Oakland, FL Homes for Sale with Pool

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  /64

  $599,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

  13067 Tollcross Way, Oakland, FL 34787

  Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  13067 Tollcross Way, Oakland, FL 34787
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  /9

  $609,990

  New Construction $38K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,911 Sq Ft

  3128 Namaste Dr, Oakland, FL 34787

  Under Construction. The Inverness is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s suite

  Ben Goldstein LENNAR REALTY

  3128 Namaste Dr, Oakland, FL 34787
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  /26

  $674,350

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft

  5576 Dr, Oakland, FL 34787

  Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home.Welcome to your dream home – the Cardinal. This stunning new construction features 4 spacious

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  5576 Dr, Oakland, FL 34787
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  /23

  $575,000

  $75K PRICE INCREASE

  • Land
  • 19,602 Sq Ft
  • $1,277,778 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787
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  /35

  $514,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,094 Sq Ft

  12308 Bracco St, Oakland, FL 34787

  Beautiful and nearly new home in the quiet and friendly Highland Ridge community. This home was built only two years ago and is in perfect condition, offering over 2,114 sq. ft. of air-conditioned space. The layout is open and bright, with a modern kitchen that overlooks the large living and dining areas, perfect for family time and hosting friends. A big plus for this property is the oversized

  Diller de Abreu Junior ELITE INTERNATIONAL REALTY INC

  12308 Bracco St, Oakland, FL 34787
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  /30

  $700,000

  New Construction $4K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,441 Sq Ft

  14780 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

  Taylor Morrison Builder

  14780 Field Daisy Dr, Oakland, FL 34787
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  /30

  $874,900

  • 4 Beds
  • 4.5 Baths
  • 3,134 Sq Ft

  1231 Foltz Loop, Oakland, FL 34787

  Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living

  Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

  1231 Foltz Loop, Oakland, FL 34787
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  /39

  $796,000

  $4K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,528 Sq Ft

  1970 Standing Rock Cir, Oakland, FL 34787

  Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1970 Standing Rock Cir, Oakland, FL 34787
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  /57

  $610,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,445 Sq Ft

  16186 Honey Harvest St, Oakland, FL 34787

  Move right into one of the most sought-after floor plans in Harvest at Ovation. This just-completed Taylor Morrison Baldwin model offers the rare opportunity to skip the build timeline and step into a never fully lived-in home loaded with designer upgrades and timeless style. Originally purchased as a long-term move, the sellers had a change of plans, creating an incredible opportunity for the

  Ken Pozek REAL BROKER, LLC

  16186 Honey Harvest St, Oakland, FL 34787
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  /13

  $2,615,320

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 4,658 Sq Ft

  1152 Prado Ln, Winter Garden, FL 34787

  Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own

  Alexis Anderson REGENCY REAL ESTATE LLC

  1152 Prado Ln, Winter Garden, FL 34787
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  /78

  $2,850,000

  • 7 Beds
  • 6.5 Baths
  • 6,400 Sq Ft

  15522 Shorebird Ln, Oakland, FL 34787

  Welcome to an extraordinary estate in Lakeshore Preserve, this exceptional lakefront estate represents a rare convergence of scale, sophistication, and resort-inspired living. Crafted by Toll Brothers, this expanded Santa Bella model stands as one of the largest and most distinguished residences in the community, offering over 6,400 square feet, 7 bedrooms, and 6.5 bathrooms. A stately tile roof

  Jack Zhao EAST PEARL REALTY

  15522 Shorebird Ln, Oakland, FL 34787
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  /68

  $1,374,990

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

  9827 Beach Port Dr, Oakland, FL 34787

  Perfectly positioned on a PREMIER WATERFRONT LOT just under half an acre, this stunning 3,910-square-foot residence delivers luxury living at every turn. Tucked away at the end of a tranquil cul-de-sac and situated on one of the few homesites in the neighborhood with no neighbors in front or behind, the property offers an exceptional sense of privacy with beautiful views of Lake Noah. A grand

  Silvia Kinkela SERHANT

  9827 Beach Port Dr, Oakland, FL 34787
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  /57

  $535,000

  • 4 Beds
  • 3.5 Baths
  • 2,486 Sq Ft

  17167 Writing Aly, Oakland, FL 34787

  Located in the heart of Horizon West, 17167 Writing Aly offers the space, flexibility, and location buyers are looking for in Winter Garden. Just minutes from Hamlin Town Center, the 429, Disney, and Downtown Winter Garden, this home is positioned in one of Central Florida’s fastest-growing areas while still offering a true neighborhood feel with community green spaces, walking paths, and

  Ken Pozek REAL BROKER, LLC

  17167 Writing Aly, Oakland, FL 34787
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  $649,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  914 Trowman Aly, Winter Garden, FL 34787

  Virtually Staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled

  Erica Diaz HOMEVEST REALTY

  914 Trowman Aly, Winter Garden, FL 34787

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