$18,000,000

10 Lari Ln, Shelter Island

• 10 Beds
• 10 Baths
• 3.2 Acres

School District: Shelter Island

Bumble Bee Manor - Unquestionably One Of The Magnificent Estates Of The East End. Luxurious Waterfront Residence Has It All: Coecles Harbor Dock, Infinity Edge Pool, Spa, Multi-story Pool House, Carriage House/garage, Lush Gardens And Tennis. The 16 Room...

$8,995,000

108 Ram Island Dr, Shelter Island

• 22 Beds
• 18 Baths
• 4.3 Acres
• 11,465 sqft

School District: Shelter Island

Own A Piece Of Shelter Island History With This One-of-a-kind Waterfront Estate In The Hamptons. The 4.3+/- Acre Property Boasts Rolling Lawn, Old Specimen Trees, Stone Patios, A Tennis Court, And 800+/- Feet Of Water Frontage With A Private Sandy Beach, De...

$3,992,000

66 Ram Island Dr, Shelter Island

• 4 Beds
• 4 Baths
• 1.16 Acres
• 2,800 sqft

School District: Shelter Island

The Perfect Hamptons Alternative! 110 Ft Dock And Private Beach Situated On Coecles Harbor. Enjoy The Afternoon Sea Breeze & Stunning Harbor Sunsets. Peter Pennoyer Designed, Decorators Interior, Oversized Living Room, New Chef's Kitchen, 3 Ensuite Bedroo...

$3,795,000

90 Peconic Ave, Shelter Island

• 5 Beds
• 4 Baths
• 1 Acres
• 3,325 sqft

School District: Shelter Island

On Peconic Bay With 190 Feet Of Waterfront With Sandy Beach, Bulkhead And Dock. This 5 Bedroom, 3.5 Bath Beautiful Shingle Beach House Enjoys Beautiful Sunsets, Magnificent Waterviews, Waterside Decks, Landscaped Lawn And Attached 2 Car Garage. Full Acre, M...

$2,988,000

28 S Menantic Rd, Shelter Island

• 4 Beds
• 6 Baths
• 2 Acres
• 4,174 sqft

School District: Shelter Island

Bucolic English Country Inspired 2-acre Estate On Secluded Parcel. Classic Interior, Gracious Common Rooms, Fireplace, Coffered Ceilings, Gourmet Country Kitchen, Butler's Pantry With Wet Bar, Built-in Window Seat & Bookshelves. Expansive Pastoral Grounds W...

$2,500,000 Under Contract

5 Westmoreland Dr, Shelter Island

• 3 Beds
• 2 Baths
• 2.7 Acres

School District: Shelter Island

Secluded 2.7 Acres And Super Sunny Home With Beautiful Waterfront And Stunning View. Cathedral Ceiling, Fireplace & 4 Skylights In Living Room With Multiple Sliders To Rear Deck And Yard. Master And One Bedroom W Sliders To Yard. House Built New In 1988 Wit...

$2,500,000 Under Contract

5 Westmoreland Dr, Shelter Island

• 2.7 Acres

School District: Shelter Island

Secluded 2.7 Acres Beautiful Waterfront And Stunning View. There Is A House Nestled On Property Built New In 1988 With 8' High Ceilings In Basement. Hardwood Floors Throughout. Main Level Laundry. Tons Of Storage And Plenty Of Room For Expansion To Create Y...

$1,795,000

69 N Cartwright Rd, Shelter Island

• 3 Beds
• 2 Baths
• 0.82 Acres
• 1,425 sqft

School District: Shelter Island

This 3-bedroom, 2-bathroom Home Is Exquisite; Exuding As Sophisticated Attention To Detail Which Perfectly Balances Historical Features With Contemporary, Smart Home Amenities And Aesthetics. A Stunning Turnkey Home For Sale On Shelter Island Featuring An ...

$1,725,000

9 Point Ln, Shelter Island

• 3 Beds
• 3 Baths
• 2.53 Acres
• 2,972 sqft

School District: Shelter Island

This Beautiful Contemporary Has 3 Bedrooms, 2.5 Baths And An Open Floor Plan Concept So That When You Enter The Home The 2 Story Living/dining Area Has A Stunning Water View Of Gardiners Bay And The North Fork. There Is A Water Side Deck Which Runs The Leng...

