MLS Listings for Sale in Oakland, FL

MLS Listings for Sale in Oakland, FL

One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36&rdquo

MLS Listings for Sale in Oakland, FL

Nestled in the highly desirable Oakland Trails community, this beautifully designed 5-bed, 3-bath "Montclair" former model home spans nearly 3,500 square feet of thoughtfully planned living space. The first floor opens with a spacious family room, separate formal living and dining areas, and a fifth bedroom with adjacent bath. The open-concept kitchen boasts an oversized island, double ovens, stainless steel appliances, walk-in pantry, Butler's pantry, a convenient breakfast nook, and access to the recently expanded and screened in paver lanai leading to a fenced in side yard. Upstairs, four additional generous bedrooms provide comfort and privacy, making this home ideal for both

MLS Listings for Sale in Oakland, FL

Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors. Built in 2019 and cared for like new, this home blends comfort, efficiency, and style. The exterior features upgraded pavers, clean neutral tones, and meticulous landscaping. Inside, you’ll find a bright, open floor plan designed for today’s lifestyle—perfect for entertaining or relaxing at home

MLS Listings for Sale in Oakland, FL

Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets paired with elegant quartz countertops installed in 2025, complemented by stainless steel appliances. The home's standout feature is the screened porch that runs the full length of the house, perfect for relaxing while overlooking the spacious backyard. This outdoor space offers plenty of room for entert