Oakland, FL Homes

/40
$3,295,000

New Construction
- 6 Beds
- 6.5 Baths
- 5,144 Sq Ft
312 Briley Ave, Oakland, FL 34760

Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern

Carolina Dumit CORCORAN PREMIER REALTY

312 Briley Ave, Oakland, FL 34760
/55
$499,990

Sold Feb 20, 2026

17621 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,791 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 9% Below List Price
- $279/SF
- 50 Days On Market
Current Estimated Value $502,000

Ashton Woods Northlake at Ovation - Estate

17621 Japonica Bloom Dr, Oakland, FL 34787

/2
Est $475,294

Not Listed For Sale

14047 Lochend Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 1,996 Sq Ft
- Built 2024
14047 Lochend Way, Oakland, FL 34787

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

/31
$414,900

Pending
- 3 Beds
- 2.5 Baths
- 1,503 Sq Ft
1321 Planted Pine St, Oakland, FL 34760

Under contract-accepting backup offers. Nestled in the highly desirable community of Longleaf at Oakland, this exquisite townhome is a blend of elegance and functionality. The open floor plan bathes the interior in natural light, creating a warm and inviting atmosphere. The kitchen, a modern culinary space, features stainless steel appliances, sleek granite countertops, and ample cabinet space.

Justin Cabral PROPERTY LOGIC RE

1321 Planted Pine St, Oakland, FL 34760
/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 $391,376

Last Listing Agent Cindy Brads COLDWELL BANKER REALTY

13298 Pontoon Rd, Oakland, FL 34787

/2
Est $478,280

Not Listed For Sale

9267 Gran Teatro Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
- Built 2024
9267 Gran Teatro Dr, Oakland, FL 34787

Last Sold Summary
- 82 Days On Market
Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

/62
$679,000

$10K PRICE DROP
- 4 Beds
- 3.5 Baths
- 2,686 Sq Ft
15174 Field Daisy Dr, Oakland, FL 34787

Welcome to this beautiful bungalow-style home in the highly desirable Osprey Ranch community in Winter Garden! Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, this thoughtfully designed residence offers comfort, style, and functionality for the whole family.Located just minutes from Disney, shopping, dining, and major highways, this home combines convenience with a peaceful

Guilherme Garcia Cavalcante REALTY ONE GROUP INSPIRATION

15174 Field Daisy Dr, Oakland, FL 34787
/19
$445,999

Sold Mar 23, 2026

12748 Brodlove Ln, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
- Built 2022
Last Sold Summary
- $248/SF
- 30 Days On Market
Current Estimated Value $452,606

Last Listing Agent Mayra Rivas Acevedo Casa Sol Realty LLC

12748 Brodlove Ln, Oakland, FL 34787

/8
Est $1,181,036

Not Listed For Sale

1080 Canyon Creek Trail, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,852 Sq Ft
- Built 2024
1080 Canyon Creek Trail, Oakland, FL 34787

Last Sold Summary
- 15 Days On Market
Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

/6
$2,210,000

New Construction Pending
- 5 Beds
- 5.5 Baths
- 4,204 Sq Ft
1164 Prado Ln, Oakland, FL 34787

Pre-Construction. To be built. Welcome to one of the most anticipated new builds at Grove at the Harvest District — the Sunburst Plan by Davila Homes, a luxury new construction masterpiece designed for those who prioritize space, style, and lifestyle.Spanning 4,204 livable square feet with 5,665 total square feet, this stunning 5-bedroom, 5.5-bath estate is thoughtfully designed from the

Alexis Anderson REGENCY REAL ESTATE LLC

1164 Prado Ln, Oakland, FL 34787
/25
$665,000

Sold Sep 11, 2026

4620 Scenic Woods Dr, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
- Built 2026
Last Sold Summary
- 5% Below List Price
- $307/SF
- 44 Days On Market
Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4620 Scenic Woods Dr, Oakland, FL 34787

/2
Est $1,015,821

Not Listed For Sale

1056 Sadler Oaks Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,711 Sq Ft
- Built 2024
1056 Sadler Oaks Way, Oakland, FL 34787

Last Sold Summary
- 129 Days On Market
Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

/25
$765,000

$15K PRICE DROP Pending
- 5 Beds
- 4 Baths
- 2,840 Sq Ft
8807 Sonoma Coast Dr, Oakland, FL 34787

