A Once-in-a-Generation Compound Opportunity in the Heart of Venice. Welcome to 1215 & 1209 Appleton Way, a truly unprecedented offering in the coveted heart of Venice - two side-by-side estate-sized properties totaling nearly 22,000 square feet of land. Opportunities of this scale and privacy are exceedingly rare, especially ones that encompass not one, but two fully independent, beautifully appointed homes, each nestled on their own nearly 11,000 square foot lot. At 1215 Appleton Way, experience over 6,500 square feet of thoughtfully designed luxury. This designer-built main residence showcases the finest materials and craftsmanship throughout, offering 5 spacious bedrooms, 2 dedicated offices, a cozy den, and a fully equipped bar perfect for entertaining. The full basement is a rare find in Venice and features a 16-seat screening room, a private gym, and expansive storage. Step outdoors into a world of resort-style living: a large swimming pool with an integrated hot tub, a fully equipped outdoor kitchen, al fresco dining room, and an elegant outdoor living room with a fireplace surrounded by a mature olive grove. A sports court (with space for a pickleball court), an expansive lawn, and a charming guest house complete the compound-like ambiance, ideal for entertaining or a quiet retreat. Next door, 1209 Appleton Way offers a charming and incredibly private 2/3-bedroom, 2-bathroom home, shielded by towering 15-foot hedges. With two fireplaces, an oversized 2-car garage, and warm, inviting interiors, this property is ideal as a guest residence, rental opportunity, or extended family compound. Together, these properties offer an extraordinary chance to own a true family estate, creative retreat, or generational investment, a sanctuary rarely available in this iconic beachside neighborhood. This is not just a home it's a legacy.