Oakland, FL Homes

/2
$545,000 Sold Jun 16, 2025
- 2,000 Sq Ft
- $272/SF
- 12 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2017
1757 Standing Rock Cir, Oakland, FL 34787

Stunning Former Model Home in Oakland Trails – Minutes from Downtown Winter Garden!Welcome to this beautifully upgraded 3-bedroom, 2.5-bathroom former model home located in the highly desirable Oakland Trails community. Situated in the heart of Oakland and just moments from the vibrant Winter Garden Downtown District, this 2,000 sq ft single-story home perfectly combines elegance, comfort, and

Shannon Christian EXP REALTY LLC

1757 Standing Rock Cir, Oakland, FL 34787

/2
Est $583,866 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

/55
$415,000 Pending
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
2203 Gopher Tortoise Terrace, Oakland, FL 34787

Under contract-accepting backup offers. .**BACK ON THE MARKET**Welcome to this exceptionally appointed town home located in Longleaf at Oakland in Oakland, Florida. This charming residence offers 3 bedrooms and 2.5 bathrooms, perfectly designed with an open-concept layout that features stylish laminate flooring in the living and dining areas. The kitchen is truly the heart of the home, boasting

Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

2203 Gopher Tortoise Terrace, Oakland, FL 34787
/2
$510,000 Sold Jun 13, 2025
- 1,689 Sq Ft
- $302/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 2023
17847 Adrift Rd, Oakland, FL 34787

WELCOME HOME to this beautiful 3-bedroom, 2-bathroom gem nestled in the heart of the highly sought-after Horizon West community of Waterleigh. Thoughtfully designed with a modern open floorplan, this home features stunning wall paneling in the living room that adds a contemporary flair, and custom shelving in both the master bedroom closet and laundry room for optimal organization. The fully

Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

17847 Adrift Rd, Oakland, FL 34787

/2
Est $544,062 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,094 Sq Ft
14387 Braemar St, Oakland, FL 34787

14387 Braemar St, Oakland, FL 34787

/61
$739,000 Pending
- 5 Beds
- 4.5 Baths
- 3,725 Sq Ft
4528 Gliding Wave St, Oakland, FL 34787

Under contract-accepting backup offers. VA assumable loan available, a great opportunity for eligible buyers. Welcome to 4528 Gliding Wave Street in Winter Garden. This Pulte Yorkshire model 5-bedroom, 4.5-bathroom home was built in 2022 and still feels brand new. With two stories of living space, there’s plenty of room for everyone to spread out, whether you need multiple bedrooms, a home

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

4528 Gliding Wave St, Oakland, FL 34787
/2
$965,000 Sold Jun 12, 2025
- 4,693 Sq Ft
- $206/SF
- 5 Days On Market
- 6 Beds
- 5 Baths
- Built 2013
427 Egret Place Dr, Oakland, FL 34787

Embrace the Florida lifestyle in this spacious, beautifully maintained home designed for both comfort and entertaining. With generous living areas inside and plenty of room to enjoy the outdoors, there’s space for everyone to spread out and make lasting memories. Ideally located in one of Winter Garden’s most sought-after communities, Johns Lake Pointe, this is a home that truly has it all. From

Denise Gregorie CLOCK TOWER REALTY

427 Egret Place Dr, Oakland, FL 34787

/56
Est $806,111 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,688 Sq Ft
5633 Orange Orchard Dr, Oakland, FL 34787

5633 Orange Orchard Dr, Oakland, FL 34787

/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
$660,000 Sold Jun 12, 2025
- 1,889 Sq Ft
- $349/SF
- 96 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
13672 Fresh Ivy St, Oakland, FL 34787

Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis will offer an

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

13672 Fresh Ivy St, Oakland, FL 34787

/34
Est $425,242 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,513 Sq Ft
9085 Legado Dr, Oakland, FL 34787

9085 Legado Dr, Oakland, FL 34787

/44
$575,000 Open Sat 12PM - 3PM
- 4 Beds
- 3.5 Baths
- 2,552 Sq Ft
8001 Sayings Dr, Winter Garden, FL 34787

Nestled on a spacious corner lot in the highly desirable community of Storey Grove, this stunning 4 bedroom, 3.5 bathroom home is move-in ready and packed with charm, functionality, and modern finishes throughout. From the moment you arrive, you'll be drawn in by the lush landscaping and the convenience of a rear detached 2-car garage offering plenty of storage. Step inside to discover pristine

