Oakland, FL Homes

/46
$999,900
- 3 Beds
- 2 Baths
- 2,214 Sq Ft
13343 Sunny Retreat Ln, Oakland, FL 34787

he neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

John Hart ENGEL & VOLKERS ORLANDO DR PHILLIPS

13343 Sunny Retreat Ln, Oakland, FL 34787
/2
$464,000 Sold Oct 29, 2025

2163 White Feather Loop, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,744 Sq Ft
- Built 2019
Last Sold Summary
- 7% Below List Price
- $266/SF
- 65 Days On Market
Current Estimated Value $461,169

Last Listing Agent Joshua Earley OPTIMA ONE REALTY, INC.

2163 White Feather Loop, Winter Garden, FL 34787

/2
Est $540,170 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,094 Sq Ft
14387 Braemar St, Oakland, FL 34787

14387 Braemar St, Oakland, FL 34787

/14
$385,000
- Land
- 0.29 Acre
- $1,327,586 per Acre
610 Simeon Rd, Oakland, FL 34787

Presenting a rare opportunity to purchase a 0.29-acre residential lot in the highly sought-after Town of Oakland. This unincorporated property offers exceptional flexibility, no HOA restrictions and agricultural zoning. Conveniently located just steps from the scenic West Orange Trail, the Oakland Nature Preserve, and downtown Oakland. Enjoy the peaceful surroundings amongst the oak trees and

Blaine Dooley REGENCY REAL ESTATE LLC

610 Simeon Rd, Oakland, FL 34787
/2
$785,000 Sold Oct 24, 2025

1212 Civitas Way, Winter Garden, FL 34787
- 4 Beds
- 2 Baths
- 2,260 Sq Ft
- Built 2022
Last Sold Summary
- 10% Below List Price
- $347/SF
- 128 Days On Market
Current Estimated Value $799,169

Last Listing Agent Kathie Glass BHHS FLORIDA REALTY

1212 Civitas Way, Winter Garden, FL 34787

/2
Est $816,576 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
1221 Wilder Oaks Way, Oakland, FL 34787

1221 Wilder Oaks Way, Oakland, FL 34787

/12
$473,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,186 Sq Ft
6056 Meditation Dr, Oakland, FL 34787

Under Construction. The Solana II has the “WOW” factor you have been searching for. There is a beautiful designer kitchen, that features an abundance of counter space that is sure to appeal to your inner-chef. The kitchen looks out to the combination dining and family rooms for the perfect open sight lines. There are a total of 3 bedrooms and 2 and a half bathrooms. The bedrooms are located on

Ben Goldstein LENNAR REALTY

6056 Meditation Dr, Oakland, FL 34787
/2
$4,383,239 Sold Dec 15, 2025

548 Walker St, Oakland, FL 34760
- 5 Beds
- 8 Baths
- 6,203 Sq Ft
- Built 2026
Last Sold Summary
- $707/SF
- 0 Days On Market
Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

548 Walker St, Oakland, FL 34760

/56
Est $767,357 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,688 Sq Ft
5633 Orange Orchard Dr, Oakland, FL 34787

5633 Orange Orchard Dr, Oakland, FL 34787

/6
$2,995,000 New Construction
- 6 Beds
- 6.5 Baths
- 5,144 Sq Ft
312 Briley Ave, Oakland, FL 34760

Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

Carolina Dumit CORCORAN PREMIER REALTY

312 Briley Ave, Oakland, FL 34760
/2
$925,000 Sold Oct 15, 2025

3179 Sailing Pier Ave, Oakland, FL 34787
- 5 Beds
- 5 Baths
- 4,272 Sq Ft
- Built 2023
Last Sold Summary
- 7% Below List Price
- $217/SF
- 70 Days On Market
Current Estimated Value $923,991

Last Listing Agent Vivian Saavedra LPT REALTY, LLC

3179 Sailing Pier Ave, Oakland, FL 34787

/2
Est $536,170 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,908 Sq Ft
13031 Tollcross Way, Oakland, FL 34787

