Oakland, FL Homes

/57
$610,000

Under Contract
- 4 Beds
- 2.5 Baths
- 2,984 Sq Ft
3247 Buoy Cir, Oakland, FL 34787

Under contract-accepting backup offers. Space, style, and a true lake-community lifestyle come together in this thoughtfully designed home in the gated community of Lakeview Preserve. With a flexible floor plan, generous living spaces, and room to grow both inside and out, this home offers the perfect blend of comfort, functionality, and Florida living. The open-concept layout is designed for

Dana Vander Meer BLUE MARLIN REAL ESTATE

3247 Buoy Cir, Oakland, FL 34787
/2
$875,000

Sold Jul 21, 2026

1269 Ridge Lake Way, Oakland, FL 34760
- Land
- 10,454 Sq Ft
- $3,645,833 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

1269 Ridge Lake Way, Oakland, FL 34760

/2
Est $549,345

Not Listed For Sale

11015 Bostwick Aly, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 2023
11015 Bostwick Aly, Oakland, FL 34787

Last Sold Summary
- 4 Days On Market
Last Listing Agent Marcos Del Nero LA ROSA REALTY KISSIMMEE

/2
$637,325

New Construction Pending
- 4 Beds
- 3 Baths
- 2,102 Sq Ft
17138 Ingram Hills Aly, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley floorplan by Dream Finders Homes features 2,102 square feet of well-designed living space across two stories. This home includes 4 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

17138 Ingram Hills Aly, Oakland, FL 34787
/2
$735,000

Sold Oct 30, 2025

2340 Standing Rock Cir, Winter Garden, FL 34787
- 5 Beds
- 3 Baths
- 3,493 Sq Ft
- Built 2019
Last Sold Summary
- 3% Below List Price
- $210/SF
- 112 Days On Market
Current Estimated Value $748,001

Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

2340 Standing Rock Cir, Winter Garden, FL 34787

/2
Est $891,000

Not Listed For Sale

16207 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
- Built 2025
16207 Point Rock Dr, Oakland, FL 34787

Last Sold Summary
- 11 Days On Market
Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

/31
$569,000

$30K PRICE DROP
- 5 Beds
- 3.5 Baths
- 3,020 Sq Ft
706 Strihal Loop, Oakland, FL 34787

Virtually Staged. BRAND NEW ROOF! This five-bedroom, three-and-a-half-bathroom residence sits in a gated community with a new roof and architectural shingles, offering security and peace of mind. The property combines thoughtful interior finishes with direct access to some of the area's most desirable outdoor recreation opportunities.Inside, the kitchen features stainless steel appliances

Patrick D'Agostino GLORY INTL. REAL ESTATE CO

706 Strihal Loop, Oakland, FL 34787
/2
$519,000

Sold May 22, 2026

2618 Bobcat Chase Blvd, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,565 Sq Ft
- Built 2020
Last Sold Summary
- $332/SF
- 7 Days On Market
Current Estimated Value $514,057

Last Listing Agent Elena Santiago THE REAL ESTATE COLLECTION LLC

2618 Bobcat Chase Blvd, Oakland, FL 34787

/2
Est $365,742

Not Listed For Sale

1312 Painted Bunting Ave, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2020
1312 Painted Bunting Ave, Oakland, FL 34760

Last Sold Summary
- 86 Days On Market
Last Listing Agent Gavin Hatch SERHANT

/78
$2,550,000

$200K PRICE DROP
- 5 Beds
- 6 Baths
- 4,373 Sq Ft
812 Johns Point Dr, Oakland, FL 34787

Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

Any Alves WRA BUSINESS & REAL ESTATE

812 Johns Point Dr, Oakland, FL 34787
/2
$470,000

Sold Feb 14, 2026

17562 Northlake Grove Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,726 Sq Ft
- Built 2025
Last Sold Summary
- $272/SF
Current Estimated Value $467,000

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

17562 Northlake Grove Dr, Oakland, FL 34787

/2
Est $1,018,322

Not Listed For Sale

936 Allendale Ln, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,711 Sq Ft
- Built 2023
936 Allendale Ln, Winter Garden, FL 34787

Last Sold Summary
- 77 Days On Market
Last Listing Agent Ken Pozek REAL BROKER, LLC

/50
$1,725,000

$84K PRICE DROP
- 5 Beds
- 4 Baths
- 3,784 Sq Ft
906 Allendale Ln, Winter Garden, FL 34787

Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden.This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range,

