Orlando
Winter Park
Brick streets, mature oaks, and walkable Park Avenue. Older housing stock with real character and strong resale.
Homes for sale in Winter Park
Pulled live from the same statewide feed as every other search on this site.
All active Winter Park listings
Nearby schools
The public elementary, middle and high schools closest to Winter Park. These are nearby schools, not a zoning guarantee — assignment depends on your exact address.
- Brookshire Elementary School
public · PK, K-5 · 4/10 GreatSchools
- Glenridge Middle School
public · 6-8 · 7/10 GreatSchools
- Winter Park High School
public · 9-12 · 7/10 GreatSchools
What the rating means: GreatSchools scores each school from 1 to 10 based largely on state test results, academic progress and how different groups of students perform. It is a summary of test data, not a judgement of teaching, programs or fit for your child.
Why this disclaimer: ratings are refreshed by GreatSchools each year and Florida districts redraw attendance boundaries, open new schools and change grade spans between school years. Verify the current assignment for the exact address with the county school district — and visit — before you rely on it in an offer.
Parks, groceries, dining and hospitals
The closest parks, supermarkets, restaurants and hospitals to the centre of Winter Park, within 5 miles — Winter Park is treated as a community-scale area, so the search radius is set accordingly. Distances are straight-line from the area centre, not driving time from a specific address.
Parks & recreation
Trismen Park
0.06 mi · 231 Brewer Ave, Winter Park, FL 32789, USA
Winter park canal
0.5 mi · 312 E Morse Blvd, Winter Park, FL 32789, USA
Park bathroom
0.5 mi · 410 Ollie Ave, Winter Park, FL 32789, USA
Dinky Dock Park
0.5 mi · 410 Ollie Ave, Winter Park, FL 32789, USA
Marvin Smiley Park
0.5 mi · 150 N Phelps Ave, Winter Park, FL 32789, USA
Groceries
The Ancient Olive Gourmet of Winter Park
0.7 mi · 324 N Park Ave, Winter Park, FL 32789, USA
Williams-Sonoma
0.7 mi · 142 S Park Ave, Winter Park, FL 32789, USA
Greater Lifestyle Foods
0.8 mi · Winter Park, FL 32789, USA
Sprouts Farmers Market
0.9 mi · 1989 Aloma Ave, Winter Park, FL 32792, USA
Publix Super Market at Aloma Shopping Center
1.1 mi · 2295 Aloma Ave, Winter Park, FL 32792, USA
Dining & cafés
Cherry Pocket
0.5 mi · 312 E Morse Blvd, Winter Park, FL 32789, USA
The Alfond Inn
0.6 mi · 300 E New England Ave, Winter Park, FL 32789, USA
Hamilton's Kitchen
0.6 mi · Located at The Alfond Inn at Rollins, 300 E New England Ave, Winter Park, FL 32789, USA
Jala Indian Cuisine
0.7 mi · 155 E Morse Blvd, Winter Park, FL 32789, USA
Luca Turci Italian Restaurant
0.7 mi · 153 E Morse Blvd, Winter Park, FL 32789, USA
Hospitals
Alternative Medical Care
0.7 mi · 315 N Lakemont Ave, Winter Park, FL 32792, USA
Royer Medical Building
0.7 mi · 111 N Lakemont Ave, Winter Park, FL 32792, USA
AdventHealth Winter Park
0.8 mi · 200 N Lakemont Ave, Winter Park, FL 32792, USA
AdventHealth Sports Concussion Program
0.8 mi · 133 Benmore Dr Ste 200, Winter Park, FL 32792, USA
Dr. Phillips Aesthetics
0.8 mi · 242 N Edinburgh Dr, Winter Park, FL 32792, USA
Sourced from Google Places and refreshed by hand. Businesses open, close and move — confirm anything you're counting on before it drives a decision.
Market dynamics
What the Orlando–Kissimmee–Sanford metro market is doing
Monthly listing statistics for the Orlando–Kissimmee–Sanford metro — the smallest geography published for Winter Park. Figures cover Sep 26 and the 36 months before it.
- Median list price
- $410,000
- Median days on market
- 77 days
- Active listings
- 13,869
- Pending ratio
- 31.9%
- Share with a price cut
- 22.7%
-2.5% year over year
-2.5% year over year
+0.3% year over year
+1.1 points year over year
-0.2 points year over year
Median list price
The midpoint asking price of homes on the market — half are listed above, half below. · Orlando–Kissimmee–Sanford metro
Market alerts
Get the Winter Park market update once a month
These figures are published monthly. Enter your email and I'll send you a short digest for Winter Park as soon as each new month lands — no more often than that.
Data provided by Redfin, a national real estate brokerage. Redfin Data Center · Source file updated September 30, 2026.