13031 Tollcross Way, Oakland, FL 34787

/55
$995,000 Pending
- 4 Beds
- 3.5 Baths
- 2,789 Sq Ft
1185 Wilder Oaks Way, Oakland, FL 34787

BETTER THAN BRAND NEW! Welcome home to 1185 Wilder Oaks Way, ideally located in the coveted and quaint neighborhood of Oakland Park. This barely lived-in highly desirable Seaside floor plan presents an exclusive opportunity to own a fully turn-key home showcasing an extensive collection of top-tier builder upgrades complemented by thoughtful owner enhancements (see attached list). Opportunities

Ashlen Hayward THE AGENCY FL

1185 Wilder Oaks Way, Oakland, FL 34787
/2
$849,628 Sold Mar 31, 2025

16193 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,837 Sq Ft
- Built 2025
Last Sold Summary
- $299/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

16193 Honey Harvest St, Oakland, FL 34787

/2
Est $631,587 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,182 Sq Ft
13109 Tollcross Way, Oakland, FL 34787

13109 Tollcross Way, Oakland, FL 34787

/17
$459,000 New Construction
- 3 Beds
- 2.5 Baths
- 1,730 Sq Ft
8937 Matriarca Aly, Oakland, FL 34787

Price adjustment! Move in ready! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring (no carpets) in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large

Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

8937 Matriarca Aly, Oakland, FL 34787
/2
$616,150 Sold Nov 01, 2025

5826 Fabry St, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- Built 2025
Last Sold Summary
- $240/SF
Current Estimated Value $619,000

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

5826 Fabry St, Oakland, FL 34787

/34
Est $429,802 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,513 Sq Ft
9085 Legado Dr, Oakland, FL 34787

9085 Legado Dr, Oakland, FL 34787

/2
$895,000 Pending
- Land
- 1.03 Acres
- $868,932 per Acre
529 N Pollard St, Winter Garden, FL 34787

Under contract-accepting backup offers. Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless

Alexis Anderson REGENCY REAL ESTATE LLC

529 N Pollard St, Winter Garden, FL 34787
/2
$410,000 Sold Jun 04, 2025

0 N Daniels St, Oakland, FL 34760
- Land
- 0.31 Acre
- $1,322,581 per Acre
Last Sold Summary
- 9% Below List Price
- 9 Days On Market
Last Listing Agent Roberta Melo SELECTA REALTY LLC

0 N Daniels St, Oakland, FL 34760

/2
Est $601,737 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
15169 Summer Harvest St, Oakland, FL 34787

15169 Summer Harvest St, Oakland, FL 34787

/33
$587,990 Pending
- 4 Beds
- 3 Baths
- 2,692 Sq Ft
2930 Good Vibes Way, Oakland, FL 34787

Under Construction. The Jagger has it all! This sleek new two-story home features a convenient game room on the second level, perfect for entertaining, relaxation and more. The first floor is host to an inviting open-concept layout shared between a modern kitchen, elegant dining room and comfortable family room. Three secondary bedrooms boast a private space near the front of the home off the

Ben Goldstein LENNAR REALTY

2930 Good Vibes Way, Oakland, FL 34787
/2
$445,000 Sold Mar 18, 2025

13311 Pontoon Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,814 Sq Ft
- Built 2023
Last Sold Summary
- 4% Below List Price
- $245/SF
- 12 Days On Market
Current Estimated Value $445,247

Last Listing Agent Ken Pozek REAL BROKER, LLC.

13311 Pontoon Rd, Oakland, FL 34787

/2
Est $643,054 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,741 Sq Ft
3303 Buoy Cir, Oakland, FL 34787

3303 Buoy Cir, Oakland, FL 34787

/2
$908,676 Pending
- 4 Beds
- 3.5 Baths
- 2,688 Sq Ft
15099 Tea Tree Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

15099 Tea Tree Dr, Oakland, FL 34787
/2
$505,000 Sold Jan 28, 2026

222 Largovista Dr, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,094 Sq Ft
- Built 2004
Last Sold Summary
- 1% Above List Price
- $241/SF
- 7 Days On Market
Last Listing Agent Sonia Jenkins ORANGE REALTY PROFESSIONALS LLC

