Luxury homes for sale & real estate in Shelter Island Heights, NY

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ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends or family. Cozy bedrooms provide comfort and privacy, while the flow of the house makes it easy to host and enjoy time together. With a separate entrance to the upstairs, this additional living space offers rental opportunity or dual living accommodation. With its retreat-like atmosphere and charmi

$1,295,000

4 beds3 baths2,618 sq ft

1 Gazon Rd, Shelter Island, NY 11964

Separate entrance • Room for a pool • New appliances

Listing by Douglas Elliman Real Estate

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There's plenty of potential here to update or expand with your own design vision. The property also includes a separate, partially completed renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests

$1,695,000

4 beds3.5 baths1,702 sq ft

26 S Menantic Rd, Shelter Island, NY 11964

Adjacent to park • Separate cottage • Inviting living area

Listing by Daniel Gale Sothebys Intl Rlty

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
6 Bedroom 6 Bath residence nestled in the heart of historic Shelter Island Heights. Over 5000 sq ft of living space Gunite Heated Pool Extensive ipe decking on main house and guest house apartment Brand New Kitchen with Monogram appliances Private Beach Club Immediate occupancy available Being sold furnished

$1,990,000

6 beds5.5 baths5,000 sq ft

4 bayview Avenue, Hampton Bays, NY 11946

Gunite heated pool • Brand new kitchen • Private beach club

Listing by Joseph W Johns

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Investors Dream! Welcome to this expansive 6-Bedroom, 4-Bath Home with Water Views on Shelter Island This spacious 6-bedroom, 4-bathroom home, nestled in one of Shelter Island’s most sought-after locations, offers a perfect blend of luxury and comfort. Featuring a grand primary suite and a versatile junior suite, it’s ideal for both relaxation and hosting guests. The very large dining room is perfect for entertaining, with plenty of space to host family gatherings or dinner parties. French doors off the dining room leads you onto the spacious deck. The chef’s kitchen boasts a Viking stove, ideal for preparing gourmet meals with ease. Enjoy breathtaking water views from mul

$1,999,000

6 beds4 baths4,949 sq ft

61 Gardiners Bay Dr, Shelter Island Heights, NY 11964

Viking stove • Large dining room • Grand primary suite

Listing by Signature Premier Properties

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ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
This Nantucket Shingle Classic with room for pool has Size, Location and Style to adorn this Rare Sunset Waterfront Green Lawns Gem. Surprisingly Bigger than it looks! Many believe the side lawn a separate lot from the spacious 5 bedroom Beach House on gorgeous Shelter Island. The only house known to be built there. The 190' of Silver Beach waterfront is fully bulk headed with dock on a level acre with generous side lawn. Perfect for entertaining or escaping as it's surrounded by mature landscaping. Reich Eklund custom built this jewel of a beach house in 1985 and it is well designed and maintained by one owner who made sure all rooms have sunset waterviews including main, living , dining

$5,415,000

5 beds3.5 baths3,325 sq ft

90 Peconic Ave, Shelter Island, NY 11964

Dock • Full bulkhead • Level acre

Listing by Susan C Cincotta

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COMING SOON

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
336 2nd St is ideally located just steps from the heart of Greenport Village, offering quick access to the harbor, Mitchell Park, and the waterfront. Residents can walk to shops, restaurants, cafés, galleries, and the LIRR station, making this one of the most convenient locations in the village. The property sits close to marinas, beaches, and ferry service to Shelter Island, and is minutes from the North Fork’s vineyards and farm stands. This desirable location provides the perfect blend of quiet residential living with all of Greenport’s amenities just a short stroll away

$1,600,000

4 beds2 baths1,800 sq ft

336 2nd Street St, Greenport, NY 11944

5,227 sq ft lot • Parking • Built 2000

Listing by Keller Williams Realty Greater

COMING SOON

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Waterfront dream! This 3-bed, 2.5-bath home boasts deep-water docking. Open floor plan on both levels features two stone fireplaces, primary en-suite, ample storage, and a large open kitchen with breakfast and dining areas. Enjoy large sliders accessing two decks overlooking the waterfront, plus a spacious waterside boat house. Benefit from a brand new bulkhead & decking completed in 2025. Built by Deck Homes for guaranteed quality!

$1,899,000

3 beds2.5 baths2,000 sq ft

630 Tarpon Dr, Southold, NY 11971

0.45 acre lot • 2 garage spots • Built 1980

Listing by Douglas Elliman Real Estate

OPEN SAT, 11:30AM TO 1PM

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Presenting a rare waterfront property in Greenport, for the serious boater. This remarkable home features over 150 feet of waterfront on protected Stirling Harbor, offering the deep water dock space you've been waiting for. The luxury floating dock can easily accommodate oversized vessels, making it ideal for large yachts. Less than 3 years old, it has both 85 feet and 30 feet deep-water sides and is fully serviced with 200 amps of power and internet. Plenty of space for multiple boats, kayaks and friends to pull up waterside. Stirling Harbor offers big-boat access with an 8 foot maintained channel and calm water protection. Also perfect for quick runs to Gardiners Bay and Shelter Island. T

$2,599,000

4 beds3 baths3,500 sq ft

340 Robinson Rd, Greenport, NY 11944

Big-boat access • Luxury floating dock • Waterfront property

Listing by Engel & Volkers North Fork

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. Whether you choose to reimagine, repurpose, or preserve this unique homestead

