Dani Kubrusly

Orange County, west of Orlando

Winter Garden

Greater OrlandoCentral Florida

A city west of Orlando with a genuine historic downtown, wrapped by newer residential communities built over the last two decades.

Talk to Dani

Identity

Winter Garden has something most of Central Florida does not: an old main street that still functions as a center. Brick sidewalks, a weekly farmers market, restaurants and shops in restored buildings, and a rail trail running through it. Around that core, the city expanded into planned residential communities, so the area mixes historic texture with recent suburban development.

Location and access

West of Orlando, near the SR-429 and Florida's Turnpike corridors, with Winter Garden Village and the Horizon West area nearby. Downtown Orlando and the theme-park corridor are both reachable by car, with commute times that depend heavily on the hour.

Everyday life

Weekends often revolve around downtown: the market, the trail, restaurants and outdoor seating. Day to day, most services are concentrated along the main commercial corridors, and the newer communities carry their own pools, playgrounds and trails.

  • Historic downtown Winter Garden and Plant Street.
  • The West Orange Trail, used for cycling, running and walking.
  • The weekly farmers market.
  • Winter Garden Village and nearby retail corridors.
  • Lake Apopka and surrounding natural areas.

Housing

  • Older homes near downtown, with smaller lots and historic character.
  • Planned communities with single-family homes and townhomes further out.
  • A wide range of construction ages within a short driving distance.
  • HOA rules and amenities differ substantially between communities.

New construction

New construction continues in the communities around the city and in the broader Horizon West area to the south, with several builders active. Inventory, phases and available floor plans change constantly, so this is checked at the moment of your search rather than described here as a fixed state.

Getting around

A car is the norm, with SR-429 and the Turnpike carrying most regional trips. Downtown itself is walkable, and the West Orange Trail makes some local trips possible by bike — a rare combination in the metro.

The area in photos

What the area looks like.

Real photographs published on Google Places for this area and its public landmarks.

Photos of the area1/12

Source: Google Places. Photos are published by Google and can change.

Real life here

What an ordinary week looks like.

The week has a real centre: Plant Street. People walk or bike the West Orange Trail into downtown for coffee, the Saturday farmers market, the Plant Street Market hall and dinner. Outside those blocks the pattern is suburban and car-based, with newer communities feeding into the same downtown.

Routines that fit

  • Wanting a walkable downtown and a weekly market within reach.
  • Cycling: the West Orange Trail runs for miles through the city.
  • Mixing an older, established core with newer construction nearby.

Outdoors and leisure

  • West Orange Trail, a paved rail-trail crossing the city centre.
  • Newton Park and Tildenville, with access to Lake Apopka.
  • Lake Apopka Wildlife Drive, a birding route a short drive north.
  • Downtown splash pad and green squares used year-round.

Eating and shopping

Plant Street is the anchor: an indoor market hall with stalls and a brewery, plus restaurants and cafés along the brick street. Chain dining and larger supermarkets sit on the SR-429 and Winter Garden Village side, a short drive away.

Winter Garden Village concentrates big-box retail, groceries and services. Health care is spread across clinics in town, with hospitals in the wider west Orange corridor.

Seasons

Downtown events cluster in the cooler months, when the market and street festivals are busiest. Summer afternoons belong to storms; mornings on the trail are the compensation.

Around here

Schools nearby

Real institutions inside this area's radius, ordered by distance. No ratings: assignment depends on the exact address, and a star average does not measure a school.