222 Largovista Dr, Oakland, FL 34787

/31
Est $455,203 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
16287 Prairie School Dr, Oakland, FL 34787

16287 Prairie School Dr, Oakland, FL 34787

/2
$852,342 Pending
- 6 Beds
- 4.5 Baths
- 3,412 Sq Ft
15093 Tea Tree Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

15093 Tea Tree Dr, Oakland, FL 34787
/2
$375,000 Sold Aug 27, 2025

5840 Meditation Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $231/SF
- 22 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

5840 Meditation Dr, Oakland, FL 34787

/11
Est $502,724 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,082 Sq Ft
2035 White Feather Loop, Oakland, FL 34787

2035 White Feather Loop, Oakland, FL 34787

/17
$399,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
Harbor Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

Dream Finders Homes Builder

14229 Lanyard Way Unit 36477638, Oakland, FL 34787
/2
$900,000 Sold Jul 11, 2025

13193 Tollcross Way, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 4,041 Sq Ft
- Built 2024
Last Sold Summary
- 18% Below List Price
- $223/SF
- 232 Days On Market
Current Estimated Value $1,007,985

Last Listing Agent Chandra Maraj CHARLES RUTENBERG REALTY ORLANDO

13193 Tollcross Way, Oakland, FL 34787

/51
Est $410,384 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
12032 Holystone St, Oakland, FL 34787

12032 Holystone St, Oakland, FL 34787

/56
$575,000 Pending
- 5 Beds
- 4 Baths
- 3,449 Sq Ft
229 Largovista Dr, Oakland, FL 34787

Under contract-accepting backup offers. **NEW PRICE – MUST-SEE LUXURY POOL HOME!** Prepare to fall in love with this stunning 5-bedroom, 4-bathroom home located in the exclusive gated community of *Johns Landing*. Offering nearly 3,500 sq. ft. of meticulously designed living space, this home is the perfect blend of elegance, comfort, and Florida living at its finest! From the moment you step

Richard Lokhnauth RL LUXURY REAL ESTATE

229 Largovista Dr, Oakland, FL 34787
/2
$810,000 Sold Aug 01, 2025

3182 Sailing Pier Ave, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
- Built 2024
Last Sold Summary
- 11% Below List Price
- $298/SF
- 76 Days On Market
Current Estimated Value $811,691

Last Listing Agent Ron Howell, II EXP REALTY LLC

3182 Sailing Pier Ave, Oakland, FL 34787

/38
Est $383,275 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
2212 Gopher Tortoise Terrace, Oakland, FL 34760

2212 Gopher Tortoise Terrace, Oakland, FL 34760

/3
$577,990 New Construction
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
Lexington Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

The Lexington floorplan is a spacious one-story design, featuring three comfortable bedrooms and two bathrooms, offering a total of 1,856 square feet. This home includes a versatile three-car garage with tandem space, perfect for extra storage or a workshop area. The open-concept layout connects the great room, cafe, and kitchen, creating a welcoming atmosphere for entertaining and everyday

Dream Finders Homes Builder

14229 Lanyard Way Unit 36464864, Oakland, FL 34787
/2
$768,390 Sold Sep 22, 2025

16107 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,837 Sq Ft
- Built 2025
Last Sold Summary
- $271/SF
- 0 Days On Market
Current Estimated Value $766,000

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

16107 Honey Harvest St, Oakland, FL 34787

/42
Est $798,865 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,561 Sq Ft
1826 Western Trailway Dr, Oakland, FL 34787

1826 Western Trailway Dr, Oakland, FL 34787

/33
$530,000
- 3 Beds
- 2.5 Baths
- 2,128 Sq Ft
6060 Glory Bower Dr, Oakland, FL 34787

Beautifully maintained home featuring 3 bedrooms plus a versatile flex room that can easily be converted into a 4th bedroom, offering the potential to increase future value. The home includes 2.5 bathrooms and a spacious private front porch, perfect for enjoying sunrise views and outdoor living. The kitchen has been thoughtfully upgraded by an interior designer, showcasing luxury finishes and

Alexandra Lattuf ANCHOR REAL ESTATE

6060 Glory Bower Dr, Oakland, FL 34787

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