Oakland, FL Homes

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  Est $778,034 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  5633 Orange Orchard Dr, Oakland, FL 34787

  5633 Orange Orchard Dr, Oakland, FL 34787
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  /2

  $852,342 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,412 Sq Ft

  15093 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15093 Tea Tree Dr, Oakland, FL 34787
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  $914,390 Sold Nov 25, 2025

  4649 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2025

  Last Sold Summary

  • $214/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  4649 Golden Birch Ave, Oakland, FL 34787
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  /2

  Est $525,514 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  13031 Tollcross Way, Oakland, FL 34787

  13031 Tollcross Way, Oakland, FL 34787
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  /17

  $399,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

  Harbor Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36477638, Oakland, FL 34787
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  /2

  $400,000 Sold Aug 18, 2025

  5693 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 2025

  Last Sold Summary

  • 11% Below List Price
  • $223/SF
  • 31 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  5693 Meditation Dr, Oakland, FL 34787
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  /2

  Est $634,227 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,182 Sq Ft

  13109 Tollcross Way, Oakland, FL 34787

  13109 Tollcross Way, Oakland, FL 34787
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  /56

  $575,000 Pending

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

  229 Largovista Dr, Oakland, FL 34787

  Under contract-accepting backup offers. **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

  Richard Lokhnauth RL LUXURY REAL ESTATE

  229 Largovista Dr, Oakland, FL 34787
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  /2

  $653,240 Sold Jul 30, 2025

  5664 Vinyasa Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft
  • Built 2025

  Last Sold Summary

  • $247/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  5664 Vinyasa Rd, Oakland, FL 34787
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  /34

  Est $433,628 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,513 Sq Ft

  9085 Legado Dr, Oakland, FL 34787

  9085 Legado Dr, Oakland, FL 34787
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  /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
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  $751,000 Sold Oct 03, 2025

  • 2,837 Sq Ft
  • $265/SF

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  16041 Honey Harvest St, Oakland, FL 34787

  Welcome to the St. Clair at 16041 Honey Harvest Street, located in Harvest at Ovation—one of the final new construction opportunities in Horizon West! This thoughtfully designed home offers gorgeous curb appeal and a designer interior with an inviting foyer that connects to two secondary bedrooms, while a third is privately located at the rear. The open-concept layout features a gourmet kitchen

  Taylor Morrison

  16041 Honey Harvest St, Oakland, FL 34787
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  /2

  Est $598,600 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft

  15169 Summer Harvest St, Oakland, FL 34787

  15169 Summer Harvest St, Oakland, FL 34787
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  /56

  $830,000

  • 5 Beds
  • 4.5 Baths
  • 4,440 Sq Ft

  3387 Current Ave, Oakland, FL 34787

  Gorgeous home at Winter Garden gated community LakeView Preserve, San Benita model with upgrade of extended lanai and a lot of home improvement, Gourmet Kitchen, open floor plan, engineer wood flooring, NO CARPET in the house, crown molding, study room, dining room, and huge game room in second floor, first floor master bedroom suite, second floor with another bedroom suite. Ceiling fans with

  Li Xue AGENT GROUP REALTY

  3387 Current Ave, Oakland, FL 34787
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  /2

  $695,000 Sold Sep 22, 2025

  1281 Ridge Lake Way, Winter Garden, FL 34787

  • Land
  • 0.39 Acre
  • $1,782,051 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 99 Days On Market

  Last Listing Agent Samantha Andrade KELLER WILLIAMS ELITE PARTNERS III REALTY

  1281 Ridge Lake Way, Winter Garden, FL 34787
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  /2

  Est $640,329 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,741 Sq Ft

  3303 Buoy Cir, Oakland, FL 34787

  3303 Buoy Cir, Oakland, FL 34787
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  /14

  $420,000

  • Land
  • 0.26 Acre
  • $1,615,385 per Acre

  1161 Prado Ln, Oakland, FL 34787

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

  Alexis Anderson REGENCY REAL ESTATE LLC

  1161 Prado Ln, Oakland, FL 34787
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  /2

  $883,656 Sold Sep 08, 2025

  16089 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2025

  Last Sold Summary

  • $311/SF

  Current Estimated Value $881,000

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  16089 Honey Harvest St, Oakland, FL 34787
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  /31

  Est $451,404 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  16287 Prairie School Dr, Oakland, FL 34787

  16287 Prairie School Dr, Oakland, FL 34787
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  /44

  $675,000

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  529 Johns Landing Way, Oakland, FL 34787

  Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary

  Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787
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  /2

