Recently Sold Oakland, FL Homes

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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 $1,469,930

  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 $791,876

  Last Listing Agent Shannon Christian EXP REALTY LLC

  934 Mckinnon Square, 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 $351,956

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

  1428 Scarlet Oak Loop, Winter Garden, FL 34787
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  $1,075,000

  Sold Apr 30, 2026

  883 Tilden Oaks Trail, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,811 Sq Ft
  • Built 2025

  Last Sold Summary

  • $382/SF
  • 0 Days On Market

  Current Estimated Value $1,061,784

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC

  883 Tilden Oaks Trail, Winter Garden, FL 34787
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  $1,295,000

  Sold Jun 30, 2026

  912 Landrum Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,834 Sq Ft
  • Built 2024

  Last Sold Summary

  • $457/SF
  • 5 Days On Market

  Current Estimated Value $1,260,908

  Last Listing Agent Lenee Magnuson DENIZ REALTY PARTNERS LLC

  912 Landrum Dr, 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 $998,993

  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 $358,906

  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 $354,136

  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 $924,827

  Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY

  1024 Kershaw Dr, Winter Garden, FL 34787
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  $1,140,000

  Sold Jul 10, 2026

  16217 Lake Johns Cir, Winter Garden, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,659 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $245/SF
  • 9 Days On Market

  Current Estimated Value $1,158,785

  Last Listing Agent Esdras Vasquez HOMEFIRST REAL ESTATE

  16217 Lake Johns Cir, 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 $567,911

  Last Listing Agent David Tanner JOSHUA UNLIMITED INC

  38 Live Oak Rd, Winter Garden, FL 34787

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