Oakland, FL Homes

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  $538,800 Sold Apr 10, 2025

  12064 Encore at Ovation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft
  • Built 2021

  Last Sold Summary

  • $232/SF
  • 2 Days On Market

  Current Estimated Value $536,650

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  12064 Encore at Ovation Way, Oakland, FL 34787
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  Not Listed For Sale

  0 Orange Ave, Winter Garden, FL 34787

  0 Orange Ave, Winter Garden, FL 34787
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  /2

  $796,191 Sold Sep 29, 2025

  16140 Point Rock Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,327 Sq Ft
  • Built 2025

  Last Sold Summary

  • $239/SF

  Current Estimated Value $796,000

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

  16140 Point Rock Dr, Oakland, FL 34787
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  /2

  Est $400,062 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  13364 Pontoon Rd, Oakland, FL 34787

  13364 Pontoon Rd, Oakland, FL 34787
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  /2

  $399,990 Sold Jun 24, 2025

  5884 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2025

  Last Sold Summary

  • $228/SF
  • 7 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  5884 Meditation Dr, Oakland, FL 34787
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  /30

  Est $481,054 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  2157 White Feather Loop, Winter Garden, FL 34787

  2157 White Feather Loop, Winter Garden, FL 34787
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  $795,000 Sold Nov 05, 2025

  9406 Bolero Rd, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,299 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $241/SF
  • 3 Days On Market

  Last Listing Agent JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

  9406 Bolero Rd, Oakland, FL 34787
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  /23

  Est $382,227 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,503 Sq Ft

  2219 Gopher Tortoise Terrace, Oakland, FL 34760

  2219 Gopher Tortoise Terrace, Oakland, FL 34760
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  $800,000 Sold Jul 10, 2025

  525 N Pollard St, Winter Garden, FL 34787

  • Land
  • 1.03 Acres
  • $776,699 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Blaine Dooley REGENCY REAL ESTATE LLC

  525 N Pollard St, Winter Garden, FL 34787
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  /30

  Est $419,690 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  6159 Juneberry Way, Oakland, FL 34787

  6159 Juneberry Way, Oakland, FL 34787
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  /2

  $695,000 Sold Mar 13, 2025

  13636 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $358/SF
  • 3 Days On Market

  Current Estimated Value $690,951

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

  13636 Fresh Ivy St, Oakland, FL 34787
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  /54

  Est $610,907 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft

  11078 Robert Frost Dr, Oakland, FL 34787

  11078 Robert Frost Dr, Oakland, FL 34787
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  $650,000 Sold May 16, 2025

  15086 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,934 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $336/SF
  • 140 Days On Market

  Current Estimated Value $638,230

  Last Listing Agent Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

  15086 Summer Harvest St, Oakland, FL 34787
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  /70

  Est $889,961 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,414 Sq Ft

  613 Cheekwood Aly, Winter Garden, FL 34787

  613 Cheekwood Aly, Winter Garden, FL 34787
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  /23

  $868,686 Sold Aug 15, 2025

  16158 Point Rock Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,327 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $261/SF
  • 10 Days On Market

  Current Estimated Value $819,000

  D.R. Horton Waterleigh

  16158 Point Rock Dr, Oakland, FL 34787
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  /2

  Est $443,444 Not Listed For Sale

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

  13958 Title Way, Winter Garden, FL 34787

  13958 Title Way, Winter Garden, FL 34787
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  $715,000 Sold Apr 28, 2025

  932 Kylee Aly, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $369/SF
  • 6 Days On Market

  Current Estimated Value $700,384

  Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

  932 Kylee Aly, Winter Garden, FL 34787
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  /65

  Est $363,743 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  1502 Sweet Apple St, Oakland, FL 34787

  1502 Sweet Apple St, Oakland, FL 34787
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  $1,000,000 Sold Jul 15, 2025

  1126 Riverway Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft
  • Built 2025

  Last Sold Summary

  • $369/SF

  Current Estimated Value $986,100

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

  1126 Riverway Dr, Oakland, FL 34787
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  /4

  Est $325,581 Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /2

  $624,000 Sold Mar 20, 2025

  15116 Dragon Fly Ct, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,449 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $255/SF
  • 133 Days On Market

  Current Estimated Value $616,488

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  15116 Dragon Fly Ct, Oakland, FL 34787
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  /43

