- 7 bds
- 6 ba
- 4,634 sqft
LISTING BY: SOTHEBY'S INTERNATIONAL REALTY
Expansive windows
Waterfront - Shelter Island NY Waterfront Homes
33 results
- 6 Harbor Ln, Shelter Island Heights, NY 11965
- 13 Winthrop Rd Unit 19, Shelter Island, NY 11964
- 1 bd
- 1 ba
- -- sqft
LISTING BY: DERING HARBOR REAL ESTATEWaterside heated pool
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- 5 N Menantic Rd, Shelter Island, NY 11964
- 5 bds
- 5 ba
- 3,157 sqft
LISTING BY: SAUNDERS & ASSOCIATESPrice cut: $525,000 (10/19)
- 66 Gardiners Bay Dr, Shelter Island, NY 11964
- 7 bds
- 9 ba
- 5,042 sqft
LISTING BY: SOTHEBY'S INTERNATIONAL REALTYPrice cut: $1,000,000 (10/14)
- Private dock
- Waterfront estate
- 171 N Ferry Rd #J/g, Shelter Island, NY 11964
- 4 bds
- 5 ba
- 3,000 sqft
LISTING BY: CORCORAN GROUPSouth facing balcony deck
- 5 Sea Gull Rd, Shelter Island, NY 11964
- 5 bds
- 5 ba
- 3,072 sqft
LISTING BY: DANIEL GALE SOTHEBY'S INTERNATIONAL REALTYExpansive primary suite
- 20 Prospect Ave, Shelter Island Heights, NY 11965
- 7 bds
- 6 ba
- 5,000 sqft
LISTING BY: HEDGEROW EXCLUSIVE PROPERTIESModern comforts
- 2 Bayview Avenue, Shelter Island Heights, NY 11965
- 4 bds
- 7 ba
- 5,377 sqft
LISTING BY: DOUGLAS ELLIMAN REAL ESTATEWide-plank light oak flooring
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- 32 Hilo Dr, Shelter Island Heights, NY 11965
- 4 bds
- 5 ba
- 2,237 sqft
LISTING BY: CORCORAN GROUPDeep-water dock
- 4 Irene Ln, Shelter Island, NY 11964
- 4 bds
- 3 ba
- 2,028 sqft
LISTING BY: DANIEL GALE SOTHEBY'S INTERNATIONAL REALTY162 days on Zillow
- West-facing waterfront retreat
- 60 Westmoreland Dr, Shelter Island Heights, NY 11965
- 4 bds
- 4 ba
- 2,854 sqft
LISTING BY: CORCORAN GROUPTwo car garage
- 15 Dickerson Dr, Shelter Island, NY 11964
- 3 bds
- 3 ba
- 3,370 sqft
LISTING BY: SAUNDERS & ASSOCIATESContemporary waterfront
- Undisclosed Address, Shelter Island, NY 11964
- 4 bds
- 4 ba
- 2,407 sqft
LISTING BY: SAUNDERS & ASSOCIATES, Penelope Moore. Listing provided by NY State MLSDramatic rooftop observation deck
- 3 Montclair Ave, Shelter Island, NY 11964
- 3 bds
- 2 ba
- 1,851 sqft
LISTING BY: SAUNDERS & ASSOCIATES, Penelope Moore. Listing provided by NY State MLS97 days on Zillow
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Fill out a short survey to help others know what it's like to live here. - 11 Dickerson Dr, Shelter Island, NY 11964
- 4 bds
- 5 ba
- 3,187 sqft
LISTING BY: SAUNDERS & ASSOCIATESFloor-to-ceiling windows
- 2 Prospect Avenue, Shelter Island, NY 11964
- 6 bds
- 3 ba
- 5,900 sqft
LISTING BY: COMPASS GREATER NY LLCThree income-producing historic cottages
- 8 Margarets Dr, Shelter Island, NY 11964
- 6 bds
- 6 ba
- 4,250 sqft
LISTING BY: HEDGEROW EXCLUSIVE PROPERTIESPrivate waterfront setting
- 7 Wheeler Rd, Shelter Island, NY 11964
- 4 bds
- 3 ba
- -- sqft
LISTING BY: WORLD PROPERTIES INT'L SEA TO SKY REALTYWaterfront in silver beach
- Wood burning fireplace
- Scenic waterfront backdrop
- 15 Menantic Rd, Shelter Island, NY 11964
- 5 bds
- 6 ba
- -- sqft
LISTING BY: DOUGLAS ELLIMAN REAL ESTATEFloating dock
- 8 Brander Pkwy, Shelter Island Heights, NY 11965
- 4 bds
- 4 ba
- 3,160 sqft
LISTING BY: DOUGLAS ELLIMAN REAL ESTATEUninterrupted views
- 64A N Midway Road, Shelter Island, NY 11964
- 5 bds
- 4 ba
- 2,642 sqft
LISTING BY: DOUGLAS ELLIMAN REAL ESTATEGas fireplace
- 23 Dickerson Dr, Shelter Island, NY 11964
- 4 bds
- 3 ba
- 3,210 sqft
LISTING BY: CORCORAN GROUPBeautiful view
- 66-A N Midway Rd, Shelter Island, NY 11964
- 2 bds
- 3 ba
- 1,488 sqft
LISTING BY: SAUNDERS & ASSOCIATES, Penelope Moore. Listing provided by NY State MLSSpring-fed pond
- 66 N Midway Rd #A, Shelter Island, NY 11964
- 2 bds
- 3 ba
- 1,488 sqft
LISTING BY: SAUNDERS & ASSOCIATESSecond fireplace
- 9 Bay Shore Dr, Shelter Island, NY 11964
- 0.62 acres lot
LISTING BY: DANIEL GALE SOTHEBY'S INTERNATIONAL REALTYSurrounded by nature
- 12 Hilo Dr, Shelter Island, NY 11964
- 0.64 acres lot
LISTING BY: DOUGLAS ELLIMAN REAL ESTATE226 days on Zillow
- 82 S Midway Rd, Shelter Island, NY 11964
- 5.6 acres lot
LISTING BY: SAUNDERS & ASSOCIATESCoveted waterfront acreage
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Based on information submitted to the MLS GRID as of 2026-11-01 15:13:23 PST 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. Some IDX listings have been excluded from this website. [Click here for more information](/mls-disclaimers/#778)
