Oakland, FL Homes

/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
$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
Current Estimated Value $2,246,297

Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

530 Largovista Dr, Oakland, FL 34787

/2
Est $797,948 Not Listed For Sale

1191 Wilder Oaks Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
- Built 2024
1191 Wilder Oaks Way, Oakland, FL 34787

Last Sold Summary
- $357/SF
- 96 Days On Market
Last Sold Price $799,000

Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC

/3
$411,995 Pending
- 3 Beds
- 2.5 Baths
- 1,863 Sq Ft
13873 Easdale Aly, Oakland, FL 34787

Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 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

Dayene Grubert ORLANDO TBI REALTY LLC

13873 Easdale Aly, 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 $457,677

Last Listing Agent Joshua Earley OPTIMA ONE REALTY, INC.

2163 White Feather Loop, Winter Garden, FL 34787

/48
Est $781,399 Not Listed For Sale

5121 Breezy Acres St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,724 Sq Ft
- Built 2021
5121 Breezy Acres St, Oakland, FL 34787

Last Sold Summary
- 7% Below List Price
- $308/SF
- 3 Days On Market
Last Sold Price $840,000

Last Listing Agent Teresa White PREMIER SOTHEBYS INT'L REALTY

/11
$1,295,000
- Land
- 1.26 Acres
- $1,027,778 per Acre
556 Walker St, Oakland, FL 34760

LAST DEVELOPER OWNED LOT IN BILEY PHASE 1. Lakefront homesite with the ability to add your own private dock. 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

Chocky Burks CORCORAN PREMIER REALTY

556 Walker St, Oakland, FL 34760
/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 $799,270

Last Listing Agent Kathie Glass BHHS FLORIDA REALTY

1212 Civitas Way, Winter Garden, FL 34787

/55
Est $469,464 Not Listed For Sale

16946 Oakboro St, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,705 Sq Ft
- Built 2020
16946 Oakboro St, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $284/SF
- 10 Days On Market
Last Sold Price $485,000

Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

/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
$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

/2
Est $483,406 Not Listed For Sale

14122 Frasier St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
- Built 2024
14122 Frasier St, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $278/SF
Last Sold Price $497,140

Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/32
$510,000
- 3 Beds
- 2.5 Baths
- 1,868 Sq Ft
15220 Blue Peacock Ln, Oakland, FL 34787

Welcome to this beautiful home featuring an open floor plan that blends comfort, style, and functionality. Filled with natural light, the spacious layout is perfect for both everyday living and entertaining. The inviting living area offers a warm setting for gatherings, while the modern kitchen boasts stainless steel appliances, abundant cabinetry, and generous counter space for the home chef.

DENILEY VALDES TALENT REALTY SOLUTIONS

15220 Blue Peacock Ln, Oakland, FL 34787
/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 $938,098

Last Listing Agent Vivian Saavedra LPT REALTY, LLC

3179 Sailing Pier Ave, Oakland, FL 34787

/2
Est $472,763 Not Listed For Sale

11361 Great Rock St, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 1,992 Sq Ft
- Built 2024
11361 Great Rock St, Oakland, FL 34787

Last Sold Summary
- 2% Below List Price
- $241/SF
Last Sold Price $480,020

Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

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

Under contract-accepting backup offers. 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

Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

717 Strihal Loop, 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 $763,776 Not Listed For Sale

14211 Lanyard Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 3,038 Sq Ft
- Built 2024
14211 Lanyard Way, Oakland, FL 34787

Last Sold Summary
- 5% Below List Price
- $263/SF
- 65 Days On Market
Last Sold Price $800,000

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/38
$390,000
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
12043 Holystone St, Oakland, FL 34787

Motivated Seller “Seller is offering $5,000 toward buyer’s closing costs.” MOVE IN READY .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 a welcoming open concept as you immediately enter the foyer, with plenty of cabinet, double sink, granite countertops and a long

Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

12043 Holystone St, 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 $663,431

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

5826 Fabry St, Oakland, FL 34787

/2
Est $745,461 Not Listed For Sale

14199 Lanyard Way, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,065 Sq Ft
- Built 2024
14199 Lanyard Way, Oakland, FL 34787

