The nuts and bolts
5 bedrooms
3.5 bathrooms
4,053 square feet
1.5 acres
House proud
Built in 1887, this home has been maintained through the years, with numerous upgrades to infrastructure and the grounds, including landscaping and the rehabbing the dock. The deep water (100 feet) dock, with a separate address of 15A Harbor Lane on Dering Harbor, comes with 50 feet of shoreline and a staircase to a sandy beach.
“The current owners have deep roots on Shelter Island with a love of boating, island life and all things pastoral,” says Penelope Moore, the Saunders agent representing the listing. “The prior owner was an artist who drew inspiration from organic textures and surrounding vistas.”




What’s the plan?
The home is entered through a 47-foot-wide wrap-around screened-in porch, which add significant living space to the layout. The center quadrant of the main floor is the entry, living and dining rooms and a den/library, all of a uniform shape and size. There’s a full bathroom and beyond the kitchen is a back screened-in porch. All five bedrooms are on the second floor, three have walk-in closets, one has a fireplace and there are one and half bathrooms in addition to the new bathroom in the primary suite. The third level has two finished rooms to be used as you like, three closets, one of which is a walk-in, and a full bathroom (currently non-operational).

What’s cooking?
Renovated in 2021, the kitchen features an updated appliance suite, navy lower cabinets with brass hardware, a white counters and open shelving. The center island seats two and there’s a 5 x 7.5 pantry. A back door leads to a screened-in back porch with additional dining,
What else?
The house retains original details such as the fireplaces, vintage French doors, stained glass windows, decorative exterior flourishes on the porch. Set up as a home office or study, the 140-square-foot third-floor cupola-style space has windows around three sides overlooking the front yard.
Amenities and more

- 20′ x 40′ heated gunite swimming pool
- Outdoor shower
- Detached two-car garage
- Screened in porch
One cool thing (or two)
The house at 8 Gardiner Way is in Dering Harbor Village, which was designed as a summer get-away for vacationers from New York City during the late 1800s who would come out by steamship to an area along Manhanset Road, and were brought by horse and buggy to a hotel that once sat at the point facing northwest toward Greenport and Southold, a block from the home.
Agent’s callout
“8 Gardiner Way was historically, and is to this day, one of the largest lots in the Village, in a commanding position along three streets, Locust Point Road, Dering Road and Gardiner Way. Over the last 138 years, the various owners have respected the natural landscape, which resembles a park,” Moore says.
Location, location, location
Dering Harbor is across from Shelter Island Heights and 1.4 miles from Hay Beach Point. Nearby are the Gardiner’s Bay Country Club, Upper Beach and the Sylvester Manor Educational Farm, which offers programming for youth and families, concerts and cultural events.
Details
The home at 8 Gardiner Way lists for $6,750,000 and the details can be seen here.