29 Winthrop Road, Shelter Island, NY 11964

Listing Provided by Daniel Gale Sotheby's International Realty




Full Baths


Half Baths



Carriage House, an extraordinary Shelter Island waterfront estate. Originally built in 1888, this magnificient home was reimagined, renovated and expanded in 2010. Sited on 1.7 acres overlooking Dering Harbor this treasure features interior and exterior spaces, with views and amenities beyond. Within the over 9000 sq foot interior are 6 en suite bedrooms and 4 additional powder rooms. Both the upper and main level primary bedrooms include expansive closets, fireplaces and private decks. Large living spaces filled with natural light include an expansive eat in kitchen and great room, 2 large living rooms, theater and a fabulous professional bar leading to the wine cellar below. There are 3 additional fireplaces throughout the main living areas of the home Outside there are gorgeous plantings and garden spaces, 166' of deep water dock and 600 feet of private beach with deeded mooring. Multiple upper and lower decks are perfect for sun worshippers and star gazers, after a swim in the gorgeous heated pool overlooking the harbor. The 4 Car garage and substantial dry storage below must be mentioned. This property is an entertainer's dream and Shelter Island is no longer a "best kept secret." Centrally located between North and South forks and less than a 5 minute ferry ride to all the Hamptons and North Fork have to offer.

Features of 29 Winthrop Road

MLS# 3466044
Price $9,499,000
Sold Price $8,750,000
Total Taxes $39,436
Bedrooms 6
Bathrooms 10
Full Baths 6
Half Baths 4
Lot Square Footage 74,488
Acres 1.71
Year Built 1888
Type Residential
Sub-Type Single Family Residence
Style Nantucket
Status Closed

Community Information

Address 29 Winthrop Road
City Shelter Island
County Suffolk
State NY
Zip Code 11964


Features Partly Wooded, Stone/Brick Wall
Parking Private, Attached, Driveway, 4+ Car Attached
# of Garages 4
Garages Private, Attached, Driveway, 4+ Car Attached
View Water
Is Waterfront Yes
Waterfront Beach Front, Harbor, Waterfront
Has Pool Yes
Pool Inground Pool


Interior Hardwood
Interior Features Den/Family Room, Eat-in Kitchen, Formal Dining Room, Living Room / Dining Room, Master Bath, Walk-In Closet(s), Entrance Foyer, Home Office, Marble Bath, Marble Countertops, Master Downstairs, Pantry, Powder Room, Storage, Wet Bar
Appliances Dishwasher, Dryer, Microwave, Oven, Washer, Wine Cooler
Heating Oil, Forced Air, Hot Water
Cooling Central Air
Fireplace Yes
# of Fireplaces 5
Has Basement Yes
Basement Partial


Exterior Advanced Framing Technique, Blown-In Insulation, Energy Star, Shingle Siding
Exterior Features Balcony, Dock, Private Entrance, Sprinkler Lawn System
Lot Description Partly Wooded, Stone/Brick Wall
Windows New Windows
Construction Advanced Framing Technique, Blown-In Insulation, Energy Star, Shingle Siding

School Information

District Shelter Island
Elementary Shelter Island School
Middle Shelter Island School
High Shelter Island School

Additional Information

Date Listed March 21st, 2023
Date Sold May 12th, 2023
Days on Market 17
Short Sale No
RE / Bank Owned No
HOA Fees $0
Broker Agency Compensation 2.5
Buyer Agency Compensation 2.5

Offer is made only to participants of the MLS where the listing is filed.

Listing Map

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