68 total properties
Did you mean the neighborhood Winter Park?
View 1640 ORANGE AVENUE Winter Park, FL MLS# O6425038
  • Recently Listed with Virtual Tour
1 of 18
$2,200
3

Beds

2.0

Baths

1,053

Sq.Ft.

1640 ORANGE AVENUE

Winter Park, FL

View 640 N PARK AVENUE 4 Winter Park, FL MLS# O6425848
  • Recently Listed with Virtual Tour
1 of 33
$2,200
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 4

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6421826
  • Recently Listed with Virtual Tour
1 of 17
$2,129
3

Beds

2.0

Baths

1,266

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TAH FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 503 KILSHORE LANE Winter Park, FL MLS# O6412456
$2,050
2

Beds

1.0

Baths

1,125

Sq.Ft.

503 KILSHORE LANE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6423856
  • Recently Listed with Virtual Tour
1 of 18
$1,997
1

Beds

1.0

Baths

650

Sq.Ft.

Address not provided

Winter Park, FL

View 3220 OAK LAWN PLACE PLACE 210 Winter Park, FL MLS# S5150258
  • Recently Listed with Virtual Tour
1 of 27
$1,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

3220 OAK LAWN PLACE PLACE 210

Winter Park, FL

View 7426 WYNNEWOOD SQUARE 195 Winter Park, FL MLS# O6410726
$1,800
3

Beds

2.0

Baths

1,117

Sq.Ft.

7426 WYNNEWOOD SQUARE 195

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES LLC
View 652 SAINT JHONS 652 Winter Park, FL MLS# TB8514256
$1,800
2

Beds

2.0

Baths

1,037

Sq.Ft.

652 SAINT JHONS 652

Winter Park, FL

View 614 SAINT JOHNS COURT 614 Winter Park, FL MLS# O6410529
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

614 SAINT JOHNS COURT 614

Winter Park, FL

View 3374 CEDAR SPRINGS PLACE 155 Winter Park, FL MLS# O6424930
  • Recently Listed with Virtual Tour
1 of 25
$1,750
2

Beds

2.1

Baths

1,031

Sq.Ft.

3374 CEDAR SPRINGS PLACE 155

Winter Park, FL

View 4812 TANGERINE AVENUE 4812 Winter Park, FL MLS# O6420610
$1,700
2

Beds

2.0

Baths

1,058

Sq.Ft.

4812 TANGERINE AVENUE 4812

Winter Park, FL

View 620 TRINIDAD COURT 620 Winter Park, FL MLS# S5150729
$1,695
2

Beds

2.0

Baths

1,120

Sq.Ft.

620 TRINIDAD COURT 620

Winter Park, FL

View 1695 LEE ROAD A101 Winter Park, FL MLS# O6419704
  • Recently Listed with Virtual Tour
1 of 22
$1,695
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

View 3045 AARON BURR AVENUE 12D Winter Park, FL MLS# S5150999
$1,650
2

Beds

2.0

Baths

1,062

Sq.Ft.

3045 AARON BURR AVENUE 12D

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1941 LANIER COURT Winter Park, FL MLS# O6404537
$1,595
2

Beds

1.0

Baths

865

Sq.Ft.

1941 LANIER COURT

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2918 ANTIQUE OAKS CIRCLE 26 Winter Park, FL MLS# O6413563
$1,575
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 26

Winter Park, FL

View 7338 SWALLOW RUN 7338 Winter Park, FL MLS# O6411093
$1,550
2

Beds

2.0

Baths

774

Sq.Ft.

7338 SWALLOW RUN 7338

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6421564
  • Recently Listed
1 of 15
$1,550
2

Beds

1.0

Baths

881

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 7340 SWALLOW RUN 7340 Winter Park, FL MLS# O6402679
$1,500
2

Beds

2.0

Baths

802

Sq.Ft.

7340 SWALLOW RUN 7340

Winter Park, FL

View 1695 LEE ROAD B204 Winter Park, FL MLS# O6418108
$1,500
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD B204

Winter Park, FL

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

281

Estimated median home price

$725,000
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 - 100K8
$100K - 200K38
$200K - 300K13
$300K - 400K14
$400K - 500K18
$500K - 600K22
$600K - 700K23
$700K - 800K8
$800K - 900K10
$900K - 1M7
$1M - Max120

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family167
Townhouse12
Condo68
Commercial7
Rental67
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/18/2026)

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 7/18/2026.