Welcome to resort-style living in Waterleigh, one of Horizon West's most sought-after master-planned communities. This stunning 5-bedroom, 4-bathroom home offers the perfect blend of space, serenity, and lifestyle, all anchored by breathtaking pond views right from your own backyard. Step outside to your private patio and take in the tranquil water view, the ideal backdrop for morning coffee,

Kerstin Crow LOKATION

8807 Sonoma Coast Dr, 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 $649,670

Last Listing Agent Keith Packey RE/MAX TITANIUM GROUP

410 E Gulley Ave, Oakland, FL 34760

/2
Not Listed For Sale

Unlisted Address
- 4 Beds
- 5 Baths
- 3,794 Sq Ft
- Built 2025
Unlisted Address

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

/33
$364,500
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
1511 Sweet Apple St, Oakland, FL 34787

Welcome to 1511 Sweet Apple Street, a well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect

Ali Yche SOUTHERN PRESTIGE REALTY INC

1511 Sweet Apple St, Oakland, 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
Current Estimated Value $700,000

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

16108 Honey Harvest St, Oakland, FL 34787

/2
Est $629,239

Not Listed For Sale

13007 Tollcross Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,160 Sq Ft
- Built 2024
13007 Tollcross Way, Oakland, FL 34787

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

/3
$2,098,000

New Construction $100K PRICE INCREASE
- 4 Beds
- 4 Baths
- 4,557 Sq Ft
1258 Ridge Lake Way, Winter Garden, FL 34787

Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The

Chris Herlihy NEW HOMES REAL ESTATE, INC.

1258 Ridge Lake Way, Winter Garden, FL 34787
/2
$730,000

Sold Jun 01, 2026

5715 Orange Orchard Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
- Built 2021
Last Sold Summary
- $326/SF
- 1 Day On Market
Current Estimated Value $722,366

Last Listing Agent Caroline De Castro Marcellini COMPASS FLORIDA, LLC

5715 Orange Orchard Dr, Oakland, FL 34787

/2
Est $801,922

Not Listed For Sale

9462 Emerald Berry Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,211 Sq Ft
- Built 2024
9462 Emerald Berry Dr, Oakland, FL 34787

Last Sold Summary
- 62 Days On Market
Last Listing Agent William Maltbie MALTBIE REALTY GROUP

/24
$995,900

$995K PRICE INCREASE
- 5 Beds
- 4 Baths
- 3,951 Sq Ft
219 Largovista Dr, Oakland, FL 34787

Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout.Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium

Durval Da Rocha NOVARE REAL ESTATE LLC

219 Largovista Dr, Oakland, FL 34787
/2
$2,675,000

Sold Oct 30, 2025

1179 Prado Ln, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 4,561 Sq Ft
- Built 2026
Last Sold Summary
- $586/SF
Current Estimated Value $2,449,500

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

1179 Prado Ln, Oakland, FL 34787

/2
Est $830,783

Not Listed For Sale

5590 Orange Orchard Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,853 Sq Ft
- Built 2021
5590 Orange Orchard Dr, Oakland, FL 34787

Last Sold Summary
- 3 Days On Market
Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

/3
$409,990

New Construction
- 3 Beds
- 2.5 Baths
- 1,715 Sq Ft
Porter Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

Dream Finders Homes Builder

14229 Lanyard Way Unit 36452383, Oakland, FL 34787
/2
$57,000

Sold Apr 29, 2026

121 S Nixon St, Oakland, FL 34760
- Land
- 4,791 Sq Ft
- $518,182 per Acre
Last Sold Summary
- 24% Below List Price
- 181 Days On Market
Current Estimated Value $164,052

Last Listing Agent Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

121 S Nixon St, Oakland, FL 34760

/2
Est $781,740

Not Listed For Sale

14205 Lanyard Way, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,076 Sq Ft
- Built 2024
14205 Lanyard Way, Oakland, FL 34787

Last Sold Summary
- 0 Days On Market
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/47
$199,000

Under Contract
- 2 Beds
- 1 Bath
- 722 Sq Ft
320 W Sadler Ave, Oakland, FL 34760

Under contract-accepting backup offers. Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town

