Experience unparalleled flexibility and private acreage living at 37153 S Pine St in Hilliard, Florida. Set upon a sprawling 0.74-acre parcel enveloped by a canopy of mature native oak trees, this unique residential compound presents two distinct, fully detached homes delivering a combined 2,478 square feet of interior living space. Whether your lifestyle calls for independent guest quarters, a dedicated professional workspace, an artist retreat, or potential long-term rental income, this Nassau County property provides a turn-key solution that is rarely available on the market.

The primary residence encompasses 1,498 square feet of thoughtfully designed single-level living, anchored by an inviting open-concept layout. The expansive central living room transitions seamlessly into a well-appointed kitchen outfitted with generous counter space and abundant cabinetry, making everyday meal preparation and hosting effortless. The primary suite serves as a relaxing private sanctuary, featuring dual vanity sinks and a custom tiled walk-in shower. Two additional generously proportioned bedrooms and a full secondary bath accommodate occupants and guests with comfort and ease.

Outdoor relaxation is a hallmark of the main home, which features both a classic covered front porch and a private rear covered porch overlooking the shaded grounds. These outdoor living areas provide ideal vantage points for enjoying North Florida's mild climate, observing local wildlife, and taking in the tranquil, peaceful woodland atmosphere of this established Hilliard setting.

Positioned just a short pathway away, the fully self-contained secondary home offers 980 square feet of private living space. This detached cottage includes an open living and dining concept, a full kitchen, a spacious private bedroom, and a complete bathroom. Complete with an interior laundry room, an independent covered porch, and an attached two-car covered carport, this second dwelling functions as an autonomous living environment ideal for extended visitor stays or passive rental opportunities.

The expansive 0.74-acre exterior grounds deliver utility and lifestyle freedom, complete with an exterior storage shed suitable for tools, lawn care equipment, or recreational gear. Located just minutes from Nassau County's premier 107-acre Westside Regional Park, residents can enjoy rapid access to lit soccer fields, pickleball courts, outdoor amphitheater entertainment, nature trails, a dog park, and freshwater kayak launches, all while remaining within easy commuting distance of Jacksonville, Callahan, and Kingsland, Georgia.