Jurgita Blake CENTURY 21 CARIOTI

906 Allendale Ln, Winter Garden, FL 34787
/2
$395,000

Sold Nov 21, 2025

13322 Pontoon Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2023
Last Sold Summary
- 1% Below List Price
- $252/SF
- 46 Days On Market
Current Estimated Value $393,564

Last Listing Agent Denise Gregorie CLOCK TOWER REALTY

13322 Pontoon Rd, Oakland, FL 34787

/2
Est $1,079,900

Not Listed For Sale

1112 Sarah Mathews Dr, Oakland, FL 34787
- 5 Beds
- 6 Baths
- 3,956 Sq Ft
- Built 2025
1112 Sarah Mathews Dr, Oakland, FL 34787

Last Sold Summary
- 0 Days On Market
Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

/56
$655,990

$124K PRICE DROP
- 5 Beds
- 3 Baths
- 3,284 Sq Ft
8114 Sayings Dr, Winter Garden, FL 34787

Virtually Staged. Beautifully maintained 5-bedroom, 3-bath home offering approximately 3,300 sq. ft. in the highly sought-after Storey Grove community of Winter Garden. Situated on a premium conservation and water-view lot with no rear neighbors, this home offers exceptional privacy and peaceful views from the screened lanai with an outdoor sink. The bright, open floor plan features a spacious

Anna Shi LPT REALTY, LLC

8114 Sayings Dr, Winter Garden, FL 34787
/2
$1,260,826

Sold Sep 26, 2025

1143 Bulwark Oaks Ln, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,046 Sq Ft
- Built 2025
Last Sold Summary
- $414/SF
Current Estimated Value $1,288,744

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

1143 Bulwark Oaks Ln, Oakland, FL 34787

/2
Est $365,514

Not Listed For Sale

1324 Painted Bunting Ave, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2019
1324 Painted Bunting Ave, Oakland, FL 34760

Last Sold Summary
- 50 Days On Market
Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

/41
$454,900

$3K PRICE DROP Under Contract
- 3 Beds
- 2.5 Baths
- 1,838 Sq Ft
2247 White Feather Loop, Oakland, FL 34787

Under contract-accepting backup offers. Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 square feet of thoughtfully designed living space with an open and functional floor plan that truly stands out in the neighborhood.From the moment you arrive, you’ll notice the

Carolina Cote Munoz LPT REALTY, LLC

2247 White Feather Loop, Oakland, FL 34787
/2
$390,000

Sold Aug 10, 2026

16461 Prairie School Dr, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 1,768 Sq Ft
- Built 2022
Last Sold Summary
- 8% Below List Price
- $221/SF
- 41 Days On Market
Current Estimated Value $398,881

Last Listing Agent Jhoana Loyo Urrutia LPT REALTY, LLC

16461 Prairie School Dr, Oakland, FL 34787

/2
Not Listed For Sale

16465 Hamlin View St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,836 Sq Ft
- Built 2025
16465 Hamlin View St, Oakland, FL 34787

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

/32
$675,900
- 4 Beds
- 2.5 Baths
- 3,652 Sq Ft
239 Largovista Dr, Oakland, FL 34787

Welcome to this beautiful and impeccably maintained 4-bedroom, 2.5-bath home in the desirable Johns Landing community of Oakland! This exceptional family home offers space, comfort, flexibility, and all the features buyers are looking for. The spacious floor plan includes a large bonus room and an additional room currently being used as an office, which can easily be converted back to a bedroom

Cathy Heighter-Moore APPROVED PATRIOT REALTY LLC

239 Largovista Dr, Oakland, FL 34787
/2
$537,000

Sold Feb 24, 2026

326 Largovista Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 3,182 Sq Ft
- Built 2004
Last Sold Summary
- 23% Below List Price
- $169/SF
- 135 Days On Market
Current Estimated Value $604,592

Last Listing Agent Chris Sanford EXP REALTY LLC

326 Largovista Dr, Oakland, FL 34787

/2
Not Listed For Sale

16459 Hamlin View St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,078 Sq Ft
- Built 2024
16459 Hamlin View St, Oakland, FL 34787

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

/10
$2,575,000

New Construction
- 5 Beds
- 7 Baths
- 4,210 Sq Ft
1155 Prado Ln, Winter Garden, FL 34787

Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless

Alexis Anderson REGENCY REAL ESTATE LLC

1155 Prado Ln, Winter Garden, FL 34787
/2
$642,120

Sold Oct 16, 2025

5810 Fabry St, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- Built 2025
Last Sold Summary
- $251/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

