Oakland, FL Homes

/50
$779,000
- 4 Beds
- 3 Baths
- 2,386 Sq Ft
309 W Oakland Ave, Oakland, FL 34760

Charming Renovated Home in the Heart of Historic Oakland! Welcome to 309 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home offers just under 2,400 square feet of thoughtfully designed living space with NO HOA restrictions!

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

309 W Oakland Ave, Oakland, FL 34760
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/30
$4,400 per month
- 5 Beds
- 4.5 Baths
- 3,227 Sq Ft
- House for Rent
8887 Sonoma Coast Dr, Oakland, FL 34787

Great opportunity!!! This magnificent home is for rent, located in the desirable community of Waterleigh in Winter Garden, The home was built in 2021, is in excellent condition, like new! It has 5 bedrooms and 4.5 bathrooms, a huge family room upstairs, custom designed closets, a large gourmet kitchen equipped with stainless steel appliances and granite countertops, a large dining room area and a

Yesenia Barrios URBAN-O REAL ESTATE SOLUTION

8887 Sonoma Coast Dr, Oakland, FL 34787
/2
$800,000 Sold Jul 10, 2025
- Land
- 1.03 Acres
- $776,699 per Acre
- 0 Days On Market
525 N Pollard St, Winter Garden, FL 34787

As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

Blaine Dooley REGENCY REAL ESTATE LLC

525 N Pollard St, Winter Garden, FL 34787

/2
Est $549,182 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
14086 Frasier St, Oakland, FL 34787

14086 Frasier St, Oakland, FL 34787

/56
$850,000
- 4 Beds
- 4 Baths
- 2,858 Sq Ft
770 Hull Island Dr, Oakland, FL 34760

Welcome to Your Stunning Pond-Front Former Model HomeFrom the moment you step through the front door, breathtaking views of a scenic pond and tranquil fountain greet you, setting the tone for this beautifully designed residence. Nestled in a prime location, this professionally curated former model home combines elegance, functionality, and serene Florida living.A charming front porch with

Phillip Hales WILSHIRE REALTY GROUP LLC

770 Hull Island Dr, Oakland, FL 34760
/41
$3,000 per month
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
- House for Rent
9588 Jacques Alley, Oakland, FL 34787

Welcome to Waterleigh in the desirable area of Horizon West located in Winter Garden, FL. “Come Here and Stay” in this stunning community situated on over 1,400 acres of land with over a dozen lakes and ponds. Check out one of Waterleigh’s most popular bungalow floor-plans the Cordale offering 4 bedrooms, 2.5 bathrooms, and an attached 2 car garage. Enjoy the water view, while sitting on the

Teresa Valdes VALSTAR REALTY LLC

9588 Jacques Alley, Oakland, FL 34787
/2
$420,000 Sold Jul 09, 2025
- 1,621 Sq Ft
- $259/SF
- 24 Days On Market
- 3 Beds
- 2 Baths
- Built 2003
709 Strihal Loop, Oakland, FL 34787

Nestled in the desirable gated community of Johns Landing in Oakland, this charming 3-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Situated on a generously sized lot of nearly a quarter acre, the property boasts a fenced backyard and mature shade trees, providing an ideal space for creating your dream outdoor oasis. Inside, the home offers two distinct living

Jessica Stone CENTURY 21 CARIOTI

709 Strihal Loop, Oakland, FL 34787

/2
Est $439,592 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,688 Sq Ft
15805 Tollington Alley, Oakland, FL 34787

15805 Tollington Alley, Oakland, FL 34787

/51
$839,900
- 3 Beds
- 2.5 Baths
- 2,348 Sq Ft
9008 Sonoma Coast Dr, Oakland, FL 34787

Welcome to your dream home! This beautifully decorated 3 Bedroom, 2 1/2 Bath + Office home where comfort meets style offers stunning lake views and a sleek tile roof. Upon entering you'll be greeted by architectural arches and a wide foyer entry. To your left, you will be greeted by architectural arches and a wide foyer entry. On your left you will find a Den/Study/Office with glass entry doors &