Shanta Navarro KELLER WILLIAMS ADVANTAGE III

8001 Sayings Dr, Winter Garden, FL 34787
/2
$455,000 Sold Jun 11, 2025
- 1,579 Sq Ft
- $288/SF
- 185 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
13418 Princess St, Oakland, FL 34787

All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis will offer an abundance of resort-style

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

13418 Princess St, Oakland, FL 34787

/26
Est $591,395 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
15169 Summer Harvest St, Oakland, FL 34787

15169 Summer Harvest St, Oakland, FL 34787

/60
$670,000
- 5 Beds
- 3 Baths
- 2,916 Sq Ft
3318 Current Ave, Oakland, FL 34787

Welcome to your dream home in the highly sought-after Lakeview Preserve, a gated community nestled near the shores of Johns Lake in Winter Garden. This beautifully appointed residence offers spacious and flexible living with 5 bedrooms and 3 full bathrooms, including a convenient guest suite or office on the first floor.Step inside to discover modern tile flooring throughout the main level, a

Geoffrey Lopez II RADIUS REALTY GROUP LLC

3318 Current Ave, Oakland, FL 34787
/2
$719,000 Sold Jun 05, 2025
- 2,113 Sq Ft
- $340/SF
- 97 Days On Market
- 4 Beds
- 3 Baths
- Built 2022
17858 Adrift Rd, Oakland, FL 34787

Prepare to be impressed with this nearly new Bellmore model home in the Waterleigh community. This lakefront beauty offers a picturesque water view with incredible sunsets and extra large backyard, perfect for relaxing or entertaining. The one-story home features 4 bedrooms, 3 full baths, and an open floor plan. The owners have upgraded and screened the oversized patio to enjoy the backyard

John R. Gordon EXP REALTY LLC

17858 Adrift Rd, Oakland, FL 34787

/31
Est $466,519 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
16287 Prairie School Dr, Oakland, FL 34787

16287 Prairie School Dr, Oakland, FL 34787

/44
$645,000
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
9576 Jacques Alley, Oakland, FL 34787

Stunning 2-Story Home with Payed off Solar System, Designer Upgrades, and A-Rated Schools in Waterleigh – Winter Garden!Welcome to this beautifully maintained 3-bedroom, 2.5-bath home featuring a versatile den/flex space—perfect for a home office, gym, or media room. The open-concept kitchen is a chef’s dream, showcasing modern wood cabinetry, waterfall stone island with under-cabinet and

Claudio Maciel NOVA REAL ESTATE SERVICES INC

9576 Jacques Alley, Oakland, FL 34787
/2
$410,000 Sold Jun 04, 2025
- Land
- 0.31 Acre
- $1,322,581 per Acre
- 9 Days On Market
0 N Daniels St, Oakland, FL 34760

Discover this RARE 0.31-acre residential lot located in the charming town of Oakland, one of the most desirable and rapidly appreciating areas in West Central Florida. Just a few blocks from Oakland’s historic downtown, this property is set on picturesque unpaved and stone roads, adding a unique character and peaceful atmosphere to the neighborhood.Oakland is known for its warm community feel,

Roberta Melo SELECTA REALTY LLC

0 N Daniels St, Oakland, FL 34760

/51
Est $418,280 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
12032 Holystone St, Oakland, FL 34787

12032 Holystone St, Oakland, FL 34787

/32
$1,450,000
- 3 Beds
- 3.5 Baths
- 2,502 Sq Ft
101 N Starr St, Oakland, FL 34760

Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious

Evan Gfeller BHHS FLORIDA REALTY

101 N Starr St, Oakland, FL 34760
/2
$2,098,500 Sold Jun 04, 2025
- 3,956 Sq Ft
- $530/SF
- 0 Days On Market
- 5 Beds
- 6 Baths
- Built 2025
1112 Sarah Mathews Dr, Oakland, FL 34787

Pre-Construction. To be built. Discover the perfect blend of old-world charm and modern luxury in this stunning custom French Farmhouse to be built by the renowned Pioneer Builders. Nestled in a picturesque setting, this home will feature classic European-inspired architecture, upscale design, and superior craftsmanship.Step through an arched entryway into an inviting open floor plan adorned with

Alexis Anderson REGENCY REAL ESTATE LLC

1112 Sarah Mathews Dr, Oakland, FL 34787

/38
Est $401,609 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
2212 Gopher Tortoise Terrace, Oakland, FL 34760

