This is one of those homes that buyers wait for, a rare opportunity to own a ONE-OF-A-KIND MID-CENTURY gem where nature, land, and character come together. Tucked into one of Longwood's most unique locations set along the former 10th hole of the historic Rolling Hills golf community, this home is nestled among rolling green space, WATER VIEWS of Lake Jeanette, & established mature landscaping. Positioned on OVER HALF AN ACRE in a DESIGNATED GOLF CART COMMUNITY with NO HOA, this retreat offers privacy & connection to nature while still being just minutes from I-4, shopping, restaurants and everything you need in the heart of Longwood. A long driveway shaded by mature trees creates a welcoming arrival, while a private canopy of trees sets the peaceful setting found throughout. The outdoor lifestyle begins the moment you arrive. A GARDEN-INSPIRED landscape welcomes you with greenery, a FIRE PIT gathering area & detached storage shed ideal for gardening or creative projects. Multiple outdoor spaces create a PARK-LIKE SETTING designed for relaxing, entertaining, & enjoying the outdoors. With a front garden retreat, private pool, backyard patio overlooking rolling hills, and side-yard screened-in patio space, you won't want to leave home! Made for easy Florida living, the SCREENED-IN SALTWATER POOL offers a private sanctuary framed by distinctive MID-CENTURY arches. Relax in a hammock, feed the ducks, or enjoy a poolside gathering. Winding pathways connect seating areas, brick patios, covered spaces, and quiet corners beneath mature trees, creating the perfect outdoor retreat. A breezeway connects the home to the OVERSIZED DETACHED TWO-CAR GARAGE, adding function & charm. The oversized garage includes a dedicated WORKSHOP SPACE for hobbies, storage, & projects. A separate dedicated GOLF CART GARAGE adds convenience and reflects the neighborhood's laid-back lifestyle. There's also a front parking area providing ample room for trailers, recreational equipment, work vehicles or additional storage needs, another advantage of living in a NO HOA community. Inside, NATURAL LIGHT pours through large windows, highlighting the residence's MID-CENTURY charm and thoughtful updates. Arched openings, wood ceilings, & built-in shelving enhance the home's character, while wood flooring complements the timeless design. The living & dining spaces flow into a kitchen featuring rich cabinetry, exposed wood detail, brick accents, & expansive windows that bring the surrounding greenery indoors. The layout includes 3 bedrooms, 2 bathrooms (one is dual entry), & WALK-IN CLOSETS in every bedroom. The area is known for its open green space, walkable streets, & being an active lifestyle neighborhood, including an annual holiday golf cart parade! The surrounding space creates a peaceful, almost country-like setting while remaining close to everything. Significant updates include NEW ROOF (2024), WHOLE HOME GENERAC PROPANE GENERATOR (2020), NEW DRAIN FIELD (2022), NEW ELECTRIC WATER HEATER (2023), NEW KITCHEN WINDOWS (2023) & new pool enclosure screens (2024). Additional improvements include waterproof laminate flooring (2022), paint/trim, baseboards, blinds/drapes, ceiling fans, & garage door openers (2021), foyer tile (2026), exterior garage lighting (2026). The home also includes an ACTIVE TRANSFERABLE TERMITE BOND. With Phase One of the Rolling Hills Community Park already underway, this amazingly unique home offers lifestyle, location, and LOTS of future potential!