Recently Sold Oakland, FL Homes

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  $615,000 Sold Apr 09, 2025

  644 Strihal Loop, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,490 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $247/SF
  • 25 Days On Market

  Current Estimated Value $608,728

  Last Listing Agent Julie Arnold REAL BROKER, LLC

  644 Strihal Loop, Oakland, FL 34787
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  $875,000 Sold Jun 30, 2025

  5319 Citrus Leaf Blvd, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,871 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $226/SF
  • 47 Days On Market

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

  5319 Citrus Leaf Blvd, Oakland, FL 34787
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  $780,000 Sold May 06, 2025

  16685 Oakboro St, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,227 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $242/SF
  • 72 Days On Market

  Current Estimated Value $785,652

  Last Listing Agent Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

  16685 Oakboro St, Oakland, FL 34787
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  $415,000 Sold Mar 07, 2026

  13902 Title Way, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft
  • Built 2023

  Last Sold Summary

  • $254/SF
  • 7 Days On Market

  Last Listing Agent Stacy Wayne FLORIDA HOME TEAM REALTY LLC

  13902 Title Way, Winter Garden, FL 34787
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  $1,490,000 Sold Mar 05, 2026

  1127 Celadon St, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,730 Sq Ft
  • Built 2023

  Last Sold Summary

  • $546/SF
  • 6 Days On Market

  Current Estimated Value $1,380,116

  Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1127 Celadon St, Winter Garden, FL 34787
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  $795,500 Sold Jan 06, 2026

  934 Mckinnon Square, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,536 Sq Ft
  • Built 2022

  Last Sold Summary

  • $314/SF
  • 5 Days On Market

  Current Estimated Value $787,370

  Last Listing Agent Shannon Christian EXP REALTY LLC

  934 Mckinnon Square, Winter Garden, FL 34787
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  $870,000 Sold Jun 18, 2025

  1024 Prosperity Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $385/SF
  • 62 Days On Market

  Current Estimated Value $857,341

  Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1024 Prosperity Dr, Winter Garden, FL 34787
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  $353,000 Sold Feb 03, 2026

  1428 Scarlet Oak Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 2013

  Last Sold Summary

  • 5% Below List Price
  • $222/SF
  • 55 Days On Market

  Current Estimated Value $351,478

  Last Listing Agent Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

  1428 Scarlet Oak Loop, Winter Garden, FL 34787
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  $475,000 Sold May 22, 2025

  16247 Lake Johns Cir, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,071 Sq Ft
  • Built 1962

  Last Sold Summary

  • 10% Below List Price
  • $229/SF
  • 100 Days On Market

  Current Estimated Value $483,830

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  16247 Lake Johns Cir, Winter Garden, FL 34787
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  $360,000 Sold Jul 31, 2025

  1356 Scarlet Oak Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,701 Sq Ft
  • Built 2013

  Last Sold Summary

  • $212/SF
  • 12 Days On Market

  Current Estimated Value $360,743

  Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

  1356 Scarlet Oak Loop, Winter Garden, FL 34787
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  $1,000,000 Sold Mar 23, 2026

  1045 Colleton Aly, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,837 Sq Ft
  • Built 2018

  Last Sold Summary

  • $352/SF
  • 1 Day On Market

  Current Estimated Value $961,429

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC

  1045 Colleton Aly, Winter Garden, FL 34787
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  $352,000 Sold Dec 15, 2025

  1386 Scarlet Oak Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • Built 2013

  Last Sold Summary

  • 5% Below List Price
  • $215/SF
  • 7 Days On Market

  Current Estimated Value $355,680

  Last Listing Agent Lisa Bennett WINDSOR REALTY GROUP INC

  1386 Scarlet Oak Loop, Winter Garden, FL 34787
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  $347,000 Sold Nov 24, 2025

  1352 Scarlet Oak Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,589 Sq Ft
  • Built 2013

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 4 Days On Market

  Current Estimated Value $351,214

  Last Listing Agent Stacy Coburn EXP REALTY LLC

  1352 Scarlet Oak Loop, Winter Garden, FL 34787
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  $925,700 Sold Mar 10, 2026

  1024 Kershaw Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,461 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $376/SF
  • 4 Days On Market

  Current Estimated Value $941,865

  Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY

  1024 Kershaw Dr, Winter Garden, FL 34787
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  $560,000 Sold Sep 08, 2025

  38 Live Oak Rd, Winter Garden, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1969

  Last Sold Summary

  • 3% Below List Price
  • $341/SF
  • 9 Days On Market

  Current Estimated Value $565,730

  Last Listing Agent David Tanner JOSHUA UNLIMITED INC

  38 Live Oak Rd, Winter Garden, FL 34787

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