Sibelys Alvarez OFFERPAD BROKERAGE FL LLC

320 W Sadler Ave, Oakland, FL 34760
/2
$745,000

Sold Jul 30, 2026

931 Kylee Aly, Winter Garden, FL 34787
- 4 Beds
- 4 Baths
- 2,831 Sq Ft
- Built 2022
Last Sold Summary
- 10% Below List Price
- $263/SF
- 46 Days On Market
Current Estimated Value $772,145

Last Listing Agent Matt McKee COMPASS FLORIDA LLC

931 Kylee Aly, Winter Garden, FL 34787

/2
Est $1,421,404

Not Listed For Sale

921 Bradenville Ln, Winter Garden, FL 34787
- 4 Beds
- 4 Baths
- 3,468 Sq Ft
- Built 2022
921 Bradenville Ln, Winter Garden, FL 34787

Last Sold Summary
- 49 Days On Market
Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

/55
$540,000
- 4 Beds
- 2.5 Baths
- 2,486 Sq Ft
223 Largovista Dr, Oakland, FL 34787

Virtually Staged. Welcome to this spacious two-story home located in the highly desirable gated community of John's Landing in beautiful Oakland. Offering 4 bedrooms, 2.5 bathrooms, and over 2486 square feet of living space, this home combines generous room sizes, a functional layout, and an exceptional location to create the perfect place to call home. Step inside to discover multiple living and

Corey Smallman MARKET CONNECT REALTY LLC

223 Largovista Dr, Oakland, FL 34787
/37
$449,990

Sold Nov 07, 2025

17681 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,577 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $285/SF
- 9 Days On Market
Current Estimated Value $3,360,085

Ashton Woods Northlake at Ovation - Estate

17681 Japonica Bloom Dr, Oakland, FL 34787

/2
Est $783,939

Not Listed For Sale

1404 High Springs Ln, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 3,059 Sq Ft
- Built 2020
1404 High Springs Ln, Winter Garden, FL 34787

Last Sold Summary
- 92 Days On Market
Last Listing Agent Kaitlin LaMacchia DENIZ REALTY PARTNERS LLC

/4
$1,975,000

New Construction
- 5 Beds
- 5.5 Baths
- 3,596 Sq Ft
1106 Sarah Mathews Dr, Oakland, FL 34787

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

Heather Spirazza REGENCY REAL ESTATE LLC

1106 Sarah Mathews Dr, Oakland, FL 34787
/2
$588,000

Sold Jul 15, 2026

12554 Westhaven Oak Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
- Built 2025
Last Sold Summary
- 13% Below List Price
- $214/SF
- 261 Days On Market
Current Estimated Value $593,104

Last Listing Agent Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

12554 Westhaven Oak Dr, Oakland, FL 34787

/2
Est $649,768

Not Listed For Sale

1382 Foltz Loop, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,268 Sq Ft
- Built 2022
1382 Foltz Loop, Oakland, FL 34787

Last Sold Summary
- 69 Days On Market
Last Listing Agent Brooke Cangro RE/MAX 200 REALTY

/22
$449,000

$20K PRICE DROP
- 3 Beds
- 3 Baths
- 1,808 Sq Ft
14014 Scarlet Aster Aly, Oakland, FL 34787

***** PRICE REDUCED *****Rare Dual Owner's Suite Townhome — Priced to Move, Near DisneyThis 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months

Jarrett Brown LPT REALTY, LLC

14014 Scarlet Aster Aly, Oakland, FL 34787
/2
$2,417,730

Sold Aug 27, 2026

1137 Prado Ln, Oakland, FL 34787
- 5 Beds
- 5.5 Baths
- 4,527 Sq Ft
- Built 2026
Last Sold Summary
- 1% Above List Price
- $534/SF
- 0 Days On Market
Current Estimated Value $2,158,667

Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

1137 Prado Ln, Oakland, FL 34787

/2
Est $812,332

Not Listed For Sale

9516 Emerald Berry Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,211 Sq Ft
- Built 2024
9516 Emerald Berry Dr, Oakland, FL 34787

Last Sold Summary
- 13 Days On Market
Last Listing Agent William Maltbie MALTBIE REALTY GROUP

/4
$498,990

New Construction
- 3 Beds
- 2.5 Baths
- 1,836 Sq Ft
Brantley Plan at Serenade at Ovation - Bungalows, 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

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