0.4 mi
Distance
Winters Landing, Oakland, FL, USA
Oakland, Florida, United States
Homes for sale near Winters Landing, Oakland, FL, USA
| Address | Bed / Bath | Listing Price |
|---|---|---|
869 BENDING OAK TRAIL
Welcome to this beautifully maintained 4-bedroom, 2-bath home located in The Oaks at Brandy Lake; Situated in the highly desirable golf cart district of Winter Garden. The home offers an open-concept layout featuring a spacious dining and living area with sliding glass doors that leads to a covered
Living Area:
1975 Sqft.
|
4
Beds,
2
Baths
|
$540,000 |
115 ZACHARY WADE STREET
One or more photo(s) has been virtually staged. In the heart of Winter Garden’s beloved Golf Cart District just moments from the charm of Plant Street where the scent of roasted coffee drifts through the air and neighbors wave as they roll past on their way to the Saturday morning Farmers Market l
Living Area:
1780 Sqft.
|
3
Beds,
2
Baths
|
$520,000 |
15201 E OAKLAND AVENUE
Step into a life of refined Southern charm and modern luxury at 15201 E Oakland Ave, nestled in the coveted Oakland Park community of Winter Garden. This custom Modern Farmhouse sits on a .44-acre fully fenced lot, anchored by two majestic oak trees, offering 4,507 square feet of thoughtfully design
Living Area:
4507 Sqft.
|
4
Beds,
5
Baths
|
$3,000,000 |
1101 EAGLES PASS WAY
One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District!
Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods
Living Area:
4104 Sqft.
|
6
Beds,
5
Baths
|
$1,850,000 |
261 ZACHARY WADE STREET
Completely Remodeled Waterfront Luxury Home – Boater’s Paradise on Lake Apopka
Experience the ultimate in lakefront living with this stunning, turnkey home on Lake Apopka in Winter Garden. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residenc
Living Area:
3728 Sqft.
|
4
Beds,
4
Baths
|
$1,895,000 |
832 EAGLE VISTA WAY
Welcome to this beautiful 4-bedroom, 3-bathroom home in the desirable Oaks at Brandy Lake community, offering 2,409 square feet of comfortable living space. Seller is willing to offer credit towards a new roof. Backing directly onto a scenic lake, this home provides stunning water views from multipl
Living Area:
2409 Sqft.
|
4
Beds,
3
Baths
|
$629,000 |
507 W OAKLAND AVENUE
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location!
Nestled in the heart of Oakland, this beautiful home offers one of the most desirable address
Living Area:
1338 Sqft.
|
3
Beds,
2
Baths
|
$375,000 |
131 RYAN COURT
Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home.
Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020
Living Area:
1513 Sqft.
|
3
Beds,
2
Baths
|
$545,000 |
2690 BOBCAT CHASE BOULEVARD
Love Where You Live — in Longleaf at Oakland! ?
Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land
Living Area:
1554 Sqft.
|
3
Beds,
2
Baths
|
$465,000 |
1428 UNION CLUB DRIVE
Welcome to Oakland Park, Winter Garden’s premier Golf Cart District — where timeless architecture, front-porch living, and modern design come together just steps from the West Orange Trail and charming downtown Winter Garden. This home exudes curb appeal with its classic front porch that invites
Living Area:
2548 Sqft.
|
4
Beds,
4
Baths
|
$850,000 |
2606 BOBCAT CHASE BOULEVARD
Stunning former MODEL HOME on a premium CORNER lot – loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both co
Living Area:
2473 Sqft.
|
4
Beds,
3
Baths
|
$670,000 |
1096 RIVERWAY DRIVE
Welcome to 1096 Riverway Drive, a fully custom home built by RCB Homes, currently under construction in the award-winning community of Oakland Park. Scheduled for completion in December 2025, this home spans 4,000 square feet of thoughtfully designed living space.
Set on a picturesque tree-lined st
Living Area:
4171 Sqft.
|
4
Beds,
4
Baths
|
$1,700,000 |
529 JOHNS LANDING WAY
Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a
Living Area:
2650 Sqft.
|
4
Beds,
3
Baths
|
$675,000 |
877 TILDEN OAKS TRAIL
Modern Craftsman Charmer in Oakland Park – Corner Lot, No Rear Neighbors, and Steps from the West Orange Trail!
