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The Goods – This stunning waterfront property has a combination of luxury, seclusion and tranquility that Shelter Island alone can offer. It includes 4.3 acres, 800 feet of westerly facing waterfront on protected Coecles Harbor, 4 blue stone patios, sweeping lawn to tennis, private beach, deep water dock and 8 moorings. The 12,000 square foot cedar shake colonial style manor house features 22 bedrooms, 14 full and 4 half baths, elegant circular drive, formal entry foyer, 4 hearths, dining room/ ballroom, living room/bar, commercial kitchen with multiple pantries, windowed porch/sunroom plus partially finished 5,000+ square foot basement with office, spa and gym. An additional 2.2 buildable acres are available across the street. This idyllic private residence is now operating as the historic Rams Head Inn. Retain commercial usage for your corporate retreats, private yacht club or exclusive gourmet events. 

Why it’s a good deal – “This is a one-of-a-kind waterfront offering with private beach and deepwater dock on 4+ acres in the coveted Ram Island neighborhood on Shelter Island. The mansion-like inn is in excellent condition and the property combines luxury amenities with commercial opportunities. There is nothing else like it,” says listing agent Peter Humphrey of Douglas Elliman Real Estate


The Goods – A charming 2 bedroom,1 bath ranch set on .70 acre with a rustic summer patio and pergola. This charming home is close to all the North Fork has to offer. 

Why it’s a good deal – “This darling home is a sweet deal because of its potential. A lovely and private yard with room for a pool and so much more. Its central location and some hidden surprises make this darling home a great deal!” says listing agent Sheila Izzo of North Fork Real Estate Inc. 


The Goods – Wake up every morning to panoramic views of the Great Peconic Bay! Feel like you are on top of the world in this spectacular home with waterfront cabana, deck and balcony. Meticulously maintained featuring master en suite, guest suite, lots of privacy and old-time details combined with timeless sophistication.

Why it’s a good deal – Listing agent Thomas McCloskey of Douglas Elliman Real Estate says, “There is not one turnkey bayfront that has this much to offer for less than $2,000,000.”


The Goods – Located in coveted Nassau Point, this chic, renovated, hideaway has its own dock, Gunite pool with spa, and gorgeous grounds. Spacious master suite, gourmet kitchen, library, living room with a fireplace. Incredible space for all! Four bedrooms, 4 bathrooms and beach rights. You must see this! Surrounded by North Fork award winning vineyards, renowned restaurants, farm stands and great shopping.

Why it’s a good deal – Listing agent Sheri Winter Parker of The Corcoran Group says, “There are so many reasons why this is such a great deal! You have a completely renovated, turn-key, gorgeous, I might add, home, complete with a Gunite pool and a dock. What more could you ask for?”


The Goods – Well-maintained, 1920s Bungalow with in-ground salt water pool. Open living/dining area with fireplace, hardwood floors, central air conditioning, large deck overlooking in-ground pool. Bay beach at the end of the street. NYC transportation, village shops and restaurants, waterfront park and marina nearby.

Why it’s a good deal – Listing agent Paul Loeb of Douglas Elliman Real Estate says, “This home is a good deal for several reasons. Most older homes in Greenport Village need a lot of work. This one does not. Another reason is, getting a pool in Greenport Village can be a tricky process due to the smaller lot sizes and most require a variance. This lot size is bigger than most village lots and your pool is already in place. This village charmer is now priced below Greenport Village sales that did not have a pool.”

Chic, Renovated Hideaway

Sheri Winter Parker of The Corcoran Group