2212 Gopher Tortoise Terrace, Oakland, FL 34760

/32
$398,500
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
2120 Gopher Tortoise Terrace, Oakland, FL 34787

***Rare Financial Advantage- Low interest rate of 2.75% ASSUMABLE LOAN is available with a negotiated offer ***Welcome Home to this charming townhouse nestled in the highly sought-after community of Longleaf at Oakland! This impressive 3-bedroom, 2.5-bathroom residence offers the perfect blend of modern living and convenience, situated just moments away from the charming downtown area of

Julia D'Arts KEY CLASSIC REALTY LLC

2120 Gopher Tortoise Terrace, Oakland, FL 34787
/2
$648,000 Sold Jun 03, 2025
- 2,278 Sq Ft
- $284/SF
- 4 Days On Market
- 4 Beds
- 2 Baths
- Built 2020
2214 Bay Line Rd, Oakland, FL 34787

WELCOME HOME TO HULL ISLAND! This home offers a serene retreat for those looking for a blend of modern living mixed with nature. Step inside to an open floor plan featuring 4 Bedrooms, 2 Baths and a dedicated home office. The HIGH ceilings and windows create a light-filled and most inviting atmosphere. Gorgeous WOOD-LOOK tile flooring throughout this OPEN-CONCEPT floor plan. Chef's kitchen is a

Kelly Zannini HOMEVEST REALTY

2214 Bay Line Rd, Oakland, FL 34787

/42
Est $798,491 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,561 Sq Ft
1826 Western Trailway Dr, Oakland, FL 34787

1826 Western Trailway Dr, Oakland, FL 34787

/99
$2,500,000
- 5 Beds
- 5 Baths
- 4,798 Sq Ft
530 Largovista Dr, Oakland, FL 34787

Extraordinary lakefront estate, where culinary excellence meets waterfront paradise. Immerse yourself in the ultimate lakefront lifestyle at this breathtaking direct waterfront estate on Johns Lake, where every morning begins with sunrise reflections dancing across 2,500 acres of pristine water and every evening concludes with golden sunsets painting the sky from your private south-facing

Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

530 Largovista Dr, Oakland, FL 34787
/2
$443,500 Sold May 30, 2025
- 1,898 Sq Ft
- $234/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
308 Largovista Dr, Oakland, FL 34787

Welcome to your Florida dream home, where location is everything. This stunning 3-bedroom, 2-bathroom home with an additional office/flex space is filled with an abundance of natural light and boasts a bright, open layout that’s perfect for both relaxing and entertaining. The spacious family room features vaulted ceilings, adding a sense of openness to the heart of the home. The updated kitchen

Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

308 Largovista Dr, Oakland, FL 34787

/57
Est $873,760 Not Listed For Sale
- 6 Beds
- 4 Baths
- 4,237 Sq Ft
15104 Heron Hideaway Cir, Oakland, FL 34787

15104 Heron Hideaway Cir, Oakland, FL 34787

/44
$498,000
- 3 Beds
- 2.5 Baths
- 1,744 Sq Ft
2163 White Feather Loop, Winter Garden, FL 34787

PRICED TO SELL! This recently built energy-efficient home, constructed by Meritage Homes in September 2019, boasts approximately $15,000 in furnishings, artwork, and pendant lighting—all negotiable with the purchase! Enjoy a large, covered front porch and a spacious open first floor. Upon entering, you'll find wood-look grey tile flooring that perfectly complements the cabinetry and walls, with

Joshua Earley OPTIMA ONE REALTY, INC.

2163 White Feather Loop, Winter Garden, FL 34787
/2
$399,990 Sold May 29, 2025
- 1,620 Sq Ft
- $247/SF
- 3 Beds
- 2.5 Baths
- Built 2025
5876 Meditation Dr, Oakland, FL 34787

Beautiful 3 bedroom, 2.5 bathroom townhome, large living room, kitchen, all bedrooms on the upper floor, master bedroom includes the master bathroom and downstairs you will find a guest bathroom. It has a backyard that leads to the two cars garage. Easy access to Fl 429 and a few minutes from US 27, where you will find restaurants, supermarkets, etc, and very close to Winter Garden.

