Dani Kubrusly

Orange County

Winter Park

Greater OrlandoCentral Florida

An established city immediately north of downtown Orlando, built around a chain of lakes, brick streets and a genuine main street rather than a master plan.

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Identity

Winter Park grew over more than a century, and it shows in a way that newer areas cannot reproduce: mature oak canopy, older homes of many different periods, a walkable commercial avenue, museums and a college campus inside the city itself. It is one of the few places in Central Florida where the centre existed long before the suburbs around it.

Location and access

North of downtown Orlando, framed by I-4 to the west and connected to the rest of the metro by US-17-92 and SR-436. Central within the region rather than at its edge, which shortens most routine trips and lengthens none of them dramatically.

Everyday life

Daily life here can genuinely include walking: Park Avenue for shops and restaurants, the parks along the lakes, the farmers market, the library and cultural venues. Beyond the central blocks the pattern becomes residential and car-based, like most of the region.

  • Park Avenue, with retail, restaurants and cafés.
  • Central Park and the lakefront parks along the chain of lakes.
  • Charles Hosmer Morse Museum of American Art.
  • Rollins College, on the shore of Lake Virginia.
  • The scenic boat tour on the Winter Park chain of lakes.
  • A SunRail commuter rail station in the centre of the city.

Housing

  • Established single-family homes spanning many decades of construction.
  • Renovated and rebuilt homes on older lots, sometimes side by side.
  • Condominiums and apartments near the commercial core.
  • Larger lakefront properties on the chain of lakes.
  • Mature trees and older infrastructure, with the maintenance that implies.

New construction

There is little room for large new communities inside Winter Park itself. New product usually appears as individual rebuilds, renovations or smaller infill projects, which means each home is evaluated on its own rather than by builder and phase.

Getting around

Walkable at the centre, car-based elsewhere, with I-4, US-17-92 and SR-436 for regional trips and a SunRail station for the north-south corridor. Access to the airport crosses the metro rather than skirting it.

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.

Genuinely walkable at the centre: Park Avenue for shops and lunch, Central Park for the weekend market, the library, museums and Rollins College. Beyond a few blocks the city becomes residential, with brick streets and mature oaks.

Routines that fit

  • Wanting culture, cafés and services within walking distance.
  • Commuting by SunRail from a station in the city centre.
  • Preferring older homes with character over new construction.

Outdoors and leisure

  • Central Park, on Park Avenue, with the weekly farmers market nearby.
  • The Winter Park chain of lakes and its scenic boat tour.
  • Mead Botanical Garden, with boardwalks and birding.
  • Lakefront parks and tree-lined running routes.

Eating and shopping

Park Avenue and Hannibal Square carry the restaurants, from cafés and bakeries to established fine dining, and the concentration means most of it is reachable on foot.

Groceries, clinics, a hospital and specialist offices are inside the city, and downtown Orlando is a short drive or a SunRail ride away.

Seasons

The art festival season and the cooler months bring crowds and parking pressure to Park Avenue; summer is quieter but stormy in the afternoons.

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.

First United Methodist Preschool

Preschool

125 N Interlachen Ave, Winter Park, FL 32789, USA

Website

All Saints School

School

338 E Lyman Ave, Winter Park, FL 32789, USA

Website
First Congregational Preschool

First Congregational Preschool

Preschool

225 S Interlachen Ave, Winter Park, FL 32789, USA

Young Innovators Academy Winter Park1/6

Young Innovators Academy Winter Park

Preschool

225 S Interlachen Ave, Winter Park, FL 32789, USA

Website
Rollins College Hamilton Holt School

Rollins College Hamilton Holt School

Educational institution

1000 Holt Ave, Winter Park, FL 32789, USA

Website

St. Margaret Mary Gym

School

631 N Knowles Ave, Winter Park, FL 32789, USA

St. Margaret Mary Catholic School1/6

St. Margaret Mary Catholic School

School

142 E Swoope Ave, Winter Park, FL 32789, USA

Website
Roy E. Crummer Hall & Bush Executive Center1/6

Roy E. Crummer Hall & Bush Executive Center

University

1000 Holt Ave, Winter Park, FL 32789, 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.

The Cheesecake Factory1/6

The Cheesecake Factory

American chain restaurant offering sizable portions from a vast menu including signature cheesecake

520 N Orlando Ave Ste 100, Winter Park, FL 32789, USA

4.2 · 7343 reviews$$
Website
Raising Cane's Chicken Fingers1/6

Raising Cane's Chicken Fingers

Fast-food chain specializing in fried chicken fingers, crinkle-cut fries & Texas toast.

