Oakland, FL Homes

/64
$999,000 Pending
- 5 Beds
- 3 Baths
- 3,563 Sq Ft
1304 Foltz Loop, Oakland, FL 34787

Under contract-accepting backup offers. Impeccably maintained 5 bed 3 bath, 3563 sq/ft home that combines luxury with natural beauty. Step outside onto the expansive screened lanai and upstairs balcony, where you can enjoy panoramic vistas of Florida’s lush scenery from this beautiful conservation lot back that backs up to Lake Apopka. The home is located on a quiet culdesac street that borders

Lisa Gould KELLER WILLIAMS WINTER PARK

1304 Foltz Loop, Oakland, 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 $461,775

Last Listing Agent Iris Lee SPRUCE QUALITY RENTALS

13885 Title Way, Winter Garden, FL 34787

/2
Est $515,593 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,838 Sq Ft
13025 Tollcross Way, Oakland, FL 34787

13025 Tollcross Way, Oakland, FL 34787

/3
$449,900
- Land
- 0.23 Acre
- $1,956,087 per Acre
1203 Ridge Lake Way, Winter Garden, FL 34787

LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

Tracey McFadden OAK AVENUE REAL ESTATE LLC

1203 Ridge Lake Way, Winter Garden, 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
Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

8001 Sayings Dr, Winter Garden, FL 34787

/2
Est $774,095 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,747 Sq Ft
3410 Buoy Cir, Oakland, FL 34787

3410 Buoy Cir, Oakland, FL 34787

/4
$498,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,836 Sq Ft
Brantley Plan at Serenade at Ovation, Oakland, FL 34787

Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

Dream Finders Homes Builder

14229 Lanyard Way Unit 36498626, 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 $1,258,769

Last Listing Agent Kelly Zannini HOMEVEST REALTY

1112 Hull Island Dr, Oakland, FL 34787

/2
Est $539,592 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,586 Sq Ft
14103 Lochend Way, Oakland, FL 34787

14103 Lochend Way, Oakland, FL 34787

/17
$2,238,120 New Construction
- 5 Beds
- 5.5 Baths
- 4,204 Sq Ft
1173 Prado Ln, Oakland, FL 34787

Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-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

Alexis Anderson REGENCY REAL ESTATE LLC

1173 Prado Ln, 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 $521,627 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
14407 Braemar St, Oakland, FL 34787

14407 Braemar St, Oakland, FL 34787

/2
$943,160 Pending
- 4 Beds
- 3 Baths
- 3,108 Sq Ft
15166 Tea Tree Dr, Oakland, FL 34787

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

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

15166 Tea Tree Dr, 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 $885,618

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

70 Millholland St, Oakland, FL 34760

/2
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,186 Sq Ft
6295 Blissful St, Oakland, FL 34787

6295 Blissful St, Oakland, FL 34787

/4
$800,000 New Construction
- 5 Beds
- 4.5 Baths
- 3,101 Sq Ft
16029 Honey Harvest St, Oakland, FL 34787

New Construction - Ready Now! Built by Taylor Morrison, America's Most Trusted Homebuilder. Welcome to the Cumberland at 16029 Honey Harvest Street in Harvest at Ovation. This spacious two-story Cumberland offers 5 bedrooms, 4.5 bathrooms, and flexible living for every stage of life. The open-concept great room, dining area, and gourmet kitchen flow effortlessly together and open to an extended

Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

16029 Honey Harvest St, 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
Last Listing Agent Cindy Brads COLDWELL BANKER REALTY

13298 Pontoon Rd, Oakland, FL 34787

/59
Est $484,754 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,082 Sq Ft
2071 White Feather Loop, Oakland, FL 34787

2071 White Feather Loop, Oakland, FL 34787

/21
$895,000 Pending
- Land
- 0.96 Acre
- $932,292 per Acre
513 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 36 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 personal

Heather Spirazza REGENCY REAL ESTATE LLC

513 N Pollard St, Winter Garden, FL 34787
/2
$545,000 Sold Jun 16, 2025

1757 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
- Built 2017
Last Sold Summary
- 3% Below List Price
- $272/SF
- 12 Days On Market
Current Estimated Value $543,986

Last Listing Agent Shannon Christian EXP REALTY LLC

1757 Standing Rock Cir, Oakland, FL 34787

/2
Est $466,171 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
2153 Standing Rock Cir, Winter Garden, FL 34787

2153 Standing Rock Cir, Winter Garden, FL 34787

/32
$480,000
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
717 Strihal Loop, Oakland, FL 34787

Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and

Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

717 Strihal Loop, Oakland, FL 34787
/21
$446,000 Sold Mar 13, 2025

2261 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,753 Sq Ft
- Built 2019
Last Sold Summary
- 4% Below List Price
- $254/SF
- 136 Days On Market
Current Estimated Value $454,793

Last Listing Agent Fernando Orsini CT HOMES REALTY CORPORATION

2261 Standing Rock Cir, Oakland, FL 34787

/2
Est $594,754 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
15109 Summer Harvest St, Oakland, FL 34787

15109 Summer Harvest St, Oakland, FL 34787

/46
$465,000 Pending
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
2690 Bobcat Chase Blvd, Oakland, FL 34787

Under contract-accepting backup offers. Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors.