Gary Berkson RE/MAX CENTRAL REALTY

9008 Sonoma Coast Dr, Oakland, FL 34787
/76
$5,500 per month
- 5 Beds
- 4.5 Baths
- 3,653 Sq Ft
- House for Rent
15511 Shorebird Ln, Oakland, FL 34787

Welcome to this open plan 5 Bedroom, 4 and a half bathroom water front home including a 3 car garage.Flooring includes tile, laminate and carpet. You will never run out of storage with the abundance of cabinets. Chef's kitchen include upgraded appliances and wall oven. Large sliders allow plenty of light and gorgeous water view and open to a covered lanai. Some of the amenities include a

Mark Volchko REALTY WORLD PREFERRED

15511 Shorebird Ln, Oakland, FL 34787
/2
$980,000 Sold Jul 08, 2025
- 2,765 Sq Ft
- $354/SF
- 6 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2022
1206 Civitas, Oakland, FL 34787

HONEY, STOP THE GOLF CART! Your opportunity to own in OAKLAND PARK! Highly desirable Seaside model built by David Weekly in 2022! From the moment you arrive, this home welcomes you with warmth and timeless elegance from the generous front porch with porch swing to enjoy your coffee from— Inside, you'll find a seamless blend of comfort and sophistication in every thoughtfully crafted space.

Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

1206 Civitas, Oakland, FL 34787

/2
Est $415,703 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,691 Sq Ft
15811 Tollington Alley, Oakland, FL 34787

15811 Tollington Alley, Oakland, FL 34787

/50
$420,000
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
13298 Pontoon Rd, Oakland, FL 34787

Built in 2023 and beautifully staged, this stylish 3-bedroom, 2.5-bath townhome offers the perfect blend of comfort, function, and low-maintenance living! Upstairs, you’ll find all three bedrooms, including a spacious primary suite with a walk-in closet and a luxurious en-suite bath featuring a double vanity and a walk-in shower. The convenient second-floor laundry area keeps chores easy and

Cindy Brads KELLER WILLIAMS CLASSIC

13298 Pontoon Rd, Oakland, FL 34787
/2
$395,890 Sold Jul 08, 2025
- 1,782 Sq Ft
- $222/SF
- 21 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
2883 Transformation Way, Oakland, FL 34787

Under Construction. Step into the beautiful contemporary yet classic Brookside. The Great Room, kitchen and dining room are situated among a convenient and contemporary open floorplan on the first level of this two-story home, with sliding glass doors that lead to a lanai. All three bedrooms occupy the second floor, including the owner’s suite which features an en-suite bathroom and walk-in

Ben Goldstein LENNAR REALTY

2883 Transformation Way, Oakland, FL 34787

/2
Est $585,489 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,149 Sq Ft
15153 Summer Harvest St, Oakland, FL 34787

15153 Summer Harvest St, Oakland, FL 34787

/63
$799,000 Open Sun 12PM - 2PM
- 5 Beds
- 4 Baths
- 2,840 Sq Ft
9518 Bolero Rd, Oakland, FL 34787

Welcome to this beautifully maintained 5-bedroom, 4-bathroom home in the highly sought-after Waterleigh community of Winter Garden. Built in 2020 and now available with a significant price improvement***This thoughtfully designed residence stands out for its rare double pond views, tranquil water scenery both in front of the home and from the backyard, offering privacy, natural beauty, and a

Olaya Guerrero Pino EXP REALTY LLC

9518 Bolero Rd, Oakland, FL 34787
/2
$394,990 Sold Jul 08, 2025
- 1,620 Sq Ft
- $244/SF
- 20 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
5860 Meditation Dr, Oakland, FL 34787

Under Construction. Refresh your lifestyle with the Wilshire! This magnificent townhome covers two stories and includes three bedrooms, two and one-half bathrooms and a two-car rear load garage. Front door opens onto the spacious open concept combination living room and dining room. There is also a laundry room with washer and dryer and a fully equipped kitchen that leads to an enticing patio.

