Recently Sold Oakland, FL Homes

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$683,000

Sold Apr 17, 2026

310 E Gulley Ave, Oakland, FL 34760
- 3 Beds
- 2 Baths
- 1,763 Sq Ft
- Built 1978
Last Sold Summary
- 2% Below List Price
- $387/SF
- 11 Days On Market
Current Estimated Value $667,790

Last Listing Agent Matt Kester THE REAL ESTATE COLLECTION LLC

310 E Gulley Ave, Oakland, FL 34760
/2
$685,000

Sold Mar 12, 2026

15133 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,908 Sq Ft
- Built 2024
Last Sold Summary
- 1% Below List Price
- $236/SF
- 10 Days On Market
Current Estimated Value $679,178

Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

15133 Summer Harvest St, Oakland, FL 34787
/2
$740,000

Sold Dec 10, 2025

14399 Wabasso Loop, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,074 Sq Ft
- Built 2022
Last Sold Summary
- 3% Below List Price
- $241/SF
- 15 Days On Market
Current Estimated Value $743,106

Last Listing Agent David Wood EXP REALTY LLC

14399 Wabasso Loop, Oakland, FL 34787
/2
$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 $2,271,000

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 $381,754

Last Listing Agent Gavin Hatch SERHANT

1312 Painted Bunting Ave, Oakland, FL 34760
/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 $578,529

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
$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
- 41,382 Sq Ft
- $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
$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
Current Estimated Value $466,000

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
- 3,920 Sq Ft
- $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 $667,790

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
- 41,817 Sq Ft
- $932,292 per Acre
Last Sold Summary
- 161 Days On Market
Current Estimated Value $912,000

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 $588,671

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 $470,327

Last Listing Agent Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

717 Strihal Loop, 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 $474,459

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 $452,250

Last Listing Agent Marnetta Arnett LPT REALTY, LLC

2690 Bobcat Chase Blvd, Oakland, FL 34787
/2
$382,000

Sold May 27, 2026

12043 Holystone St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2023
Last Sold Summary
- 8% Below List Price
- $244/SF
- 221 Days On Market
Current Estimated Value $390,664

Last Listing Agent Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

12043 Holystone St, 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 $795,000

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

16140 Point Rock Dr, Oakland, FL 34787
/2
$1,700,000

Sold Apr 09, 2026

1207 Ridge Lake Way, Winter Garden, FL 34787
- 5 Beds
- 3.5 Baths
- 3,909 Sq Ft
- Built 2026
Last Sold Summary
- $435/SF
- 291 Days On Market
Last Listing Agent Chris Herlihy NEW HOMES REAL ESTATE, INC.

1207 Ridge Lake Way, Winter Garden, 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 $808,139

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
/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
/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 $635,731

Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

829 Cura Ct, Oakland, FL 34787
/2
$664,740

Sold Apr 13, 2026

4520 Scenic Woods Dr, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- Built 2026
Last Sold Summary
- $259/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4520 Scenic Woods Dr, Oakland, 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 $1,660,140

Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

854 Tilden Oaks Trail, Winter Garden, FL 34787
/2
$1,032,585

Sold Apr 28, 2026

12904 Westhaven Oak Dr, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,894 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $265/SF
- 70 Days On Market
Toll Brothers, Inc. Westhaven at Ovation - Retreat Collection

12904 Westhaven Oak 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 $1,021,831

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 $930,603

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
- 10,890 Sq Ft
- $1,500,000 per Acre
Last Sold Summary
- 14% Below List Price
- 82 Days On Market
Current Estimated Value $379,441

Last Listing Agent Darby Shields HAVEN PROPERTY GROUP LLC

1225 Water Maple Dr, Oakland, FL 34760
/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 $506,893

Last Listing Agent Vincent Cordaro SERHANT

1143 Bobcat Chase Blvd, Oakland, FL 34787
/2
$475,990

Sold Feb 06, 2026

Unlisted Address
- 4 Beds
- 3 Baths
- 2,023 Sq Ft
- Built 2026
Last Sold Summary
- $235/SF
Current Estimated Value $473,373

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

Unlisted Address
/2
$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
/2
$2,050,000

Sold Feb 13, 2026

1017 Johns Point Dr, Oakland, FL 34787
- 5 Beds
- 6 Baths
- 6,141 Sq Ft
- Built 2001
Last Sold Summary
- 5% Below List Price
- $334/SF
- 6 Days On Market
Current Estimated Value $2,075,930

Last Listing Agent peipei Qiao BAY STREET GROUP FLORIDA LLC

1017 Johns Point Dr, Oakland, FL 34787
/2
$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 $747,259

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

8935 Sonoma Coast Dr, Oakland, FL 34787
/32
$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 $750,000

D.R. Horton Waterleigh

16195 Point Rock Dr, Oakland, FL 34787

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