The Learning Center

Preschool

125 N Lakeview Ave #2710, Winter Garden, FL 34787, USA

Website
Winter Garden Academy1/6

Winter Garden Academy

Preschool

72 N Woodland St, Winter Garden, FL 34787, USA

Website
Winter Garden's First Baptist1/6

Winter Garden's First Baptist

Church

125 E Plant St, Winter Garden, FL 34787, USA

Website
Foundation Academy - Plant Street Campus1/6

Foundation Academy - Plant Street Campus

Elementary school

125 E Plant St, Winter Garden, FL 34787, USA

Website
Young Star Musical Theatre1/6

Young Star Musical Theatre

Performing arts theater

67 S Dillard St, Winter Garden, FL 34787, USA

Website

Children of the Messiah Preschool

Preschool

241 N Main St, Winter Garden, FL 34787, USA

Website

SLV High School

High school

213 S Dillard St, Winter Garden, FL 34787, USA

Winter Garden Music Academy1/4

Winter Garden Music Academy

Educational institution

330 E Plant St, Winter Garden, FL 34787, USA

Website

Source: Google Places. Names, addresses, photos and ratings are published by Google and can change.

Around here

Restaurants around

Real addresses nearby, with public Google ratings where they exist.

Wawa1/6

Wawa

Convenience store chain known for sandwiches & coffee. Many offer fuel & are open 24/7.

13501 W Colonial Dr, Winter Garden, FL 34787, USA

3.8 · 446 reviews$
Website
The Hangry Bison - Winter Garden1/6

The Hangry Bison - Winter Garden

American restaurant

250 W Plant St, Winter Garden, FL 34787, USA

4.4 · 2361 reviews$$
Website
Miller's Ale House1/6

Miller's Ale House

Casual sports-pub chain with basics from bar snacks to steaks & a large selection of tap beers.

12175 W Colonial Dr, Winter Garden, FL 34787, USA

4.3 · 4420 reviews$$
Website
Rosallie Le French Cafe1/6

Rosallie Le French Cafe

Restaurant

141 W Plant St, Winter Garden, FL 34787, USA

4.2 · 2030 reviews$$
Website
MANGONI Italian Market Pizza1/6

MANGONI Italian Market Pizza

Pizza restaurant

251 Tremaine St, Winter Garden, FL 34787, USA

4.6 · 3372 reviews$$
Website
The Whole Enchilada Fresh Mexican Grill & Bar1/6

The Whole Enchilada Fresh Mexican Grill & Bar

Airy & trendy spot dishing up updated takes on classic Mexican offerings such as tacos & enchiladas.

129 W Plant St, Winter Garden, FL 34787, USA

4.2 · 2967 reviews$
Website
Culver’s1/6

Culver’s

Fast-food chain specializing in frozen custard & signature burgers made with Midwest beef & dairy.

13649 W Colonial Dr, Winter Garden, FL 34787, USA

4.4 · 2479 reviews$$
Website
4 Rivers Smokehouse1/6

4 Rivers Smokehouse

Counter-serve chain eatery featuring Texas-style BBQ, homestyle sides & sweet treats.

1047 S Dillard St, Winter Garden, FL 34787, USA

4.4 · 2540 reviews$$
Website
El Tequila Sunrise Mexican Restaurant1/6

El Tequila Sunrise Mexican Restaurant

Mexican restaurant

443 W Silver Star Rd, Ocoee, FL 34761, USA

4.0 · 202 reviews$$

Source: Google Places. Names, addresses, photos and ratings are published by Google and can change.

Around here

Parks and green space

Public parks inside this area's radius.

Newton Park1/6

Newton Park

Popular lakefront park features a playground, boat launch, covered picnic pavilion & fishing pier.

31 W Garden Ave, Winter Garden, FL 34787, USA

Website
Encore Winter Garden1/6

Encore Winter Garden

RV resort featuring a pool & a fitness center, plus a playground, basketball & a game room.

13905 W Colonial Dr, Winter Garden, FL 34787, USA

Website
Veterans Memorial Park1/6

Veterans Memorial Park

Park

420 S Park Ave, Winter Garden, FL 34787, USA

Website
Chapin Station1/6

Chapin Station

Park

501 Crown Point Cross Rd, Winter Garden, FL 34787, USA

West Orange Soccer Complex1/6

West Orange Soccer Complex

Sports complex

150 Windermere Rd, Winter Garden, FL 34787, USA

Tucker Ranch Recreation and Nature Complex1/6

Tucker Ranch Recreation and Nature Complex

Park

100 Avalon Rd, Winter Garden, FL 34787, USA

Website

Source: Google Places. Names, addresses, photos and ratings are published by Google and can change.

