Oakland, FL Homes

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  /51

  Est $394,287 Not Listed For Sale

  12032 Holystone St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2022

  12032 Holystone St, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $271/SF
  • 39 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Marcelo Lopes Santana FLORIDA CONNEXION PROPERTIES
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  /55

  $499,990 Pending

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft

  17621 Japonica Bloom Dr, Oakland, FL 34787

  Enjoy comfortable and convenient living in Northlake at Ovation, where this thoughtfully designed home features a private primary suite with a spacious walk-in closet, creating a peaceful retreat at the end of the day. Ideally located, the community offers easy access to everyday conveniences and popular destinations—just 37 minutes from Orlando International Airport, 20 minutes from world-famous

  Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  17621 Japonica Bloom Dr, Oakland, FL 34787
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  /2

  $1,025,000 Sold Jul 21, 2025

  936 Allendale Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $378/SF
  • 77 Days On Market

  Current Estimated Value $1,008,836

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  936 Allendale Ln, Winter Garden, FL 34787
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  /38

  Est $375,075 Not Listed For Sale

  2212 Gopher Tortoise Terrace, Oakland, FL 34760

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2020

  2212 Gopher Tortoise Terrace, Oakland, FL 34760

  Last Sold Summary

  • 9% Below List Price
  • $253/SF
  • 2 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Cristina Ireland THE SIMON SIMAAN GROUP
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  /2

  $852,342 Pending

  • 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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  /2

  $394,990 Sold Jul 08, 2025

  5860 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $244/SF
  • 20 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  5860 Meditation Dr, Oakland, FL 34787
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  /42

  Est $774,119 Not Listed For Sale

  1826 Western Trailway Dr, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,561 Sq Ft
  • Built 2021

  1826 Western Trailway Dr, Oakland, FL 34787

  Last Sold Summary

  • $218/SF
  • 5 Days On Market

  Last Sold Price $776,000

  Last Listing Agent Rick Martin COLDWELL BANKER REALTY
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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

  $575,000 Sold May 16, 2025

  11015 Bostwick Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $261/SF
  • 4 Days On Market

  Current Estimated Value $571,355

  Last Listing Agent Marcos Del Nero LA ROSA REALTY KISSIMMEE

  11015 Bostwick Aly, Oakland, FL 34787
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  /2

  Est $443,979 Not Listed For Sale

  11337 Great Rock St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft
  • Built 2023

  11337 Great Rock St, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $268/SF

  Last Sold Price $461,000

  Last Listing Agent Denise Batista ALLUX REAL ESTATE LLC
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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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  /2

  $886,000 Sold Jul 31, 2025

  9068 Sonoma Coast Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,267 Sq Ft
  • Built 2020

  Last Sold Summary

  • 6% Below List Price
  • $271/SF
  • 11 Days On Market

  Current Estimated Value $880,510

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  9068 Sonoma Coast Dr, Oakland, FL 34787
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  /2

  Est $1,110,287 Not Listed For Sale

  111 Millholland St, Oakland, FL 34760

  • 4 Beds
  • 3 Baths
  • 3,333 Sq Ft
  • Built 2001

  111 Millholland St, Oakland, FL 34760

  Last Sold Summary

  • 1% Above List Price
  • $330/SF
  • 7 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY
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  /53

  $875,000

  • 4 Beds
  • 4 Baths
  • 2,831 Sq Ft

  931 Kylee Aly, Winter Garden, FL 34787

  There is a specific frequency to life in Oakland Park that exists nowhere else in Central Florida. It is a rare, rhythmic harmony between the nostalgia of Old Florida and the crisp, clean lines of modern luxury. As you cross into the community, the atmosphere shifts. The air feels lighter, filtered through the canopy of ancient oaks and manicured greenery of a village designed for connection.

  Barbara Vance PA PREMIER SOTHEBYS INT'L REALTY

  931 Kylee Aly, Winter Garden, FL 34787
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  /20

  $705,000 Sold Mar 31, 2025

  13714 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $339/SF
  • 65 Days On Market

  Current Estimated Value $676,963

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13714 Fresh Ivy St, Oakland, FL 34787
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  /2

  Est $629,058 Not Listed For Sale

  13121 Tollcross Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft
  • Built 2024

  13121 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 9% Below List Price
  • $335/SF
  • 37 Days On Market

  Last Sold Price $689,995

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
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  /14

  $440,000

  • Land
  • 0.26 Acre
  • $1,692,308 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

  $937,239 Sold Mar 26, 2025

  1179 Wilder Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,773 Sq Ft
  • Built 2025

  Last Sold Summary

  • $338/SF

  Current Estimated Value $939,507

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

  1179 Wilder Oaks Way, Oakland, FL 34787
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  /57

  Est $831,378 Not Listed For Sale

  15104 Heron Hideaway Cir, Oakland, FL 34787

  • 6 Beds
  • 4 Baths
  • 4,237 Sq Ft
  • Built 2012

  15104 Heron Hideaway Cir, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $202/SF
  • 2 Days On Market

  Last Sold Price $857,500

  Last Listing Agent Denise Gregorie CLOCK TOWER REALTY
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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

  $795,000 Sold Jul 18, 2025

  101 W Oakland Ave, Oakland, FL 34760

  • 4 Beds
  • 3 Baths
  • 2,505 Sq Ft
  • Built 2014

  Last Sold Summary

  • 1% Below List Price
  • $317/SF
  • 25 Days On Market

  Current Estimated Value $791,623

  Last Listing Agent Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  101 W Oakland Ave, Oakland, FL 34760
• 

