165 total properties
Did you mean the neighborhood Winter Park?
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
$395,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Adult Community with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5147382
$140,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of NAIM REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$439,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1695 LEE ROAD D211 Winter Park, FL MLS# O6396190
$99,900
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD D211

Winter Park, FL

Courtesy of LOKATION
View 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
  • Virtual Tour
1 of 36
$630,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

Courtesy of AROD PARTNERS REALTY
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$419,000
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2918 ANTIQUE OAKS CIRCLE 25 Winter Park, FL MLS# O6389113
$189,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 25

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$449,900
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
$499,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
$680,000
4

Beds

3.1

Baths

2,664

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 230 STRATHY LANE Winter Park, FL MLS# O6371054
  • Virtual Tour
1 of 12
$499,000
2

Beds

1.0

Baths

920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
  • Virtual Tour
1 of 19
$499,000
3

Beds

2.0

Baths

1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$459,900
0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
$184,400
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

Courtesy of HOMESMART
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$285,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 311 SCOTTSDALE SQUARE 311 Winter Park, FL MLS# O6355536
$109,000
1

Beds

1.0

Baths

785

Sq.Ft.

311 SCOTTSDALE SQUARE 311

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 311 E MORSE BOULEVARD 7-11 Winter Park, FL MLS# O6337061
$279,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 7-11

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
$619,500
3

Beds

2.1

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 3370 CEDAR SPRINGS PLACE 156 Winter Park, FL MLS# O6326460
$179,990
2

Beds

2.1

Baths

1,031

Sq.Ft.

3370 CEDAR SPRINGS PLACE 156

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES LLC

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

357

Estimated median home price

$825,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

PriceCount
$0 - 100K4
$100K - 200K32
$200K - 300K23
$300K - 400K18
$400K - 500K32
$500K - 600K24
$600K - 700K26
$700K - 800K18
$800K - 900K17
$900K - 1M12
$1M - Max151

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family210
Townhouse25
Condo80
Commercial15
Rental96
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 11/11/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 11/12/2026.