Penelope Moore
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Home > Listings > 1887 Dering Harbor Village Victorian with Pool and Dock

1887 Dering Harbor Village Victorian with Pool and Dock

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Pending

This charming, renovated 1887 Victorian is located on a quiet lane on 1.44+/- acres in the Village of Dering Harbor on Shelter Island in a park-like setting. A delightful screened porch which serves as an outdoor living and lounge area, wraps almost entirely around the home, greeting you as you ascend up the path through the privet hedges from the road. The entry foyer is spacious and welcoming, flowing to the living room which has French doors to the screened porch. The dining room has a fireplace, doors to screened porch, butlers pantry, beautiful sunlight. The kitchen, new in 2021, has a center island and high end appliances including a range installed in August 2025, with a delightful screened-in back porch with outdoor dining with views to the harbor and gardens. A library, outfitted with comfortable couch and media, has a full bath with marble tile adjacent with easy access to the pool area. The second floor has five bedrooms. The primary bedroom has a new full bath. The additional four guest bedrooms have access to a hall full bath, which was renovated in July 2025 with new plywood subfloor and marble tile, with an original ball and claw tub and a separate half bath. The third floor is finished with two bonus rooms and a full bath, a summer bathroom that is currently not in use. The 20′ x 40′ heated Gunite pool, which has new retaining walls, coping and brickwork completed in June 2025, is surrounded by hedges, gardens and established landscapes, with outdoor shower close by. A stone’s throw away is the deep water dock on Dering Harbor with 50 ft. of shoreline, bulkhead, an approximately 100-foot deep water dock, with 4 feet+/- at low mean tide and a staircase to sandy beach. Bounded by hedge with wonderful shade trees, there is seating facing the dock, offering privacy and incredible sunset views to one of the most scenic vantage points on Shelter Island. There have been many other upgrades since 2022, including central air, primary bathroom construction, outdoor shower, fresh painting throughout and replacement of dock planks and pilings as needed. In October 2025, the exterior was power washed, shingles installed where needed, and touched-up. Annual Town taxes are: 8 Gardiner Way: $19,014.74 and 15A Harbor Lane: $627.57. Annual Village taxes which include water are: 8 Gardiner Way: $4,448.86 and 15A Harbor Lane: $146.84

Property Details

Price: $5,195,000
Address: 8 Gardiner Way & 15A Harbor Lane
City: Shelter Island
State: NY
Zip: 11965
MLS#: 11441620
Pool: Yes
Waterfront: Yes
Beds: 5
Baths: 3.5
Square Feet: 4053
Garage: Detached, 2 spaces
Year Built: 1887, Reno 2024
Acres: 1.50
Status: Pending

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Penelope Moore

Penelope Moore

Since 1998, Penelope has been the driving force and leader in the Shelter Island real estate market, and is the go-to real estate broker for discerning buyers and sellers. She has experienced record-breaking sales in multiple categories over successive years, and her success has been distinguished not just by benchmark sales, but by volume in all categories.

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Penelope Moore, Licensed Associate Real Estate Broker

9 Grand Avenue, PO Box 100
Shelter Island Heights, NY 11965-0100

(631) 749-5801
(917) 208-5519 Mobile

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