Ben Goldstein LENNAR REALTY

5860 Meditation Dr, Oakland, FL 34787

/2
Est $525,671 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
14407 Braemar St, Oakland, FL 34787

14407 Braemar St, Oakland, FL 34787

/51
$746,000
- 4 Beds
- 4.5 Baths
- 2,908 Sq Ft
15133 Summer Harvest St, Oakland, FL 34787

**Seller is offering closing cost assistance with a full-price offer.** Discover this like-new Baldwin floor plan from the Taylor Morrison Bungalow Series, offering a rare and highly desirable detached garage den. This versatile space includes a wet bar, full bathroom, and private entrance—ideal for use as a guest suite, home office, or kids’ retreat. Ideally positioned on one of the best

Nick Whitehouse RE/MAX PRIME PROPERTIES

15133 Summer Harvest St, Oakland, FL 34787
/2
$388,000 Sold Jul 03, 2025
- 1,620 Sq Ft
- $240/SF
- 86 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2020
1312 Painted Bunting Ave, Oakland, FL 34760

NEW PRICE! Discover the most spacious 2-bedroom townhome in Winter Garden! Unlike most 2-bedroom homes in the area averaging around 1,250 square feet, this 1,620-square-foot residence features a versatile loft space that’s ideal for a home office, guest area, or bonus living zone. Built in 2020 and meticulously maintained by its original owner, every detail and upgrade was carefully selected in

Gavin Hatch SERHANT

1312 Painted Bunting Ave, Oakland, FL 34760

/59
Est $481,145 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,082 Sq Ft
2071 White Feather Loop, Oakland, FL 34787

2071 White Feather Loop, Oakland, FL 34787

/56
$760,000
- 5 Beds
- 3 Baths
- 3,493 Sq Ft
2340 Standing Rock Cir, Winter Garden, FL 34787

Welcome to an extraordinary residence nestled in the highly sought-after Oakland Trails community—just steps from the scenic West Orange Trail and moments from the charm of downtown Winter Garden. This beautifully appointed home showcases sophisticated upgrades, including a striking custom stone accent wall in the main living and dining areas and matching stonework along the staircase, creating a

Jennifer Coon KELLER WILLIAMS WINTER PARK

2340 Standing Rock Cir, Winter Garden, FL 34787
/2
$852,105 Sold Jul 02, 2025
- 3,300 Sq Ft
- $258/SF
- 33 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2025
5307 Citrus Leaf Blvd, Oakland, FL 34787

Brand new, energy-efficient home ready NOW! This functional floorplan has a spacious family room that’s open to an expansive kitchen. A combination dining and living room provides ideal space for indoor entertaining or moving the party outdoors to the private lanai. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit for every lifestyle. Located in the

Tatiana Souza MERITAGE HOMES OF FL REALTY

5307 Citrus Leaf Blvd, Oakland, FL 34787

/2
Est $607,809 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
15101 Summer Harvest St, Oakland, FL 34787

15101 Summer Harvest St, Oakland, FL 34787

/58
$765,000
- 4 Beds
- 3 Baths
- 2,106 Sq Ft
17936 Adrift Rd, Oakland, FL 34787

This impressive 4BR/3BA/2CG 2023 Bellmore Model in Waterleigh is a modern lakefront beauty. Expansive water views & vibrant sunsets are visible from the spacious living room, dining room, gourmet kitchen, master bedroom, & private covered lanai. The open layout is ideal for your entertaining needs. Its well-appointed kitchen features SS appliances, quartz countertops, a walk-in pantry, & large

Cheryl Schweigart The Keyes Company

17936 Adrift Rd, Oakland, FL 34787
/2
$1,400,000 Sold Jun 27, 2025
- 3,497 Sq Ft
- $400/SF
- 72 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2002
141 Millholland St, Oakland, FL 34760

Live the "Lake Life" in a Tropical Paradise – Key West Vibes in Oakland, Florida!Welcome to your own slice of paradise in the heart of The Town of Oakland – one of Central Florida’s most desirable and fastest-growing communities. Situated on a sprawling 1.12-acre lot along the shores of Lake Apopka – Florida’s 4th largest lake – this gorgeous custom home spans nearly 4,000 square feet of

