Rare opportunity to own a 20-acre multi-home farm estate offering privacy, versatility, and income potential. This exceptional property features two residences across multiple parcels, making it ideal for multigenerational living, rental income, or a private rural compound with thoughtfully designed equestrian amenities. The custom-built main residence sits on a scenic 14-acre parcel and offers 3,564 sq ft with 4 bedrooms and 2.5 baths. Both stories are concrete block and complete with double pane glass windows and doors. Inside, the home is anchored by a striking two-story stacked NC Cherry Long stone fireplace, creating a dramatic focal point in the main living area. It is flanked by a wall of windows for an abundance of natural light. A floating oak staircase adds warmth and craftsmanship, while the new kitchen installed in 2022 flows seamlessly into generous living spaces designed for everyday comfort and entertaining. Outdoor highlights include a custom resort-style pool with slide, firepit, pool equipment house, two tranquil koi ponds with a waterfall and expansive grounds framed by mature trees and open pasture views. The 2 story, 864 sq ft detached garage features a finished, screened-in Florida room above, ideal for gatherings, hobbies, or enjoying the outdoors year-round bug-free. You'll enjoy walking across the bridge from the primary bedroom to the Florida room. The property also includes an additional income-producing residences: 27750 Debbie Rd with ~6 acres, 3-bed/2-bath mobile home, 1,152 sq ft (1993). There is an additional 3rd parcel also available at 27720 Debbie Rd with ~5 acres, 3-bed/2-bath mobile home, 1,560 sq ft (2010). Both homes are currently tenant-occupied offering immediate income opportunities. Designed with equestrian use in mind, the property offers a comprehensive layout including a 72' x 144' riding arena shaded by mature oak trees, a 60' round pen, and lighting throughout the property and into multiple pastures (may need updating). An extra-wide pole barn with metal roof and center aisle allows for configurable stall layouts ranging from 7 to 13 stalls (currently 10x20), complete with a wash rack. Ask about the farm equipment included. The land is thoughtfully arranged with eight total pastures, two small turnout paddocks, and is cross-fenced with no-climb fencing for safety and ease of management. A pond with viewing gazebo adds both function and a peaceful gathering space. This property offers the ideal balance of country living with modern convenience, located just minutes from shopping, dining, and services in The Villages. Publix and Aldi's are just down the road. For active equestrians, it is also well positioned near established venues including Sumter Equestrian (24mi), Grand Oaks (14mi), Rocking Horse (29mi), Three Lakes (13), Florida Horse Park (31mi) and the World Equestrian Center WEC Ocala (44mi). The Florida Turnpike is approximately two miles away, providing efficient access throughout Central Florida. With expansive acreage, multiple residences, immediate income, and well-appointed equestrian infrastructure, this property presents a rare combination of lifestyle, flexibility, and accessibility in a highly desirable setting.