One or more photo(s) has been virtually staged. Discover luxury living in Wyndham at Lake Winterset, one of Winter Haven’s most prestigious gated and guarded lakefront communities. Welcome to 105 Wyndham Drive, an elegant waterfront residence on a sprawling 0.80-acre lot with peaceful pond views, mature landscaping, and timeless architectural appeal. Stately wrought-iron gates, a brick-paved entry, and manicured grounds set the tone for the executive lifestyle this enclave is known for. Inside, the beautifully maintained 4-bedroom, 3-bath layout offers refined living spaces filled with natural light, soaring ceilings, crown moldings, upgraded wood flooring, and wide windows framing serene water views. A flexible executive office can easily function as a fourth bedroom. The chef-inspired kitchen features custom cabinetry, glass-front displays, granite countertops, stainless-steel appliances, and a built-in desk nook. The adjoining family room includes a cozy fireplace and custom wine storage, while the formal living and dining rooms add sophistication for gatherings. The private primary suite is a true retreat with room for a sitting area, dual walk-in closets, and a spa-like bath with jetted tub, walk-in shower, dual sinks, and elegant sconce lighting. Additional bedrooms are generously sized and well-separated for privacy. Step outside to enjoy resort-style Florida waterfront living. A covered lanai with audio/TV connections opens to an expansive paver patio, lagoon-style heated pool and spa, outdoor firepit, and tranquil pond and fountain views—ideal for entertaining or quiet evenings at home. The oversized two-car garage includes epoxy floors and extensive built-in storage. Recent upgrades include new wood flooring in all bedrooms and the office, new tile in both baths, expanded patios, upgraded irrigation, refreshed landscaping, and new interior/exterior paint. Wyndham residents enjoy tennis and pickleball courts, basketball, a playground, and manned security—all in a beautifully maintained lakefront setting near the Winter Haven Chain of Lakes, shopping, dining, medical care, and major highways. Disney World is under an hour away, with convenient access to Tampa and Orlando airports. A rare opportunity to own one of Wyndham’s finest waterfront executive homes, offering luxury, privacy, and a stunning natural setting.