5810 Fabry St, Oakland, FL 34787

/2
Est $390,745

Not Listed For Sale

16926 Reseda Aly, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2020
16926 Reseda Aly, Oakland, FL 34787

Last Sold Summary
- 63 Days On Market
Last Listing Agent Eve Metlis WATSON REALTY CORP

/33
$787,000

Under Contract Pre-Foreclosure
- 5 Beds
- 4 Baths
- 2,840 Sq Ft
16771 Oakboro St, Oakland, FL 34787

Under contract-accepting backup offers. Virtually Staged. Built in 2020, this beautifully designed five-bedroom, four-bathroom home offers 2,840 square feet of thoughtfully planned living space in the sought-after Waterleigh community. The private outdoor retreat features a heated saltwater pool, screened enclosure, and covered lanai, perfect for year-round relaxation and entertaining.Inside,

Misty Griffin DOUGLAS ELLIMAN

16771 Oakboro St, Oakland, FL 34787
/2
$826,850

Sold Jan 27, 2026

4684 Golden Birch Ave, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,810 Sq Ft
- Built 2026
Last Sold Summary
- $217/SF
Current Estimated Value $837,744

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

4684 Golden Birch Ave, Oakland, FL 34787

/2
Not Listed For Sale

1113 Prado Ln, Oakland, FL 34787
1113 Prado Ln, Oakland, FL 34787

Last Sold Summary
- 0 Days On Market
Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

/2
$606,440

New Construction Pending
- 4 Beds
- 3 Baths
- 2,102 Sq Ft
17156 Ingram Hills Aly, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

17156 Ingram Hills Aly, Oakland, FL 34787
/2
$635,000

Sold Dec 01, 2025

546 Egret Place Dr, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,156 Sq Ft
- Built 2014
Last Sold Summary
- 2% Below List Price
- $201/SF
- 44 Days On Market
Current Estimated Value $658,707

Last Listing Agent Matthew Blanco MARK SPAIN REAL ESTATE

546 Egret Place Dr, Oakland, FL 34787

/2
Est $381,247

Not Listed For Sale

1509 Sweet Apple St, Oakland, FL 34787
- 3 Beds
- 3 Baths
- 1,809 Sq Ft
- Built 2019
1509 Sweet Apple St, Oakland, FL 34787

Last Sold Summary
- 144 Days On Market
Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

/12
$799,999
- 5 Beds
- 3 Baths
- 3,413 Sq Ft
16 Oakland Pointe Cir, Oakland, FL 34760

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new

Jack Keller JACK KELLER INC

16 Oakland Pointe Cir, Oakland, FL 34760
/2
$787,000

Sold Feb 23, 2026

3375 Hanging Tide St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,741 Sq Ft
- Built 2021
Last Sold Summary
- 9% Below List Price
- $287/SF
- 62 Days On Market
Current Estimated Value $776,246

Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

3375 Hanging Tide St, Oakland, FL 34787

/2
Est $878,051

Not Listed For Sale

932 Tilden Oaks Trail, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,362 Sq Ft
- Built 2021
932 Tilden Oaks Trail, Winter Garden, FL 34787

Last Sold Summary
- 6 Days On Market
Last Listing Agent Tony Marino CHARLES RUTENBERG REALTY ORLANDO

/59
$515,000

$30K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,204 Sq Ft
2259 White Feather Loop, Oakland, FL 34787

INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by

Chuck Burt YOUNG REAL ESTATE

2259 White Feather Loop, Oakland, FL 34787
/2
$925,000

Sold Jul 01, 2026

4632 Golden Birch Ave, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 4,313 Sq Ft
- Built 2025
Last Sold Summary
- 12% Below List Price
- $214/SF
- 189 Days On Market
Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4632 Golden Birch Ave, Oakland, FL 34787

/2
Not Listed For Sale

3119 Armstrong Ave, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 1,867 Sq Ft
- Built 2025
3119 Armstrong Ave, Oakland, FL 34787

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

/3
$674,000

New Construction Pending
- 4 Beds
- 3.5 Baths
- 2,508 Sq Ft
12919 Westhaven Oak Dr, Oakland, FL 34787

Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026Bungalow featuring a private in-law suite above a detached 2-car garage. A charming covered entry welcomes you into an open and expansive floor plan with seamless flow between the great room, kitchen, and dining area — ideal for both everyday living and entertaining.Enjoy

Dayene Grubert ORLANDO TBI REALTY LLC

12919 Westhaven Oak Dr, Oakland, FL 34787

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