Recently Sold Oakland, FL Homes

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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

  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 $868,350

  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

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

  1428 Scarlet Oak Loop, Winter Garden, FL 34787
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  $340,000 Sold Feb 28, 2025

  1468 Scarlet Oak Loop, Winter Garden, FL 34787

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

  Last Sold Summary

  • 6% Below List Price
  • $214/SF
  • 81 Days On Market

  Current Estimated Value $348,308

  Last Listing Agent Sandy Jones CLOCK TOWER REALTY

  1468 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 $489,812

  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 $360,829

  Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

  1356 Scarlet Oak Loop, Winter Garden, FL 34787
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  $339,500 Sold Feb 28, 2025

  1342 Scarlet Oak Loop, Winter Garden, FL 34787

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

  Last Sold Summary

  • 4% Below List Price
  • $213/SF
  • 31 Days On Market

  Current Estimated Value $344,440

  Last Listing Agent Mark Anthony Buot ROI AVE LLC

  1342 Scarlet Oak Loop, 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

  Last Listing Agent Lisa Bennett WINDSOR REALTY GROUP INC

  1386 Scarlet Oak Loop, Winter Garden, FL 34787
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  $790,000 Sold Mar 27, 2025

  934 Mckinnon Square, Winter Garden, FL 34787

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

  Last Sold Summary

  • 4% Below List Price
  • $312/SF
  • 104 Days On Market

  Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  934 Mckinnon Square, 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 $564,584

  Last Listing Agent David Tanner JOSHUA UNLIMITED INC

  38 Live Oak Rd, Winter Garden, FL 34787

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