Homes with Pools for Sale in Fire Island, NY

Home with a Pool for sale in Fire Island, NY:

Set amongst lush landscaping, 208 Midway Walk is a commanding presence with a storied history and architectural pedigree attributed to Bates Masi+ Architects. Cedar detailing inside and out presents 3 bedrooms and 2 full baths, double height ceilings and large windows bringing the indoors out. Extra deep lot and large pool + morning and afternoon decks, sun and shade options, makes for the ideal Fire Island retreat.

Home with a Pool for sale in Fire Island, NY:

Impeccably maintained, secluded Bay Walk property located eight minutes from the Waterfront. Renovated in 2025 including kitchen appliances; cabinetry; refinished hardwood floors; heated XL saltwater pool; hot tub; gas water heater; roof and fully serviced Andersen windows & doors. New furnishings throughout. Extensive mahogany decking. Wood burning fireplace and propane fire pit. Fully air conditioned. Generously proportioned primary en-suite features with additional fireplace. Three guest bedrooms (one king & two queen beds) with ample closets. Low operating expenses and $185k in 2026 gross rent; several weeks pre-booked in 2027. Straightforward mortgage financing – n

Home with a Pool for sale in Fire Island, NY:

A quintessential Cherry Grove cottage, cozy and unfussy, perfect for a relaxing beach vacation. There are three bedrooms and two bathrooms (the primary bedroom is en suite), Entertaining is easy with the kitchen open to the living area as well as the dining area. And the house features a spacious deck for outside dining, sunbathing, and lounging by the pool. Refresh yourself with an invigorating outdoor shower. Located in a quiet neighborhood, but still convenient to the nightlife and restaurants, the beach is just 4 houses off the beach, as is the trail through the Sunken Forest. The heated pool completes this lovely property.

Home with a Pool for sale in Fire Island, NY:

One of Fire Island Pines’ most recognizable residences, the Pyramid House is an extraordinary expression of the experimental modernism that came to define the Pines. Designed circa 1960 by Buenos Aires–born architect Julio Kaufman, the house was later thoughtfully reimagined while preserving Kaufman’s iconic silhouette. A monumental steel-and-glass wall opens the soaring upper-level great room to sweeping views across the protected dunes of Fire Island National Seashore toward the Atlantic and bay beyond. Set at the quiet eastern edge of the Pines and bordering protected landscape, the approximately 2,100-square-foot residence offers an unusual degree of privacy. Built to