Once in a generation - 56 years of devoted ownership, offered for the very first time. Meticulously maintained by a single family for over five decades, 220 Rollingwood Trail is a rare opportunity to own a generational home in one of Central Florida's most coveted guard-gated communities, Spring Lake Hills. Offered on the open market for the very first time, this 5-bedroom, 3-bathroom, 3-car garage pool home sits on a beautifully landscaped 0.35-acre lot and has been thoughtfully upgraded throughout, delivering a truly move-in ready lifestyle with nothing left to do but make it your own. This home is a standout for the energy-conscious buyer. A fully paid-off solar system installed in 2024 powers the home with virtually no monthly electric bill. A whole-house standby generator with dedicated hookup provides peace of mind through any Florida storm season. The upgraded electrical panel, energy-efficient water heater, high-efficiency variable-speed pool equipment, and double-pane energy-efficient windows complete a mechanical package that is simply unmatched at this price point. New roof installed May 2020. Step inside to warm hardwood and tile floors, a charming dry bar perfect for entertaining, and a kitchen anchored by classic Chicago brick detailing that gives the space a timeless, character-rich feel. The generous 2,845 square feet of living space is spread across five bedrooms and three full bathrooms, offering ideal flexibility for families, guests, or a dedicated home office. The three-car garage features extensive built-in storage and workshop, a rare find in this community. The backyard is a true Florida retreat - a screened pool and expansive covered patio invite year-round outdoor living, while a propane hookup on the side yard serves both the grill and a gas-burning fireplace for those cooler evenings. A lifetime paver driveway adds curb appeal from the moment you arrive. The 8-zone irrigation system and covered gutter system keep the property in pristine condition with minimal upkeep. CPVC plumbing throughout. City water and city sewer. Spring Lake Hills is among Seminole County's most prestigious addresses - a 24-hour guard-gated community with a single staffed entry and exit point, offering an unmatched level of security and privacy. Residents enjoy deeded access to two lakes - Spring Lake and Lake Destiny - via two private community boat ramps, plus pickleball courts, basketball courts, and a community playground. Within minutes of three of Central Florida's top-rated private schools, major shopping and dining at Altamonte Mall and Cranes Roost Park, and seamless Interstate 4 access to Orlando and beyond. Homes with this combination of pedigree, mechanical upgrades, community amenities, and first-time-on-market status simply do not come available often. It is a lovingly cared-for family home being passed forward. Schedule your private showing before this chapter closes.
- Built in 1970
- 3 garage spaces
- $261.86/sqft
- Lot size: 15,212 sqft
- 53 days on market
- Directions: Take Exit 92 from I-4 - SR-436 West / Altamonte Springs Head west on SR-436 (Altamonte Avenue) Turn LEFT onto S. Westmonte Drive heading south Turn RIGHT onto Wymore Road - Spring Lake Hills will be on your right Enter through the 24-hr guard gate - have your ID ready and let them know you're visiting 220 Rollingwood Trail Follow Spring Lake Hills Drive, then turn onto Rollingwood Trail - home will be on your right
- County: Seminole
- Geo subdivision: SPRING LAKE HILLS
Nearby Schools
Spring Lake Elementary
Milwee Middle
Lyman High
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Community Info
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Niles Harrison Pfeiffer
Central Florida REALTOR®
- Source: Stellar MLS
- MLS #: O6414914
Listing updated: August 3, 2026 at 4:43PM
Listing provided by: Tyler Deans, CREEGAN GROUP
Last checked 5 hours ago
Listing provided by: Tyler Deans, CREEGAN GROUP
Last checked 5 hours ago
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