Oakland Houses for Sale

Custom Entertainer’s Dream Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living.From the

David Dorman CENTURY 21 CARIOTI

LOCATION, LOCATION, LOCATION! This fantastic home is located in the highly sought after community of OAKLAND PARK! Enjoy the quaint historic Town of Oakland or a short golf cart or bike ride to enjoy bustling downtown Winter Garden with its shops, restaurants and weekly farmers market. The 22 mile West Orange Trail meanders through the community for enjoying tree lined walks or bike rides! When

Kathie Glass BHHS FLORIDA REALTY

Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious

Evan Gfeller BHHS FLORIDA REALTY

Welcome to 619 Largovista Dr—a custom-built, recently remodeled home in the highly desirable, gated community of Johns Landing on Johns Lake. This one-of-a-kind property features luxury finishes and a beautifully designed layout, along with mature fruit trees for a touch of natural charm. Step into the grand foyer and take in the stunning light fixtures cascading from the soaring ceilings. To

Farhad Haniff WEICHERT REALTORS HALLMARK PRO

Welcome to a home that blends comfort, function, and fun for all behind the gates of a peaceful, well-kept neighborhood just minutes from the turnpike. This spacious residence features a smart split floor plan with four generously sized bedrooms and five full bathrooms plus one half bathroom, including a guest suite perfect for visiting friends or extended family. Inside, custom cabinets and

Mark Bridges CHARLES RUTENBERG REALTY ORLANDO

Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

Chris Herlihy NEW HOMES REAL ESTATE, INC.

Under Construction. UPDATE: Ahead of schedule with an estimated completion in Sept.–Oct. 2025, 166 Hammock Preserve Loop offers one of the finest new construction custom homes in Winter Garden, FL. Built by AR Homes—celebrating over 40 years of luxury homebuilding—this Carrabelle model sits in the highly sought-after Oakland Park community. Boasting 3,186 sq ft of impeccably crafted living space,

AJ Lash CORCORAN PREMIER REALTY

Extraordinary lakefront estate, where culinary excellence meets waterfront paradise. Immerse yourself in the ultimate lakefront lifestyle at this breathtaking direct waterfront estate on Johns Lake, where every morning begins with sunrise reflections dancing across 2,500 acres of pristine water and every evening concludes with golden sunsets painting the sky from your private south-facing

Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

PRICED TO SELL! This recently built energy-efficient home, constructed by Meritage Homes in September 2019, boasts approximately $15,000 in furnishings, artwork, and pendant lighting—all negotiable with the purchase! Enjoy a large, covered front porch and a spacious open first floor. Upon entering, you'll find wood-look grey tile flooring that perfectly complements the cabinetry and walls, with

Joshua Earley OPTIMA ONE REALTY, INC.

229 Largovista Drive – A Dream Address You'll Be Thrilled to Call HOME! Step into a world of elegance and leisure at this stunning pool home located in the highly coveted gated community of Johns Landing. This beautiful home boasts 5 spacious bedrooms, 4 full bathrooms, and almost 3,500 sq. ft. of living space, offering both luxury and comfort in every detail. As you enter, you’ll be impressed by

Richard Lokhnauth RL LUXURY REAL ESTATE

Step into this exquisite ONE-STORY residence, where love at first sight is inevitable. Nestled in the serene, LAKEFRONT community of Hull Island, this home offers enchanting VIEWS of the NATURE PRESERVE and is ideally located within close proximity to Winter Garden’s historic downtown, the charming town of Oakland, and the lively town of Clermont. Here, you’ll relish waterfront dining, local

Ashley Boyd BHHS FLORIDA REALTY

Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the

Celestino De Cicco CENTRAL FLORIDA REALTY

Luxury, Convenience, and Comfort in John’s Landing! This thoughtfully updated and move-in ready 4-bedroom, 2-bath home offers flexible living in one of Oakland/Winter Garden’s most desirable gated communities, the gorgeous John’s Landing. You will feel welcomed home with mature landscaping, an extended driveway, a covered entry, Ring doorbell, and exterior lighting—perfect for a warm arrival day

Rachael Segarra EXP REALTY LLC

Welcome to 2035 White Feather Loop, a stunning haven nestled in the serene community of Oakland Trails. This meticulously crafted residence offers an unparalleled blend of modern elegance and timeless charm, providing a sanctuary for luxurious living. Upon arrival, you'll be captivated by the impeccable curb appeal of this home, showcasing lush landscaping and a grand entrance. Step inside to

James Goodyear REAL BROKER, LLC

**This property qualifies for a closing cost credit up to $8,400 through the Seller’s preferred lender.** Welcome to a beautifully designed two-story single-family home featuring 3 bedrooms, 2.5 bathrooms, and a detached garage, nestled in a serene and manicured community. As you arrive, you're greeted by a welcoming front porch and an upstairs balcony offering peaceful views of a sleekly

Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

Welcome to an extraordinary residence nestled in the highly sought-after Oakland Trails community—just steps from the scenic West Orange Trail and moments from the charm of downtown Winter Garden. This beautifully appointed home showcases sophisticated upgrades, including a striking custom stone accent wall in the main living and dining areas and matching stonework along the staircase, creating a

