Shelter Island Heights, NY Homes

/43
$2,750,000
- 6 Beds
- 4 Baths
- 4,949 Sq Ft
61 Gardiners Bay Dr, Shelter Island Heights, NY 11965

Welcome to this stunning 6-Bedroom, 4-Bath Home with Water Views on Shelter IslandThis expansive 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

Marie Catanzano

Signature Premier Properties

(844) 791-3908

61 Gardiners Bay Dr, Shelter Island Heights, NY 11965
/20
$60,000 per month
- 3 Beds
- 2 Baths
- House for Rent
16 Little Ram Island Dr, Shelter Island, NY 11964

In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.

16 Little Ram Island Dr, Shelter Island, NY 11964
$1,250,000 Sold Feb 07, 2025
- 2,380 Sq Ft
- $525/SF
- 304 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1986
5 Country Club Dr, Shelter Island, NY 11964

Nestled on 1.06 acres of serene beauty, this charming ranch-style home offers the perfect blend of comfort and coastal living. Enjoy easy access to pristine beaches, world-class golf courses, and all the amenities Hay Beach has to offer. Inside, you'll find a spacious and inviting interior with hardwood floors, vaulted ceilings, and a skylight-lit eat-in kitchen. The primary suite features a

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

5 Country Club Dr, Shelter Island, NY 11964

Est $1,460,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
75 W Neck Rd, Shelter Island Heights, NY 11965

75 W Neck Rd, Shelter Island Heights, NY 11965

/48
$2,895,000
- 3 Beds
- 2.5 Baths
- 1,901 Sq Ft
7 Gazon Rd, Shelter Island, NY 11964

Immerse yourself in the serene charm of 7 Gazon Road, a Zen-inspired retreat tucked away on Shelter Island. This waterfront sanctuary offers the perfect balance of modern luxury and tranquil living. With three bedrooms and two-and-a-half baths, you can choose between a first or second-floor primary suite, each thoughtfully updated to exude sophistication and comfort. Nestled on 1.6 acres of lush

Terry Thompson

Douglas Elliman Real Estate

(631) 800-7430

7 Gazon Rd, Shelter Island, NY 11964
/27
$50,000 per month
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
- House for Rent
28 Gardiners Bay Dr, Shelter Island Heights, NY 11965

Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to

Michael Brennan Douglas Elliman Real Estate

28 Gardiners Bay Dr, Shelter Island Heights, NY 11965
$1,850,000 Sold Oct 29, 2024
- 2,628 Sq Ft
- $704/SF
- 96 Days On Market
- 4 Beds
- 4 Baths
- Built 2005
45 New York Ave, Shelter Island, NY 11964

No details spared in this impeccably renovated Village Classic 4-bedroom spacious home with water views of Chase Creek in the heart of Shelter Island Heights and down the street from shops, restaurants, The Chequit Hotel, Eccentric Bagel, Stars Caf?, Marie Eiffel, Leon 1901, Sunset Beach, Shelter Island Golf Club and more. The first floor graciously flows from the living room with new raised

David Tenenbaum Brown Harris Stevens Hamptons

45 New York Ave, Shelter Island, NY 11964

Est $2,967,000 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,200 Sq Ft
12 Terry Dr, Shelter Island, NY 11964

12 Terry Dr, Shelter Island, NY 11964

/12
$2,750,000
- 6 Beds
- 4 Baths
- 2,418 Sq Ft
14 Freds Ln, Shelter Island, NY 11964

Tucked away on a shy acre, this private retreat features a heated Gunite pool framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the stage for alfresco dining and

Melina Wein M WEIN REALTY INC

14 Freds Ln, Shelter Island, NY 11964
/25
$50,000 per month
- 5 Beds
- 6 Baths
- House for Rent
37 Tuthill Dr, Shelter Island, NY 11964

WHEN AN ARTIST MAKES A HOME Serena Dugan, Co-Founder of Serena&Lily has completed her renovation of 37 Tuthill Drive, Shelter Island. This property is a robust representation of Serena's vision as an artist and a designer. Each detail was carefully considered and selected, and her point of view is visible throughout the house. The artwork, fabrics, and wallpapers are of her design. In some