Real indicators

Market in Orange County, with sources.

These numbers are published per county, not per neighbourhood or community. They show the direction of the market around this area — they do not estimate the price of a specific home.

Median listing price (county)

The midpoint asking price of homes listed across the whole county that month. It is what sellers ask, not what buyers pay, and a county is far larger than a single community — a specific neighbourhood can sit well above or below it.

$439,450

median asking price (USD)

−0.4% vs. a year earlier

July 2026 · monthly series

Median listing price (county) · Orange County, FL

Median listing price (county): from $375,000 in July 2021 to $439,450 in July 2026 — higher over the period. Low of $375,000 in July 2021 and high of $495,000 in June 2023. 61 real observations.

July 2021July 2026 · 61 observations

Realtor.com via FRED · St. Louis Fed
View data table

Showing 1 in every 2 real observations from the selected period.

Median listing price (county)
PeriodMedian listing price
July 2021$375,000
September 2021$382,500
November 2021$386,000
January 2022$389,990
March 2022$416,750
May 2022$462,000
July 2022$484,945
September 2022$465,824
November 2022$448,450
January 2023$434,900
March 2023$447,000
May 2023$474,973
July 2023$495,000
September 2023$479,999
November 2023$465,000
January 2024$437,000
March 2024$439,900
May 2024$450,000
July 2024$455,000
September 2024$447,748
November 2024$436,490
January 2025$422,450
March 2025$419,000
May 2025$444,850
July 2025$441,250
September 2025$430,000
November 2025$430,000
January 2026$425,000
March 2026$430,000
May 2026$437,990
July 2026$439,450

Realtor.com via FRED · St. Louis Fed · Housing Inventory: Median Listing Price in Orange County, FL

Median listing price per square foot (county)

Asking price divided by interior area, at the county midpoint. It travels better between areas than a total price because it partly removes house size from the comparison — but it still ignores lot, age, finish level and view.

$244

USD per square foot

−1.2% vs. a year earlier

July 2026 · monthly series

Median listing price per square foot (county) · Orange County, FL

Median listing price per square foot (county): from $203 in July 2021 to $244 in July 2026 — higher over the period. Low of $203 in July 2021 and high of $257 in October 2023. 61 real observations.

July 2021July 2026 · 61 observations

Realtor.com via FRED · St. Louis Fed
View data table

Showing 1 in every 2 real observations from the selected period.

Median listing price per square foot (county)
PeriodPrice per sq ft
July 2021$203
September 2021$208
November 2021$212
January 2022$220
March 2022$234
May 2022$249
July 2022$249
September 2022$245
November 2022$242
January 2023$243
March 2023$248
May 2023$251
July 2023$255
September 2023$256
November 2023$255
January 2024$252
March 2024$254
May 2024$256
July 2024$256
September 2024$252
November 2024$249
January 2025$247
March 2025$247
May 2025$249
July 2025$247
September 2025$246
November 2025$245
January 2026$243
March 2026$245
May 2026$244
July 2026$244

Realtor.com via FRED · St. Louis Fed · Housing Inventory: Median Listing Price per Square Feet in Orange County, FL

Active listings (county)

How many homes were actively listed for sale in the county during the month: a snapshot of available supply. It says nothing about how many sold and excludes homes already under contract.

5,563

active listings

−4.6% vs. a year earlier

July 2026 · monthly series

Active listings (county) · Orange County, FL

Active listings (county): from 1,952 in July 2021 to 5,563 in July 2026 — higher over the period. Low of 1,141 in February 2022 and high of 5,836 in June 2025. 61 real observations.

July 2021July 2026 · 61 observations

Realtor.com via FRED · St. Louis Fed
View data table

Showing 1 in every 2 real observations from the selected period.

