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9 / 7 Westmoreland Drive, Shelter Island Heights

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.

6 Beds ⋅ 5 Baths ⋅ 899084 MLS

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.

9 / 7 Westmoreland Drive, Shelter Island Heights

31 Grand Ave and 20 Spring Garden Ave, Shelter Island Heights

Historic Shelter Island Heights Home with Pool and Cottage. This beautifully renovated 1890's Victorian home is located in the heart of the Heights Historic District. Ideally located right off the North Ferry, and within a block of the private beach club and tennis courts. And just a stones throw to the Yacht Club. Beautiful architectural details remain throughout the exterior and interior of this Classic Historic home. The main house features 4 Bedrooms with 3 of them having their own balcony thru beautiful arched doorways. The primary bedroom is spacious with a full bath. Gorgeous wide plank pine floors are featured in every room. First floor includes a cozy parlor with fireplace, large den, custom eat-in-kitchen with high-end appliances and easy access to dining area and large wrap around porch for outdoor entertaining. Back deck overlooks the beautiful gardens and heated gunite salt water pool. Beyond the pool is an adorable 2-bedroom guest cottage. Adjacent to the cottage is a detached garage for car, storage, or game room. This home is a Gem. Rare find!

6 Beds ⋅ 5 Baths ⋅ 829868 MLS

Historic Shelter Island Heights Home with Pool and Cottage. This beautifully renovated 1890's Victorian home is located in the heart of the Heights Historic District. Ideally located right off the North Ferry, and within a block of the private beach club and tennis courts. And just a stones throw to the Yacht Club. Beautiful architectural details remain throughout the exterior and interior of this Classic Historic home. The main house features 4 Bedrooms with 3 of them having their own balcony thru beautiful arched doorways. The primary bedroom is spacious with a full bath. Gorgeous wide plank pine floors are featured in every room. First floor includes a cozy parlor with fireplace, large den, custom eat-in-kitchen with high-end appliances and easy access to dining area and large wrap around porch for outdoor entertaining. Back deck overlooks the beautiful gardens and heated gunite salt water pool. Beyond the pool is an adorable 2-bedroom guest cottage. Adjacent to the cottage is a detached garage for car, storage, or game room. This home is a Gem. Rare find!

31 Grand Ave and 20 Spring Garden Ave, Shelter Island Heights

5 Spring Garden Avenue, Shelter Island Heights

Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by America’s earliest landscape architects. Originally described as a “2.5-story Gothic Revival cottage with hipped roof, segmental arch window heads and two-tier veranda,” the residence retains an extraordinary collection of original details rarely found today. Highlights include 39 original working double-hung windows complete with storms and screens, four original attic “cross-breeze” windows designed to naturally cool the home, original solid oak interior and exterior doors, spacious 10-foot ceilings, and plaster walls throughout the main house. Three spacious front bedrooms — including the primary — open directly onto a covered second-story wraparound sleeping porch, capturing the breezes and relaxed elegance of Shelter Island summers. Cottage-style clapboard accents in the kitchen and rear bedroom add warmth and authenticity to the historic interiors. Thoughtful infrastructure improvements complement the home’s historic integrity, including a new roof (2006), a newly excavated full-footprint extra-deep basement with radiant heat slab (2008), and a complete rebuild of the secondary upstairs bath (2010). The property may also qualify for the New York State Historic Homeownership Rehabilitation Credit Program, offering a potential tax credit on qualified rehabilitation expenditures. A truly special opportunity to own an architecturally significant home in one of New York’s most cherished historic communities.

5 Beds ⋅ 3 Baths ⋅ 1004894 MLS

Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by America’s earliest landscape architects. Originally described as a “2.5-story Gothic Revival cottage with hipped roof, segmental arch window heads and two-tier veranda,” the residence retains an extraordinary collection of original details rarely found today. Highlights include 39 original working double-hung windows complete with storms and screens, four original attic “cross-breeze” windows designed to naturally cool the home, original solid oak interior and exterior doors, spacious 10-foot ceilings, and plaster walls throughout the main house. Three spacious front bedrooms — including the primary — open directly onto a covered second-story wraparound sleeping porch, capturing the breezes and relaxed elegance of Shelter Island summers. Cottage-style clapboard accents in the kitchen and rear bedroom add warmth and authenticity to the historic interiors. Thoughtful infrastructure improvements complement the home’s historic integrity, including a new roof (2006), a newly excavated full-footprint extra-deep basement with radiant heat slab (2008), and a complete rebuild of the secondary upstairs bath (2010). The property may also qualify for the New York State Historic Homeownership Rehabilitation Credit Program, offering a potential tax credit on qualified rehabilitation expenditures. A truly special opportunity to own an architecturally significant home in one of New York’s most cherished historic communities.

5 Spring Garden Avenue, Shelter Island Heights

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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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