Oakland, FL Homes

/42
$630,000
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
12554 Westhaven Oak Dr, Oakland, FL 34787

This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

12554 Westhaven Oak Dr, Oakland, FL 34787
/2
$852,105 Sold Jul 02, 2025

5307 Citrus Leaf Blvd, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,300 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $258/SF
- 33 Days On Market
Last Listing Agent Tatiana Souza MERITAGE HOMES OF FL REALTY

5307 Citrus Leaf Blvd, Oakland, FL 34787

/34
Est $570,963 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,148 Sq Ft
12832 Lavender Bloom Aly, Oakland, FL 34787

12832 Lavender Bloom Aly, Oakland, FL 34787

/21
$610,690 Pending
- 4 Beds
- 3.5 Baths
- 2,911 Sq Ft
3088 Namaste Dr, Oakland, FL 34787

Under Construction. The Inverness II is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s

Ben Goldstein LENNAR REALTY

3088 Namaste Dr, Oakland, FL 34787
/2
$448,750 Sold Apr 28, 2025

9109 Legado Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,687 Sq Ft
- Built 2020
Last Sold Summary
- 6% Below List Price
- $266/SF
- 126 Days On Market
Current Estimated Value $453,366

Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC

9109 Legado Dr, Oakland, FL 34787

/2
Est $828,349 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,254 Sq Ft
1204 Oak Fort Ln, Oakland, FL 34787

1204 Oak Fort Ln, Oakland, FL 34787

/55
$2,350,000
- 5 Beds
- 4.5 Baths
- 4,436 Sq Ft
9014 Morgana Ct, Oakland, FL 34787

This is more than a house ~ it is a fully furnished, turnkey lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare

Jennifer Wemert WEMERT GROUP REALTY LLC

9014 Morgana Ct, Oakland, FL 34787
/2
$455,000 Sold Mar 07, 2025

1769 White Feather Loop, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
- Built 2017
Last Sold Summary
- 3% Below List Price
- $248/SF
- 18 Days On Market
Current Estimated Value $461,947

Last Listing Agent Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

1769 White Feather Loop, Oakland, FL 34787

/2
Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,455 Sq Ft
6259 Blissful St, Oakland, FL 34787

6259 Blissful St, Oakland, FL 34787

/60
$997,000
- 5 Beds
- 3.5 Baths
- 3,910 Sq Ft
9549 Bolero Rd, Oakland, FL 34787

The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

9549 Bolero Rd, Oakland, FL 34787
/2
$828,296 Sold Sep 29, 2025

16146 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $257/SF
- 48 Days On Market
Current Estimated Value $825,000

Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

16146 Point Rock Dr, Oakland, FL 34787

/2
Est $418,589 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,717 Sq Ft
17005 Volume Aly, Oakland, FL 34787

17005 Volume Aly, Oakland, FL 34787

/41
$642,990 New Construction
- 5 Beds
- 4 Baths
- 3,011 Sq Ft
2982 Good Vibes Way, Oakland, FL 34787

Under Construction. The Dylan is all the rage! This stylish two-story home features a first-floor owner’s suite, offering a private retreat with a full bathroom and walk-in closet. An additional bedroom is located near the front of the home, steps from a full bathroom. A spacious and flexible open-concept layout blends the kitchen, living and dining areas, while a nearby flex space provides the

Ben Goldstein LENNAR REALTY

2982 Good Vibes Way, Oakland, FL 34787
/2
$900,000 Sold Jun 25, 2025

13202 Spring Grove Way, Oakland, FL 34787
- 4 Beds
- 4 Baths
- 2,930 Sq Ft
- Built 2020
Last Sold Summary
- 5% Below List Price
- $307/SF
- 54 Days On Market
Current Estimated Value $891,966

Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

13202 Spring Grove Way, Oakland, FL 34787

/2
Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,043 Sq Ft
6301 Blissful St, Oakland, FL 34787

6301 Blissful St, Oakland, FL 34787

/44
$560,000
- 3 Beds
- 2.5 Baths
- 2,089 Sq Ft
2065 White Feather Loop, Oakland, FL 34787

Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential

Denis Bochkov PINK MIAMI

2065 White Feather Loop, Oakland, FL 34787
/2
$389,000 Sold Dec 23, 2025

2218 Gopher Tortoise Terrace, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
- Built 2020
Last Sold Summary
- $264/SF
- 36 Days On Market
Last Listing Agent Chelsea Eckert CAM REALTY & PROPERTY MANAGEME

2218 Gopher Tortoise Terrace, Oakland, FL 34760

/2
Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,455 Sq Ft
6253 Blissful St, Oakland, FL 34787

6253 Blissful St, Oakland, FL 34787

/5
$455,000
- Land
- 0.28 Acre
- $1,625,000 per Acre
1227 Ridge Lake Way, Winter Garden, FL 34787

Lot 249 is located in the final phase of Oakland Park at The Reserve, a highly sought-after golf cart community nestled along the shores of Lake Apopka. Enjoy close proximity to the West Orange Trail and the charming Downtown Winter Garden, known for its local shops, dining, and events. This is a rare opportunity to build your FULLY CUSTOM dream home in one of the area’s most desirable

Dawn Pickard THE C SMITH REAL ESTATE GROUP LLC

1227 Ridge Lake Way, Winter Garden, FL 34787
/2
$520,000 Sold Aug 29, 2025

1877 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
- Built 2018
Last Sold Summary
- $259/SF
- 9 Days On Market
Current Estimated Value $516,588

Last Listing Agent James Goodyear REAL BROKER, LLC.

