3,195

Oakland, FL Homes

Section Image Section Image
    • 2042 South Old Killarney St, Winter Garden, FL 34787
      2042 South Old Killarney St, Winter Garden, FL 34787
      2042 South Old Killarney St, Winter Garden, FL 34787
      /34

      Est $709,772 Not Listed For Sale

      2042 South Old Killarney St, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 3,314 Sq Ft
      • Built 2023
      2042 South Old Killarney St, Winter Garden, FL 34787

      Last Sold Summary

      • 2% Above List Price
      • $211/SF
      • 85 Days On Market

      Last Sold Price $697,990

      Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 513 N Pollard St, Winter Garden, FL 34787
    513 N Pollard St, Winter Garden, FL 34787
    /2

    $895,000 Sold Jan 02, 2026

    513 N Pollard St, Winter Garden, FL 34787

    • Land
    • 0.96 Acre
    • $932,292 per Acre

    Last Sold Summary

    • 161 Days On Market

    Last Listing Agent Heather Spirazza REGENCY REAL ESTATE LLC

    513 N Pollard St, Winter Garden, FL 34787
    • 2025 South Old Killarney St, Winter Garden, FL 34787
      2025 South Old Killarney St, Winter Garden, FL 34787
      2025 South Old Killarney St, Winter Garden, FL 34787
      /21

      Est $629,894 Not Listed For Sale

      2025 South Old Killarney St, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,787 Sq Ft
      • Built 2023
      2025 South Old Killarney St, Winter Garden, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $227/SF
      • 38 Days On Market

      Last Sold Price $633,990

      Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 1219 Foltz Loop, Oakland, FL 34787
    1219 Foltz Loop, Oakland, FL 34787
    /2

    $592,500 Sold Sep 05, 2025

    1219 Foltz Loop, Oakland, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft
    • Built 2022

    Last Sold Summary

    • 4% Below List Price
    • $319/SF
    • 27 Days On Market

    Current Estimated Value $580,351

    Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

    1219 Foltz Loop, Oakland, FL 34787
    • 2021 South Old Killarney St, Winter Garden, FL 34787
      2021 South Old Killarney St, Winter Garden, FL 34787
      2021 South Old Killarney St, Winter Garden, FL 34787
      /38

      Est $564,720 Not Listed For Sale

      2021 South Old Killarney St, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,108 Sq Ft
      • Built 2023
      2021 South Old Killarney St, Winter Garden, FL 34787

      Last Sold Summary

      • 2% Below List Price
      • $275/SF
      • 50 Days On Market

      Last Sold Price $578,990

      Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 17847 Adrift Rd, Oakland, FL 34787
    17847 Adrift Rd, Oakland, FL 34787
    /2

    $510,000 Sold Jun 13, 2025

    17847 Adrift Rd, Oakland, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,689 Sq Ft
    • Built 2023

    Last Sold Summary

    • 3% Below List Price
    • $302/SF
    • 12 Days On Market

    Current Estimated Value $496,238

    Last Listing Agent Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

    17847 Adrift Rd, Oakland, FL 34787
    • 15926 Moonlight Bay St, Oakland, FL 34787
      15926 Moonlight Bay St, Oakland, FL 34787
      15926 Moonlight Bay St, Oakland, FL 34787
      /55

      Est $506,862 Not Listed For Sale

      15926 Moonlight Bay St, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,029 Sq Ft
      • Built 2021
      15926 Moonlight Bay St, Oakland, FL 34787

      Last Sold Summary

      • 3% Below List Price
      • $256/SF
      • 83 Days On Market

      Last Sold Price $520,000

      Last Listing Agent Buyana Espad Espada CHARLES RUTENBERG REALTY ORLANDO

  • 312 W Hull Ave, Oakland, FL 34760
    312 W Hull Ave, Oakland, FL 34760
    /2

    $480,000 Sold Sep 19, 2025

    312 W Hull Ave, Oakland, FL 34760

    • 4 Beds
    • 2 Baths
    • 1,681 Sq Ft
    • Built 2006

    Last Sold Summary

    • 12% Below List Price
    • $286/SF
    • 74 Days On Market

    Current Estimated Value $469,385

    Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

    312 W Hull Ave, Oakland, FL 34760
    • 2037 South Old Killarney St, Winter Garden, FL 34787
      2037 South Old Killarney St, Winter Garden, FL 34787
      2037 South Old Killarney St, Winter Garden, FL 34787
      /34