Jennifer Coon KELLER WILLIAMS WINTER PARK

Welcome to your beautifully updated home in the coveted gated community of John’s Landing in Oakland, Florida! Nestled near the shores of Johns Lake, this stylish residence combines modern upgrades with timeless appeal, all in one of Central Florida’s most desirable locations.Step inside to discover an open and airy floor plan, highlighted by a completely renovated kitchen featuring sleek

Julie Arnold REAL BROKER, LLC

Welcome to this beautifully updated 4-bedroom, 2-bath home located in the heart of Oakland.Nestled in the golf cart district of the charming local town, this home has the blend of small-town charm and modern convenience.Within a short 10-minute walk, youll enjoy local shopping, the West Orange Biking Trail, and a quaint downtown area. Conveniently located 2 miles from the main highway

Steven Koleno BEYCOME OF FLORIDA LLC

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space.Inside, enjoy a warm and functional layout with 1,419 sq ft of living

Liam Lugo KELLER WILLIAMS WINTER PARK

One or more photo(s) has been virtually staged. Exceptional POOL HOME with SOLAR PANELS and Many Other ENERGY-EFFICIENT FEATURES!Welcome to a home that truly impresses from the moment you arrive. As you step inside, you’re greeted by seamless WOOD PLANK TILE FLOORING that flows throughout the home, creating a warm and cohesive aesthetic. The heart of the home is a show-stopping kitchen

Melissa Vance MAINFRAME REAL ESTATE

***ASSUMABLE VA MORTGAGE AT A 5.375 INTEREST RATE*** Absolute model condition—and that’s not said lightly. From the moment you arrive, the charm and care put into this home are undeniable. A cozy front porch with ample seating and attractive brick pavers sets the tone, leading to an upgraded 9-foot leaded glass front door that opens into a meticulously maintained interior.The upgraded

Brooke Cangro RE/MAX 200 REALTY

Discover the charm of this custom-built home, completed in 2010, with no HOA!Step inside this spacious two-story, 3-bedroom, 2-bathroom home and fall in love with the open floor plan and modern updates. The brand-new flooring and fresh interior paint create a bright, clean, and welcoming feel throughout.The heart of the home is the completely renovated chef’s kitchen, featuring

Angela Worachek REAL BROKER, LLC

Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the

Erica Diaz HOMEVEST REALTY

Welcome to 235 Largovista Dr, tucked inside the gated Johns Landing community in Oakland, FL! This spacious 4-bedroom, 3-bath home includes a flex space already set up for a 5th bedroom perfect for guests, a home office, or extra room to grow.Outside, enjoy your private pool and outdoor living area, made for relaxing weekends and fun-filled gatherings. The new pool pump (2022) and fresh sod give

Liam Lugo KELLER WILLIAMS WINTER PARK

NEW PRICE ...Highly MOTIVATED owner !! Welcome to this stunning designed 4-bedrooms, 3-full bathrooms + office, nestled in one of Oakland / Winter Garden’s most desirable communities! With over 2400 sqft of thoughtfully designed living space, this home offers modern elegance and functional spaces.Spacious Open Layout: High ceilings, abundant natural light, and a seamless flow between living,

Ana Bruder FLORIDA CONNEXION PROPERTIES

This BRAND NEW CONSTRUCTION home directly on John's Lake is one of a kind with over 2 acres behind, high and dry, over 500 feet of direct lake frontage, plus 4700 sqft of living space, 5 spacious bedrooms, 4 full bathrooms, one half bath and a true open concept design. As you walk in the front door, you're greeted by tons of natural light from all the sliding glass doors and oversized windows,

David Johnston CREEGAN GROUP

Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and lifestyles.Step inside and experience an open-concept layout that combines elegance with

Alexis Anderson REGENCY REAL ESTATE LLC

Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this home is thoughtfully designed to create ample space for both private retreats and vibrant social

Alexis Anderson REGENCY REAL ESTATE LLC

Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

Heather Spirazza REGENCY REAL ESTATE LLC

Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features four spacious bedrooms and four luxurious bathrooms, providing ample space for relaxation and

Matt McKee COMPASS FLORIDA LLC

Under Construction. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. This custom-built masterpiece by Pioneer Builders blends timeless elegance with modern convenience, offering a quintessential French farmhouse style that exudes warmth and charm. Step inside this 5-bedroom,

Heather Spirazza REGENCY REAL ESTATE LLC

Pre-Construction. To be built. Introducing Briley Farm, an exquisite 111-acre sanctuary nestled in the historic charm of Oakland, Florida. Designed by renowned Element Home Builders, this brand-new architectural design evokes a Modern Farmhouse vibe, epitomizing luxury with a touch of heritage. A welcoming front porch creates small-town charm. The open kitchen connects to the family gathering

Matthew Burks CORCORAN PREMIER REALTY

Pre-Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders – A Stunning New Home in Oakland's Premier Community!Discover your dream home with the Clementine Floorplan, a thoughtfully designed residence nestled in Oakland's newest, most sought-after community. This spacious, modern home combines elegance, functionality, and comfort to create the perfect

Blaine Dooley REGENCY REAL ESTATE LLC