37 Tuthill Dr, Shelter Island, NY 11964
$2,515,000 Sold Oct 18, 2024
- 2,800 Sq Ft
- $898/SF
- 96 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2017
8 Crescent Way, Shelter Island, NY 11964

Located in a desirable area of Shelter Island known as Hay beach, This traditional home is ready for it's new owner. The home offers an open floor plan with vaulted ceilings, a chef's kitchen with a large island and dining area. The master suite offers substancial closets, double sinks with a large shower with a bench seat. The two additional bedrooms share a bathroom, the second floor has a

Christine Beckwith Douglas Elliman Real Estate

8 Crescent Way, Shelter Island, NY 11964

Est $2,837,000 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,450 Sq Ft
6 Behringer Ln, Shelter Island, NY 11964

6 Behringer Ln, Shelter Island, NY 11964

/20
$3,600,000
- 4 Beds
- 2.5 Baths
- 2,890 Sq Ft
24 Rocky Point Rd, East Marion, NY 11939

This architecturally distinctive home, inspired by the mid-century California Case Study Houses and designed by AC Hocek, is set on two acres of gently sloping land in the prestigious estate area, "Greenlawns". Designed with a thoughtful balance of form and function, the property includes a main house and a separate guest house, offering a unique blend of modern design and natural

Penelope Moore SAUNDERS & ASSOCIATES

24 Rocky Point Rd, East Marion, NY 11939
/31
$18,000 per month
- 3 Beds
- 3 Baths
- 1,675 Sq Ft
- House for Rent
5 Bay Ave, Shelter Island, NY 11964

Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan living room with sunroom, dining and eat in kitchen. This home offers two bedrooms with two full baths and another bedroom with a full bath over the two car garage. In addition the master bedroom has

Michael Brennan Douglas Elliman Real Estate

5 Bay Ave, Shelter Island, NY 11964
$1,579,000 Sold Oct 10, 2024
- 1,637 Sq Ft
- $965/SF
- 390 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1985
16 Great Circle Dr, Shelter Island, NY 11964

Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

16 Great Circle Dr, Shelter Island, NY 11964

Est $5,056,696 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,500 Sq Ft
6 Club Dr, Shelter Island, NY 11964

6 Club Dr, Shelter Island, NY 11964

/36
$2,990,000 Open Sat 1PM - 2:30PM
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
5 Bay Shore Dr, Shelter Island Heights, NY 11965

This waterfront home with deep water dock is a boater's dream. A cozy beach home featuring 3 bedrooms, 2 full baths, a 2 car garage, and outdoor shower, all tucked down a quiet dead-end road, in the sought after Silver Beach area. Enjoy breathtaking sunrises from this spacious yard overlooking West Neck Creek, and a nature preserve. This wonderful home is near the most desirable beaches on

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

5 Bay Shore Dr, Shelter Island Heights, NY 11965
/29
$20,030 per month
- 5 Beds
- 5 Baths
- 3,874 Sq Ft
- Condo for Rent
13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964

Welcome to Sandpoint, an exclusive Shelter Island retreat nestled on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds.

13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964
$2,475,000 Sold Oct 02, 2024
- 1,795 Sq Ft
- $1379/SF
- 307 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1979
3 Bevan Place, Shelter Island, NY 11964

Shelter Island Heights Waterfront Property ! This contemporary 3-bedroom home with stunning sunset and water views, perched above trees, is fantastic place for someone looking for a serene and picturesque setting. Decks surrounding the living areas providing plenty of outdoor spaces for relaxation and entertainment. The bright and open living room with a fireplace, dining room, and eat-in

Mary Elizabeth Galle Corcoran

3 Bevan Place, Shelter Island, NY 11964

Est $787,000 Not Listed For Sale
169 N Ferry Rd, Shelter Island, NY 11964

169 N Ferry Rd, Shelter Island, NY 11964

/16
$2,750,000
- 3 Beds
- 3 Baths
- 2,000 Sq Ft
5 Grand Ave, Shelter Island Heights, NY 11965

