Dani Kubrusly

Orange County, southwest of Orlando

Windermere

Greater OrlandoFlorida

A low-density, lake-oriented area on the Butler Chain of Lakes, known for large lots, mature oaks and privacy.

Talk to Dani

Identity

Windermere is defined by water and trees. The town itself is small, with unpaved residential streets in parts of the historic core, and the surrounding area holds estate-style homes and gated communities set between lakes. Density is low and the overall feeling is residential rather than commercial.

Location and access

Southwest of Orlando, between Dr. Phillips and the Horizon West growth corridor, with reasonable access to the theme-park area and the SR-429 corridor. Everyday shopping tends to happen in the neighboring commercial areas rather than in town.

Everyday life

Life here is quieter and more private than in the planned communities nearby. Boating and lake access shape a lot of the routine for waterfront owners, and much of the social and commercial life happens a short drive away in Dr. Phillips or Horizon West.

  • The Butler Chain of Lakes.
  • The small historic town center of Windermere.
  • Golf communities in the surrounding area.
  • Nearby commercial corridors in Dr. Phillips and Horizon West.

Housing

  • Estate homes on large lots, several with lake frontage.
  • Gated communities with controlled access and their own amenities.
  • Older homes in the historic core, on smaller and more irregular lots.
  • Fewer listings overall than in higher-density communities.

New construction

New construction here is typically individual: custom homes, rebuilds on existing lots, or smaller enclaves, rather than large multi-phase communities. That changes the process considerably compared with buying from a production builder.

Getting around

Entirely car-dependent. Roads in and around the historic core are narrow and residential, which keeps traffic slow inside town and pushes through-traffic to the surrounding arteries.

Windermere, Florida

The area

Chain-of-lakes estates linked by canals beneath a canopy of oaks.

Real life here

What an ordinary week looks like.

Life is quiet and residential, organised around the Butler Chain of Lakes: boats, docks, and unhurried streets under oak canopy. Errands and dining happen a few minutes away in Dr. Phillips or Winter Garden, the town itself keeps a very small commercial core.

Routines that fit

  • Boating and lake access as part of the weekly routine.
  • Preferring space, privacy and larger lots over walkability.
  • Accepting a short drive for almost every service.

Outdoors and leisure

  • Butler Chain of Lakes, a connected chain used for boating and fishing.
  • Public boat ramps and lakefront parks around the chain.
  • Golf courses across the surrounding communities.
  • Tibet-Butler Preserve, a quiet nature preserve with boardwalks.

Eating and shopping

The town has a handful of local spots; the concentrated dining is on Restaurant Row in Dr. Phillips, roughly a ten-minute drive, which covers everything from casual to fine dining.

Groceries, pharmacies and medical offices are mostly in Dr. Phillips and along Winter Garden Vineland Road. Nothing is far, but almost nothing is walkable.

Seasons

Lake life peaks from spring to early autumn. Afternoon storms are frequent in summer, and lakefront homes require attention to docks, seawalls and insurance requirements.

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.

Joseph house

Elementary school

Windermere, FL 34786, USA

Colegio de Isa

High school

Windermere, FL 34786, USA

Windermere Elementary School

Windermere Elementary School

Elementary school

11125 Park Ave, Windermere, FL 34786, USA

Website
Olympia High School

Olympia High School

High school

4301 S Apopka Vineland Rd, Orlando, FL 32835, USA

Website
Chain of Lakes Middle School1/6

Chain of Lakes Middle School

School

8700 Conroy Windermere Rd, Orlando, FL 32835, 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.

Hawkers Asian Street Food1/6

Hawkers Asian Street Food

Asian restaurant

9100 Conroy Windermere Rd Ste 110, Windermere, FL 34786, USA

4.8 · 4579 reviews$$
Website
Sakura Ramen Orlando1/6

Sakura Ramen Orlando

Restaurant

4848 S Apopka Vineland Rd Ste 208, Orlando, FL 32819, USA

4.6 · 238 reviews$$
Website
Sukoy Hibachi Express1/6

Sukoy Hibachi Express

Japanese restaurant

320 Moore Rd, Ocoee, FL 34761, USA

4.6 · 157 reviews$$
Website
Dim Dim Sum1/6

Dim Dim Sum

Asian restaurant

4750 The Grove Dr, Windermere, FL 34786, USA

4.2 · 386 reviews$$
Website
Keke's Breakfast Cafe1/6

Keke's Breakfast Cafe

Local chain serving American breakfasts & comfort-food lunches in a modern diner with booth seating.

282 Moore Rd, Ocoee, FL 34761, USA

4.7 · 5141 reviews$
Website

Fastax and Accounting

Consultant

2739 Maguire Rd, Ocoee, FL 34761, USA

4.6 · 57 reviews
Website
Dixie Cream Cafe1/6

Dixie Cream Cafe

Bright cafe adorned with lively artwork serving American food like pancakes & sandwiches, plus cake.

434 Main St, Windermere, FL 34786, USA

4.5 · 879 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.

R.D. Keene Park1/6

R.D. Keene Park

Park

10900 Chase Rd, Windermere, FL 34786, USA

Website
Windermere Recreation Area1/6

Windermere Recreation Area

Park

11465 Park Ave, Windermere, FL 34786, USA

Website
Freedom Park1/6

Freedom Park

Park

351 Thornebrooke Dr, Ocoee, FL 34761, USA

Website
Gotha Park1/6

Gotha Park

Park

10013 Park Ridge Gotha Rd, Windermere, FL 34786, USA

Website
Central Park1/6

Central Park

Park

Oakdale St, Windermere, FL 34786, USA

Lake Down Boat Ramp1/6

Lake Down Boat Ramp

Public park and green space

9619 Conroy Windermere Rd, Windermere, FL 34786, 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.

Smart Fitness1/6

Smart Fitness

Health

324 Moore Rd, Ocoee, FL 34761, USA

5.0 · 161 reviews
Website
Holy Family Catholic Church1/6

Holy Family Catholic Church

Church

5125 S Apopka Vineland Rd, Orlando, FL 32819, USA

4.8 · 1111 reviews
Website
Isleworth Golf & Country Club1/6

Isleworth Golf & Country Club

Association / Organization

6100 Payne Stewart Dr, Windermere, FL 34786, USA

4.8 · 226 reviews
Website
Body Coach Personal Training1/6

Body Coach Personal Training

Gym

625 Main St #25, Windermere, FL 34786, USA

5.0 · 41 reviews
Website
Zero Gravity Fitness1/6

Zero Gravity Fitness

Health

2910 Maguire Rd #1007, Ocoee, FL 34761, USA

5.0 · 33 reviews
Website

Jeff Coleman Memorial Gymnasium

Gym

4851 S Apopka Vineland Rd, Orlando, FL 32819, USA

Rock N Body Wellness

Health

8815 Conroy Windermere Rd, Orlando, FL 32835, USA

LUXE TOURS

Marina

10900 Chase Rd, Windermere, FL 34786, USA

Orangetheory Fitness1/6

Orangetheory Fitness

Gym

2883 Maguire Rd Unit Ste A1004-A1005, Windermere, FL 34786, USA

4.7 · 147 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

  • Fewer comparable sales, which can make pricing and resale cycles slower.
  • Larger lots and waterfront mean higher maintenance responsibility.
  • Limited walkable services; most errands require driving out.
  • Waterfront ownership carries specific insurance and permitting considerations.

Next step

A thirty-minute conversation.

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

Talk to Dani