity — permanently protected views no neighbor can ever build out. Every current use remains fully intact: horses, livestock, vineyard, organic produce. The two building lots are not part of it and remain fully buildable.

What can the buildings become?

20,209 sq ft across six structures. The 6,615 sq ft former riding arena works as built for equestrian training or adapts to cathedral-ceiling commercial, working-pasture, or workshop use. The 20-stall stable is turn-key. The multi-use barn carries residence-conversion plans. See every future we’ve mapped →

Can the property produce income?

The configuration supports several approaches buyers model: boarding and training with twenty stalls, the arena and four paddocks; agricultural use of the protected acres; or building on one residential lot while holding the other. The two single-and-separate lots are what make the two-home strategy possible.

Is this one property or three?

Three contiguous tax parcels, offered together as MLS #853864 — 17.4 acres in total. That structure is the flexibility: one private compound, a working farm with a residence, or build-and-hold across the two lots.

What’s actually nearby?

Orient is the quiet end of the North Fork — and we mapped it: 250 restaurants, wineries, farm stands, beaches and marinas, searchable on the Location page, with the village, Orient Beach State Park and the Cross Sound Ferry minutes away.

How do I see it?

Privately, with Alexander. Walking all three parcels takes about 45 minutes. Call or text 631·902·7351, or use the form below — and the property documents hold the full particulars.

Seventeen acres,
three parcels, one rare opportunity.

The Land

What It Could Become

The Buildings

Plans & Surveys

The Gallery

Location & History

A rare estate of two building lots and 11.9 agricultural acres.

A look across all three parcels.

Same estate. Two futures.

Alexander Aquino

What buyers ask.

A private showing of the estate.