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27 Country Club DriveShelter Island, NY 11964

For Sale

$1,850,000

Smart Buyer Rebate $18,500

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm and inviting ambiance. The gourmet kitchen is equipped with high-end appliances, and a granite island seating 10, a spacious breakfast/bar with ample counter space, perfect for cooking and entertaining. A large adjacent sunroom, with double doors opening to beautifully landscaped gardens and a patio, provides an ideal setting for gatherings or quiet relaxation. The first floor boasts a luxurious primary suite with custom-built storage, two walk-in closets, and a spacious en-suite bath with a dedicated vanity area. A second bedroom, a full bath, and a versatile art studio with skylights—also with double doors leading to the patio—complete the main level. Upstairs, you’ll find an additional large bedroom, and a 12'x30' framed out space for a theater, office, gym, game room, or whatever you desire. The home also includes a generous two-car garage, ensuring ample space for vehicles and equipment, a whole house generator, 1000 gallon propane tank, and radiant heat flooring. With its thoughtful design, high-quality finishes, and prime location near sought-after beaches and golf courses, this exceptional home is a must-see.

Listed by Tina Marika Kaasik

·

Daniel Gale Sothebys Intl Rlty

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631-749-1155

Last updated August 17, 2025

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Source: OneKey #842082

Listing Facts

  • TypeSingle-family
  • NeighborhoodShelter Island Heights
  • Bedrooms3
  • Bathrooms2
  • Days on Prevu156
  • Taxes$7,382.92/year
  • Size3,170 sqft
  • Price per sqft$584

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

08/16/2025
Price Decreased
$1,850,000
04/03/2025
Listed by Daniel Gale Sothebys Intl Rlty
$1,990,000

Property Details for 27 Country Club Drive

Exterior

Construction

  • Year Built: 2011
  • Architectural Style: Traditional
  • Construction Materials: Frame

Features

  • Other Structures: Shed(s)
  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 3,170
  • Building Area Units: Square Feet
  • Lot Size Dimensions: 1
  • Lot Size Square Feet: 45,738

Financial

Taxes

  • Parcel Number: 0700-001-00-01-00-099-000
  • Tax Annual Amount: $7,382.92
  • Tax Year: 2025

Interior

Features

  • Appliances: Dishwasher, Dryer, Electric Water Heater, Washer
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Hardwood
  • Interior Features: Primary Bathroom, Cathedral Ceiling(s), Eat-in Kitchen, Entrance Foyer, Master Downstairs, Walk-In Closet(s), Formal Dining

Measurements

  • Living Area: 3,170
  • Living Area Source: Public Records

Rooms

  • Basement: Partial, Partially Finished
  • Bathrooms Full: 2
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 3
  • Rooms Total: 9

Other

Location

  • Tax Block: 1
  • Tax Lot: 99

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Features: Private, Attached

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: Oil, Forced Air, Radiant
  • Sewer: Septic Tank
  • Utilities: Trash Collection Private
  • Water Source: Well, Private

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2025, OneKey™ MLS. All Rights Reserved.

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.