Dani Kubrusly

Orange County, west of Orlando

Winter Garden

Greater OrlandoFlorida

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 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.

Winter Garden, Florida

The area

A brick downtown along a rail-trail, framed by lakes and old groves.

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.

SLV High School

High school

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

Dillard Street Elementary School

Dillard Street Elementary School

Elementary school

311 N Dillard St, Winter Garden, FL 34787, USA

Website
Maxey Elementary School1/6

Maxey Elementary School

Elementary school

602 E Story Rd, 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.

Eggs Up Grill1/6

Eggs Up Grill

Relaxed chain serving a menu of breakfast, burgers & sandwiches in a colorful setting.

13750 W Colonial Dr, Winter Garden, FL 34787, USA

4.7 · 1876 reviews$$
Website
Sizzlin' Greens1/6

Sizzlin' Greens

Restaurant

12639 W Colonial Dr C, Winter Garden, FL 34787, USA

4.7 · 474 reviews$$
Website
MANGONI Italian Market Pizza1/6

MANGONI Italian Market Pizza

Pizza restaurant

251 Tremaine St, Winter Garden, FL 34787, USA

4.6 · 3412 reviews$$
Website
Yummy Crab Juicy Seafood1/6

Yummy Crab Juicy Seafood

Seafood restaurant

13383 W Colonial Dr, Winter Garden, FL 34787, USA

4.6 · 452 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 · 2563 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 · 2378 reviews$$
Website
Indian Pavilion1/6

Indian Pavilion

Indian restaurant

13770 W Colonial Dr #120, Winter Garden, FL 34787, USA

4.9 · 933 reviews
Website
AJ's Pizza Joint1/6

AJ's Pizza Joint

Convivial eatery with playful decor, offering NY-style pizzas, calzones, pasta & sub sandwiches.

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

4.3 · 2033 reviews$$
Website
Rosallie Le French Cafe1/6

Rosallie Le French Cafe

Restaurant

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

4.2 · 2041 reviews$$
Website

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.

Around here

Things to do here

Cinema, bowling, activities for the children, culture and sport around here, without repeating the parks. I list what actually exists, with the public Google rating where there is one.

The Escape Ventures Winter Garden1/6

The Escape Ventures Winter Garden

Amusement center

1165 E Plant St #2, Winter Garden, FL 34787, USA

5.0 · 1607 reviews
Website
Athletic Motion Golf Club1/6

Athletic Motion Golf Club

Indoor golf course

1230 Winter Garden Vineland Rd, Winter Garden, FL 34787, USA

5.0 · 288 reviews
Website
Apex Functional Fitness1/6

Apex Functional Fitness

Gym

1015 S Dillard St C, Winter Garden, FL 34787, USA

4.9 · 181 reviews
Rise Athletics1/6

Rise Athletics

Gym

1232 Winter Garden Vineland Rd #116, Winter Garden, FL 34787, USA

4.9 · 153 reviews
Website
Downtown Winter Garden1/6

Downtown Winter Garden

Tourist attraction

320 Windford Ct, Winter Garden, FL 34787, USA

4.8 · 1147 reviews
Website
Central Florida Railroad Museum1/6

Central Florida Railroad Museum

Circa-1913 railroad station housing locomotive memorabilia & old train cars, plus displays for kids.

101 S Boyd St, Winter Garden, FL 34787, USA

4.8 · 250 reviews
Website
The Williams Holiday House1/6

The Williams Holiday House

Museum

15304 E Oakland Ave, Winter Garden, FL 34787, USA

4.8 · 212 reviews
Hardcore Fitness Winter Garden1/6

Hardcore Fitness Winter Garden

Gym

1401 Beulah Rd Ste 100, Winter Garden, FL 34787, USA

4.8 · 127 reviews
Website
Roper YMCA Family Center1/6

Roper YMCA Family Center

Gym

100 Windermere Rd, Winter Garden, FL 34787, USA

4.5 · 339 reviews
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.

$430,000

median asking price (USD)

−0.9% vs. a year earlier

August 2026 · monthly series

Median listing price (county) · Orange County, FL

Median listing price (county): from $380,026 in August 2021 to $430,000 in August 2026, higher over the period. Low of $380,026 in August 2021 and high of $497,300 in July 2023. 61 real observations.

