Dani Kubrusly

Orange County, southwest of Orlando

Windermere

Greater OrlandoCentral Florida

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

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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.

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.

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

New Academy Inc

School

436 Oakdale St, Windermere, FL 34786, USA

Windermere Preschool (Family Church)

Preschool

300 Main St, Windermere, FL 34786, USA

Website
Windermere Elementary School

Windermere Elementary School

Elementary school

11125 Park Ave, Windermere, FL 34786, USA

Website

Windermere Union Church Preschool

Preschool

10710 Park Ridge Gotha Rd, Windermere, FL 34786, USA

Website

Inspiring Minds Day School

School

4950 S Apopka Vineland Rd, Orlando, FL 32819, USA

Website

The Parenting Experience Cooperative Preschool's

Preschool

4950 S Apopka Vineland Rd, Orlando, FL 32819, USA

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.

Yellow Dog Eats1/6

Yellow Dog Eats

American joint serving BBQ, sandwiches & craft brews in a colorful, relaxed setting with a patio.

1236 Hempel Ave, Windermere, FL 34786, USA

4.8 · 3769 reviews$$
Website
Hawkers Asian Street Food1/6

Hawkers Asian Street Food

Asian restaurant

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

4.8 · 4566 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 · 4989 reviews$
Website
Panera Bread1/6

Panera Bread

Counter-serve bakery/cafe chain serving sandwiches, salads & more, known for its bread & free WiFi.

4700 S Apopka Vineland Rd, Orlando, FL 32819, USA

3.9 · 493 reviews$$
Website
Dim Dim Sum1/6

Dim Dim Sum

Asian restaurant

4750 The Grove Dr, Windermere, FL 34786, USA

4.2 · 382 reviews$$
Website
Sakura Ramen Orlando1/6

Sakura Ramen Orlando

Restaurant

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

4.6 · 234 reviews$$
Website
Starbucks1/6

Starbucks

Welcoming coffeehouse with handcrafted coffee, espresso & tea, plus breakfast, lunch & pastries.

9100 Conroy Windermere Rd, Windermere, FL 34786, USA

4.1 · 366 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 · 874 reviews$
Website
Chipotle Mexican Grill1/6

Chipotle Mexican Grill

Casual restaurant offering Mexican fare, including design-your-own burritos, tacos & bowls.

9100 Conroy Windermere Rd, Windermere, FL 34786, USA

3.6 · 532 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.

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

  • 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