288 total properties
Did you mean the neighborhood Winter Park?
View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Virtual Tour
1 of 28
$1,450,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 100 S VIRGINIA AVENUE 201 Winter Park, FL MLS# O6442678
$1,450,000
3

Beds

3.0

Baths

2,756

Sq.Ft.

100 S VIRGINIA AVENUE 201

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
  • Virtual Tour
1 of 48
$1,449,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

Courtesy of SAFFORD REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1546 MILLER AVENUE Winter Park, FL MLS# O6428019
  • New Construction with Virtual Tour
1 of 36
$1,429,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1546 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1581 MAGNOLIA AVE Winter Park, FL MLS# O6396118
  • Virtual Tour
1 of 76
$1,425,000
4

Beds

4.0

Baths

2,642

Sq.Ft.

1581 MAGNOLIA AVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2237 WOODCREST DRIVE Winter Park, FL MLS# TB8563139
  • Recently Listed
1 of 5
$1,425,000
4

Beds

4.1

Baths

3,563

Sq.Ft.

2237 WOODCREST DRIVE

Winter Park, FL

Courtesy of WEEKLEY HOMES REALTY COMPANY
View 328 W MORSE BOULEVARD 105 Winter Park, FL MLS# O6448119
$1,420,000
1,862

Sq.Ft.

328 W MORSE BOULEVARD 105

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1737 INDIANA AVENUE Winter Park, FL MLS# S5158760
  • Recently Listed with Virtual Tour
1 of 38
OPEN HOUSE: Sunday 11/1 1:00 PM - 4:00 PM
$1,399,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1737 INDIANA AVENUE

Winter Park, FL

Courtesy of LOKATION
View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 150 E READING WAY Winter Park, FL MLS# O6430223
  • Virtual Tour
1 of 21
$1,399,000
0.0

Baths

150 E READING WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 150 E READING WAY Winter Park, FL MLS# O6435809
  • Virtual Tour
1 of 21
$1,399,000
3

Beds

2.1

Baths

2,080

Sq.Ft.

150 E READING WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1751 GOODRICH AVENUE Winter Park, FL MLS# O6377936
$1,380,000
4

Beds

3.1

Baths

2,170

Sq.Ft.

1751 GOODRICH AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1534 MILLER AVENUE Winter Park, FL MLS# O6454003
  • Recently Listed with Virtual Tour
1 of 8
$1,379,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1534 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 330 W MORSE BOULEVARD 104 Winter Park, FL MLS# O6448115
$1,379,000
1,790

Sq.Ft.

330 W MORSE BOULEVARD 104

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • New Construction with Virtual Tour
1 of 38
OPEN HOUSE: Sunday 11/1 11:00 AM - 2:00 PM
$1,369,000
5

Beds

4.0

Baths

2,446

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 1320 ORCHID AVENUE Winter Park, FL MLS# O6438656
  • Virtual Tour
1 of 33
$1,350,000
4

Beds

4.0

Baths

2,998

Sq.Ft.

1320 ORCHID AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 436 N WYMORE ROAD Winter Park, FL MLS# O6440396
  • Virtual Tour
1 of 24
$1,350,000
3,021

Sq.Ft.

436 N WYMORE ROAD

Winter Park, FL

Courtesy of HOMEVEST REALTY
View 1939 WOODCREST DRIVE Winter Park, FL MLS# O6449666
  • Recently Listed with Virtual Tour
1 of 58
OPEN HOUSE: Sunday 11/1 9:00 AM - 5:00 PM
$1,349,000
4

Beds

3.1

Baths

2,575

Sq.Ft.

1939 WOODCREST DRIVE

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 952 MOSS LANE Winter Park, FL MLS# TB8545586
  • Virtual Tour
1 of 49
$1,319,950
4

Beds

2.3

Baths

3,474

Sq.Ft.

952 MOSS LANE

Winter Park, FL

Courtesy of MERIDIAN RESIDE
View 504 W SWOOPE AVENUE Winter Park, FL MLS# O6440582
  • Virtual Tour
1 of 32
$1,300,000
3

Beds

2.1

Baths

2,563

Sq.Ft.

504 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA 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

360

Estimated median home price

$799,999
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 3
$100K - 200K 35
$200K - 300K 20
$300K - 400K 15
$400K - 500K 31
$500K - 600K 26
$600K - 700K 35
$700K - 800K 16
$800K - 900K 15
$900K - 1M 13
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 215
Townhouse 22
Condo 77
Commercial 15
Rental 90
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/30/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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

Data is updated as of 10/31/2026.

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 10/31/2026.