1988 West Lake Shore Drive is a multi-home property that offers one of the most unique opportunities in Wilmington. Positioned directly across from Greenfield Lake and approximately 220 yards from Greenfield Lake Amphitheater, this remarkable property blends historic character, established income potential, and a private compound-style setting rarely found close to downtown. The property features three separate living spaces, each thoughtfully positioned to provide privacy and flexibility. The 'Main House,' a beautifully preserved 1935-era residence, serves as the primary home and offers 3 bedrooms and 3 full bathrooms with hardwood floors, fiber cement siding, generator setup, and timeless architectural charm. The outdoor living experience is equally impressive with a beautifully landscaped backyard, outdoor kitchen, enclosed exterior bathroom, tranquil fountain, 23 blueberry bushes, and a private retreat-like setting. The 'Lake House,' originally built around 1945, features 2 bedrooms and 2 full bathrooms. Thoughtfully renovated with modern conveniences while maintaining its character and warmth, it has become a highly successful Airbnb Guest Favorite with an exceptional 4.96-star rating across 332 reviews. The property also includes an additional detached cottage-style structure currently utilized by the owners as the 'Lake Cottage,' offering additional flexibility for guests or extended stays. This space has also earned Airbnb Guest Favorite status with a 4.93-star rating across 123 reviews. The Lake House and Lake Cottage generated over $51,000 in gross income during 2025, presenting an exceptional opportunity for investors, multigenerational living, or buyers seeking a personal residence with supplemental income potential. Whether envisioned as a private family compound, income-producing retreat, or combination of both, 1988 West Lake Shore Drive represents a truly rare Wilmington offering. The above-ground pool and 'Lake Cottage' were not permitted.