Introducing an extraordinary new construction completed in 2024, nestled in the Historic Business District of Shelter Island Heights. Allowing for both residential and commercial uses, the offering was constructed in a traditional Heights vernacular with all modern amenities, seamlessly integrating historic charm with functionality. The main building, currently permitted as a primary residence

Hedgerow Exclusive Team Hedgerow Exclusive Properties

5 Grand Ave, Shelter Island Heights, NY 11965
/35
$75,000 per month
- 6 Beds
- 4.5 Baths
- 4,600 Sq Ft
- House for Rent
15 Montclair Ave, Shelter Island, NY 11964

Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

Margot Reutter Corcoran

15 Montclair Ave, Shelter Island, NY 11964
$999,999 Sold Sep 13, 2024
- 1,411 Sq Ft
- $709/SF
- 100 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1992
36 Rocky Point Rd, East Marion, NY 11939

Discover this custom-built contemporary home nestled on 1.47 acres of serene beauty. Crafted with love, it boasts cedar siding, wide plank pine floors, and hand-hewn timbers. Approach the meandering driveway, greeted by vibrant gardens and majestic trees-a perfect outdoor oasis. Inside, soak in the timeless charm of pine floors and abundant natural light. A passive solar design ensures energy

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

36 Rocky Point Rd, East Marion, NY 11939

Est $2,192,000 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,350 Sq Ft
148E N Ferry Rd, Shelter Island, NY 11964

148E N Ferry Rd, Shelter Island, NY 11964

/35
$3,200,000
- 4 Beds
- 4 Baths
- 3,420 Sq Ft
156 Ram Island Dr, Shelter Island, NY 11964

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom

Mary Elizabeth Galle Corcoran

156 Ram Island Dr, Shelter Island, NY 11964
/16
$55,000 per month
- 5 Beds
- 4 Baths
- House for Rent
4 Bay Ave, Shelter Island, NY 11964

This clean and modern harborfront home is located in an area that features glorious sunsets. There are lovely gardens and shade trees with meditation areas to read or relax in, and the main home offers an open floor plan, with an L-shaped living room that maximizes views of the water, a fireplace for chilly nights, dining area overlooking the water, and efficient kitchen. There is a first floor

4 Bay Ave, Shelter Island, NY 11964
$2,000,000 Sold Sep 12, 2024
- 1,296 Sq Ft
- $1543/SF
- 73 Days On Market
- 3 Beds
- 1 Bath
- Built 1953
74 Peconic Ave, Shelter Island, NY 11964

Enjoy this original 1953 waterfront summer cottage with southwest prevailing breezes. The deck and covered porch are great for entertaining off the main living areas. This home is situated on .46 acres and offers original wood panelled walls and vaulted ceilings with oak floors throughout. The living room has a wood burning fireplace and open floorplan. This property is being sold "As Is". There

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

74 Peconic Ave, Shelter Island, NY 11964

Est $1,395,000 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,270 Sq Ft
10 Penny's Path, Shelter Island, NY 11964

10 Penny's Path, Shelter Island, NY 11964

/14
$3,600,000
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
24 Rocky Point Rd, East Marion, NY 11939

This exquisite, light-filled, four bedroom, three-and-a-half bathroom architecturally designed mid-century modern is sited on two private acres in the Nostrand Estate section of Shelter Island, a short distance to Sunset Beach, Perlman Music Center, and the Pridwin Hotel. The main house offers spectacular open plan living with an expansive great room incorporating generous living (including a

Melina Wein M WEIN REALTY INC

24 Rocky Point Rd, East Marion, NY 11939
/10
$50,000 per month
- 3 Beds
- 2 Baths
- 1,691 Sq Ft
- House for Rent
21 Peconic Ave, Shelter Island, NY 11964

Impeccable cottage ideally located in the heart of Silver Beach. Very Closeto the secluded association beach and a short distance to Shell Beach. Lovely deck with water view and cool summer breezes. Three bedrooms and two bath. Ref. R103 MD - LD $50,000 June - LD $50,000, June $10,000, July $20,000, and August $25,000

Melina Wein M WEIN REALTY INC

21 Peconic Ave, Shelter Island, NY 11964
$850,000 Sold Aug 15, 2024
- Land
- 1.00 Acre
- $850,000 per Acre
- 111 Days On Market
39 Gardiners Bay Dr, Shelter Island Heights, NY 11965

Opportunity to build your dream home. Located in coveted Hay Beach of Shelter Island. Pristine neighborhood, close proximity to beaches, boating and golf. Only 250 yards to Town beach access on Gardiners Bay overlooking Bug Lighthouse.

