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5 N Menantic RoadShelter Island, NY 11964

For Sale

$5,950,000

Smart Buyer Rebate $59,500

A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West Neck Creek, this timeless model of Federal-style architecture offers 3,206 +/- sq. ft. of living space on 2 levels, 5 bedrooms, 4.5 baths, an attached 2-car garage, 3 fireplaces, a waterside heated gunite pool and room for expansion. The first level has a traditional floor plan with a living room, dining room, kitchen, ensuite primary and guest bedroom. Enjoy all-day sun from the patios, including a beautiful attached gazebo porch for dining al fresco and morning coffee. Bedrooms are each well-sized and bathrooms have been updated. Upstairs, the open third floor awaits your imagination. The restored interiors have been beautifully preserved, the original high ceilings with crown molding, wide-plank pine floors, marble mantelpieces, and even bannisters and newel posts-imbuing the estate with provenance and character and ready to be improved and updated to suit your lifestyle. The estate's park-like grounds showcase everything that makes summers on Shelter Island so special - peace, privacy, with direct access to the water in West Neck Creek. This outdoor oasis is the ultimate luxury, a highlight of every season with brilliant color changes, migrating songbirds, and extraordinary all-day light. The exceptionally well-considered heated gunite pool features a Hydrazzo finish that combines a silky-smooth texture with the proven durability of exposed aggregates. The bluestone patio is located perfectly to capture western light and water views without interrupting the open vista lawn stretching down to the water. Here, find a boaters' paradise with a deepwater dock and 250 feet of western-facing waterfrontage on West Neck Creek. From lawn games and late-night dancing under the stars to elegant dinners with guests arriving by boat, the property has long served as both a vibrant social hub and a serene private retreat. Shelter Island offers an abundance of seasonal pleasures-sailing, fishing, nature trails, and beaches so peaceful they often feel private. The island's charm extends beyond summer; when West Neck Creek glows with shifting light and the surrounding landscape turns vibrant with spring blossoms or autumn foliage. A haven for wildlife and inspiration alike, it's a rare retreat that feels both expansive and deeply personal, year-round.

Listed by Myles Reilly

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Saunders & Associates

·

631-537-5454

Listed by Nancy Mizrahi

·

Saunders & Associates

Last updated September 05, 2025

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Source: OneKey #884679

Listing Facts

  • TypeSingle-family
  • NeighborhoodShelter Island Heights
  • Bedrooms6
  • Bathrooms5
  • Days on Prevu66
  • Taxes$26,438.74/year
  • Size3,157 sqft
  • Price per sqft$1,885

Amenities

  • Dishwasher
  • Washer/Dryer
  • Air Conditioning
  • Swimming Pool

Location

Mortgage Calculator

Listing History

08/05/2025
Price Decreased
$5,950,000
07/02/2025
Listed by Saunders & Associates
$6,750,000

Property Details for 5 N Menantic Road

Exterior

Construction

  • Property Attached: Yes
  • Year Built: 1860
  • Architectural Style: Other
  • Construction Materials: Frame

Features

  • Pool Features: In Ground, Other
  • Pool Private: Yes
  • Waterfront Features: Waterfront
  • Waterfront: Yes

Measurements

  • Building Area Total: 3,206
  • Building Area Units: Square Feet
  • Lot Size Acres: 2.94
  • Lot Size Square Feet: 128,066

Financial

Taxes

  • Parcel Number: 0700-018-00-02-00-022-000
  • Tax Annual Amount: $26,438.74
  • Tax Assessed Value: $3,788,000.00
  • Tax Year: 2024

Interior

Features

  • Appliances: Dishwasher, Dryer, Other, Refrigerator
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Interior Features: Other

Measurements

  • Living Area: 3,157
  • Living Area Source: Other

Rooms

  • Basement: Full
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 6
  • Rooms Total: 9

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes

Schools

Elementary School

  • Elementary School: Shelter Island School
  • Elementary School District: Shelter Island

High School

  • High School: Shelter Island School
  • High School District: Shelter Island

Middle or Junior School

  • Middle Or Junior School: Shelter Island School
  • Middle Or Junior School District: Shelter Island

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Forced Air, Other
  • Sewer: Septic Tank
  • Utilities: See Remarks
  • Water Source: Other

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.