Recently Sold Oakland, FL Homes

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$2,300,000 Sold Feb 23, 2026

1118 Sarah Mathews Dr, Oakland, FL 34787
- 4 Beds
- 6 Baths
- 3,902 Sq Ft
- Built 2025
Last Sold Summary
- $589/SF
- 26 Days On Market
Current Estimated Value $2,275,667

Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

1118 Sarah Mathews Dr, Oakland, FL 34787
/2
$629,745 Sold Oct 24, 2025

16198 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,904 Sq Ft
- Built 2025
Last Sold Summary
- 4% Above List Price
- $217/SF
- 23 Days On Market
Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

16198 Honey Harvest St, Oakland, FL 34787
/2
$388,000 Sold Jul 03, 2025

1312 Painted Bunting Ave, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2020
Last Sold Summary
- 3% Below List Price
- $240/SF
- 86 Days On Market
Current Estimated Value $372,911

Last Listing Agent Gavin Hatch SERHANT

1312 Painted Bunting Ave, Oakland, FL 34760
/2
$600,000 Sold Apr 25, 2025

1011 Johns Cove Ln, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,579 Sq Ft
- Built 2001
Last Sold Summary
- 6% Below List Price
- $233/SF
- 96 Days On Market
Current Estimated Value $605,170

Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

1011 Johns Cove Ln, Oakland, FL 34787
/2
$585,000 Sold Aug 13, 2025

1740 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,995 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $293/SF
- 50 Days On Market
Current Estimated Value $573,812

Last Listing Agent Melissa Vance MAINFRAME REAL ESTATE

1740 Standing Rock Cir, Oakland, FL 34787
/2
$422,240 Sold Aug 29, 2025

5689 Meditation Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,647 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $256/SF
- 17 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

5689 Meditation Dr, Oakland, FL 34787
/2
$890,000 Sold May 12, 2025

896 Tilden Oaks Trail, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,268 Sq Ft
- Built 2022
Last Sold Summary
- 9% Below List Price
- $392/SF
- 57 Days On Market
Current Estimated Value $884,300

Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

896 Tilden Oaks Trail, Winter Garden, FL 34787
/2
$1,835,000 Sold May 27, 2025

625 Cheekwood Aly, Winter Garden, FL 34787
- 6 Beds
- 4.5 Baths
- 3,796 Sq Ft
- Built 2022
Last Sold Summary
- 5% Below List Price
- $483/SF
- 17 Days On Market
Current Estimated Value $1,793,358

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

625 Cheekwood Aly, Winter Garden, FL 34787
/2
$865,000 Sold Jun 05, 2025

9554 Bolero Rd, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,916 Sq Ft
- Built 2021
Last Sold Summary
- $297/SF
- 0 Days On Market
Current Estimated Value $869,620

Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

9554 Bolero Rd, Oakland, FL 34787
/2
$395,890 Sold Jul 08, 2025

2883 Transformation Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $222/SF
- 21 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

2883 Transformation Way, Oakland, FL 34787
/2
$800,000 Sold Jul 10, 2025

517 N Pollard St, Winter Garden, FL 34787
- Land
- 0.95 Acre
- $842,105 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent Blaine Dooley REGENCY REAL ESTATE LLC

517 N Pollard St, Winter Garden, FL 34787
/2
$489,990 Sold Apr 14, 2025

6672 Juneberry Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,846 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $265/SF
- 155 Days On Market
Current Estimated Value $491,072

Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

6672 Juneberry Way, Oakland, FL 34787
/2
$460,252 Sold Nov 20, 2025

17693 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,635 Sq Ft
- Built 2025
Last Sold Summary
- $281/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

17693 Japonica Bloom Dr, Oakland, FL 34787
/2
$750,000 Sold Jan 28, 2026

16029 Honey Harvest St, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,101 Sq Ft
- Built 2025
Last Sold Summary
- 9% Below List Price
- $242/SF
- 176 Days On Market
Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

16029 Honey Harvest St, Oakland, FL 34787
/2
$45,000 Sold Feb 12, 2026

515 W Herriot Ave, Oakland, FL 34760
- Land
- 0.09 Acre
- $500,000 per Acre
Last Sold Summary
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

515 W Herriot Ave, Oakland, FL 34760
/2
$450,000 Sold Oct 08, 2025

310 E Gulley Ave, Oakland, FL 34760
- 3 Beds
- 2 Baths
- 1,419 Sq Ft
- Built 1978
Last Sold Summary
- 8% Below List Price
- $317/SF
- 82 Days On Market
Current Estimated Value $454,402

Last Listing Agent Liam Lugo KELLER WILLIAMS WINTER PARK

310 E Gulley Ave, Oakland, FL 34760
/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
/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 $579,077

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

1219 Foltz Loop, Oakland, FL 34787
/2
$474,000 Sold Mar 31, 2026

717 Strihal Loop, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
- Built 2002
Last Sold Summary
- 1% Below List Price
- $230/SF
- 62 Days On Market
Current Estimated Value $473,521

Last Listing Agent Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

717 Strihal Loop, 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
/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 $461,666

Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

312 W Hull Ave, Oakland, FL 34760
/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
/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 $449,881

Last Listing Agent Marnetta Arnett LPT REALTY, LLC

2690 Bobcat Chase Blvd, 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 $542,264

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

12064 Encore at Ovation Way, 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 $798,000

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

16140 Point Rock 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
/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 $798,726

Last Listing Agent JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

9406 Bolero Rd, Oakland, 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
/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 $627,433

Last Listing Agent Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

15086 Summer Harvest St, 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 $822,000

D.R. Horton Waterleigh

16158 Point Rock Dr, 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 $625,317

Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

829 Cura Ct, Oakland, FL 34787
/2
$530,000 Sold May 23, 2025

321 E Gulley Ave, Oakland, FL 34760
- 3 Beds
- 1 Bath
- 1,515 Sq Ft
- Built 1958
Last Sold Summary
- 1% Below List Price
- $350/SF
- 1 Day On Market
Current Estimated Value $411,807

Last Listing Agent Rebecca Hall KELLER WILLIAMS WINTER PARK

321 E Gulley Ave, Oakland, FL 34760
/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 $1,674,793

Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

854 Tilden Oaks Trail, 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 $705,739

Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

932 Kylee Aly, Winter Garden, 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 $1,005,154

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

1126 Riverway Dr, Oakland, 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 $913,388

Last Listing Agent Matt McKee COMPASS FLORIDA LLC

908 Tilden Oaks Trail, Winter Garden, FL 34787
/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
/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 $632,901

Last Listing Agent Millie Gwin Coldwell Banker Coast Realty

632 Strihal Loop, Oakland, FL 34787
/2
$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
/2
$500,000 Sold Oct 09, 2025

1143 Bobcat Chase Blvd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,811 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $276/SF
- 15 Days On Market
Current Estimated Value $494,856

Last Listing Agent Vincent Cordaro SERHANT

1143 Bobcat Chase Blvd, Oakland, FL 34787

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