Oakland, FL Houses for Sale

• 

  

  

  /40

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  2023 White Feather Loop, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Partial flooring replacement in some areas. Discover a bright interior tied together with a neutral color palette. You'll love cooking in this kitchen, complete with a spacious center island and a sleek backsplash. Relax in your primary suite with a walk in closet included. The primary bathroom

  Karen Albright OPENDOOR BROKERAGE LLC

  2023 White Feather Loop, Oakland, FL 34787
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /60

  $670,000

  • 5 Beds
  • 3 Baths
  • 2,916 Sq Ft

  3318 Current Ave, Oakland, FL 34787

  Welcome to your dream home in the highly sought-after Lakeview Preserve, a gated community nestled near the shores of Johns Lake in Winter Garden. This beautifully appointed residence offers spacious and flexible living with 5 bedrooms and 3 full bathrooms, including a convenient guest suite or office on the first floor.Step inside to discover modern tile flooring throughout the main level, a

  Geoffrey Lopez II RADIUS REALTY GROUP LLC

  3318 Current Ave, Oakland, FL 34787
• 

  

  

  /44

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  9576 Jacques Alley, Oakland, FL 34787

  Stunning 2-Story Home with Payed off Solar System, Designer Upgrades, and A-Rated Schools in Waterleigh – Winter Garden!Welcome to this beautifully maintained 3-bedroom, 2.5-bath home featuring a versatile den/flex space—perfect for a home office, gym, or media room. The open-concept kitchen is a chef’s dream, showcasing modern wood cabinetry, waterfall stone island with under-cabinet and

  Claudio Maciel NOVA REAL ESTATE SERVICES INC

  9576 Jacques Alley, Oakland, FL 34787
• 

  

  

  /32

  $1,450,000

  • 3 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  101 N Starr St, Oakland, FL 34760

  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

  101 N Starr St, Oakland, FL 34760
• 

  

  

  /99

  $2,500,000

  • 5 Beds
  • 5 Baths
  • 4,798 Sq Ft

  530 Largovista Dr, Oakland, FL 34787

  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

  530 Largovista Dr, Oakland, FL 34787
• 

  

  /56

  $619,900

  • 5 Beds
  • 4 Baths
  • 3,449 Sq Ft

  229 Largovista Dr, Oakland, FL 34787

  **NEW PRICE – MUST-SEE LUXURY POOL HOME!** Prepare to fall in love with this stunning 5-bedroom, 4-bathroom home located in the exclusive gated community of *Johns Landing*. Offering nearly 3,500 sq. ft. of meticulously designed living space, this home is the perfect blend of elegance, comfort, and Florida living at its finest! From the moment you step inside, you'll be captivated by

  Richard Lokhnauth RL LUXURY REAL ESTATE

  229 Largovista Dr, Oakland, FL 34787
• 

  

  /29

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  2435 Standing Rock Cir, Oakland, FL 34787

  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

  2435 Standing Rock Cir, Oakland, FL 34787
• 

  

  /45

  $534,900

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft

  233 Largovista Dr, Oakland, FL 34787

  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

  233 Largovista Dr, Oakland, FL 34787
• 

  

  /37

  $540,000

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft

  2035 White Feather Loop, Oakland, FL 34787

  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

  2035 White Feather Loop, Oakland, FL 34787
• 

  

  /38

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  1787 White Feather Loop, Oakland, FL 34787

  **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing available for qualified buyers. Seller also offering additional $5000 credit towards new flooring.** 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

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1787 White Feather Loop, Oakland, FL 34787
• 

  

  /30

  $585,000

  • 4 Beds
  • 2 Baths
  • 2,490 Sq Ft

  610 Strihal Loop, Oakland, FL 34787

  * Seller is giving $10,000 in concessions for closing costs/prepaids or a rate buy down. 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

  Julie Arnold REAL BROKER, LLC

  610 Strihal Loop, Oakland, FL 34787
• 

  

  /29

  $375,000 Open Sun 1AM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,336 Sq Ft

  500 W Oakland Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed

  Angela Worachek REAL BROKER, LLC

  500 W Oakland Ave, Oakland, FL 34760
• 

  

  /44

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  409 E Gulley Ave, Oakland, FL 34760

  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

  409 E Gulley Ave, Oakland, FL 34760
• 

  

  /18

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  13748 Werrington Dr, Oakland, FL 34787

  Seller offering concessions to compete with new construction in the area! 13748 Werrington Drive isn’t just a house — it’s your next chapter waiting to be written. Tucked inside the vibrant, amenity-rich community of Encore at Ovation, this stylish 3-bedroom, 2.5-bath gem offers the perfect mix of comfort, design, and location. From the moment you step through the door, you’ll fall in love with

  Kimberly Ann Zeidner, LLC CHARLES RUTENBERG REALTY ORLANDO

  13748 Werrington Dr, Oakland, FL 34787
• 

  

  /39

  $579,000 Open Sun 12PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  1873 White Feather Loop, Oakland, FL 34787

  This well-designed 4-bedroom, 3-bathroom home with a private office is located in one of Oakland/Winter Garden’s most desirable communities. Offering over 2,400 square feet of living space, the property combines modern features with functional design to suit a variety of lifestyles. The open-concept floor plan includes high ceilings, abundant natural light, and a seamless connection between the

  Ana Bruder FLORIDA CONNEXION PROPERTIES

  1873 White Feather Loop, Oakland, FL 34787
• 

  

  /32

  $674,900

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  13557 Parkfield Way, Oakland, FL 34787

  Amazing highly desirable single story home in the popular Encore at Ovation in Winter Garden just minutes from Walt Disney World! This home sits on a beautiful lot ( only one side neighbor) with no one behind you. It has a gorgeous water and wooded view. The home has a wonderful front porch perfect for enjoying a cup of coffee along with a beautiful back patio overlooking the peaceful water.