  Est $673,902 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,117 Sq Ft

  9418 Bolero Rd, Oakland, FL 34787

  9418 Bolero Rd, Oakland, FL 34787
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  $915,000 Sold Aug 15, 2025

  908 Tilden Oaks Trail, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,683 Sq Ft
  • Built 2022

  Last Sold Summary

  • 6% Below List Price
  • $341/SF
  • 94 Days On Market

  Current Estimated Value $921,560

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC

  908 Tilden Oaks Trail, Winter Garden, FL 34787
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  /2

  Est $435,730 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,691 Sq Ft

  15739 Tollington Aly, Oakland, FL 34787

  15739 Tollington Aly, Oakland, FL 34787
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  $375,000 Sold Sep 25, 2025

  1225 Water Maple Dr, Oakland, FL 34760

  • Land
  • 0.25 Acre
  • $1,500,000 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 82 Days On Market

  Last Listing Agent Darby Shields HAVEN PROPERTY GROUP LLC

  1225 Water Maple Dr, Oakland, FL 34760
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  /36

  Est $1,022,738 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 4,674 Sq Ft

  3175 Sailing Pier Ave, Oakland, FL 34787

  3175 Sailing Pier Ave, Oakland, FL 34787
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  /35

  $645,000 Sold Jun 18, 2025

  632 Strihal Loop, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,311 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Above List Price
  • $279/SF
  • 13 Days On Market

  Current Estimated Value $637,818

  Last Listing Agent Millie Gwin Coldwell Banker Coast Realty

  632 Strihal Loop, Oakland, FL 34787
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  /2

  Est $438,584 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  13304 Pontoon Rd, Oakland, FL 34787

  13304 Pontoon Rd, Oakland, FL 34787
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  $419,990 Sold May 28, 2025

  2895 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft
  • Built 2025

  Last Sold Summary

  • $255/SF
  • 0 Days On Market

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

  2895 Transformation Way, Oakland, FL 34787
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  /48

  Est $914,510 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,265 Sq Ft

  15311 Arcadia Bluff Loop, Oakland, FL 34787

  15311 Arcadia Bluff Loop, Oakland, FL 34787
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  $950,000 Sold Sep 25, 2025

  544 Walker St, Oakland, FL 34760

  • Land
  • 1.23 Acres
  • $772,358 per Acre

  Last Sold Summary

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

  544 Walker St, Oakland, FL 34760
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  /30

  Est $1,873,443 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,340 Sq Ft

  1091 Eaglecrest Dr, Oakland, FL 34787

  1091 Eaglecrest Dr, Oakland, FL 34787
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  $569,830 Sold Mar 28, 2025

  12736 Lavender Bloom Aly Unit 170, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $259/SF
  • 235 Days On Market

  Last Listing Agent Gretta Akellino K HOVNANIAN FLORIDA REALTY

  12736 Lavender Bloom Aly Unit 170, Oakland, FL 34787
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  /55

  Est $515,260 Not Listed For Sale

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

  15735 Fountain Springs Rd, Oakland, FL 34787

  15735 Fountain Springs Rd, Oakland, FL 34787
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  $750,000 Sold Sep 18, 2025

  8935 Sonoma Coast Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,181 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $344/SF
  • 56 Days On Market

  Current Estimated Value $744,044

  Last Listing Agent Bruno Dasilva, LLC MS LAND & BUILDING LLC

  8935 Sonoma Coast Dr, Oakland, FL 34787
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  /36

  Est $380,880 Not Listed For Sale

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

  1412 Planted Pine St, Oakland, FL 34760

  1412 Planted Pine St, Oakland, FL 34760
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  $794,990 Sold Sep 16, 2025

  16195 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $277/SF
  • 7 Days On Market

  Current Estimated Value $751,000

  D.R. Horton Waterleigh

  16195 Point Rock Dr, Oakland, FL 34787
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  /50

  Est $885,337 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,178 Sq Ft

  15326 Heron Hideaway Cir, Oakland, FL 34787

  15326 Heron Hideaway Cir, Oakland, FL 34787
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  $578,000 Sold Feb 06, 2026

  1808 Western Trailway Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,857 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $311/SF
  • 45 Days On Market

  Last Listing Agent Daniel McGrath UNLOCK REALTY GROUP INC

  1808 Western Trailway Dr, Oakland, FL 34787
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  /2

  Est $452,206 Not Listed For Sale

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

  15769 Tollington Aly, Oakland, FL 34787

  15769 Tollington Aly, Oakland, FL 34787

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