0.49 mi
Distance
Winter Oaks, Winter Garden, FL, USA
Winter Garden, Florida, United States
Homes for sale near Winter Oaks, Winter Garden, FL, USA
| Address | Bed / Bath | Listing Price |
|---|---|---|
111 LAKEVIEW RESERVE BOULEVARD
Move-in ready! From the extra wide paver driveway, Bahama shutters, modern sculptures, the double door custom front doors, and new windows you realize you are at your ideal home. Through the front doors, you enter a gracious and welcoming dining room, and see all the way though the back of the hou
Living Area:
2882 Sqft.
|
4
Beds,
3
Baths
|
$634,900 |
417 S MAIN STREET
Experience the perfect blend of historic charm and modern comfort in this home nestled in the sought-after golf cart district of Downtown Winter Garden. This residence captures the character of the hip historic neighborhood while offering the convenience and style of newer construction.
Step instid
Living Area:
2172 Sqft.
|
3
Beds,
3
Baths
|
$775,000 |
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 |
627 AUTUMN OAKS LOOP
THE HEART OF WINTER GARDEN… Shopping and Dining just blocks away.
Located in the Golf Cart District, the community of Winter Oaks is a hidden gem offering this beautiful 5-Bedroom, 3-Bath Traditional Home with 3000 sq/ft of living space. The rear alley garages allow for timeless architecture, m
Living Area:
3000 Sqft.
|
5
Beds,
3
Baths
|
$739,000 |
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
|
$1,890,000 |
40 W SMITH STREET
Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's
Living Area:
2225 Sqft.
|
4
Beds,
2
Baths
|
$750,000 |
750 S PARK AVENUE
Welcome to 750 S Park Avenue, a beautifully maintained and fully RENOVATED home offering comfort, charm, and modern convenience in one of Winter Garden’s most desirable neighborhoods.This 3-bedroom, 1.5-bath residence spans approximately 1,186 square feet and sits on a well-kept lot with mature FR
Living Area:
1086 Sqft.
|
3
Beds,
2
Baths
|
$430,000 |
241 N DILLARD STREET
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden
Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart Distr
Living Area:
3507 Sqft.
|
3
Beds,
3
Baths
|
$1,800,000 |
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 |
229 N HIGHLAND AVENUE
Completely Renovated 4BR/2BA Home – Walk to Downtown Winter Garden located just steps from the vibrant heart of Downtown Winter Garden. This move-in-ready property has been thoughtfully renovated from top to bottom, offering modern comfort and timeless style.4 spacious bedrooms and 2 full bathroom
Living Area:
1720 Sqft.
|
4
Beds,
2
Baths
|
$749,000 |
100 TEMPLE GROVE DRIVE
Welcome home to a true Winter Garden gem that perfectly blends modern comfort, timeless design, and small-town charm. Nestled on a spacious private lot with no HOA, this beautifully expanded and reimagined residence captures the spirit of historic Winter Garden while delivering every modern luxury.
Living Area:
3182 Sqft.
|
4
Beds,
3
Baths
|
$1,050,000 |
329 W BAY STREET
Investor special or perfect project home just steps from historic Downtown Winter Garden! This 2-bedroom, 1-bath bungalow sits on a generous lot and offers tons of potential for renovation or redevelopment. Bring your vision to life—restore its original charm or reimagine the space entirely. The l
Living Area:
1004 Sqft.
|
2
Beds,
1
Bath
|
$420,000 |
351 FLORAL DRIVE
PRICE IMPROVEMENT - Stunning Renovated Ranch on Prime Corner Lot in Historic Downtown Winter Garden - Welcome to a prime corner lot property in Historic Downtown Winter Garden that perfectly blends modern luxury with small-town charm! While this beautiful home has been lovingly maintained in the sel
Living Area:
1722 Sqft.
|
3
Beds,
2
Baths
|
$689,000 |
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 |
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
|
$1,775,000 |
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 |
312 N PARK AVENUE
One or more photo(s) has been virtually staged. Welcome to your downtown Winter Garden dream. This updated three-bedroom, two-bath pool home sits right in the golf cart district, just minutes from Plant Street Market, Crooked Can Brewery, and the Saturday Farmers Market. Picture weekend strolls with
Living Area:
1701 Sqft.
|
3
Beds,
2
Baths
|
$600,000 |
618 FOSTER AVENUE
Newly renovated INCOME PRODUCING 3-bedroom, 2-bathroom home nestled in the heart of downtown Winter Garden! Hop onto your golf cart or take a few moments' walk towards numerous shops, restaurants, the local farmer's market and all of the other charm that downtown has to offer. This home has been ful
Living Area:
1010 Sqft.
|
3
Beds,
2
Baths
|
$375,000 |
327 S LAKEVIEW AVENUE
Charming Winter Garden Home with In-Law Suite & Botanical Backyard Retreat
Welcome to this beautifully crafted single-family home built in 2014, where quality workmanship, thoughtful design, and everyday convenience come together. Located in the heart of Winter Garden’s desirable golf cart dist
Living Area:
2225 Sqft.
|
3
Beds,
3
Baths
|
$894,900 |
711 BURCH AVENUE
Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all
Living Area:
1154 Sqft.
|
3
Beds,
2
Baths
|
$450,000 |
213 W TILDEN STREET
Located in the heart of DOWNTOWN WINTER GARDEN!!
This beautifully renovated single story home combines charm with modern upgrades.
Completely redesigned in 2021, this home showcases numerous upgrades, including new roof,
new HVAC, recently installed Whole-House Water Filtration
Living Area:
2100 Sqft.
|
4
Beds,
2
Baths
|
$789,000 |
113 W DIVISION STREET
Beautifully remodeled 4BR/2BA home with an open-concept kitchen,top in appliances ,quartz countertops, sleek modern bathrooms,new windows, and durable waterproof laminate floors,excellent screen porch. Perfectly located close to the best schools, City Hall, highways, dining, and parks—ideal for fa
Living Area:
1487 Sqft.
|
4
Beds,
2
Baths
|
$629,900 |
524 S LAKEVIEW AVENUE
One or more photo(s) has been virtually staged. ***NEW REDUCED PRICE!***MOVE IN BEFORE THE HOLIDAYS & TAKE ADVANTAGE OF THE LOWER INTEREST RATES!
The sellers are motivated and ready for the next chapter—creating an incredible opportunity for you to own this beautifully updated Craftsman-style ho
Living Area:
2204 Sqft.
|
3
Beds,
3
Baths
|
$890,000 |
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 |
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 |
636 COKE AVENUE
Updated 2 Bedroom, 1 Bath Home Near Downtown Winter Garden. Welcome to your dream home! This beautifully updated 2-bedroom, 1-bath home is located just minutes from the heart of downtown Winter Garden, Florida.
Property Highlights:
Fully updated with brand-new cabinetry throughout the home, givin
Living Area:
914 Sqft.
|
2
Beds,
1
Bath
|
$339,999 |
166 HAMMOCK PRESERVE LOOP
Under Construction. UPDATE: Ahead of schedule with an estimated completion is FEB 2026. 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 years o
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 |
634 BURCH AVENUE
Welcome to your dream home in the heart of Downtown Winter Garden’s golf cart district—where small-town charm meets modern living. This newly built home is packed with thoughtful design and high-end finishes. Step inside to wide plank luxury vinyl floors, an airy open-concept layout, and sunligh
Living Area:
2448 Sqft.
|
4
Beds,
4
Baths
|
$664,000 |
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 |
515 N BOYD STREET
One or more photo(s) has been virtually staged. Discover the charm and convenience of luxurious living in this stunning 5-bedroom, 3-bathroom home, perfectly located in the heart of downtown Winter Garden. With a spacious and thoughtfully designed layout, this residence offers a blend of elegance an
Living Area:
3152 Sqft.
|
5
Beds,
4
Baths
|
$900,000 |