  /2

  Est $2,367,294 Not Listed For Sale

  15522 Shorebird Ln, Oakland, FL 34787

  • 7 Beds
  • 6.5 Baths
  • 6,400 Sq Ft
  • Built 2020

  15522 Shorebird Ln, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $380/SF
  • 12 Days On Market

  Last Sold Price $2,430,000

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY
• 

  /2

  $459,006 Sold Nov 25, 2025

  17705 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 2025

  Last Sold Summary

  • $266/SF

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

  17705 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Est $512,888 Not Listed For Sale

  14347 Braemar St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 1,897 Sq Ft
  • Built 2024

  14347 Braemar St, Oakland, FL 34787

  Last Sold Summary

  Last Listing Agent Linda O'Grady PREMIER SOTHEBYS INT'L REALTY
• 

  /2

  $692,000 Sold Mar 13, 2026

  570 Johns Landing Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 4,030 Sq Ft
  • Built 2003

  Last Sold Summary

  • $172/SF
  • 6 Days On Market

  Current Estimated Value $685,666

  Last Listing Agent Ashley Pun DENIZ REALTY PARTNERS LLC

  570 Johns Landing Way, Oakland, FL 34787
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  /27

  Est $680,008 Not Listed For Sale

  16265 Misty Hills Ave, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft
  • Built 2020

  16265 Misty Hills Ave, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $317/SF
  • 23 Days On Market

  Last Sold Price $720,000

  Last Listing Agent xTroy Nowak MANGROVE BAY REALTY LLC
• 

  /2

  $775,000 Sold Sep 29, 2025

  8972 Sonoma Coast Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft
  • Built 2021

  Last Sold Summary

  • $281/SF
  • 27 Days On Market

  Current Estimated Value $777,828

  Last Listing Agent Gabriella Sadler SERHANT

  8972 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  Est $637,681 Not Listed For Sale

  14084 Lochend Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,109 Sq Ft
  • Built 2024

  14084 Lochend Way, Oakland, FL 34787

  Last Sold Summary

  • 10% Below List Price
  • $337/SF
  • 78 Days On Market

  Last Sold Price $710,000

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  /2

  $500,000 Sold Dec 03, 2025

  16695 Herongate Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $297/SF
  • 3 Days On Market

  Current Estimated Value $498,532

  Last Listing Agent Claire Jesso SERHANT

  16695 Herongate Dr, Oakland, FL 34787
• 

  

  /4

  Est $308,247 Not Listed For Sale

  411 W Hull Ave, Oakland, FL 34760

  • 3 Beds
  • 1.5 Baths
  • 1,029 Sq Ft
  • Built 1999

  411 W Hull Ave, Oakland, FL 34760

  Last Sold Summary

  • 21% Above List Price
  • $248/SF
  • 17 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
• 

  /2

  $1,284,682 Sold May 08, 2025

  1245 Wilder Oaks Way, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,852 Sq Ft
  • Built 2025

  Last Sold Summary

  • $334/SF

  Current Estimated Value $1,179,166

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

  1245 Wilder Oaks Way, Oakland, FL 34787
• 

  

  /19

  Est $452,956 Not Listed For Sale

  15817 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,833 Sq Ft
  • Built 2024

  15817 Tollington Aly, Oakland, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 16 Days On Market

  Last Sold Price $475,800

  Last Listing Agent Eusebio Salas LA ROSA REALTY LLC
• 

  /2

  $1,057,482 Sold Mar 27, 2025

  1216 Oak Fort Ln, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • $347/SF

  Current Estimated Value $1,016,507

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

  1216 Oak Fort Ln, Oakland, FL 34787
• 

  /2

  Est $924,208 Not Listed For Sale

  14054 Lochend Way, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,094 Sq Ft
  • Built 2024

  14054 Lochend Way, Oakland, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 48 Days On Market

  Last Sold Price $974,995

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  /2

  $537,000 Sold Jan 29, 2026

  2090 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • Built 2019

  Last Sold Summary

  • 17% Below List Price
  • $267/SF
  • 147 Days On Market

  Current Estimated Value $565,332

  Last Listing Agent Tim Boon CREEGAN GROUP

  2090 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  Est $779,072 Not Listed For Sale

  14090 Lochend Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,256 Sq Ft
  • Built 2024

  14090 Lochend Way, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 268 Days On Market

  Last Sold Price $790,000

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  /2

  $1,575,000 Sold Jan 23, 2026

  1096 Riverway Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 4,171 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $378/SF
  • 32 Days On Market

  Current Estimated Value $1,596,274

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  1096 Riverway Dr, Oakland, FL 34787
• 

  

  /5

  Est $522,161 Not Listed For Sale

  15105 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 2023

  15105 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $274/SF
  • 30 Days On Market

  Last Sold Price $546,335

  Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC
• 

  /2

  $450,000 Sold Jan 25, 2026

  510 N Nixon St, Oakland, FL 34760

  • Land
  • 0.45 Acre
  • $1,000,000 per Acre

  Last Sold Summary

  • 90% Below List Price
  • 0 Days On Market

  Current Estimated Value $448,965

  Last Listing Agent Chocky Burks CORCORAN PREMIER REALTY

  510 N Nixon St, Oakland, FL 34760
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  /17

  Est $573,978 Not Listed For Sale

  15113 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft
  • Built 2024

  15113 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 5 Days On Market

  Last Sold Price $602,480

  Last Listing Agent Ayrys Torres TALENT REALTY SOLUTIONS

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