1877 Standing Rock Cir, Oakland, FL 34787

/2
Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,023 Sq Ft
6379 Blissful St, Oakland, FL 34787

6379 Blissful St, Oakland, FL 34787

/49
$1,199,000 Pending
- 4 Beds
- 3 Baths
- 2,563 Sq Ft
1120 Civitas Way, Winter Garden, FL 34787

Under contract-accepting backup offers. Nestled on a corner lot in the heart of Oakland Park and thoughtfully custom designed and built by J&J Builders, this fully turnkey home is impeccably finished and flooded with natural light, thanks to an abundance of large sun-filled windows that create an airy, welcoming atmosphere throughout. A flexible floor plan offers 4 true bedrooms PLUS an

Ashlen Hayward THE AGENCY FL

1120 Civitas Way, Winter Garden, FL 34787
/2
$455,000 Sold Apr 25, 2025

13885 Title Way, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,042 Sq Ft
- Built 2022
Last Sold Summary
- 1% Above List Price
- $223/SF
- 2 Days On Market
Current Estimated Value $462,786

Last Listing Agent Iris Lee SPRUCE QUALITY RENTALS

13885 Title Way, Winter Garden, FL 34787

/2
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
6391 Blissful St, Oakland, FL 34787

6391 Blissful St, Oakland, FL 34787

/14
$415,000 Pending
- Land
- 0.27 Acre
- $1,537,037 per Acre
15738 E Oakland Ave, Oakland, FL 34787

Under contract-accepting backup offers. Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood

Alexis Anderson REGENCY REAL ESTATE LLC

15738 E Oakland Ave, Oakland, FL 34787
/2
$530,000 Sold Oct 15, 2025

8001 Sayings Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,552 Sq Ft
- Built 2022
Last Sold Summary
- 8% Below List Price
- $208/SF
- 66 Days On Market
Current Estimated Value $531,455

Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

8001 Sayings Dr, Winter Garden, FL 34787

/2
Est $424,556 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,688 Sq Ft
15805 Tollington Aly, Oakland, FL 34787

15805 Tollington Aly, Oakland, FL 34787

/61
$665,000
- 4 Beds
- 3 Baths
- 2,274 Sq Ft
2169 Bay Line Rd, Oakland, FL 34787

Welcome home to Hull Island, where refined design meets serene Florida living. This impeccably maintained 4-bedroom, 3-bath home offers the rare combination of conservation privacy, thoughtful upgrades, and resort-style community amenities—truly better than new. Backing to a protected nature preserve with no rear neighbors, the home provides a peaceful retreat while still being moments from

Mariana Wartella LPT REALTY, LLC

2169 Bay Line Rd, Oakland, FL 34787
/2
$1,272,000 Sold Apr 29, 2025

1112 Hull Island Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,562 Sq Ft
- Built 2021
Last Sold Summary
- 2% Below List Price
- $357/SF
- 49 Days On Market
Current Estimated Value $1,259,309

Last Listing Agent Kelly Zannini HOMEVEST REALTY

1112 Hull Island Dr, Oakland, FL 34787

/2
Est $421,142 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,691 Sq Ft
15811 Tollington Aly, Oakland, FL 34787

15811 Tollington Aly, Oakland, FL 34787

$1,675,000 New Construction
- 5 Beds
- 5 Baths
- 4,819 Sq Ft
166 Hammock Preserve Loop, Oakland, FL 34787

AR Homes Builder

166 Hammock Preserve Loop, Oakland, FL 34787
/2
$599,200 Sold Sep 25, 2025

4727 Forest Haven Way, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 2025
Last Sold Summary
- $310/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4727 Forest Haven Way, Oakland, FL 34787

/2
Est $597,480 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,149 Sq Ft
15153 Summer Harvest St, Oakland, FL 34787

15153 Summer Harvest St, Oakland, FL 34787

/16
$2,130,760 New Construction
- 5 Beds
- 5.5 Baths
- 3,992 Sq Ft
1146 Prado Ln, Oakland, FL 34787

Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

Heather Spirazza REGENCY REAL ESTATE LLC

1146 Prado Ln, Oakland, FL 34787
/2
$865,000 Sold Jul 25, 2025

70 Millholland St, Oakland, FL 34760
- 5 Beds
- 3 Baths
- 2,534 Sq Ft
- Built 2009
Last Sold Summary
- 15% Below List Price
- $341/SF
- 261 Days On Market
Current Estimated Value $885,651

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

70 Millholland St, Oakland, FL 34760

/2
Est $437,748 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,663 Sq Ft
2315 Standing Rock Cir, Oakland, FL 34787

2315 Standing Rock Cir, Oakland, FL 34787

/79
$3,575,000 New Construction
- 5 Beds
- 7 Baths
- 5,478 Sq Ft
510 Briley Ave, Oakland, FL 34787

Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two

Alexis Anderson REGENCY REAL ESTATE LLC

510 Briley Ave, Oakland, FL 34787
/2
$395,000 Sold Sep 30, 2025

13298 Pontoon Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2023
Last Sold Summary
- 6% Below List Price
- $252/SF
- 51 Days On Market
Current Estimated Value $394,831

Last Listing Agent Cindy Brads COLDWELL BANKER REALTY

13298 Pontoon Rd, Oakland, FL 34787

/2
Est $670,515 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,248 Sq Ft
1540 Stone Arrow Ct, Winter Garden, FL 34787

1540 Stone Arrow Ct, Winter Garden, FL 34787

/62
$1,650,000
- 6 Beds
- 7.5 Baths
- 5,614 Sq Ft
620 N Tubb St, Oakland, FL 34760

This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant

Jennifer Wilson OAKSTRAND REALTY

620 N Tubb St, Oakland, FL 34760

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