Located in the desirable waterfront community of Winterset Gardens, this uniquely designed SE Winter Haven pool home is set on an oversized half-acre-plus lot and offers community lake access to the beautiful Winter Haven Chain of Lakes. Important system upgrades provide added peace of mind including a newer architectural shingle roof (2024), new electrical panels (2025), new water heaters (2025), and a new A/C system (2025). The home offers over 2,600 square feet of spacious living and showcases distinctive architectural character, including arched openings, beautiful parquet wood flooring, generous room dimensions, and an elegant wood-burning fireplace. The floor plan includes spacious rooms throughout including a family room, formal living room and a formal dining room, creating a natural flow for everyday living and entertaining. The upgraded kitchen is conveniently positioned just off the foyer and features a dedicated breakfast nook, sleek all-wood custom cabinetry, granite countertops, stainless steel appliances, and a professional-style gas range with a stainless hood. The primary bedroom suite is generously sized with en-suite bath access, while the guest bedroom offers comfortable proportions and a walk-in closet. The formal living room provides excellent flexibility for use as a home office, sitting room or conversion into a third bedroom to suit individual living needs. Outdoor living is highlighted by an open-air pool, ample deck space, and a private backyard setting framed by mature plantings, with plenty of room to create your own backyard retreat. The expansive 0.64-acre lot offers exceptional versatility, allowing space for boat or overflow parking, expanded outdoor living areas, or the creation of a garden or vegetable oasis. Winterset Gardens features an optional POA (only $100 per year), with members enjoying access to the community boat ramp on Little Lake Winterset—part of the Winter Haven Chain of Lakes, a system of 20 canal-connected lakes offering some of Central Florida’s best boating, skiing, fishing, and waterfront dining. Ideally located just minutes from shopping, Publix grocery stores, Walmart, dining, and medical facilities, the home is also centrally positioned between Tampa and Orlando for convenient access to major airports and attractions. While the property does require some updating, the combination of architectural character, oversized lot, pool, major system upgrades, and Chain of Lakes access presents a compelling opportunity to create a truly special residence in one of Winter Haven’s most sought-after waterfront communities.