The Top Five Most Expensive Homes For Sale In Montauk

Owning a property in Montauk is what it’s all about these days. This week’s Real Estate Top 5 checks out Montauk to see what the options are for the wealthiest real estate buyers of the East End.

The historic Startop Ranch offers the most stunning vistas of the East End with panoramic views from Long Island Sound across the Montauk Moorlands to the Atlantic Ocean. The mystical hilltop setting with 13-plus acres of rolling paddocks echoes grand English country estates and presents a unique opportunity to create a private retreat with regal home, pool, gardens and tennis. A long winding drive through fragrant honeysuckle and pear trees leads up to the main 5-bedroom house. The 120-foot elevation with views of Lake Montauk and the harbor, Long Island Sound, Gardiner’s Bay, Block Island Sound and the Atlantic Ocean as well as a state park sets the perfect canvas to compose an architectural masterpiece.


This contemporary 1.5-acre oceanfront property in Montauk boasts a rare 125-foot setback from the bluff, affording astounding water views from its close proximity to the ocean. This is a special opportunity to acquire a prime Montauk oceanfront parcel where “grandfathered” setbacks are fully intact, allowing for incredible flexibility in development options. The existing residence could easily be expanded to 4,000 square feet, or the current building envelope could accommodate an all-new 6,000-square-foot home, pool, pool house and garage. The present interior features 2700 square feet of sunny, bright living space with floor-to-ceiling ocean-view windows, 5 bedrooms and 3 baths, living room, dining and eat-in kitchen. There is an expansive oceanside deck complete with stunning views and a delightful beach cabana that sits at the toe of the bluff. Private stairs lead to one of the best beaches in the world. The setting is truly spectacular.


Situated down a stately private drive sits this stunning shingle-style traditional on more than 10 acres. This is a rare opportunity to own this gorgeous Hollenbeck designed home built with the finest quality by Hummel, surrounded by over 100 acres of preserve. This spacious property features 4,000 square feet of perfection. It was designed to capture the beautiful views of the ocean from the house and grounds. This spacious 4-bedroom home includes wonderful details such as stone fireplaces and gourmet kitchen.


Enjoy unspoiled ocean views and deeded ocean access from this 4,700-square-foot, 6-bedroom, 5.5-bath modern beach bungalow set on 11 acres in the exclusive Montauk Moorlands. Rarely do residences become available within the Montauk Moorlands community. This is one of only a very few houses that are surrounded by hundreds of acres of open space and which have access to the dramatic cliffs and remote beaches of the tip of Long Island. The floor plan places the living spaces, master suite and two guest bedrooms on the second story to take advantage of the sweeping views. Enter the double-height entrance foyer, ascend the curved stair to the great room and you are immediately drawn across the room and out through the floor-to-ceiling sliding glass doors to the oversized deck with covered outdoor dining room, multiple seating and lounging areas and a view of the vast Atlantic Ocean.


This inimitable offering includes two homes situated on two ocean view parcels in Hither Hills, directly across from private deeded ocean beach and access. The main house offers 6 bedrooms, 6 bathrooms, exposed beam cathedral ceiling living area, chef’s central island stone kitchen, walk-in pantry, ocean view private deck, fireplace, deep and heated gunite pool, sauna, gym, rainmaker outdoor shower and extensive brick patio, all encapsulated with stone-accented lush landscape. The cottage offers 5 bedrooms, 2 baths, 2 living rooms, 2 kitchens, exterior deck, outdoor shower, central air, expansive lawn and ocean views. All located on street to street Hither Hills parcels just steps to deeded ocean access and beach.

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