Are short-term rentals (Airbnb/VRBO) allowed in Winter Garden?

It depends on zoning and approvals. Verify with Winter Garden Planning and Zoning before listing. The City provides FAQs and direct contacts.

Is Winter Garden Florida a good place to live?

Winter Garden consistently ranks among Central Florida's most desirable communities, offering a walkable historic downtown on Plant Street, the West Orange Trail, strong schools through OCPS, and a wide range of housing from Horizon West new construction to lakefront estates. ZIP code 34787 is one of the fastest-growing in the country.

Winter Garden, FL Real Estate | Homes for Sale in Winter Garden, Florida

Winter Garden’s Best Homes & Neighborhoods

Downtown charm meets Horizon West growth—watch the full tour.

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Inside Orlando’s HOTTEST Zip Code – From 400k to 2 MILLION!

34787 is one of the fastest-growing ZIP codes in the country, covering areas from Horizon West to Downtown Winter Garden. The range of home prices here is vast — from multi-million-dollar estates to entry-level properties. Over the next week, viewers are taken through four new listings ranging from $2.25 million to $475,000.

What $2.25M Gets You in Winter Garden, Florida

The first tour showcases a 2019 Toll Brothers home with over $1 million in upgrades on a half-acre lakefront lot. The property features black-framed windows, high-end doors, and an infinity-edge pool overlooking Panther Lake and Disney fireworks views. Inside, the home has level-five wall finishes, wide-plank flooring, Gen Air appliances, and a redesigned open-concept layout. Custom beams, upgraded drywall curves, and cohesive design flow between floors add to the luxury. Smart-home technology with iPads controls lighting and audio throughout. Upstairs, multiple suites, California Closets, and a spa-like primary with a balcony complete the design.

What $1.15M Gets You in Winter Garden, Florida

The second home, located in Oakland Park, is a 2,600+ sq. ft. David Weekley “Mabel” plan listed by Susanna. With four bedrooms and three baths, this home offers 10-foot ceilings, custom cabinetry, quartz counters, upgraded lighting, and coastal-style shiplap accents. The first-floor primary suite features a soaker tub and detailed finishes. Upstairs includes a loft/media room and another full bedroom and bath. Outdoor amenities include a wraparound patio and a three-car epoxy garage — rare for the community. Only five homes of this plan were ever built, making it a standout at $1.15 million.

What $879K Gets You in Winter Garden, Florida

This Rockwell Homes “Jackson” model, built in 2023, offers just over 2,000 sq. ft. with three bedrooms, a loft, and an office. The open kitchen features quartz countertops, herringbone backsplash, a gas cooktop, and double ovens. The primary suite is on the first floor with an ensuite bathroom and walk-in closet. A flexible upstairs loft can convert to a fourth bedroom. The detached three-car garage provides ample space — a rare find in Oakland Park — and the extended backyard adds versatility within the $879K range.

What $475K Gets You in Winter Garden, Florida

The final property, located in Hamlin inside Horizon West, comes from DRB Homes with Ashton Woods developing next door. The 1,846 sq. ft. end-unit townhome features flexible ground-floor space that can serve as an office, gym, or fourth bedroom. Upstairs, a chef’s kitchen with luxury finishes, vinyl plank flooring, and tall baseboards adds style. The third floor includes a spacious owner’s suite, guest bedrooms, and full laundry. With HOA-covered landscaping, no CDD, and prices starting at $475K, it’s a strong entry point into the Winter Garden market.

Closing Thoughts

From luxury estates to modern townhomes, Winter Garden offers remarkable variety in architecture, design, and pricing. Each listing showcases distinct craftsmanship and lifestyle benefits — from golf-course views to walkable retail access. Viewers are encouraged to comment on their favorite home and reach out to the team at theorlando.com for buying or selling assistance across Central Florida.

Winter Garden

Winter Garden blends small-town main-street energy with one of Central Florida’s fastest-growing suburban districts. On Plant Street, you get a true downtown: Plant Street Market/Crooked Can, a bustling Farmers Market, coffee and bakeries, boutique retail, and an easygoing, golf-cart-friendly vibe. The West Orange Trail cuts directly through downtown, so riders and runners from neighborhoods like Oakland Park roll straight into the action. Head south and you reach Horizon West/Hamlin, where targeted retail and entertainment continue to fill in around SR-429, putting daily essentials close to new-construction communities. Housing spans updated mid-century cottages and townhomes near Plant Street, production builds across Horizon West villages, and custom/lakefront options—including seven-figure properties—featured in our videos.

For deeper context and neighborhood shopping, see our pieces on Horizon West’s villages, an Oakland Park neighborhood spotlight , and a Downtown Winter Garden dining guide.

Real Estate Statistics

Average Price	$704K
Lowest Price	$139K
Highest Price	$6M
Total Listings	972
Avg. Days On Market	95
Avg. Price/SQFT	$276

Property Types (active listings)

Winter Garden Highlights

01
Plant Street’s walkable core—Plant Street Market/Crooked Can, weekly Farmers Market, and seasonal events
02
West Orange Trail runs through downtown—ride or run without loading a bike rack
03
Downtown is evolving: The Exchange, Hangry Bison, Foxtail/Kelly’s, boutique hotel, and seven-figure townhomes on key blocks
04
Horizon West/Hamlin growth: expanding retail, dining, and services along SR-429 for everyday convenience.
05
Homes for every stage: renovated cottages, townhomes, production builds, and custom lakefront estates featured across our tours.
06
Real-world scale: 34787 spans historic downtown to Ovation/Flamingo Crossings—varied HOA styles, amenities, and commute patterns.