$1,700,000

72 S Ferry Rd, Shelter Island

• 1 Beds
• 1 Baths
• 5.5 Acres
• 1,800 sqft

School District: Shelter Island

Ultimate Privacy And Potential Await You On 5.5 Acres Of Rolling Lawns, Woods, Vegetable And Perennial Gardens, Fruit Trees And Large Stocked Pond All At The End Of A 1000' Private Driveway. Less Then A Mile From The South Ferry And A Short Distance To Wade...

$1,495,000

157 N Ferry Rd, Shelter Island

• 8 Beds
• 4 Baths
• 0.87 Acres
• 4,183 sqft

School District: Shelter Island

Beautifully Renovated 1900's Home Offers Open Plan Living With Grand Woodworking Details. The Eat In Kitchen Is Light Filled And Leads To The Spacious Deck, Great Space For Entertaining With Steps To The Pool. The 9' Ceiling Height On The First Floor Expan...

$1,325,000

9 Wheeler Rd, Shelter Island

• 5 Beds
• 4 Baths
• 0.78 Acres

School District: Shelter Island

Silver Beach Waterfront Shy Of 1 Acre. 5br/3.5ba Home. Ist Floor Features Cathedral Ceilings W Skylights For A Bright Sun Filled Space. Hardwood Floors. Viking Stove Kitchen. Fp. Sliders Open To A 20x40 Gunite Pool Overlooking Floating Dock, 6' At Low Tide...

$1,299,000 Under Contract

11 Dickerson Dr, Shelter Island

• 3 Beds
• 4 Baths
• 1.3 Acres
• 3,300 sqft

School District: Shelter Island

Now Is The Time To Create Your Waterfront Dream Home-waterfront Property On Menantic Creek. Boasts 2 Waterfront Master En-suites.3rd Bedroom Has Water & Dock View. Floor To Ceiling Windows In Living Room & Dining Room. Surrounded By Water W/ Eastern & Weste...

$1,295,000

32 Ram Island Dr, Shelter Island

• 9.74 Acres

School District: Shelter Island

This Irreplaceable Estate On The Historic Isle Of Shelter Island Asserts A Total Of 9.74 Acres, Faces South, Boasts Over 1400' Of Road Frontage, & An Unbelievable 1/3 Mile Of Water Frontage! Directly On Coecles Harbor W/ 360 Degree Water Views Encompassing ...

$1,199,000 Under Contract

3 Conrad Rd, Shelter Island

• 4 Beds
• 3 Baths
• 0.7 Acres
• 1,895 sqft

School District: Shelter Island

Chic & Timeless Design Meet Efficient Modern Living In This Newly Renovated 4 Bedroom, 3 Bath Home. The Open Floor Plan Seamlessly Integrates With The Spacious & Private .7 Acre Property Creating An Ideal Entertaining Environment. Custom Cabinetry & Bertazo...

$1,100,000

39 Lake Dr, Shelter Island

• 4 Beds
• 4 Baths
• 0.63 Acres
• 1,822 sqft

School District: Shelter Island

Updated Contemporary Close To Beach. Modern Open Plan, Vaulted Ceilings, Kitchen With Stainless Appliances. Two Guest Rooms On Main Floor, 2nd Fl Master. Finished 1000 Sq Ft Lower Level Guest Suite W Walkout, Kitchenette. Home Sits Up From Road Surrounded B...

$999,999

11 Spring Garden Ave, Shelter Island

• 4 Beds
• 2 Baths
• 0.12 Acres
• 2,268 sqft

School District: Shelter Island

This 1887 Carpenter Gothic Victorian Is As Sweet As Its Porch Swing And Blue Hydrangeas. The Front Porch, Chapel Style Doors And Guest Parlor Welcome You To This Historic Home. Simple Gatherings Are Easy To Create In The Open Dining Room And Kitchen. Surrou...

$975,000

12 Tims Trl, Shelter Island

• 4 Beds
• 5 Baths
• 0.5 Acres

School District: Shelter Island

Island Getaway Farmhouse. Start Your Day With Coffee On The Charming Porch. Enjoy Gatherings In The Sun Filled Open Kitchen, Dining Room & Family Room. Outside Entertaining Is Easily Accomplished On The Spacious Deck That Stepping Down To A Private, & Fence...

