Oakland, FL Homes

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  /2

  $591,290

  Sold Jan 09, 2026

  2823 Haze Rd, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 2,201 Sq Ft
  • Built 2025

  Last Sold Summary

  • $269/SF
  • 0 Days On Market

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

  2823 Haze Rd, Oakland, FL 34787
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  /48

  Est $778,481

  Not Listed For Sale

  5121 Breezy Acres St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,724 Sq Ft
  • Built 2021

  5121 Breezy Acres St, Oakland, FL 34787

  Last Sold Summary

  • 3 Days On Market
• 

  

  

  /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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  /2

  $819,006

  Sold Sep 17, 2025

  16125 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2024

  Last Sold Summary

  • $289/SF
  • 0 Days On Market

  Current Estimated Value $818,000

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

  16125 Honey Harvest St, Oakland, FL 34787
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  /55

  Est $463,649

  Not Listed For Sale

  16946 Oakboro St, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft
  • Built 2020

  16946 Oakboro St, Oakland, FL 34787

  Last Sold Summary

  • 10 Days On Market
• 

  

  /49

  $799,900

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  13343 Sunny Retreat Ln, Oakland, FL 34787

  The neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

  John Hart ENGEL & VOLKERS CLERMONT

  13343 Sunny Retreat Ln, 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 $1,032,507

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  936 Allendale Ln, Winter Garden, FL 34787
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  /2

  Est $481,633

  Not Listed For Sale

  14122 Frasier St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 2024

  14122 Frasier St, Oakland, FL 34787

  Last Sold Summary
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  /56

  $629,999

  New Construction $119K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  38 S Pollard St, Oakland, FL 34760

  Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current

  Cassia Barros MS LAND & BUILDING LLC

  38 S Pollard St, Oakland, FL 34760
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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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  /2

  Est $474,232

  Not Listed For Sale

  11361 Great Rock St, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 2024

  11361 Great Rock St, Oakland, FL 34787

  Last Sold Summary
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  /3

  $1,032,000

  New Construction $23K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 3,894 Sq Ft

  12904 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026 The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

  Dayene Grubert ORLANDO TBI REALTY LLC

  12904 Westhaven Oak Dr, 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 $900,902

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  9068 Sonoma Coast Dr, Oakland, FL 34787
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  /2

  Est $752,369

  Not Listed For Sale

  14211 Lanyard Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,038 Sq Ft
  • Built 2024

  14211 Lanyard Way, Oakland, FL 34787

  Last Sold Summary

  • 65 Days On Market
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  /12

  $465,490

  New Construction $9K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft

  6056 Meditation Dr, Oakland, FL 34787

  Under Construction. The Solana II has the “WOW” factor you have been searching for. There is a beautiful designer kitchen, that features an abundance of counter space that is sure to appeal to your inner-chef. The kitchen looks out to the combination dining and family rooms for the perfect open sight lines. There are a total of 3 bedrooms and 2 and a half bathrooms. The bedrooms are located on

  Ben Goldstein LENNAR REALTY

  6056 Meditation Dr, Oakland, 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 $796,306

  Last Listing Agent Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  101 W Oakland Ave, Oakland, FL 34760
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  /2

  Est $742,853

  Not Listed For Sale

  14199 Lanyard Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,065 Sq Ft
  • Built 2024

  14199 Lanyard Way, Oakland, FL 34787

  Last Sold Summary

  • 185 Days On Market
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  /31

  $550,000

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

  14123 Frasier St, Oakland, FL 34787

  SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon

  Yornelly Sanchez Manrique LEVO REAL ESTATE LLC

  14123 Frasier St, Oakland, FL 34787
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  /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

  Current Estimated Value $465,000

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

  17705 Japonica Bloom Dr, Oakland, FL 34787
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  /69

  Est $741,944

  Not Listed For Sale

  11168 Robert Frost Dr, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,332 Sq Ft
  • Built 2021

  11168 Robert Frost Dr, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  /2

  $858,120

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 3,498 Sq Ft

  15142 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15142 Tea Tree Dr, Oakland, FL 34787
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  /2