$1,499,000

4 beds1.5 baths1,880 sq ft

1760 Albertson Ln, Greenport, NY 11944

Mechanics pit • 2 car garage • Workshop

Listing by Douglas Elliman Real Estate

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
I am proud to bring 605 Gus Drive in East Marion to the market. A custom-built, classic Hamptons style home, nestled on a shy acre at the end of a serene cul de sac. This enchanting property, completed in 2022, offers an exquisite blend of elegance, comfort, and luxury, wrapped in an abundance of natural light. Enter through the front door into a grand foyer boasting elegant 20-foot ceilings. The rest of the groundfloor features 10-foot ceilings, creating an airy, spacious atmosphere throughout the sprawling 3400sq ft of living space(excluding the basement). Oak hardwood floors add a touch of warmth and sophistication to each room and add to the sense of grandeur throughout. The home compri

$2,595,000

5 beds4.5 baths3,400 sq ft

605 Gus Dr, East Marion, NY 11939

Grand foyer • 20 foot ceilings • 10 foot ceilings

Listing by Douglas Elliman Real Estate

ABOUT THIS HOME
Luxury Home for sale in Shelter Island Heights, NY:
Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for

$869,000

5 beds3 baths1,805 sq ft

35 Washington Ave, Greenport, NY 11944

8,712 sq ft lot • Built 1928 • Listed 15 days

Listing by Coldwell Banker American Homes

Property at 210 Bennett Rd, Greenport, NY 11944, 4 beds, 3 baths

$998,500

4 beds3 baths2,000 sq ft

210 Bennett Rd, Greenport, NY 11944

Listing by Douglas Elliman Real Estate

Property at 530 Sunset Way, Southold, NY 11971, 5 beds, 2 baths

$1,699,000

5 beds2 baths1,688 sq ft

530 Sunset Way, Southold, NY 11971

Listing by Thomas J McCarthy Real Estate

Property at 450 Sterling Woods Ln, Southold, NY 11971, 4 beds, 3 baths

$2,295,000

4 beds3 baths3,769 sq ft

450 Sterling Woods Ln, Southold, NY 11971

Listing by Douglas Elliman Real Estate

Property at 1455 Cedar Point Dr, Southold, NY 11971, 3 beds, 2 baths

$2,750,000

3 beds2 baths1,250 sq ft

1455 Cedar Point Dr, Southold, NY 11971

Listing by Daniel Gale Sothebys Intl Rlty

Property at 250 Osprey Nest Rd, Greenport, NY 11944, 4 beds, 6 baths

$2,999,000

4 beds6 baths5,220 sq ft

250 Osprey Nest Rd, Greenport, NY 11944

Listing by BERKSHIRE HATHAWAY

Property at 141A N Ferry Rd, Shelter Island, NY 11964, 4 beds, 6 baths

$4,250,000

4 beds6 baths5,500 sq ft

141A N Ferry Rd, Shelter Island, NY 11964

Listing by Atlas Sales Realty

Property at 73 N Midway Rd, Shelter Island, NY 11964, 4 beds, 3 baths

$1,895,000

4 beds3 baths2,296 sq ft

73 N Midway Rd, Shelter Island, NY 11964

Listing by Daniel Gale Sothebys Intl Rlty

Property at 2820 Shipyard Ln Unit 3M, East Marion, NY 11939, 2 beds, 2.5 baths

$1,275,000

2 beds2.5 baths1,800 sq ft

2820 Shipyard Ln Unit 3M, East Marion, NY 11939

Listing by Compass Greater NY LLC

Property at 13 Tarkettle Rd, Shelter Island, NY 11964, 3 beds, 2 baths

$3,175,000

3 beds2 baths1,373 sq ft

13 Tarkettle Rd, Shelter Island, NY 11964

Listing by Daniel Gale Sothebys Intl Rlty

Property at 240 August Ln, Greenport, NY 11944, 4 beds, 3 baths

$1,750,000

4 beds3 baths2,600 sq ft

240 August Ln, Greenport, NY 11944

Listing by Sothebys Int'l Realty Hamptons

Property at 619 Bailey Ave, Greenport, NY 11944, 4 beds, 2.5 baths

$1,645,000

4 beds2.5 baths2,300 sq ft

619 Bailey Ave, Greenport, NY 11944

Listing by Douglas Elliman Real Estate

Property at 412 Atlantic Ave, Greenport, NY 11944, 3 beds, 2 baths

$1,495,000

3 beds2 baths1,671 sq ft

412 Atlantic Ave, Greenport, NY 11944

Listing by Engel & Volkers North Fork

Property at 435 Maple Ln, Greenport, NY 11944, 4 beds, 4 baths

$2,250,000

4 beds4 baths4,500 sq ft

435 Maple Ln, Greenport, NY 11944

Listing by Corcoran

Property at 380 Homestead Way, Greenport, NY 11944, 3 beds, 2 baths

$1,200,000

3 beds2 baths1,650 sq ft

380 Homestead Way, Greenport, NY 11944

Listing by Locqube New York, Inc.

Based on information submitted to the MLS GRID as of Tue Dec 02 2025. 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.

Luxury Homes for Sale in Shelter Island Heights

There are currently 5 luxury homes for sale in Shelter Island Heights at a median listing price of $1.99M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Shelter Island Heights stay on the market for 227 days. Popular neighborhoods include North Fork, The Hamptons, and Long Island. This map is refreshed with the newest listings in Shelter Island Heights every 15 minutes.

In the past month, 1 home has been sold in Shelter Island Heights. Find your dream home in Shelter Island Heights using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Shelter Island Heights are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Shelter Island Heights. Our Shelter Island Heights real estate stats and trends will give you more information about home buying and selling trends in Shelter Island Heights. If you're looking to sell your home in the Shelter Island Heights area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Shelter Island Heights with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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