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 · 1934 reviews$$
Website
Sizzlin' Greens1/6

Sizzlin' Greens

American restaurant

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

4.7 · 487 reviews$$
Website
MANGONI Italian Market Pizza1/6

MANGONI Italian Market Pizza

Pizza restaurant

251 Tremaine St, Winter Garden, FL 34787, USA

4.6 · 3524 reviews$$
Website
Yummy Crab Juicy Seafood1/6

Yummy Crab Juicy Seafood

Seafood restaurant

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

4.6 · 456 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 · 2600 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 · 2395 reviews$$
Website
Indian Pavilion1/6

Indian Pavilion

Indian restaurant

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

4.9 · 953 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 · 2049 reviews$$
Website
Rosallie Le French Cafe1/6

Rosallie Le French Cafe

Restaurant

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

4.2 · 2050 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
Winter Garden - Winter Garden, FL1/6

Winter Garden - Winter Garden, FL

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 · 1646 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 · 300 reviews
Website
Rise Athletics1/6

Rise Athletics

Gym

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

5.0 · 152 reviews
Website
Downtown Winter Garden1/6

Downtown Winter Garden

Tourist attraction

320 Windford Ct, Winter Garden, FL 34787, USA

4.9 · 1163 reviews
Website
Apex Functional Fitness1/6

Apex Functional Fitness

Gym

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

4.9 · 181 reviews
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 · 252 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 · 349 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.

$424,950

median asking price (USD)

−1.2% vs. a year earlier

September 2026 · monthly series

Median listing price (county) · Orange County, FL

Median listing price (county): from $382,500 in September 2021 to $424,950 in September 2026, higher over the period. Low of $382,500 in September 2021 and high of $497,300 in July 2023. 61 real observations.

September 2021, September 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
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$465,448
November 2022$448,950
January 2023$434,900
March 2023$447,000
May 2023$474,950
July 2023$497,300
September 2023$480,000
November 2023$465,500
January 2024$436,850
March 2024$439,900
May 2024$450,000
July 2024$455,000
September 2024$447,861
November 2024$436,490
January 2025$422,450
March 2025$419,000
May 2025$444,900
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
September 2026$424,950

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

September 2026 · monthly series

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

Median listing price per square foot (county): from $208 in September 2021 to $242 in September 2026, higher over the period. Low of $208 in September 2021 and high of $257 in September 2023. 61 real observations.

September 2021, September 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
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$257
November 2023$255
January 2024$252
March 2024$254
May 2024$255
July 2024$256
September 2024$252
November 2024$249
January 2025$247
March 2025$246
May 2025$249
July 2025$247
September 2025$246
November 2025$245
January 2026$243
March 2026$245
May 2026$244
July 2026$244
September 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.

5,554

active listings

−0.9% vs. a year earlier

September 2026 · monthly series

Active listings (county) · Orange County, FL

Active listings (county): from 1,987 in September 2021 to 5,554 in September 2026, higher over the period. Low of 1,141 in February 2022 and high of 5,836 in June 2025. 61 real observations.

September 2021, September 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
September 20211,987
November 20211,689
January 20221,237
March 20221,152
May 20221,542
July 20222,996
September 20223,259
November 20223,136
January 20232,637
March 20232,168
May 20232,060
July 20232,371
September 20232,635
November 20233,097
January 20243,196
March 20243,367
May 20243,791
July 20244,382
September 20244,694
November 20244,952
January 20254,732
March 20255,249
May 20255,597
July 20255,831
September 20255,603
November 20255,373
January 20264,901
March 20265,210
May 20265,340
July 20265,562
September 20265,554

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.

1,650

new listings in the month

+1.1% vs. a year earlier

September 2026 · monthly series

New listings (county) · Orange County, FL

New listings (county): from 2,002 in September 2021 to 1,650 in September 2026, lower over the period. Low of 1,140 in December 2022 and high of 2,440 in June 2022. 61 real observations.

September 2021, September 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
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 20231,528
May 20231,684
July 20231,644
September 20231,664
November 20231,432
January 20241,626
March 20241,876
May 20242,020
July 20241,816
September 20241,604
November 20241,548
January 20251,810
March 20251,992
May 20251,896
July 20251,828
September 20251,632
November 20251,528
January 20261,772
March 20261,946
May 20262,052
July 20261,732
September 20261,650

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.

73

days on market

−3.9% vs. a year earlier

September 2026 · monthly series

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

Median days on market (county): from 38 in September 2021 to 73 in September 2026, higher over the period. Low of 27 in June 2022 and high of 86 in January 2026. 61 real observations.

September 2021, September 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
September 202138
November 202142
January 202242
March 202231
May 202228
July 202230
September 202247
November 202263
January 202371
March 202350
May 202343
July 202342
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
September 202673

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

Metro and statewide context

Median listing price

$410,000

median asking price (USD)

−2.5% vs. a year earlier

September 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

7.28%

annual rate

+0.94 percentage points vs. a year earlier

Week ending Oct 01, 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