Active listings (county)
PeriodActive listings
July 20211,952
September 20211,987
November 20211,689
January 20221,237
March 20221,152
May 20221,542
July 20222,999
September 20223,260
November 20223,140
January 20232,638
March 20232,170
May 20232,061
July 20232,376
September 20232,640
November 20233,099
January 20243,199
March 20243,367
May 20243,793
July 20244,385
September 20244,696
November 20244,954
January 20254,734
March 20255,249
May 20255,597
July 20255,831
September 20255,605
November 20255,375
January 20264,906
March 20265,211
May 20265,339
July 20265,563

Realtor.com via FRED · St. Louis Fed · Housing Inventory: Active Listing Count in Orange County, FL

New listings (county)

Homes that entered the county market for the first time that month. It measures how much new supply arrived, which is what usually changes negotiating room from one season to the next.

1,734

new listings in the month

−5.2% vs. a year earlier

July 2026 · monthly series

New listings (county) · Orange County, FL

New listings (county): from 2,244 in July 2021 to 1,734 in July 2026 — lower over the period. Low of 1,140 in December 2022 and high of 2,440 in June 2022. 61 real observations.

July 2021July 2026 · 61 observations

Realtor.com via FRED · St. Louis Fed
View data table

Showing 1 in every 2 real observations from the selected period.

New listings (county)
PeriodNew listings
July 20212,244
September 20212,002
November 20211,678
January 20221,560
March 20221,972
May 20222,278
July 20222,344
September 20221,852
November 20221,288
January 20231,454
March 20231,530
May 20231,686
July 20231,644
September 20231,664
November 20231,436
January 20241,626
March 20241,876
May 20242,020
July 20241,818
September 20241,604
November 20241,548
January 20251,810
March 20252,000
May 20251,896
July 20251,830
September 20251,634
November 20251,528
January 20261,772
March 20261,946
May 20262,052
July 20261,734

Realtor.com via FRED · St. Louis Fed · Housing Inventory: New Listing Count in Orange County, FL

Median days on market (county)

The midpoint of how long county listings stayed on the market that month: half were listed for less, half for more. It measures pace, not price.

69

days on market

−1.4% vs. a year earlier

July 2026 · monthly series

Median days on market (county) · Orange County, FL

Median days on market (county): from 35 in July 2021 to 69 in July 2026 — higher over the period. Low of 27 in June 2022 and high of 86 in January 2026. 61 real observations.

July 2021July 2026 · 61 observations

Realtor.com via FRED · St. Louis Fed
View data table

Showing 1 in every 2 real observations from the selected period.

Median days on market (county)
PeriodDays on market
July 202135
September 202138
November 202142
January 202242
March 202231
May 202228
July 202230
September 202247
November 202263
January 202371
March 202350
May 202343
July 202343
September 202345
November 202349
January 202460
March 202447
May 202448
July 202455
September 202462
November 202470
January 202576
March 202557
May 202560
July 202570
September 202576
November 202578
January 202686
March 202664
May 202665
July 202669

Realtor.com via FRED · St. Louis Fed · Housing Inventory: Median Days on Market in Orange County, FL

Metro and statewide context

Median listing price

$419,450

median asking price (USD)

−1.8% vs. a year earlier

July 2026 · monthly series

Florida house price index

827.9

index · base 1980:Q1 = 100

+1.9% vs. a year earlier

Q1 2026 · quarterly series

30-year fixed mortgage rate

6.65%

annual rate

+0.07 percentage points vs. a year earlier

Week ending Aug 20, 2026 · weekly average

Honest trade-offs

What you accept when you choose this area.

Trade-offs

  • Popular weekends mean downtown parking and traffic can be tight.
  • Commutes east into Orlando vary a lot by time of day.
  • Homes near downtown are older and may need more maintenance.
  • Growth to the south continues to change traffic patterns.

Next step

A thirty-minute conversation.

Goals, budget, timing and the regions that fit you — with no obligation.

Talk to Dani