  $2,275,000 Sold Nov 24, 2025

  530 Largovista Dr, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,798 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $474/SF
  • 110 Days On Market

  Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

  530 Largovista Dr, Oakland, FL 34787
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  /11

  Est $504,808 Not Listed For Sale

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

  2035 White Feather Loop, Oakland, FL 34787

  2035 White Feather Loop, Oakland, FL 34787
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  /3

  $374,900

  • Land
  • 0.24 Acre
  • $1,562,083 per Acre

  1215 Ridge Lake Way, Winter Garden, FL 34787

  LOT 247: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1215 Ridge Lake Way, Winter Garden, FL 34787
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  /2

  $464,000 Sold Oct 29, 2025

  2163 White Feather Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 65 Days On Market

  Last Listing Agent Joshua Earley OPTIMA ONE REALTY, INC.

  2163 White Feather Loop, Winter Garden, FL 34787
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  /51

  Est $406,934 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  12032 Holystone St, Oakland, FL 34787

  12032 Holystone St, Oakland, FL 34787
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  /2

  $523,905 Sold Jan 27, 2025

  12494 Westhaven Oak Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft
  • Built 2024

  Last Sold Summary

  • $275/SF

  Current Estimated Value $531,933

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  12494 Westhaven Oak Dr, Oakland, FL 34787
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  /38

  Est $383,685 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  2212 Gopher Tortoise Terrace, Oakland, FL 34760

  2212 Gopher Tortoise Terrace, Oakland, FL 34760
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  /2

  $785,000 Sold Oct 24, 2025

  1212 Civitas Way, Winter Garden, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,260 Sq Ft
  • Built 2022

  Last Sold Summary

  • 10% Below List Price
  • $347/SF
  • 128 Days On Market

  Last Listing Agent Kathie Glass BHHS FLORIDA REALTY

  1212 Civitas Way, Winter Garden, FL 34787
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  /42

  Est $785,604 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,561 Sq Ft

  1826 Western Trailway Dr, Oakland, FL 34787

  1826 Western Trailway Dr, Oakland, FL 34787
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  /2

  $4,383,239 Sold Dec 15, 2025

  548 Walker St, Oakland, FL 34760

  • 5 Beds
  • 8 Baths
  • 6,203 Sq Ft
  • Built 2026

  Last Sold Summary

  • $707/SF
  • 0 Days On Market

  Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

  548 Walker St, Oakland, FL 34760
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  /2

  Est $465,390 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft

  11337 Great Rock St, Oakland, FL 34787

  11337 Great Rock St, Oakland, FL 34787
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  /2

  $925,000 Sold Oct 15, 2025

  3179 Sailing Pier Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2023

  Last Sold Summary

  • 7% Below List Price
  • $217/SF
  • 70 Days On Market

  Last Listing Agent Vivian Saavedra LPT REALTY, LLC

  3179 Sailing Pier Ave, Oakland, FL 34787
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  /2

  Est $632,792 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  13121 Tollcross Way, Oakland, FL 34787

  13121 Tollcross Way, Oakland, FL 34787
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  /2

  $849,628 Sold Mar 31, 2025

  16193 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2025

  Last Sold Summary

  • $299/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  16193 Honey Harvest St, Oakland, FL 34787
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  /57

  Est $873,697 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,237 Sq Ft

  15104 Heron Hideaway Cir, Oakland, FL 34787

  15104 Heron Hideaway Cir, Oakland, FL 34787
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  /2

  $616,150 Sold Nov 01, 2025

  5826 Fabry St, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 2,563 Sq Ft
  • Built 2025

  Last Sold Summary

  • $240/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  5826 Fabry St, Oakland, FL 34787
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  /2

  Est $2,439,075 Not Listed For Sale

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

  15522 Shorebird Ln, Oakland, FL 34787

  15522 Shorebird Ln, Oakland, FL 34787
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  /2

  $410,000 Sold Jun 04, 2025

  0 N Daniels St, Oakland, FL 34760

  • Land
  • 0.31 Acre
  • $1,322,581 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 9 Days On Market

  Last Listing Agent Roberta Melo SELECTA REALTY LLC

  0 N Daniels St, Oakland, FL 34760
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  /2

  Est $537,472 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,897 Sq Ft

  14347 Braemar St, Oakland, FL 34787

  14347 Braemar St, Oakland, FL 34787
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  /2

  $445,000 Sold Mar 18, 2025

  13311 Pontoon Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2023

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 12 Days On Market

  Current Estimated Value $446,298

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  13311 Pontoon Rd, Oakland, FL 34787

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