$899,000

2 Wheeler Rd, Shelter Island

• 4 Beds
• 4 Baths
• 0.57 Acres
• 2,933 sqft

School District: Shelter Island

This Water-view Silver Beach Expanded Ranch Is Much More Than Meets The Eye! Its Newly Constructed Addition Allows For A Large 4+br Home With Bonus Family Room W/water View; Or A Spacious 3-br Home With A 1+br Guest Suite W/wv. Bright, Airy & Fresh Spaces, ...

$819,000 Under Contract

18 Manhanset Rd, Shelter Island

• 3 Beds
• 3 Baths
• 0.77 Acres
• 2,706 sqft

School District: Shelter Island

This 3br/3ba Expanded Ranch Is Turnkey With A Complete, New Renovation Throughout. Located Across From Sylvester Manor Farmlands, The Sunsets Are Spectacular Year Round Over The Fields. The Grounds Host An Expansive Backyard With Room For A Pool. Raised Bed...

$725,000

57 N Midway Rd, Shelter Island

• 2 Beds
• 1 Baths
• 2.2 Acres

School District: Shelter Island

This Type Of Property Doesn't Become Available Very Often. This Property Is 2.2 Acres With A 2 Bedroom, One Bath Home With A Detached 1 Car Garage Located Along The Front Of The Property. Behind The Home Is A 4 Car Garage Which Is Amazing Storage Or A Great...

$699,000

20f S Ferry Rd, Shelter Island

• 3 Beds
• 2 Baths
• 0.5 Acres
• 1,161 sqft

School District: Shelter Island

Private Country Lane Setting Off South Ferry Rd. Spacious Open Ranch Floor Plan. Additional Garage Space On Lower Level With Garage Door.

$675,000

7 Dering Woods Rd, Shelter Island

• 3.1 Acres

School District: Shelter Island

In The Historic Village Of Dering Harbor, This 3.1 Acre Property Is Down A Scenic, Wooded, Private Lane. This Acreage Awaits Your New Home. Assured Of Privacy, One Side Of The Property Abuts A 17 Acre Preserve And Another Backs Up To The 6th Tee Box At Gard...

$450,000

16 Osprey Rd, Shelter Island

• 0.9 Acres

School District: Shelter Island

Huge Opportunity To Build Your Dream Home On Beautiful, Tranquil Shelter Island. Just Shy Of An Acre With Beach Rights And Private Tennis Court Use When Joining The Shorewood Civic Association.

$425,000

11 Margarets Dr, Shelter Island

• 0.94 Acres

School District: Shelter Island

Residental Wooded Level Vacant Lot In Waterfront Neighborhood. Possible Second Floor Waterview As Waterfront Properties Across The Street. Opportunity To Own Withl With Waterfront Across The Street.

$409,000

139 S Midway Rd, Shelter Island

• 0.95 Acres

School District: Shelter Island

Shy Of 1 Acre Lot On Beautiful Shelter Island, Build Your Dream Home On Your Dream Island.

$409,000

137 S Midway Rd, Shelter Island

• 1 Acres

School District: Shelter Island

$409,000

141 S Midway Rd, Shelter Island

• 0.95 Acres

School District: Shelter Island

Build Your Dream Home On Your Dream Island

$399,000

13 Tims Trl, Shelter Island

• 0.62 Acres

School District: Shelter Island

From Nothing Comes An Amazing Memory Keeper....make This Blank Canvas Your Dream Come True! .62 Acres ~ 27,007sf Lot, Land Waiting For Your Creativity!

$375,000

13 Winthrop Rd 15, Shelter Island

• 1 Beds
• 1 Baths
• 625 sqft

School District: Shelter Island

Spectacular Bay View 1 Bedroom, 1 Bath Unit With Porch In 7.9 Acre Dering Harbor Inn Waterfront Property. Bright And Roomy With Private Porch On Lawn With Adirondack Chairs Over Bluff And Association Dock. Heated Pool, Two Tennis Courts, Fully Equiped Gym I...