  Paula Dale SOTERA LIVING

  13557 Parkfield Way, Oakland, FL 34787
• 

  

  /57

  $1,046,000

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9849 Lost Creek Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience.From the moment you arrive, the immaculate

  Jennifer Ibarra REAL BROKER, LLC

  9849 Lost Creek Dr, Oakland, FL 34787
• 

  

  /7

  $832,126 New Construction

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft

  16152 Point Rock Dr, Oakland, FL 34787

  Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a flex room perfect for work or play and downstairs powder room.The well-appointed kitchen

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16152 Point Rock Dr, Oakland, FL 34787
• 

  

  /3

  $577,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  Lexington Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Lexington floorplan is a spacious one-story design, featuring three comfortable bedrooms and two bathrooms, offering a total of 1,856 square feet. This home includes a versatile three-car garage with tandem space, perfect for extra storage or a workshop area. The open-concept layout connects the great room, cafe, and kitchen, creating a welcoming atmosphere for entertaining and everyday

  

  Dream Finders Homes

  Builder

  14229 Lanyard Way Unit 36464864, Oakland, FL 34787
• 

  

  /3

  $655,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  Captiva Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

  

  Dream Finders Homes

  Builder

  14229 Lanyard Way Unit 36490537, Oakland, FL 34787
• 

  

  /3

  $508,990 New Construction

  • 3 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation, Oakland, FL 34787

  Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

  

  Dream Finders Homes

  Builder

  14229 Lanyard Way Unit 36490206, Oakland, FL 34787
• 

  

  /79

  $1,800,000 New Construction

  • 6 Beds
  • 5 Baths
  • 3,911 Sq Ft

  102 Hammock Preserve Loop, Oakland, FL 34787

  Welcome to 102 Hammock Preserve Loop—a beautifully crafted custom, J&J Home tucked away in the heart of Oakland Park, one of Winter Garden's most sought-after communities. Owners never fully moved into this new home due to change in family circumstances. This spacious corner-lot property is framed by mature oak trees that make you feel like you're living in your own forest oasis. Inside, the

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  102 Hammock Preserve Loop, Oakland, FL 34787
• 

  

  /7

  $1,700,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,909 Sq Ft

  1207 Ridge Lake Way, Winter Garden, FL 34787

  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.

  1207 Ridge Lake Way, Winter Garden, FL 34787
• 

  

  /15

  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  1244 Water Maple Dr, Oakland, FL 34787

  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

  1244 Water Maple Dr, Oakland, FL 34787
• 

  

  /15

  $2,175,000 New Construction

  • 5 Beds
  • 8 Baths
  • 4,433 Sq Ft

  1232 Water Maple Dr, Oakland, FL 34787

  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

  1232 Water Maple Dr, Oakland, FL 34787
• 

  

  /15

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  1238 Water Maple Dr, Oakland, FL 34787

  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

  1238 Water Maple Dr, Oakland, FL 34787
• 

  

  /62

  $1,675,000 New Construction

  • 4 Beds
  • 4 Baths
  • 3,186 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  Under Construction. UPDATE: Ahead of schedule with an estimated completion in Sept.–Oct. 2025. Please see attached package for full renderings and finishes. 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

  AJ Lash CORCORAN PREMIER REALTY

  166 Hammock Preserve Loop, Oakland, FL 34787
• 

  

  /5

  $1,996,500 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  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

  1258 Ridge Lake Way, Winter Garden, FL 34787
• 

  /2

  $617,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,278 Sq Ft

  Lexington w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

  

  Dream Finders Homes

  Builder

  14229 Lanyard Way Unit 36473362, Oakland, FL 34787
• 

  $498,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft

  Brantley Plan at Serenade at Ovation, Oakland, FL 34787

  Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

  

  Dream Finders Homes

  Builder

  14229 Lanyard Way Unit 36498626, Oakland, FL 34787
• 

  /2

  $565,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft

  14111 Frasier St, Oakland, FL 34787

  We present this beautiful new bungalow-style home, located in the Highland Ridge condominium, in Winter Garden – one of the most valued and desired areas to live in.With a charming façade and a welcoming porch at the entrance, this residence combines comfort, elegance and functionality in one place.The project has an open-concept floor plan, perfectly integrating the kitchen with an island with

  Erika Castellani WRA BUSINESS & REAL ESTATE

  14111 Frasier St, Oakland, FL 34787
• 

  

  /15

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1149 Dr, Oakland, FL 34787

  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

  1149 Dr, Oakland, FL 34787
• 

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  The Clementine Plan at The Grove, Oakland, FL 34760

  

  Element Home Builders

  Builder

  15752 E Oakland Ave St Unit 36498057, Oakland, FL 34760
• 

  $2,175,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,433 Sq Ft

  The Citrus Plan at The Grove, Oakland, FL 34760

  

  Element Home Builders

  Builder

  15752 E Oakland Ave St Unit 36480892, Oakland, FL 34760
• 

  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  The Hamlin Plan at The Grove, Oakland, FL 34760

  

  Element Home Builders

  Builder

  15752 E Oakland Ave St Unit 36487597, Oakland, FL 34760
• 

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  The Blossom Plan at The Grove, Oakland, FL 34760

  

  Element Home Builders

  Builder

  15752 E Oakland Ave St Unit 36481095, Oakland, FL 34760

Showing Results 41 - 76, Page 2 of 2