      Est $691,370 Not Listed For Sale

      2037 South Old Killarney St, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 3,345 Sq Ft
      • Built 2023
      2037 South Old Killarney St, Winter Garden, FL 34787

      Last Sold Summary

      • 3% Above List Price
      • $201/SF
      • 96 Days On Market

      Last Sold Price $672,990

      Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 3090 Mindfullness Dr, Oakland, FL 34787
    3090 Mindfullness Dr, Oakland, FL 34787
    /2

    $524,540 Sold Oct 14, 2025

    3090 Mindfullness Dr, Oakland, FL 34787

    • 6 Beds
    • 3 Baths
    • 2,643 Sq Ft
    • Built 2025

    Last Sold Summary

    • $198/SF

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

    3090 Mindfullness Dr, Oakland, FL 34787
    • 5977 Painted Leaf Dr, Oakland, FL 34787
      5977 Painted Leaf Dr, Oakland, FL 34787
      5977 Painted Leaf Dr, Oakland, FL 34787
      /26

      Est $540,494 Not Listed For Sale

      5977 Painted Leaf Dr, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,128 Sq Ft
      • Built 2020
      5977 Painted Leaf Dr, Oakland, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $257/SF
      • 15 Days On Market

      Last Sold Price $546,100

      Last Listing Agent Melquisedec Martins NOVA REAL ESTATE SERVICES INC

  • 2690 Bobcat Chase Blvd, Oakland, FL 34787
    2690 Bobcat Chase Blvd, Oakland, FL 34787
    /2

    $450,000 Sold Jan 23, 2026

    2690 Bobcat Chase Blvd, Oakland, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $290/SF
    • 59 Days On Market

    Current Estimated Value $451,913

    Last Listing Agent Marnetta Arnett LPT REALTY, LLC

    2690 Bobcat Chase Blvd, Oakland, FL 34787
    • 7718 Bowery Dr, Oakland, FL 34787
      7718 Bowery Dr, Oakland, FL 34787
      7718 Bowery Dr, Oakland, FL 34787
      /28

      Est $441,573 Not Listed For Sale

      7718 Bowery Dr, Oakland, FL 34787

      • 3 Beds
      • 3 Baths
      • 2,032 Sq Ft
      • Built 2019
      7718 Bowery Dr, Oakland, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $220/SF
      • 36 Days On Market

      Last Sold Price $447,000

      Last Listing Agent Jennifer Carson Mark Spain Real Estate

  • 12064 Encore at Ovation Way, Oakland, FL 34787
    12064 Encore at Ovation Way, Oakland, FL 34787
    /2

    $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 $539,406

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

    12064 Encore at Ovation Way, Oakland, FL 34787
    • 2511 Sky Stone Ct, Winter Garden, FL 34787
      2511 Sky Stone Ct, Winter Garden, FL 34787
      2511 Sky Stone Ct, Winter Garden, FL 34787
      /57

      Est $644,516 Not Listed For Sale

      2511 Sky Stone Ct, Winter Garden, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 3,449 Sq Ft
      • Built 2018
      2511 Sky Stone Ct, Winter Garden, FL 34787

      Last Sold Summary

      • 10% Above List Price
      • $170/SF
      • 72 Days On Market

      Last Sold Price $585,500

      Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  • 16140 Point Rock Dr, Oakland, FL 34787
    16140 Point Rock Dr, Oakland, FL 34787
    /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 $794,000

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

    16140 Point Rock Dr, Oakland, FL 34787
    • 126 Hammock Preserve Loop, Oakland, FL 34787
      126 Hammock Preserve Loop, Oakland, FL 34787
      /2

      Est $970,622 Not Listed For Sale

      126 Hammock Preserve Loop, Oakland, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,811 Sq Ft
      • Built 2023
      126 Hammock Preserve Loop, Oakland, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $349/SF
      • 19 Days On Market

      Last Sold Price $980,000

      Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY

  • 5884 Meditation Dr, Oakland, FL 34787
    5884 Meditation Dr, Oakland, FL 34787
    /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
    • 2093 Standing Rock Cir, Winter Garden, FL 34787
      2093 Standing Rock Cir, Winter Garden, FL 34787
      2093 Standing Rock Cir, Winter Garden, FL 34787
      /21

