84 total properties
Did you mean the neighborhood Winter Park?
View 541 N CAPEN AVENUE Winter Park, FL MLS# O6379695
  • Recently Listed
1 of 14
$2,295
3

Beds

2.0

Baths

1,251

Sq.Ft.

541 N CAPEN AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2580 EUSTON ROAD Winter Park, FL MLS# O6384808
  • Recently Listed
1 of 15
$2,500
3

Beds

2.0

Baths

1,158

Sq.Ft.

2580 EUSTON ROAD

Winter Park, FL

Courtesy of LOKATION
View 1130 WASHINGTON AVENUE 11C Winter Park, FL MLS# O6384586
  • Recently Listed with Virtual Tour
1 of 52
$5,995
3

Beds

2.1

Baths

2,069

Sq.Ft.

1130 WASHINGTON AVENUE 11C

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 2907 LITTLE JOHN ROAD Winter Park, FL MLS# O6381254
  • Recently Listed with Virtual Tour
1 of 31
$3,200
4

Beds

3.0

Baths

2,070

Sq.Ft.

2907 LITTLE JOHN ROAD

Winter Park, FL

Courtesy of SOTERA LIVING
View 3651 N GOLDENROD ROAD A103 Winter Park, FL MLS# O6381710
  • Recently Listed with Virtual Tour
1 of 13
$1,595
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD A103

Winter Park, FL

Courtesy of CFRP REALTY LLC
View 283 N RANGER BOULEVARD Winter Park, FL MLS# O6380889
  • Recently Listed with Virtual Tour
1 of 22
$2,650
3

Beds

2.0

Baths

1,542

Sq.Ft.

283 N RANGER BOULEVARD

Winter Park, FL

Courtesy of BELMONT REALTY
View 612 MONTEGO BAY COURT 612 Winter Park, FL MLS# O6381197
  • Recently Listed with Virtual Tour
1 of 14
$1,850
2

Beds

2.0

Baths

1,037

Sq.Ft.

612 MONTEGO BAY COURT 612

Winter Park, FL

Courtesy of JEXOR LLC
View 612 TRINIDAD COURT 612 Winter Park, FL MLS# O6381198
  • Recently Listed with Virtual Tour
1 of 12
$1,850
2

Beds

2.0

Baths

1,037

Sq.Ft.

612 TRINIDAD COURT 612

Winter Park, FL

Courtesy of JEXOR LLC
View 421 W FAIRBANKS AVENUE Winter Park, FL MLS# O6381970
  • Recently Listed with Virtual Tour
1 of 21
$3,750
3

Beds

3.0

Baths

1,750

Sq.Ft.

421 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 1815 BARKER DRIVE Winter Park, FL MLS# A4681550
  • Recently Listed with Virtual Tour
1 of 25
$5,500
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

Courtesy of FLATFEE.COM
View 3044 ANTIQUE OAKS CIRCLE APT 177 Winter Park, FL MLS# S5143190
  • Recently Listed with Virtual Tour
1 of 16
$1,600
1

Beds

1.0

Baths

749

Sq.Ft.

3044 ANTIQUE OAKS CIRCLE APT 177

Winter Park, FL

Courtesy of ROBERT MICHAEL & COMPANY INC.
View 503 W CANTON AVENUE Winter Park, FL MLS# O6380490
  • Recently Listed with Virtual Tour
1 of 45
$6,000
3

Beds

3.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 782 S PENNSYLVANIA AVENUE 1 Winter Park, FL MLS# O6380197
  • Recently Listed with Virtual Tour
1 of 25
$5,770
3

Beds

2.1

Baths

2,354

Sq.Ft.

782 S PENNSYLVANIA AVENUE 1

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 1695 LEE ROAD ROAD C110 Winter Park, FL MLS# O6377466
  • Recently Listed with Virtual Tour
1 of 12
$1,400
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD ROAD C110

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1380 INDIANA AVENUE 3 Winter Park, FL MLS# R4910620
  • Recently Listed with Virtual Tour
1 of 23
$1,495
2

Beds

1.0

Baths

3,822

Sq.Ft.

1380 INDIANA AVENUE 3

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1812 PINEVIEW CIRCLE Winter Park, FL MLS# O6379940
  • Recently Listed with Virtual Tour
1 of 21
$2,375
3

Beds

2.0

Baths

1,238

Sq.Ft.

1812 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 1278 MILLER AVENUE Winter Park, FL MLS# O6378898
  • Recently Listed with Virtual Tour
1 of 25
$3,000
3

Beds

2.1

Baths

1,659

Sq.Ft.

1278 MILLER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 3355 RIVER VIEW WAY 42 Winter Park, FL MLS# O6379394
$1,650
2

Beds

1.1

Baths

990

Sq.Ft.

3355 RIVER VIEW WAY 42

Winter Park, FL

Courtesy of EPIQUE REALTY, INC.
View Address not provided Winter Park, FL MLS# O6379158
$2,500
Studio

Beds

0.0

Baths

Address not provided

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1925 S LAKEMONT AVENUE Winter Park, FL MLS# O6378656
$1,100
1

Beds

1.0

Baths

850

Sq.Ft.

1925 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY 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

319

Estimated median home price

$699,000
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 - 100K7
$100K - 200K38
$200K - 300K33
$300K - 400K19
$400K - 500K25
$500K - 600K16
$600K - 700K22
$700K - 800K20
$800K - 900K7
$900K - 1M7
$1M - Max125

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family178
Townhouse17
Condo88
Commercial5
Rental82
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 2/23/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 2/23/2026.