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| 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 |
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 |
626 OXFORD CHASE DRIVE
Welcome to this truly exceptional estate home in the exclusive gated community of Oxford Chase, a residence that blends thoughtful design, upscale finishes, and resort-style living. Nestled on a serene lot, this 5-bedroom (all ensuite) home offers a rare combination of space, privacy, and family-for
Living Area:
4478 Sqft.
|
5
Beds,
5
Baths
|
$1,250,000 |
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 |
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
|
$550,000 |
14373 BLACK LAKE PRESERVE STREET
!!BACK ON MARKET WITH A RECENT PRICE REDUCTION!! Seller may consider buyer concessions if made in an offer
****Located in the desirable GATED COMMUNITY of Black Lake Preserve, this spacious two-story POOL HOME offers style, comfort, and a prime Winter Garden location! Built in 2017 and thoughtfu
Living Area:
3690 Sqft.
|
5
Beds,
3
Baths
|
$725,000 |
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 |
14008 JOMATT LOOP
Presenting 14008 Jomatt Loop in the highly desirable Cypress Reserve community of Winter Garden. Priced at $699,000, this spacious single-family home offers four bedrooms, three full bathrooms, and a dedicated den, with nearly 3,000 square feet of living space under air on a .19-acre lot. Built in 2
Living Area:
2952 Sqft.
|
4
Beds,
3
Baths
|
$699,000 |
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 |
514 LYNDON PLACE
Your Winter Garden dream home awaits! This 4 bedroom, 3 bathroom property offers 2,600 sq ft of thoughtfully designed living space on a spacious corner lot, blending elegance with everyday comfort. From the moment you arrive, the brick paver driveway, 3-car garage, and inviting covered front patio c
Living Area:
2600 Sqft.
|
4
Beds,
3
Baths
|
$749,000 |
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 |
617 MARSH REED DRIVE
Stunning 5BR/4BA pool home in the highly desirable Johns Lake Pointe community. Built in 2016 by Meritage Homes, this 3,100+ sq ft property is loaded with upgrades and move-in ready. The gourmet kitchen features granite counters, tile backsplash, stainless steel appliances, double ovens, and a walk-
Living Area:
3100 Sqft.
|
5
Beds,
4
Baths
|
$789,000 |
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 |
813 MARSH REED DRIVE
Welcome to this beautifully maintained residence in the highly desirable Johns Lake Pointe community of Winter Garden—where comfort, style, and convenience converge.
This spacious home showcases elegant porcelain tiles in the main living areas and luxury vinyl plank flooring throughout all bedroo
Living Area:
3148 Sqft.
|
5
Beds,
4
Baths
|
$629,000 |
15058 SAWGRASS BLUFF DRIVE
Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.22-acre corner lot.
Enjoy the comfort of a brand new A/C unit installed in January 2025 and freshly painted interiors (2022) that create a cr
Living Area:
2626 Sqft.
|
4
Beds,
3
Baths
|
$620,000 |
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 |
349 MORNING VIEW DRIVE
One or more photo(s) has been virtually staged. PRICE REDUCTION !!! Welcome home to 349 Morning View Drive Winter Garden in the much sought after community of Johns Lake Pointe. Huge price drop - you will be walking in with over $100,000 equity from last appraisal !!! This well cared for home has t
Living Area:
4693 Sqft.
|
7
Beds,
4
Baths
|
$750,000 |
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 |