      Est $455,725 Not Listed For Sale

      2093 Standing Rock Cir, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 2020
      2093 Standing Rock Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 3% Below List Price
      • $269/SF
      • 5 Days On Market

      Last Sold Price $470,000

      Last Listing Agent Randy Fontanez, II CHARLES RUTENBERG REALTY ORLANDO

  • 9406 Bolero Rd, Oakland, FL 34787
    9406 Bolero Rd, Oakland, FL 34787
    /2

    $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

    Current Estimated Value $797,434

    Last Listing Agent JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

    9406 Bolero Rd, Oakland, FL 34787
    • Unlisted Address
      Unlisted Address
      /2

      Est $450,451 Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 2.5 Baths
      • 1,992 Sq Ft
      • Built 2023
      Unlisted Address

      Last Sold Summary

      • 6% Below List Price
      • $241/SF

      Last Sold Price $480,785

      Last Listing Agent Iris Sanchez LA ROSA REALTY LLC

  • 525 N Pollard St, Winter Garden, FL 34787
    525 N Pollard St, Winter Garden, FL 34787
    /2

    $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
    • 10623 Words Dr, Oakland, FL 34787
      10623 Words Dr, Oakland, FL 34787
      /2

      Est $443,928 Not Listed For Sale

      10623 Words Dr, Oakland, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 1,992 Sq Ft
      • Built 2023
      10623 Words Dr, Oakland, FL 34787

      Last Sold Summary

      • 2% Below List Price
      • $228/SF
      • 0 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Adrian Antunes, Sr GLASSTONE GROUP INC

  • 15086 Summer Harvest St, Oakland, FL 34787
    15086 Summer Harvest St, Oakland, FL 34787
    /2

    $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 $632,886

    Last Listing Agent Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

    15086 Summer Harvest St, Oakland, FL 34787
    • 50 Demens St, Oakland, FL 34760
      50 Demens St, Oakland, FL 34760
      50 Demens St, Oakland, FL 34760
      /35

      Est $731,434 Not Listed For Sale

      50 Demens St, Oakland, FL 34760

      • 4 Beds
      • 3.5 Baths
      • 2,652 Sq Ft
      • Built 2003
      50 Demens St, Oakland, FL 34760

      Last Sold Summary

      • 16% Above List Price
      • $238/SF
      • 1 Day On Market

      Last Sold Price $630,000

      Last Listing Agent Jason Asa LPT REALTY, LLC

  • 16158 Point Rock Dr, Oakland, FL 34787
    16158 Point Rock Dr, Oakland, FL 34787
    16158 Point Rock Dr, Oakland, FL 34787
    /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 $817,000

    D.R. Horton Waterleigh

    16158 Point Rock Dr, Oakland, FL 34787
    • 3295 Hanging Tide St, Oakland, FL 34787
      3295 Hanging Tide St, Oakland, FL 34787
      3295 Hanging Tide St, Oakland, FL 34787
      /28

      Est $508,731 Not Listed For Sale

      3295 Hanging Tide St, Oakland, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 2021
      3295 Hanging Tide St, Oakland, FL 34787

      Last Sold Summary

      • 2% Above List Price
      • $298/SF
      • 46 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Franshely Calero LUXE HUNTER REAL ESTATE

  • 829 Cura Ct, Oakland, FL 34787
    829 Cura Ct, Oakland, FL 34787
    /2

    $645,000 Sold Sep 24, 2025

    829 Cura Ct, Oakland, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,329 Sq Ft
    • Built 2002

    Last Sold Summary

    • $277/SF
    • 3 Days On Market

    Current Estimated Value $626,966

    Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

    829 Cura Ct, Oakland, FL 34787
    • 17167 Writing Aly, Oakland, FL 34787
      17167 Writing Aly, Oakland, FL 34787
      17167 Writing Aly, Oakland, FL 34787
      /64

      Est $548,887 Not Listed For Sale

      17167 Writing Aly, Oakland, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,502 Sq Ft
      • Built 2020
      17167 Writing Aly, Oakland, FL 34787

      Last Sold Summary

      • 4% Below List Price
      • $229/SF
      • 5 Days On Market

      Last Sold Price $572,500

      Last Listing Agent Ana Afshin GERMEROTH REALTY LLC

  • 854 Tilden Oaks Trail, Winter Garden, FL 34787
    854 Tilden Oaks Trail, Winter Garden, FL 34787
    /2