Welcome to 877 Tilden Oaks Trail, a beautifully designed David Weekley Modern Craftsman home in the heart of Oakland Park—one of Winter Garden’s most sought-after communities. Featu
Living Area:
3084 Sqft.
|
5
Beds,
4
Baths
|
$1,050,000 |
326 LARGOVISTA DRIVE
Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring
Living Area:
3182 Sqft.
|
4
Beds,
3
Baths
|
$649,900 |
854 TILDEN OAKS TRAIL
This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offeri
Living Area:
3991 Sqft.
|
5
Beds,
5
Baths
|
$1,795,000 |
1368 UNION CLUB DRIVE
**NEW ROOF WILL BE PLACED PRIOR TO CLOSING**3/2.5 FOLK VICTORIAN HOME WITH OFFICE AND LOFT, AVAILABLE IN OAKLAND PARK. Located in the golf-cart district and only minutes from downtown Winter Garden and the Turnpike. Access to the West Orange Trail right within this waterfront, certified green commun
Living Area:
2484 Sqft.
|
3
Beds,
3
Baths
|
$849,000 |
14804 COSCESTER STREET
Welcome to your dream home in the highly sought-after community of Winter Garden! This beautiful New Constitution home with NO HOA maintained 3-bedroom, 2.5- bathroom residence offers the perfect blend of comfort, style, and convenience. Featuring an open-concept layout with abundant natural light,
Living Area:
1456 Sqft.
|
3
Beds,
3
Baths
|
$409,999 |
219 LARGOVISTA DRIVE
Investor Special! Located in the highly desirable, gated lakefront community of Johns Landing. This spacious 5-bedroom, 4-bathroom pool home offers nearly 4,000 sq. ft. of living space (excluding garage) and features two upstairs primary suites, additional bedrooms with a loft and bathroom, plus a d
Living Area:
3903 Sqft.
|
5
Beds,
4
Baths
|
$610,000 |
101 N STARR STREET
Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney.
Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida?
Living Area:
2502 Sqft.
|
3
Beds,
4
Baths
|
$1,450,000 |
229 LARGOVISTA DRIVE
**NEW PRICE – MUST-SEE LUXURY POOL HOME!**
Prepare to fall in love with this stunning 5-bedroom, 4-bathroom home located in the exclusive gated community of *Johns Landing*. Offering nearly 3,500 sq. ft. of meticulously designed living space, this home is the perfect blend of elegance, comfort,
Living Area:
3449 Sqft.
|
5
Beds,
4
Baths
|
$619,900 |
1207 RIDGE LAKE WAY
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
Living Area:
3909 Sqft.
|
5
Beds,
4
Baths
|
$1,700,000 |
610 STRIHAL LOOP
***MOTIVATED SELLERS!!! ***Don’t Miss This One. Welcome home to John’s Landing, one of Oakland’s most loved gated lakefront communities near beautiful Johns Lake. This stunningly updated home feels fresh, modern, and move-in ready, yet still warm and welcoming from the moment you step inside.
Living Area:
2490 Sqft.
|
4
Beds,
2
Baths
|
$555,000 |
1244 WATER MAPLE DRIVE
Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and
Living Area:
4859 Sqft.
|
6
Beds,
6
Baths
|
$2,295,000 |
1238 WATER MAPLE DRIVE
Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertain
Living Area:
4388 Sqft.
|
5
Beds,
6
Baths
|
$2,150,000 |
1149 PRADO LANE DRIVE
Pre-Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders – A Stunning New Home in Oakland's Premier Community!
Discover your dream home with the Clementine Floorplan, a thoughtfully designed residence nestled in Oakland's newest, most sought-after community. T
Living Area:
3596 Sqft.
|
5
Beds,
6
Baths
|
$1,975,000 |
1232 WATER MAPLE DRIVE
Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this ho
Living Area:
4433 Sqft.
|
5
Beds,
8
Baths
|
$2,175,000 |
985 HUNTSPOINT STREET
This stunning 5-bedroom, 4-bathroom single-family home is located in the highly desirable Oakland Park community, offering resort-style amenities such as a clubhouse, zero-entry pool, community firepit, and fireplace. Situated in the heart of Winter Garden, this home is part of the popular golf-cart
Living Area:
3084 Sqft.
|
5
Beds,
4
Baths
|
$929,500 |
166 HAMMOCK PRESERVE LOOP
Under Construction. UPDATE: Ahead of schedule with an estimated completion in NOV.-DEC. 2025. Please see attached package for full renderings and finishes. 166 Hammock Preserve Loop offers one of the finest new construction custom homes in Winter Garden, FL. Built by AR Homes—celebrating over 40 y
Living Area:
3186 Sqft.
|
4
Beds,
4
Baths
|
$1,675,000 |
931 KYLEE ALLEY
JUST REDUCED! Welcome to this exceptional David Weekley “Stoneybrook” residence in the highly sought-after Oakland Park community—just two years young and thoughtfully designed for both comfort and style. This four-bedroom, four-bath home spans 2,831 square feet of beautifully appointed living
Living Area:
2831 Sqft.
|
4
Beds,
4
Baths
|
$835,000 |
1258 RIDGE LAKE WAY
Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features fou
Living Area:
4557 Sqft.
|
4
Beds,
4
Baths
|
$1,996,500 |
1136 BRICK RD
Don’t miss this rare opportunity to own almost 5 acres in the heart of downtown Winter Garden. Privacy at its best yet just a short golf cart ride to downtown for your restaurants retail therapy and fun, YES IT IN THE GOLF CART DISTRICT! 2019 custom built home sits on 4.89 acres of privacy. Two s
Living Area:
2535 Sqft.
|
4
Beds,
3
Baths
|
$1,899,999 |
