A Rare Shelter Island Gem with Timeless Soul
Welcome to a truly extraordinary waterfront estate where history, elegance, and coastal luxury converge. Set on the coveted Westmoreland Drive, this stunning 1901 Tudor has been masterfully restored - blending old-world charm with modern sophistication.
Inside, you’ll be transported by original plaster walls and six dramatic fireplaces, thoughtfully paired with today’s comforts: central air, upgraded heating, and energy-conscious insulation throughout the upper floors. The chef’s kitchen, the heart of the home, has been reimagined with top-tier finishes and a newly added butler’s pantry - perfect for hosting with ease.
With six bedrooms and four and a half baths, there’s ample space for family, friends, and guests to gather and unwind. Whether you’re curling up by the fire, hosting summer soirées on the classic brick patio, or floating in the 20x50 heated Gunite pool, every moment here feels timeless.
Beyond the manicured grounds, a deep-water dock awaits - ideal for multiple boats and offering direct access to Shelter Island’s pristine waters.
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Listing Snapshot
Price
$4,300,000
Days On Site
14 Days
Bedrooms
6
Inside Area (SqFt)
4,957 sqft
Total Baths
5
Full Baths
4
Partial Baths
1
Lot Size
2.02 Acres
Year Built
1901
MLS® Number
899084
Status
Active
Property Tax
$22,697.66
HOA/Condo/Coop Fees
N/A
Sq Ft Source
N/A
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Recent Activity
2 weeks ago
Listing first seen on site
2 weeks ago
Listing updated with changes from the MLS®
General Features
Acres
2.02
Property Sub Type
Single Family Residence
Sewer
Septic Tank
SqFt Total
4957
Style
Tudor
Utilities
Electricity Available
Water Source
PrivateWell
Interior Features
Appliances
Stainless Steel Appliance(s)
Cooling
Central Air
Fireplace
Yes
Fireplace Features
BedroomFamily RoomLiving RoomWood Burning
Fireplaces
6
Heating
Forced Air
Interior
Beamed CeilingsBuilt-in FeaturesChandelier
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Exterior Features
Construction Details
Frame
Pool Features
Electric HeatIn GroundPrivate
Private Pool
Yes
Waterfront Features
River AccessWaterfront Access
Community Features
School District
Shelter Island
Schools
School District
Shelter Island
Elementary School
Shelter Island School
Middle School
Shelter Island School
High School
Shelter Island School
Listing courtesy of Compass Greater NY LLC carl.gambino@compass.com
Based on information submitted to the MLS GRID as of 2025-08-23 05:23 PM EDT.
All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied
Open House Information is subject to change without notice. All information should be independently reviewed
and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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