Oakland, FL Homes

/48
Est $773,802 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

/77
$489,900 Pending
- 3 Beds
- 2.5 Baths
- 1,909 Sq Ft
2029 White Feather Loop, Winter Garden, FL 34787

Under contract-accepting backup offers. Welcome to an exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bed, 2.5-bath residence boasts an open and functional floor plan that truly sets it apart from others in the neighborhood. With approximately 1,909 sq. ft. of thoughtfully laid-out living space, this home offers modern comfort with everyday

Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

2029 White Feather Loop, Winter Garden, FL 34787
/2
$460,000 Sold Sep 23, 2025

17055 Wynford Ln, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,345 Sq Ft
- Built 2021
Last Sold Summary
- 16% Below List Price
- $196/SF
- 160 Days On Market
Current Estimated Value $479,006

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

17055 Wynford Ln, Oakland, FL 34787

/55
Est $485,780 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,705 Sq Ft
16946 Oakboro St, Oakland, FL 34787

16946 Oakboro St, 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
$580,109 Sold Dec 23, 2025

17597 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,791 Sq Ft
- Built 2025
Last Sold Summary
- $324/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

17597 Japonica Bloom Dr, Oakland, FL 34787

/2
Est $502,140 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
14122 Frasier St, Oakland, FL 34787

14122 Frasier St, 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
$500,000 Sold Apr 08, 2025

16257 Prairie School Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,070 Sq Ft
- Built 2021
Last Sold Summary
- 3% Below List Price
- $242/SF
- 54 Days On Market
Current Estimated Value $496,846

Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC

16257 Prairie School Dr, Oakland, FL 34787

/2
Est $491,683 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,992 Sq Ft
11361 Great Rock St, Oakland, FL 34787

11361 Great Rock St, 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
$785,000 Sold Oct 24, 2025

16152 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 2,866 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $274/SF
- 48 Days On Market
Current Estimated Value $785,000

Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

16152 Point Rock Dr, Oakland, FL 34787

/2
Est $828,816 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,038 Sq Ft
14211 Lanyard Way, Oakland, FL 34787

14211 Lanyard Way, Oakland, FL 34787

/66
$2,300,000 Pending
- 4 Beds
- 6 Baths
- 3,902 Sq Ft
1118 Sarah Mathews Dr, Oakland, FL 34787

Under contract-accepting backup offers. Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept

Alexis Anderson REGENCY REAL ESTATE LLC

1118 Sarah Mathews Dr, Oakland, FL 34787
/52
$580,000 Sold Oct 31, 2025

2642 Bobcat Chase Blvd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,811 Sq Ft
- Built 2019
Last Sold Summary
- 6% Below List Price
- $320/SF
- 38 Days On Market
Current Estimated Value $577,589

Last Listing Agent Johna Jennings Coastal Life Properties LLC

2642 Bobcat Chase Blvd, Oakland, FL 34787

/2
Est $743,123 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,065 Sq Ft
14199 Lanyard Way, Oakland, FL 34787

14199 Lanyard Way, Oakland, FL 34787

/3
$461,995 New Construction
- 3 Beds
- 2.5 Baths
- 1,863 Sq Ft
13873 Easdale Aly, Oakland, FL 34787

Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 2026. Our Crowley Townhome features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual

Alicea Salgado ORLANDO TBI REALTY LLC

13873 Easdale Aly, Oakland, FL 34787
/2
$900,000 Sold Sep 12, 2025

619 Largovista Dr, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,728 Sq Ft
- Built 2005
Last Sold Summary
- 9% Below List Price
- $241/SF
- 52 Days On Market
Current Estimated Value $901,764

Last Listing Agent Farhad Haniff EXP REALTY LLC

619 Largovista Dr, Oakland, FL 34787

/69
Est $745,189 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,332 Sq Ft
11168 Robert Frost Dr, Oakland, FL 34787

11168 Robert Frost Dr, Oakland, 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
/2
$914,390 Sold Nov 25, 2025

4649 Golden Birch Ave, Oakland, FL 34787
- 5 Beds
- 5 Baths
- 4,272 Sq Ft
- Built 2025
Last Sold Summary
- $214/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4649 Golden Birch Ave, Oakland, FL 34787

/2
Est $782,484 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,950 Sq Ft
16225 Silver Brook Way, Oakland, FL 34787

16225 Silver Brook Way, Oakland, FL 34787

/38
$395,000
- 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 offers

Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

12043 Holystone St, Oakland, FL 34787
/2
$400,000 Sold Aug 18, 2025

5693 Meditation Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,795 Sq Ft
- Built 2025
Last Sold Summary
- 11% Below List Price
- $223/SF
- 31 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

5693 Meditation Dr, Oakland, FL 34787

/2
Est $634,857 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 2,789 Sq Ft
15022 Summer Harvest St, Oakland, FL 34787

15022 Summer Harvest St, Oakland, FL 34787

/18
$895,000
- Land
- 0.89 Acre
- $1,005,618 per Acre
537 N Pollard St, Winter Garden, FL 34787

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 personal oasis—whether that’s a timeless farmhouse, a

Blaine Dooley REGENCY REAL ESTATE LLC

537 N Pollard St, Winter Garden, FL 34787
/2
$653,240 Sold Jul 30, 2025

5664 Vinyasa Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,650 Sq Ft
- Built 2025
Last Sold Summary
- $247/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

5664 Vinyasa Rd, Oakland, FL 34787

/2
Est $602,280 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,450 Sq Ft
15141 Summer Harvest St, Oakland, FL 34787

15141 Summer Harvest 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
/36
$751,000 Sold Oct 03, 2025

16041 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,837 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $265/SF
- 26 Days On Market
Taylor Morrison Harvest at Ovation

16041 Honey Harvest St, Oakland, FL 34787

/2
Est $852,349 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,247 Sq Ft
1215 Wilder Oaks Way, Oakland, FL 34787

1215 Wilder Oaks Way, Oakland, FL 34787

/28
$1,775,000 Pending
- 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
$695,000 Sold Sep 22, 2025

1281 Ridge Lake Way, Winter Garden, FL 34787
- Land
- 0.39 Acre
- $1,782,051 per Acre
Last Sold Summary
- 13% Below List Price
- 99 Days On Market
Last Listing Agent Samantha Andrade SERHANT

1281 Ridge Lake Way, Winter Garden, FL 34787

/2
Est $520,066 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,985 Sq Ft
14114 Frasier St, Oakland, FL 34787

14114 Frasier St, Oakland, FL 34787

/64
$625,000
- 3 Beds
- 2.5 Baths
- 1,906 Sq Ft
13067 Tollcross Way, Oakland, FL 34787

Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to

Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

13067 Tollcross Way, Oakland, FL 34787
/2
$883,656 Sold Sep 08, 2025

16089 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,837 Sq Ft
- Built 2025
Last Sold Summary
- $311/SF
Current Estimated Value $873,000

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

16089 Honey Harvest St, Oakland, FL 34787

/2
Est $525,712 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,114 Sq Ft
14078 Frasier St, Oakland, FL 34787

14078 Frasier 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
/2
$2,275,000 Sold Nov 24, 2025

530 Largovista Dr, Oakland, FL 34787
- 5 Beds
- 5 Baths
- 4,798 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $474/SF
- 110 Days On Market
Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

530 Largovista Dr, Oakland, FL 34787

/2
Est $1,398,565 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,747 Sq Ft
100 Millholland St, Oakland, FL 34760

100 Millholland St, Oakland, FL 34760

Showing Results 241 - 280, Page 7 of 18

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