August 2021, August 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
August 2021$380,026
October 2021$393,715
December 2021$385,495
February 2022$395,475
April 2022$429,900
June 2022$485,000
August 2022$477,000
October 2022$456,495
December 2022$440,000
February 2023$437,475
April 2023$464,000
June 2023$495,000
August 2023$487,500
October 2023$474,999
December 2023$445,000
February 2024$439,248
April 2024$445,875
June 2024$455,000
August 2024$454,900
October 2024$439,950
December 2024$425,473
February 2025$422,450
April 2025$430,000
June 2025$445,000
August 2025$433,990
October 2025$429,950
December 2025$428,625
February 2026$427,000
April 2026$435,000
June 2026$443,995
August 2026$430,000

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.

$242

USD per square foot

−1.6% vs. a year earlier

August 2026 · monthly series

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

Median listing price per square foot (county): from $207 in August 2021 to $242 in August 2026, higher over the period. Low of $207 in August 2021 and high of $257 in September 2023. 61 real observations.

August 2021, August 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
August 2021$207
October 2021$209
December 2021$215
February 2022$225
April 2022$244
June 2022$250
August 2022$248
October 2022$245
December 2022$241
February 2023$244
April 2023$250
June 2023$255
August 2023$255
October 2023$257
December 2023$254
February 2024$253
April 2024$254
June 2024$256
August 2024$254
October 2024$251
December 2024$249
February 2025$246
April 2025$249
June 2025$248
August 2025$246
October 2025$246
December 2025$243
February 2026$243
April 2026$243
June 2026$245
August 2026$242

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.

5,577

active listings

−2.7% vs. a year earlier

August 2026 · monthly series

Active listings (county) · Orange County, FL

Active listings (county): from 2,057 in August 2021 to 5,577 in August 2026, higher over the period. Low of 1,141 in February 2022 and high of 5,836 in June 2025. 61 real observations.

August 2021, August 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
August 20212,057
October 20211,866
December 20211,454
February 20221,141
April 20221,228
June 20222,089
August 20223,221
October 20223,097
December 20222,865
February 20232,379
April 20232,086
June 20232,189
August 20232,474
October 20232,878
December 20233,145
February 20243,266
April 20243,590
June 20244,096
August 20244,611
October 20244,819
December 20244,717
February 20254,978
April 20255,442
June 20255,836
August 20255,731
October 20255,532
December 20255,188
February 20265,044
April 20265,233
June 20265,474
August 20265,577

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.

1,760

new listings in the month

+9.2% vs. a year earlier

August 2026 · monthly series

New listings (county) · Orange County, FL

New listings (county): from 2,186 in August 2021 to 1,760 in August 2026, lower over the period. Low of 1,140 in December 2022 and high of 2,440 in June 2022. 61 real observations.

August 2021, August 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
August 20212,186
October 20211,836
December 20211,544
February 20221,864
April 20221,996
June 20222,440
August 20222,008
October 20221,492
December 20221,140
February 20231,524
April 20231,584
June 20231,740
August 20231,634
October 20231,526
December 20231,376
February 20241,770
April 20241,958
June 20241,936
August 20241,768
October 20241,724
December 20241,250
February 20252,060
April 20252,106
June 20252,046
August 20251,612
October 20251,608
December 20251,178
February 20261,844
April 20261,954
June 20262,004
August 20261,760

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.

71

days on market

−1.4% vs. a year earlier

August 2026 · monthly series

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

Median days on market (county): from 36 in August 2021 to 71 in August 2026, higher over the period. Low of 27 in June 2022 and high of 86 in January 2026. 61 real observations.

August 2021, August 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
August 202136
October 202141
December 202156
February 202232
April 202231
June 202227
August 202239
October 202257
December 202266
February 202358
April 202347
June 202341
August 202343
October 202345
December 202354
February 202453
April 202447
June 202451
August 202458
October 202466
December 202477
February 202568
April 202558
June 202565
August 202572
October 202578
December 202580
February 202678
April 202664
June 202666
August 202671

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

Metro and statewide context

Median listing price

$415,000

median asking price (USD)

−1.9% vs. a year earlier

August 2026 · monthly series

Florida house price index

825.7

index · base 1980:Q1 = 100

+1.4% vs. a year earlier

Q2 2026 · quarterly series

30-year fixed mortgage rate

6.76%

annual rate

+0.41 percentage points vs. a year earlier

Week ending Sep 10, 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