Luxury homes for sale & real estate in Oakland, FL

Luxury Home for sale in Oakland, FL:

Stunning upgraded model home with an oversized kitchen in highly desirable Oakland Park. The Sunset Model—a neighborhood favorite known for its award-winning design—is no longer available to build, making this a rare opportunity to own a customized, seldom-available gem! This home features 3 bedrooms + an additional flex room with French doors, 2.5 baths, a fenced yard, oversized quartz island with granite kitchen counters, custom lighting, wood flooring, gas stove, tile backsplash, a loft, inviting front porch, and a fully finished backyard complete with a fire pit, pavers, and bistro lights—perfect for entertaining. The yard also has room for a pool should a future owne

Luxury Home for sale in Oakland, FL:

Exquisite Lakefront Residence: 5 Beds, 5 Baths! This striking home, constructed by DR Horton in 2023, sits on over half an acre, boasting panoramic views of the picturesque Lake Apopka. This property sits directly on the 5th Largest Lake in the entire state and the lot is already approved for a full dock and a pool!!! A chef's dream, the kitchen is luxuriously equipped, seamlessly flowing into the expansive family room. On the main level, discover a full bedroom and bath, while the primary suite and additional bedrooms await upstairs. Upgraded with smart fans in every bedroom, the movie room, and the upper deck, this home also features new lighting fixtures throughout, including the bathroo

Luxury Home for sale in Oakland, FL:

Spectacular Lakefront Living on Johns Lake in Winter Garden, Florida - Pool, Spa & Stunning Sunset Views - Welcome to this extraordinary Standard Pacific executive home, perfectly positioned on over a quarter acre with 87 feet of pristine lakefront along beautiful Johns Lake. From the instant you walk in, the openness, elegance, and sweeping lake view reveal that this is a home unlike any other. Providing more than 4,000 square feet of elegant one-story living with a dedicated upstairs bonus room, this residence offers 4 bedrooms, 4½ baths, and a 3-car garage. This exceptional floor plan reflects the builder’s distinguished craftsmanship and masterfully planned design, el

Luxury Home for sale in Oakland, FL:

Completely Remodeled Waterfront Luxury Home – Boater’s Paradise on Lake Apopka Experience the ultimate in lakefront living with this stunning, turnkey home on Lake Apopka in Winter Garden. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm, offering breathtaking sunrise and sunset views every day. Every inch of this home has been meticulously upgraded with nearly $450,000 invested in recent renovations, creating a move-in-ready oasis with high ceilings, spacious open-concept living, and designer finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly ac

Luxury Home for sale in Oakland, FL:

Welcome to Oakland Park, Winter Garden’s premier Golf Cart District — where timeless architecture, front-porch living, and modern design come together just steps from the West Orange Trail and charming downtown Winter Garden. This home exudes curb appeal with its classic front porch that invites you to relax and take in the neighborhood’s vibrant, walkable atmosphere. Inside, the open-concept main level showcases ceramic tile flooring throughout, granite countertops, and high ceilings that create a bright, spacious feel perfect for entertaining or everyday living. Upstairs, you’ll find all bedrooms thoughtfully designed for comfort and functionality, each featuring w

Luxury Home for sale in Oakland, FL:

Welcome to a truly exceptional custom home, perfectly situated in a private, gated community on the shores of breathtaking John’s Lake. Set on over an acre of beautifully landscaped property with panoramic water views throughout the island, this 4-bedroom estate offers the ultimate Florida lifestyle — complete with resort-style amenities and convenient access to Historic Downtown Winter Garden, as well as Downtown Orlando and major attractions just 30 minutes or less away. From the moment you arrive, charm and craftsmanship are evident in every detail. Step through the front door into an inviting floor plan that seamlessly blends elegance with functionality. The spacious living