Annmarie Seddio Atlas Sales Realty

39 Gardiners Bay Dr, Shelter Island Heights, NY 11965

Est $972,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,217 Sq Ft
1 Worthy Way, Shelter Island, NY 11964

1 Worthy Way, Shelter Island, NY 11964

/23
$4,995,000 Open Sat 10AM - 11:30AM
- 7 Beds
- 6 Baths
- 5,000 Sq Ft
20 Prospect Ave, Sag Harbor, NY 11963

Introducing Aquarelle at 20 Prospect Ave, an iconic piece of Shelter Island Heights history. Built in 1883, this distinguished home holds a cherished place among the original residences in this esteemed neighborhood, now classified as a national historic district. When upon Prospect Avenue, once known as Divinity Hill, you'll find yourself transported to a time when Methodist ministers from New

Hedgerow Exclusive Team Hedgerow Exclusive Properties

20 Prospect Ave, Sag Harbor, NY 11963
/20
$23,000 per month
- 4 Beds
- 3 Baths
- House for Rent
71 Gardiners Bay Dr, Shelter Island, NY 11964

Beautiful home across the street from beach access, relax and unwind in this 4 bedroom 3 bath home steps to beach. Back deck off the dining room for additional entertaining space. Additional playroom on the lower level. The kitchen and baths are recently updated. [[Rental Registration # 2025-V0002]]

71 Gardiners Bay Dr, Shelter Island, NY 11964
$495,000 Sold May 28, 2024
- Land
- 0.68 Acre
- $727,941 per Acre
- 18 Days On Market
11 Sylvan Rd, Shelter Island, NY 11964

Build your dream home on this lovely lot on a quiet road overlooking Ice Pond. Close proximity to beach, golf course and Shelter Island Heights. Don't miss this opportunity.

Annmarie Seddio Atlas Sales Realty

11 Sylvan Rd, Shelter Island, NY 11964

Est $2,070,661 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,228 Sq Ft
1 Country Club Dr, Shelter Island Heights, NY 11965

1 Country Club Dr, Shelter Island Heights, NY 11965

/29
$2,145,000 Open Sat 12PM - 1:30PM
- 3 Beds
- 3 Baths
- 1,897 Sq Ft
40 Dinah Rock Rd, Shelter Island, NY 11964

Picture a rural drive through farm fields and vineyards to a short ferry boat ride from Greenport's harbor, then a scenic meander along Shelter Island's picturesque coves. Continue passing through a golf course and arrive at your home in Hay Beach, across the street from a sandy shoreline with a magnificent sunset and bay views directly in front of your home. This could be you this year. The 1900

Caroline Sarraf Compass

40 Dinah Rock Rd, Shelter Island, NY 11964
/8
$5,000 per month
- 3 Beds
- 3 Baths
- House for Rent
17 Wade Rd, Shelter Island, NY 11964

Located near Coecles Harbor and Sylvester Manor farm, this 3 bedroom 3 bath ranch home has 2 newly updated bathrooms and central air conditioning. A great place to spend your summer days. [[Rental Registration # 2024-L-0037]]

17 Wade Rd, Shelter Island, NY 11964

Est $1,385,000 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,098 Sq Ft
27 Terry Dr, Shelter Island, NY 11964

27 Terry Dr, Shelter Island, NY 11964

/35
$1,990,000
- 3 Beds
- 2 Baths
- 3,170 Sq Ft
27 Country Club Dr, Shelter Island, NY 11964

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant Traditional home was lovingly crafted by a local artist in 2011. Spanning 3,170 square feet, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. Designed to maximize natural light, the home features vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

27 Country Club Dr, Shelter Island, NY 11964

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