Stellar Non-Member Agent Stellar Non-Member Office

5876 Meditation Dr, Oakland, FL 34787

/2
Est $545,104 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,897 Sq Ft
14347 Braemar St, Oakland, FL 34787

14347 Braemar St, Oakland, FL 34787

/61
$989,000 Open Sat 1PM - 4PM
- 5 Beds
- 3.5 Baths
- 3,728 Sq Ft
619 Largovista Dr, Oakland, FL 34787

Welcome to 619 Largovista Dr—a custom-built, recently remodeled home in the highly desirable, gated community of Johns Landing on Johns Lake. This one-of-a-kind property features luxury finishes and a beautifully designed layout, along with mature fruit trees for a touch of natural charm. Step into the grand foyer and take in the stunning light fixtures cascading from the soaring ceilings. To

Farhad Haniff WEICHERT REALTORS HALLMARK PRO

619 Largovista Dr, Oakland, FL 34787
/2
$1,835,000 Sold May 27, 2025
- 3,796 Sq Ft
- $483/SF
- 17 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2022
625 Cheekwood Alley, Winter Garden, FL 34787

Welcome to this stunning custom-built POOL & PARK-FRONT home with IN-LAW SUITE located in the highly sought-after community of Oakland Park. Designed for both luxury & functionality, this exceptional residence boasts impeccable craftsmanship, high-end finishes, & a thoughtfully designed layout perfect for modern living. The main home includes 5 bedrooms (one does not have a closet) & 3.5 baths

Ashley Boyd BHHS FLORIDA REALTY

625 Cheekwood Alley, Winter Garden, FL 34787

/27
Est $693,121 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,270 Sq Ft
16265 Misty Hills Ave, Oakland, FL 34787

16265 Misty Hills Ave, Oakland, FL 34787

/86
$649,963
- 5 Beds
- 4 Baths
- 3,449 Sq Ft
229 Largovista Dr, Oakland, FL 34787

229 Largovista Drive – A Dream Address You'll Be Thrilled to Call HOME! Step into a world of elegance and leisure at this stunning pool home located in the highly coveted gated community of Johns Landing. This beautiful home boasts 5 spacious bedrooms, 4 full bathrooms, and almost 3,500 sq. ft. of living space, offering both luxury and comfort in every detail. As you enter, you’ll be impressed by

Richard Lokhnauth RL LUXURY REAL ESTATE

229 Largovista Dr, Oakland, FL 34787
/2
$530,000 Sold May 23, 2025
- 1,515 Sq Ft
- $350/SF
- 1 Day On Market
- 3 Beds
- 1 Bath
- Built 1958
321 E Gulley Ave, Oakland, FL 34760

DOUBLE LOT .55 - GREAT LOCATION!- NO HOA - GOLF CART FRIENDLY COMMUNITY - ACCESS TO WINTER GARDEN'S HISTORICAL DOWNTOWN - CLOSE TO WEST ORANGE TRAIL - Spacious 3 Bedroom 1 Bathroom home. Open Concept Living with High Ceilings - Wood Floors - Plenty of Natural Light - Oversized Lot Offering Ample Room to Expand or Build New. Large Storage Shed - Newer Roof and A/C - Take Advantage of this Rare

Rebecca Hall KELLER WILLIAMS WINTER PARK

321 E Gulley Ave, Oakland, FL 34760

/4
Est $278,520 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,029 Sq Ft
411 W Hull Ave, Oakland, FL 34760

411 W Hull Ave, Oakland, FL 34760

/93
$610,000 Open Sat 10:30AM - 12:30PM
- 3 Beds
- 2 Baths
- 1,860 Sq Ft
1219 Foltz Loop, Oakland, FL 34787

Step into this exquisite ONE-STORY residence, where love at first sight is inevitable. Nestled in the serene, LAKEFRONT community of Hull Island, this home offers enchanting VIEWS of the NATURE PRESERVE and is ideally located within close proximity to Winter Garden’s historic downtown, the charming town of Oakland, and the lively town of Clermont. Here, you’ll relish waterfront dining, local

Ashley Boyd BHHS FLORIDA REALTY

1219 Foltz Loop, Oakland, FL 34787
/2
$522,000 Sold May 23, 2025
- 1,685 Sq Ft
- $310/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
15657 Pelican Cay Dr, Oakland, FL 34787

This immaculate, 3 bedroom, 2 bath block constructed home has been perfectly kept and appars like a model home located in the desirable Horizon West community of WATERLIEGH. The home has 1,685 square feet under air and is situated on a beautiful OVERSIZED CORNER LOT. The home is very inviting and is bright inside with an open floor plan making it perfect for any lifestyle. The home has curb

Kevin Pribell ACRES INC

15657 Pelican Cay Dr, Oakland, FL 34787

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