Last Sold Summary
- 1% Below List Price
- $245/SF
- 185 Days On Market
Last Sold Price $749,407

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/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
$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

/69
Est $747,259 Not Listed For Sale

11168 Robert Frost Dr, Oakland, FL 34787
- 5 Beds
- 3 Baths
- 3,332 Sq Ft
- Built 2021
11168 Robert Frost Dr, Oakland, FL 34787

Last Sold Summary
- 10% Above List Price
- $204/SF
- 4 Days On Market
Last Sold Price $680,000

Last Listing Agent Iluska Kruse ORLANDO BROTHERS REAL ESTATE LLC

/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
$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
Current Estimated Value $496,295

Last Listing Agent Sonia Jenkins ORANGE REALTY PROFESSIONALS LLC

222 Largovista Dr, Oakland, FL 34787

/2
Est $753,540 Not Listed For Sale

16225 Silver Brook Way, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,950 Sq Ft
- Built 2024
16225 Silver Brook Way, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $263/SF
- 28 Days On Market
Last Sold Price $776,995

Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

$1,032,585 New Construction
- 5 Beds
- 4.5 Baths
- 3,894 Sq Ft
12904 Westhaven Oak Dr, Oakland, FL 34787

The Griffin's welcoming extended covered porch, and inviting covered entry and foyer, flow past the lovely dining room to the spacious great room and views of the desirable covered lanai beyond. The well-designed kitchen overlooks a bright casual dining area, and is highlighted by a large center island with breakfast bar, plenty of counter and cabinet space, and roomy walk-in pantry. The graceful

Toll Brothers, Inc. Builder

12904 Westhaven Oak 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

/2
Est $564,724 Not Listed For Sale

15129 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
- Built 2024
15129 Summer Harvest St, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $248/SF
Last Sold Price $579,655

Last Listing Agent Antonio Cardoso Desmarais TALENT REALTY SOLUTIONS

/64
$599,000
- 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
$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
Last Listing Agent Chandra Maraj CHARLES RUTENBERG REALTY ORLANDO

13193 Tollcross Way, Oakland, FL 34787

/2
Est $622,473 Not Listed For Sale

15022 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,789 Sq Ft
- Built 2024
15022 Summer Harvest St, Oakland, FL 34787

Last Sold Summary
- $224/SF
- 12 Days On Market
Last Sold Price $625,430

Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

/2
$605,455 Pending
- 4 Beds
- 3.5 Baths
- 2,520 Sq Ft
17144 Ingram Hills Aly, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Carter offers a well-designed living space with 3 bedrooms, 3.5 baths, and a 2-car garage. The open-concept layout features a spacious family room, a gourmet kitchen with a large island and pantry, and a dining area. The primary suite includes a luxurious bath and walk-in closet, while additional

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

17144 Ingram Hills Aly, 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 $792,871

Last Listing Agent Ron Howell, II EXP REALTY LLC

3182 Sailing Pier Ave, Oakland, FL 34787

/2
Est $562,227 Not Listed For Sale

15141 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,450 Sq Ft
- Built 2024
15141 Summer Harvest St, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $228/SF
Last Sold Price $558,990

Last Listing Agent Elaine Garcia GARCIA REALTY GROUP

/34
$565,000
- 4 Beds
- 3.5 Baths
- 2,477 Sq Ft
16140 Harbor Mist Aly, Oakland, FL 34787

Priced to sell — don't miss this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious

Jeanine Louis-Alcime EXP REALTY LLC

16140 Harbor Mist Aly, 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 $783,000

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

16107 Honey Harvest St, Oakland, FL 34787

/2
Est $802,651 Not Listed For Sale

1215 Wilder Oaks Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,247 Sq Ft
- Built 2024
1215 Wilder Oaks Way, Oakland, FL 34787

Last Sold Summary
- $356/SF
- 21 Days On Market
Last Sold Price $799,000

Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC

/23
$575,000
- Land
- 0.45 Acre
- $1,277,778 per Acre
514 N Pollard St, Winter Garden, FL 34787

Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

Alexis Anderson REGENCY REAL ESTATE LLC

514 N Pollard St, Winter Garden, FL 34787

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Florida Orange County Oakland

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