101 total properties
Did you mean the neighborhood Winter Park?
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
$500,000
3

Beds

2.0

Baths

1,413

Sq.Ft.

512 N LAKEMONT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7509 GLENMOOR LANE Winter Park, FL MLS# O6421887
  • Virtual Tour
1 of 45
$499,500
3

Beds

2.0

Baths

2,067

Sq.Ft.

7509 GLENMOOR LANE

Winter Park, FL

View 3718 N Goldenrod Road Winter Park, FL MLS# A11792799
$499,000
Studio

Beds

0.0

Baths

3718 N Goldenrod Road

Winter Park, FL

Courtesy of PROCLOSE REALTY, LLC.
The time to sell is now! THE TIME TO SELL IS NOW!
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

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

View 2560 Franklin Avenue Winter Park, FL MLS# F10431070
$499,000
4

Beds

2.0

Baths

1,514

Sq.Ft.

2560 Franklin Avenue

Winter Park, FL

View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
$499,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
$498,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$495,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

View 4887 N MAGNOLIA AVENUE Winter Park, FL MLS# O6420961
  • Recently Listed with Virtual Tour
1 of 52
$495,000
4

Beds

3.0

Baths

1,955

Sq.Ft.

4887 N MAGNOLIA AVENUE

Winter Park, FL

Courtesy of LUXE PROPERTIES
View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
$475,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

346 S RANGER BOULEVARD

Winter Park, FL

View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$475,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
  • Recently Listed with Virtual Tour
1 of 32
$475,000
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

Winter Park, FL

View 240 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6330690
$470,000
4

Beds

2.0

Baths

1,718

Sq.Ft.

240 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View 2041 JEWELL AVENUE Winter Park, FL MLS# O6420660
  • Recently Listed with Virtual Tour
1 of 30
$470,000
3

Beds

1.0

Baths

1,508

Sq.Ft.

2041 JEWELL AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$469,000
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

View 259 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6419225
  • Recently Listed with Virtual Tour
1 of 26
$465,500
3

Beds

2.0

Baths

1,248

Sq.Ft.

259 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$460,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Virtual Tour
1 of 7
$459,900
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 316 BECKETT COURT Winter Park, FL MLS# O6411108
  • Virtual Tour
1 of 33
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of ITS REALTY

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

273

Estimated median home price

$695,000
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

Price Count
$0 - 100K 5
$100K - 200K 40
$200K - 300K 17
$300K - 400K 14
$400K - 500K 24
$500K - 600K 19
$600K - 700K 22
$700K - 800K 12
$800K - 900K 8
$900K - 1M 4
$1M - Max 108

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 158
Townhouse 10
Condo 70
Commercial 7
Rental 73
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/12/2026)

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 7/12/2026.