A canopy of oaks lines the entrance to these TWO HOMES on five acres in rural east-Sarasota. Situated on a private cul-de-sac, this multi-generational property offers a 4-bedroom, 3-bathroom main home and a 3-bedroom, 1.5-bathroom guest home, with separate driveway and fenced side yard. NEW ROOF (2025) and hurricane-impact windows (2021) on main house; owners recently renovated and expanded guest house (2018). This estate also offers a screened, oversized, heated saltwater pool with a sunshelf and waterfall. Also included are a barn with tack room, a stocked fishing pond, and cross-fencing for horses. Entire property is fenced. Ample extras include a neat fire pit by the pond perfect for s'mores and camp-outs, a zip line from treehouse, and a kids' soccer field apart from pastures with shady seating nearby for spectators. Current owners added a separate HVAC system and insulation to the garage of the main home, creating a flex space for media and gaming, crafting, working out, or even an overnight guest. A generous carport offers an additional parking option if new ownership maintains the flex space. What sets property apart is its unique privacy: situated on a private cul-de-sac at the end of a quiet byroad, enclosed in a perimeter of oak and pine, this property feels like your own clearing in the woods. Yet no swampy conservation areas or heavy brush to contend with-- once inside the oak-lined drive, open pasture provides a clear view from one property boundary line to the other. White-tailed deer, whistling ducks (late Spring), sand-hill cranes, white ibises and blue herons are a regular occurrence, and the occasional Bald Eagle can even be seen. Bern Creek Ranches is an equestrian community offering a rural lifestyle still close to shopping and beaches. The barebones HOA keeps neighboring properties nice, but doesn't burden property owners with a lengthy list of do's and don'ts. Horses, chickens, cattle and sheep are all welcome. These two homes on five acres will serve new owners and guests well for years to come.