Welcome to 1 Fairwind Court, an exceptional waterfront residence located in the highly sought-after Water Pointe community of Oakdale. Perfectly positioned on scenic Water Pointe Pond, this elegant and spacious Colonial offers over 3,000 square feet of luxury living with 5 bedrooms, 3.5 baths, and a lifestyle designed for both relaxation and entertaining. Combining refined interiors, resort-style amenities, and direct boating access to the Great South Bay, this is South Shore living at its finest. The home is a beautifully updated throughout. Featuring an eat-in kitchen featuring premium Wolf appliances, including a Wolf oven, along with Sub-Zero refrigerator and freezer systems that blend sophistication with top-tier performance. Granite counter tops in the kitchen area carries into the powder room, wet bar and fireplace surround. Designed with both functionality and style in mind, the kitchen opens seamlessly into expansive living and dining spaces filled with natural light, hardwood flooring, elegant crown molding, wainscoting, and custom mill work throughout. The luxurious primary suite serves as a private retreat with two walk-in closets, a spa-inspired bath, and a private balcony overlooking the tranquil pond. Additional highlights include spacious guest accommodations, a main-floor office, central air conditioning, natural gas heating, high ceilings, and a fully finished basement offering a lounge area and work out room. Outdoor living is equally impressive. Residents enjoy a deeded boat slip with direct canal access to the Connetquot River and Great South Bay, making this home ideal for boating enthusiasts and waterfront lovers alike. The beautifully maintained Water Pointe community offers resort-style amenities including an in-ground pool, tennis courts, professionally landscaped grounds, snow removal, lawn maintenance, and trash removal for truly carefree living year-round. Situated on a quiet cul-de-sac in one of Oakdale’s most desirable waterfront communities, 1 Fairwind Court delivers the perfect blend of luxury, convenience, and coastal charm — all with low-maintenance living and no flood insurance currently required. This is a rare opportunity to experience the very best of waterfront living on Long Island’s South Shore.