  $1,790,000

  Sold Apr 27, 2026

  15198 E Oakland Ave, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 3,616 Sq Ft
  • Built 2023

  Last Sold Summary

  • 3% Below List Price
  • $495/SF
  • 9 Days On Market

  Current Estimated Value $1,797,431

  Last Listing Agent Melody Niederst IAD REAL ESTATE

  15198 E Oakland Ave, Winter Garden, FL 34787
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  /2

  Est $748,054

  Not Listed For Sale

  16225 Silver Brook Way, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft
  • Built 2024

  16225 Silver Brook Way, Oakland, FL 34787

  Last Sold Summary

  • 28 Days On Market
• 

  

  /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
• 

  /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 $690,359

  Last Listing Agent Ashley Pun DENIZ REALTY PARTNERS LLC

  570 Johns Landing Way, Oakland, FL 34787
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  /2

  Est $567,639

  Not Listed For Sale

  15129 Summer Harvest St, Oakland, FL 34787

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

  15129 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary
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  /68

  $1,399,990

  $25K PRICE INCREASE

  • 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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  /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 $801,583

  Last Listing Agent Gabriella Sadler SERHANT

  8972 Sonoma Coast Dr, Oakland, FL 34787
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  /2

  Est $630,161

  Not Listed For Sale

  15022 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,789 Sq Ft
  • Built 2024

  15022 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 12 Days On Market
• 

  

  /57

  $535,000

  Open Sat 11AM - 2PM

  • 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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  /2

  $415,000

  Sold Jun 23, 2026

  2222 Gopher Tortoise Terrace, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft
  • Built 2020

  Last Sold Summary

  • $229/SF
  • 71 Days On Market

  Current Estimated Value $411,932

  Last Listing Agent Wagner ferreira LPT REALTY, LLC

  2222 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  /2

  Est $593,239

  Not Listed For Sale

  15141 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,450 Sq Ft
  • Built 2024

  15141 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary
• 

  

  /20

  $294,990

  New Construction Pending

  • 2 Beds
  • 2 Baths
  • 1,421 Sq Ft

  3148 Repose Dr, Oakland, FL 34787

  This new single-story Napa villa is designed to maximize space while delivering low-maintenance living. Upon entry are two comfortable bedrooms flanking the foyer, one of which is the owner’s suite with a private bathroom and walk-in closet. Further down the hallway is the open-concept kitchen, a lovely dining area and a sunny living room with lanai access. Tucked to the side is a flex space for

  Ben Goldstein LENNAR REALTY

  3148 Repose Dr, Oakland, FL 34787
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  /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 $507,891

  Last Listing Agent Claire Jesso SERHANT

  16695 Herongate Dr, Oakland, FL 34787
• 

  /2

  Est $804,202

  Not Listed For Sale

  1215 Wilder Oaks Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2024

  1215 Wilder Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • 21 Days On Market
• 

  

  /50

  $774,900

  $25K PRICE DROP

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

  3367 Hanging Tide St, Oakland, FL 34787

  Stunning, meticulously maintained home in the sought-after Lakeview Preserve community of Winter Garden! This spacious residence is situated on a premium lot close to cul-de-sac limiting through traffic and offers a thoughtfully designed layout ideal for both everyday living and entertainment. A grand two-story foyer welcomes you inside and features a Maitland-Smith designer chandelier with

  Jeffrey Petch GECKO REALTY, INC

  3367 Hanging Tide St, Oakland, FL 34787
• 

  /2

  $850,000

  Sold May 27, 2026

  8 Winters Landing Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $298/SF
  • 44 Days On Market

  Current Estimated Value $868,097

  Last Listing Agent Danielle Norvell REGENCY REAL ESTATE LLC

  8 Winters Landing Dr, Oakland, FL 34787
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  /2

  Est $514,705

  Not Listed For Sale

  14114 Frasier St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,985 Sq Ft
  • Built 2024

  14114 Frasier St, Oakland, FL 34787

  Last Sold Summary

  • 105 Days On Market
• 

  

  /17

  $401,990

  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
• 

  /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 $531,112

  Last Listing Agent Tim Boon CREEGAN GROUP

  2090 Standing Rock Cir, Oakland, FL 34787

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