Set on a generous lot framed by mature landscaping, 24 Pine Lane offers four bedrooms across two distinct dwellings in a private, rural setting, yet in a surprisingly convenient location. Lovingly built and maintained by a longtime Island family with decades of experience landscaping and caring for beautiful Island properties, the three-bedroom main residence features gorgeous pine floors, post-and-beam detailing, and distinctive cedar ceilings. A finished lower level with an air-exchange system provides additional flexible space, ideal for a home gym, recreation room, or other uses. A separate apartment at the garage adds a second living space and enhances the property's versatility. Thoughtful upgrades include solar, a reverse-osmosis drinking system, water filtration system, a backup generator that powers the apartment's well during outages, and a 2024 roof. An outdoor wood-fired furnace provides heat and hot water to both dwellings, while the original oil and gas heating systems remain operational. A three-year firewood reserve is also included, offering significant potential heating-cost savings. Two gardens, mature perimeter plantings, and generous room for vehicle parking add to the property's privacy and versatility. The apartment above the garage features radiant heat, a first-floor office, kitchen, washer and dryer, private deck, and outdoor shower. The deck wraps around a mature tree, creating a charming “treehouse” feel. Each dwelling is served by its own 1,000-gallon septic system, with a three-bedroom design capacity per system. According to the West Tisbury Board of Health, the systems have a combined capacity to accommodate up to six bedrooms, subject to applicable zoning and permitting requirements. A unique additional opportunity exists for an interested buyer to separately acquire the seller's established Island landscaping business, including certain vehicles and equipment; details available upon request. With solar power helping to keep electric costs low, radiant heat in the garage and apartment, two septic systems, generous parking, multiple work-from-home spaces, and a separate second dwelling, 24 Pine Lane offers a unique combination of character, practicality, and flexibility. Conveniently located for access to Vineyard Haven, Oak Bluffs, Edgartown, and Up-Island destinations. Exclusions: Bertazzoni stove, clawfoot tub in the apartment. Owner occupied; 24-hour notice for showings.