Quick Facts

Price range: Entry tier from the mid-$400Ks to $2M+ for custom and lakefront homes; seven-figure townhomes now appear near downtown (as shown in our clips).
Home types: Historic cottages and townhomes near Plant Street; master-planned and new-build options in Horizon West and Hamlin; semi-custom and custom homes in lake and estate pockets.
Commute: Primary arteries SR-429 and Florida’s Turnpike connect to Disney-area employers and Downtown Orlando; MCO access via 429/408/528 links.
Schools: Established OCPS options plus newer schools serving Horizon West; most families choose based on program fit, commute, and neighborhood proximity.

Explore Winter Garden Homes

Browse the newest Winter Garden homes—from entry-level new builds to larger hillside plans with scenic elevation. Create a Save Search to get instant alerts when matching homes hit the market.

Historic Winter Garden city hall, Florida

Properties in Winter Garden

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$385,000

16920 Reseda Alley, WINTER GARDEN

3 Beds 3 Baths 1,568 SqFt Residential MLS® # O6400124

$725,000

10705 Petrillo Way, WINTER GARDEN

4 Beds 3 Baths 2,528 SqFt Residential MLS® # O6391807

$670,000

16283 Honey Harvest Street, WINTER GARDEN

4 Beds 4 Baths 2,927 SqFt Residential MLS® # O6399528

$670,000

16277 Honey Harvest Street, WINTER GARDEN

4 Beds 5 Baths 2,930 SqFt Residential MLS® # O6400235

$900,000

15828 Shorebird Lane, WINTER GARDEN

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6398059

$319,900

431 Southern Pecan Circle 201, WINTER GARDEN

3 Beds 2 Baths 1,499 SqFt Residential MLS® # O6397663

$495,000

16716 Wingspread Loop, WINTER GARDEN

3 Beds 2 Baths 1,676 SqFt Residential MLS® # O6397108

$580,000

$580,000

15408 Lebeau Loop, WINTER GARDEN

4 Beds 3 Baths 2,415 SqFt Residential MLS® # O6383534

$649,900

↓ $25,100

13846 Fresh Ivy Street, WINTER GARDEN

2 Beds 3 Baths 2,108 SqFt Residential MLS® # O6346706

View All 987 Results

Winter Garden Real Estate FAQs

Is Downtown Winter Garden truly walkable, and what’s there?

Yes. Plant Street anchors a designated historic downtown with shops, dining, weekly events, museums, and a popular farmers market.

Can I drive a golf cart downtown? What are the rules?

Golf carts are allowed only on streets the City designates for cart use. To qualify as a golf cart, the vehicle must not be capable of exceeding 20 mph, and carts may not operate on roads signed over 25 mph. Always confirm the latest City guidance and maps.

Where does the West Orange Trail run, and where do I start?

The paved trail runs directly through downtown; the Winter Garden Station trailhead at 455 E. Plant St. offers parking and facilities. Trail hours are generally sunrise to sunset.

Which public schools serve my address?

Attendance is address-based. Use Orange County Public Schools’ “Find My School” tool and the current attendance boundary maps to confirm your zoned schools.

Are short-term rentals (Airbnb/VRBO) allowed?

It depends on zoning and approvals. Verify with Winter Garden Planning & Zoning before listing; the City provides FAQs and direct contacts.

Do I need a permit for renovations, pools, or additions? Which code applies?

Most structural/mechanical/electrical/plumbing work requires a permit. Winter Garden enforces the Florida Building Code (current edition); the City’s Building FAQ outlines what needs a permit.

Who provides utilities and how do I set up service?

The City of Winter Garden provides water/sewer/stormwater. Utility Billing runs through the City’s BS&A online portal for account setup and payments.

Is my address in a flood zone or Special Flood Hazard Area?

Check the FEMA Flood Map Service Center by address for official designations.

Start searching for your Winter Garden dream home today.

From Horizon West to Downtown Winter Garden, explore the latest listings anytime, anywhere. Our site works flawlessly on any device so you never miss a home that fits your lifestyle.

Talk to a Local Agent

Winter Garden, FL Real Estate.

Winter Garden’s Best Homes & Neighborhoods

Inside Orlando’s HOTTEST Zip Code – From 400k to 2 MILLION!

What $2.25M Gets You in Winter Garden, Florida

What $1.15M Gets You in Winter Garden, Florida

What $879K Gets You in Winter Garden, Florida

What $475K Gets You in Winter Garden, Florida

Closing Thoughts

Winter Garden

Real Estate Statistics

Winter Garden Highlights

Quick Facts

Explore Winter Garden Homes

Properties in Winter Garden

$385,000

16920 Reseda Alley, WINTER GARDEN

$725,000

10705 Petrillo Way, WINTER GARDEN

$670,000

16283 Honey Harvest Street, WINTER GARDEN

$670,000

16277 Honey Harvest Street, WINTER GARDEN

$900,000

15828 Shorebird Lane, WINTER GARDEN

$319,900

431 Southern Pecan Circle 201, WINTER GARDEN

$495,000

16716 Wingspread Loop, WINTER GARDEN

$580,000

15444 Lebeau Loop, WINTER GARDEN

$560,000

10043 Sequel Alley, WINTER GARDEN

$568,000

15306 Lebeau Loop, WINTER GARDEN

$580,000

15408 Lebeau Loop, WINTER GARDEN

$649,900

13846 Fresh Ivy Street, WINTER GARDEN

Winter Garden Real Estate FAQs

Start searching for your Winter Garden dream home today.