About This Home

This 5-bedroom, 4-bathroom single family at 64A N Midway Road in Shelter Island, NY is listed for $2,199,000 ($832 per sqft). Built in 1977, the home offers 2,642 sqft of living space on a 1.00 acres lot.

Key Features

  • Built in 1977
  • 1.00 acre lot
  • Fireplace
  • Waterfront

Property Details

4 full
3-car garage
1977

Amenities

SolarFireplaceWaterfrontHardwoodA/C
Listing Description

A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm.

This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining.

The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons. Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings.

A welcoming front porch, an attached one-car garage, and a carport. Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light.

The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind.

The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home's appeal.

The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island.

Monthly Cost Estimate

$11,761/mo

20% down · 6.5% · 30 years

Principal$1,590
Interest$9,529
Insurance$641

Estimates only. Actual payments may vary.

Location

64A N Midway Road

Shelter Island, NY 11964

Features & Amenities

Interior Features

First Floor BedroomFirst Floor Full BathBeamed CeilingsCathedral Ceiling(s)Ceiling Fan(s)Central VacuumCrown MoldingEat-in KitchenGranite CountersHigh CeilingsOpen FloorplanOpen KitchenPantryPrimary BathroomRecessed LightingSoaking TubStorageWalk Through Kitchen

Property Details

Flooring

CombinationHardwoodTile - Ceramic

Construction

Batts Insulation Cedar Frame HardiPlank Type

Heating

OilHot Water(Heating)Forced Air

Cooling

Central Air

Appliances

Convection OvenDishwasherDryerElectric CooktopElectric RangeElectric Water HeaterExhaust FanFreezerMicrowaveRefrigeratorStainless Steel Appliance(s)WasherTankless Water Heater

Questions & Answers

This 5-bedroom, 4-bathroom single family at 64A N Midway Road is listed at $2,199,000 ($832/sqft). The estimated monthly payment is $11,760 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1977, 1.00 acre lot, Fireplace, Waterfront. Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings.

This property is listed by Christine M. Beckwith.

CB

Christine M. Beckwith

Agent at Douglas Elliman Real Estate

Listed by Douglas Elliman Real Estate · Broker phone: 6313548100 · View on Broker Site · Broker website

MLS# 1029569· Source: OneKey MLS· 102 days on PropertySimple

Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

64A N Midway Road, Shelter Island, NY 11964

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