    $1,695,000 Sold Feb 13, 2026

    854 Tilden Oaks Trail, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,991 Sq Ft
    • Built 2020

    Last Sold Summary

    • 10% Below List Price
    • $425/SF
    • 119 Days On Market

    Current Estimated Value $1,718,401

    Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

    854 Tilden Oaks Trail, Winter Garden, FL 34787
    • 11072 Robert Frost Dr, Oakland, FL 34787
      11072 Robert Frost Dr, Oakland, FL 34787
      11072 Robert Frost Dr, Oakland, FL 34787
      /54

      Est $674,571 Not Listed For Sale

      11072 Robert Frost Dr, Oakland, FL 34787

      • 4 Beds
      • 4 Baths
      • 2,722 Sq Ft
      • Built 2021
      11072 Robert Frost Dr, Oakland, FL 34787

      Last Sold Summary

      • 2% Below List Price
      • $253/SF
      • 7 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Pan Pan JWJ REALTY LLC

  • 932 Kylee Aly, Winter Garden, FL 34787
    932 Kylee Aly, Winter Garden, FL 34787
    /2

    $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 $702,811

    Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

    932 Kylee Aly, Winter Garden, FL 34787
    • 8186 Sayings Dr, Oakland, FL 34787
      8186 Sayings Dr, Oakland, FL 34787
      8186 Sayings Dr, Oakland, FL 34787
      /44

      Est $617,246 Not Listed For Sale

      8186 Sayings Dr, Oakland, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 2,704 Sq Ft
      • Built 2022
      8186 Sayings Dr, Oakland, FL 34787

      Last Sold Summary

      • 3% Below List Price
      • $235/SF
      • 4 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Helen Thompson RE/MAX SELECT GROUP

  • 1126 Riverway Dr, Oakland, FL 34787
    1126 Riverway Dr, Oakland, FL 34787
    /2

    $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 $958,646

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

    1126 Riverway Dr, Oakland, FL 34787
    • 11307 Great Rock St, Winter Garden, FL 34787
      11307 Great Rock St, Winter Garden, FL 34787
      11307 Great Rock St, Winter Garden, FL 34787
      /10

      Est $455,329 Not Listed For Sale

      11307 Great Rock St, Winter Garden, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2023
      11307 Great Rock St, Winter Garden, FL 34787

      Last Sold Summary

      • 6% Below List Price
      • $243/SF
      • 14 Days On Market

      Last Sold Price $485,070

      Last Listing Agent Ben Goldstein LENNAR REALTY

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

    $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 $909,523

    Last Listing Agent Matt McKee COMPASS FLORIDA LLC

    908 Tilden Oaks Trail, Winter Garden, FL 34787
    • 11301 Great Rock St, Oakland, FL 34787
      11301 Great Rock St, Oakland, FL 34787
      11301 Great Rock St, Oakland, FL 34787
      /12

      Est $435,238 Not Listed For Sale

      11301 Great Rock St, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,755 Sq Ft
      • Built 2023
      11301 Great Rock St, Oakland, FL 34787

      Last Sold Summary

      • 8% Below List Price
      • $269/SF
      • 9 Days On Market

      Last Sold Price $471,440

      Last Listing Agent Ben Goldstein LENNAR REALTY

  • 1225 Water Maple Dr, Oakland, FL 34760
    1225 Water Maple Dr, Oakland, FL 34760
    /2

    $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
    • 12338 Bracco St, Oakland, FL 34787
      12338 Bracco St, Oakland, FL 34787
      /2

      Est $487,268 Not Listed For Sale

      12338 Bracco St, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,788 Sq Ft
      • Built 2023
      12338 Bracco St, Oakland, FL 34787

      Last Sold Summary

      • 2% Above List Price
      • $268/SF
      • 132 Days On Market

      Last Sold Price $480,000

      Last Listing Agent Christine Kim SOGO REAL ESTATE SERVICES LLC

  • 632 Strihal Loop, Oakland, FL 34787
    632 Strihal Loop, Oakland, FL 34787
    632 Strihal Loop, Oakland, FL 34787
    /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 $626,184

    Last Listing Agent Millie Gwin Coldwell Banker Coast Realty

    632 Strihal Loop, Oakland, FL 34787

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