Matthew Matin CLOCK TOWER REALTY

141 Millholland St, Oakland, FL 34760

/48
Est $824,659 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

/32
$674,900
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
13557 Parkfield Way, Oakland, FL 34787

Amazing highly desirable single story home in the popular Encore at Ovation in Winter Garden just minutes from Walt Disney World! This home sits on a beautiful lot ( only one side neighbor) with no one behind you. It has a gorgeous water and wooded view. The home has a wonderful front porch perfect for enjoying a cup of coffee along with a beautiful back patio overlooking the peaceful water.

Paula Dale SOTERA LIVING

13557 Parkfield Way, Oakland, FL 34787
/2
$862,000 Sold Jun 25, 2025
- 2,808 Sq Ft
- $307/SF
- 47 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2024
13133 Sunny Retreat Ln, Oakland, FL 34787

Elegant & Upgraded Luxury Living in Winter Garden's Premier 55+ Community – Del Webb Oasis Welcome to Sunny Retreat —a stunning, move-in-ready 3-bedroom with additional FLEX space, 3.5-bathroom single-family home in highly desirable Del Webb Oasis of Winter Garden, FL. Thoughtfully designed with $110,000+ in custom upgrades, PREMIUM lot, Renown model, this home offers resort-style

Roo Klaers COLDWELL BANKER REALTY

13133 Sunny Retreat Ln, Oakland, FL 34787

/55
Est $487,315 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
$409,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,729 Sq Ft
Sage, Oakland, FL 34787

The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

Dream Finders Homes

Sage, Oakland, FL 34787
/2
$900,000 Sold Jun 25, 2025
- 2,930 Sq Ft
- $307/SF
- 54 Days On Market
- 4 Beds
- 4 Baths
- Built 2020
13202 Spring Grove Way, Oakland, FL 34787

Experience the finest of Winter Garden living in this exceptional 4-bedroom, 4-bathroom pool home, featuring a generous bonus room in a vibrant, resort-style community. Combining the excitement of being just minutes from Disney with the tranquility of a peaceful suburban retreat, this one-of-a-kind residence offers the best of both worlds. With nearly 3,000 square feet of living space on a

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

13202 Spring Grove Way, Oakland, FL 34787

/2
Est $501,624 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

/3
$508,990 New Construction
- 3 Beds
- 3 Baths
- 2,083 Sq Ft
Newbury, Oakland, FL 34787

Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

Dream Finders Homes

Newbury, Oakland, FL 34787
/2
$399,990 Sold Jun 24, 2025
- 1,755 Sq Ft
- $228/SF
- 7 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
5884 Meditation Dr, Oakland, FL 34787

Welcome to the light & bright Landcaster! This elegant townhome covers two stories and includes three bedrooms, two and one-half bathrooms with a two-car rear load garage. The front door opens onto the spacious open concept combination living room and dining room. There is also a laundry room with washer and dryer and a fully equipped kitchen that leads to an beautiful patio. The luxurious

Ben Goldstein LENNAR REALTY

5884 Meditation Dr, Oakland, FL 34787

/2
Est $500,382 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
$399,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
Harbor, Oakland, FL 34787

The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

Dream Finders Homes

Harbor, Oakland, FL 34787
/2
$1,475,000 Sold Jun 20, 2025
- 3,468 Sq Ft
- $425/SF
- 49 Days On Market
- 4 Beds
- 4 Baths
- Built 2022
921 Bradenville Ln, Winter Garden, FL 34787

An unparalleled opportunity awaits to step into refined luxury without the delay or uncertainty of building. This bespoke residence, masterfully crafted by J&J Builders, graces an oversized corner lot directly across from the resort-caliber clubhouse of Oakland Park. From the moment you arrive, the home makes a commanding impression with its grand front porch—a quintessential feature of Oakland

Ronald Ziolkowski RE/MAX PRIME PROPERTIES

921 Bradenville Ln, Winter Garden, FL 34787

/69
Est $724,419 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

/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

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