2186 Lakeside Dr

Take the helm at Regatta Retreat, a custom lakefront home in one of Highland Lakes premier waterfront locations, with front-row views of the start and finish line for summer sailing races. This elevated 3-bed, 2-bath retreat was thoughtfully renovated by the designers behind Ralph Lauren stores, blending timeless character with sophisticated design. Dramatic ceilings, 300-year-old reclaimed wood walls, and black walnut, copper, and zinc accents bring warmth, texture, and distinction throughout. The modern chefs kitchen makes entertaining effortless, while the first-floor primary suite offers lake views, a walk-in closet, and a spa-like ensuite bath. A nearby den and office add flexibility, while upstairs guest rooms also enjoy lake views, including one with Murphy beds that easily transforms from daytime workspace to welcoming guest accommodations. The walk-out basement is set up as a workshop and storage. Oversized sliders create a seamless indoor-outdoor connection, opening to an expansive ipe deck with pergola, a firepit area with pizza oven, and a serene lakeside patio perfect for sunset cocktails. Lush perennial gardens add beauty and privacy. Life here revolves around the water, with a private dock for swimming, boating, and fishing. Less than a quarter mile from the clubhouse, enjoy beaches, tennis, pickleball, and year-round community activities. With designer finishes, included furnishings, and a premium waterfront setting, this is more than a home - its a lifestyle.