Marnetta Arnett LPT REALTY, LLC

2690 Bobcat Chase Blvd, Oakland, FL 34787
/2
$420,000 Sold Jul 09, 2025

709 Strihal Loop, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,621 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $259/SF
- 24 Days On Market
Current Estimated Value $421,170

Last Listing Agent Jessica Stone CENTURY 21 CARIOTI

709 Strihal Loop, Oakland, FL 34787

/2
Est $609,434 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
15101 Summer Harvest St, Oakland, FL 34787

15101 Summer Harvest St, Oakland, FL 34787

/38
$399,000
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
12043 Holystone St, Oakland, FL 34787

“The property is currently active for sale but is rented for $2500 monthly, with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.”Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It

Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

12043 Holystone St, Oakland, FL 34787
/2
$604,000 Sold Sep 19, 2025

410 E Gulley Ave, Oakland, FL 34760
- 5 Beds
- 3 Baths
- 2,458 Sq Ft
- Built 1959
Last Sold Summary
- 8% Below List Price
- $246/SF
- 30 Days On Market
Current Estimated Value $618,317

Last Listing Agent Keith Packey RE/MAX TITANIUM GROUP

410 E Gulley Ave, Oakland, FL 34760

/2
Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,455 Sq Ft
6271 Blissful St, Oakland, FL 34787

6271 Blissful St, Oakland, FL 34787

/7
$1,700,000 New Construction
- 5 Beds
- 3.5 Baths
- 3,909 Sq Ft
1207 Ridge Lake Way, Winter Garden, FL 34787

Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

Chris Herlihy NEW HOMES REAL ESTATE, INC.

1207 Ridge Lake Way, Winter Garden, FL 34787
/2
$652,316 Sold Nov 14, 2025

16108 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
- Built 2025
Last Sold Summary
- $267/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

16108 Honey Harvest St, Oakland, FL 34787

/2
Est $910,251 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
1191 Wilder Oaks Way, Oakland, FL 34787

1191 Wilder Oaks Way, Oakland, FL 34787

/28
$1,775,000
- 5 Beds
- 4.5 Baths
- 3,991 Sq Ft
854 Tilden Oaks Trail, Winter Garden, FL 34787

This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended

Tracey McFadden OAK AVENUE REAL ESTATE LLC

854 Tilden Oaks Trail, Winter Garden, FL 34787
/2
$1,100,000 Sold Mar 17, 2025

111 Millholland St, Oakland, FL 34760
- 4 Beds
- 3 Baths
- 3,333 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $330/SF
- 7 Days On Market
Current Estimated Value $1,101,421

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

111 Millholland St, Oakland, FL 34760

/48
Est $794,611 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,724 Sq Ft
5121 Breezy Acres St, Oakland, FL 34787

5121 Breezy Acres St, Oakland, FL 34787

/47
$700,000
- 5 Beds
- 3.5 Baths
- 3,381 Sq Ft
729 Strihal Loop, Oakland, FL 34787

One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is

Dylan Stanley MARK SPAIN REAL ESTATE

729 Strihal Loop, Oakland, FL 34787
/2
$804,990 Sold Jan 05, 2025

9462 Emerald Berry Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,211 Sq Ft
- Built 2024
Last Sold Summary
- 2% Below List Price
- $251/SF
- 62 Days On Market
Current Estimated Value $793,701

Last Listing Agent William Maltbie MALTBIE REALTY GROUP

9462 Emerald Berry Dr, Oakland, FL 34787

/55
Est $484,518 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,705 Sq Ft
16946 Oakboro St, Oakland, FL 34787

16946 Oakboro St, Oakland, FL 34787

/60
$2,160,000 Pending
- 5 Beds
- 6 Baths
- 6,141 Sq Ft
1017 Johns Point Dr, Oakland, FL 34787

Under contract-accepting backup offers. A rare lakefront estate on one of Central Florida?s most celebrated lakes, John?s Lake. Positioned on nearly one acre in a private, gated enclave, this custom 5-bedroom, 6-bath residence offers sweeping open-water views, dramatic sunsets, and direct access to boating, jet skiing, and year-round fishing from its private dock. With approximately 250 feet of

peipei Qiao BAY STREET GROUP FLORIDA LLC

1017 Johns Point Dr, Oakland, FL 34787

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