Oakland, FL Houses for Sale

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  $575,000

  • 4 Beds
  • 3 Baths
  • 2,820 Sq Ft

  235 Largovista Dr, Oakland, FL 34787

  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

  235 Largovista Dr, Oakland, FL 34787
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  $599,000

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

  1873 White Feather Loop, Oakland, FL 34787

  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

  1873 White Feather Loop, Oakland, FL 34787
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  $625,000

  • 2 Beds
  • 2 Baths
  • 1,889 Sq Ft

  13732 Fresh Ivy St, Oakland, FL 34787

  One or more photo(s) has been virtually staged. BEST VALUE IN THE COMMUNITY!! Why wait months for new construction when the magic is already waiting for you—just 5 minutes from Disney? This nearly new, designer-upgraded home in Del Webb Oasis is a Disney enthusiast’s dream come true. Whether you’re a lifelong fan of the parks, or simply love the joy and nostalgia Disney brings, you’ll be living

  Nicola Ansons COLDWELL BANKER RESIDENTIAL RE

  13732 Fresh Ivy St, Oakland, FL 34787
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  $524,988

  • 3 Beds
  • 2.5 Baths
  • 2,345 Sq Ft

  17055 Wynford Ln, Oakland, FL 34787

  *****Buyer incentive!! up to $10,000 towards closing costs! ***** Why wait to build when you can MOVE RIGHT IN to this pristine home, shows like a model!!! Welcome to your beautiful 3 bedroom 2 1/2 bathrooms with spacious loft, window treatments and blinds! This beautiful home is where luxury meets comfort! Upon entering, you are greeted with stunning lighting fixtures and an open floor plan

  Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  17055 Wynford Ln, Oakland, FL 34787
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  $685,900

  • 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
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  $614,000

  • 3 Beds
  • 2.5 Baths
  • 2,341 Sq Ft

  12754 Brodlove Ln, Oakland, FL 34787

  **This property qualifies for a closing cost credit up to 1% of the loan amount through the Seller’s preferred lender.** Make This Stunning Home YOURS! Experience the comfort you deserve in this 3 bed/2.5 bath home, featuring a 2-car garage with a paved driveway. With over $55K in enhancements, this home in a prime location near Disney World is a showcase of modern luxury and refined living. The

  Carlinhos Fregonezi TALENT REALTY SOLUTIONS

  12754 Brodlove Ln, Oakland, FL 34787
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  $1,050,000

  • 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
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  $1,060,000

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

  9747 Lost Creek Dr, Oakland, FL 34787

  Qualify with preferred lender for a lower-than-the-market rates *****Seller provides 10,000 dollars towards buyer's closing cost! *****Welcome to 9747 Lost Creek! Located in the highly sought-after HORIZON WEST community of Waterleigh, this gorgeous WATERFRONT beauty is ready to welcome a new family! Built in 2021, everything is in PRISTINE condition, and the home is truly MOVE-IN READY! Mature

  Kim Goldin KELLER WILLIAMS ADVANTAGE REALTY

  9747 Lost Creek Dr, Oakland, FL 34787
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  $821,829 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,101 Sq Ft

  16029 Honey Harvest St, Oakland, FL 34787

  Under Construction. New Construction - October Completion! Built by Taylor Morrison, America's Most Trusted Homebuilder. Welcome to the Cumberland at 16029 Honey Harvest Street in Harvest at Ovation. This spacious two-story Cumberland offers 5 bedrooms, 4.5 bathrooms, and flexible living for every stage of life. The open-concept great room, dining area, and gourmet kitchen flow effortlessly

  Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  16029 Honey Harvest St, Oakland, FL 34787
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  $848,296 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft

  16146 Point Rock Dr, Oakland, FL 34787

  Under Construction. Waterleigh presents the Torrey. 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 are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16146 Point Rock Dr, Oakland, FL 34787
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  $868,686 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,327 Sq Ft

  16158 Point Rock Dr, Oakland, FL 34787

  Under Construction. Waterleigh presents the Seacliff. 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 are greeted with a formal dining room. Go down the hallway and you’ll find a powder room and laundry room tucked

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16158 Point Rock Dr, Oakland, FL 34787
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  $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
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  $877,356 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft

  16164 Point Rock Dr, Oakland, FL 34787

  Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 5 bedrooms and 4.5 bathrooms optimizing living space with an open concept feel.A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16164 Point Rock Dr, Oakland, FL 34787
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  $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
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  $2,175,000 New Construction

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

  1256 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

  1256 Water Maple Dr, Oakland, FL 34787
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  $2,150,000 New Construction

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

  1250 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

  1250 Water Maple Dr, Oakland, FL 34787
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  $617,990 New Construction

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

  Lexington w/ Bonus, 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

  Lexington w/ Bonus, Oakland, FL 34787
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  $577,990 New Construction

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

  Lexington, 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, café, and kitchen, creating a welcoming atmosphere for entertaining and everyday

  Dream Finders Homes

  Lexington, Oakland, FL 34787
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  $505,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  Cooper, Oakland, FL 34787

  Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the

  Dream Finders Homes

  Cooper, Oakland, FL 34787
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  $649,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  Biscayne, Oakland, FL 34787

  The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

  Dream Finders Homes

  Biscayne, Oakland, FL 34787
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  $603,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  Anna Maria, Oakland, FL 34787

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes

  Anna Maria, Oakland, FL 34787
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  $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, 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

  166 Hammock Preserve Loop, Oakland, FL 34787
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  $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
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  $2,200,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,876 Sq Ft

  110 W Railway Ave, Oakland, FL 34760

  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

  110 W Railway Ave, Oakland, FL 34760
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  $1,895,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  511 Briley Ave, Oakland, FL 34787

  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

  511 Briley Ave, Oakland, FL 34787
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  $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
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  $498,990 New Construction

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

  Brantley, 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

  Brantley, Oakland, FL 34787
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  $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

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