100 S Semoran Blvd, Winter Park, FL 32792, USA

4.3 · 970 reviews$
Website
The Alfond Inn1/6

The Alfond Inn

Polished, understated rooms with free Wi-Fi, plus a casual restaurant & an outdoor pool.

300 E New England Ave, Winter Park, FL 32789, USA

4.6 · 2200 reviews
Website
Briarpatch Restaurant1/6

Briarpatch Restaurant

Breakfast fare such as waffles & eggs Benedict plus homemade ice cream served in an airy setting.

252 N Park Ave #3814, Winter Park, FL 32789, USA

4.5 · 4137 reviews$$
Website
AVA MediterrAegean Winter Park1/6

AVA MediterrAegean Winter Park

Greek restaurant

290 S Park Ave, Winter Park, FL 32789, USA

4.8 · 11891 reviews$$$$
Website
Hillstone Restaurant1/6

Hillstone Restaurant

Upscale chain eatery serving burgers, steaks & other American fare in stylish, spacious surrounds.

215 S Orlando Ave, Winter Park, FL 32789, USA

4.3 · 3860 reviews
Website
Chick-fil-A1/6

Chick-fil-A

Fast-food chain serving chicken sandwiches & nuggets along with salads & sides.

700 S Orlando Ave, Winter Park, FL 32789, USA

4.3 · 2957 reviews$
Website
Prato1/6

Prato

Stylish Italian eatery offering modern takes on classic dishes in rustic-chic surrounds.

124 N Park Ave, Winter Park, FL 32789, USA

4.5 · 3332 reviews$$
Website
The Glass Knife1/6

The Glass Knife

This counter-service dessert shop sells sweets, savories and coffees in a bright feminine space.

276 S Orlando Ave, Winter Park, FL 32789, USA

4.6 · 3816 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.

Downtown Winter Park1/6

Downtown Winter Park

Popular shopping district featuring eateries & boutiques in a charming, pedestrian-friendly setting.

110 N Park Ave, Winter Park, FL 32789, USA

Website
Blue Jacket Park1/6

Blue Jacket Park

Sports, recreation, loop path & picnic areas amid stone structures & a fountain on 75 acres.

2501 General Rees Ave, Orlando, FL 32814, USA

Website
Lake Baldwin Dog Park1/6

Lake Baldwin Dog Park

Park

1864-2018 S Lakemont Ave, Winter Park, FL 32789, USA

Website
Ward Park1/6

Ward Park

Public 66-acre sports-focused park (baseball, soccer, football & track) with a wetlands trail.

Cady Way & Perth Ln, Winter Park, FL 32792, USA

Website
Martin Luther King, Jr. Park1/6

Martin Luther King, Jr. Park

23 acres set around a lake, with a big playground, walking trail, sports facilities & picnic tables.

1050 W Morse Blvd, Winter Park, FL 32789, USA

Website
Lake Baldwin Park1/6

Lake Baldwin Park

23-acre dog-friendly lakeside park offering a beach, pavilions, picnic areas & a boat ramp.

2000 S Lakemont Ave, Winter Park, FL 32789, 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

  • Older homes mean older systems: roof, plumbing, electrical and trees all deserve close inspection.
  • Lot sizes and street patterns vary block to block; two nearby homes can be very different products.
  • Limited new construction, so buyers who want a new home usually look elsewhere.
  • Central location comes with the traffic of a central location, especially near I-4.

Next step

A thirty-minute conversation.

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

Talk to Dani