43 total properties
Did you mean the neighborhood Winter Park?
View 890 N PHELPS AVENUE Winter Park, FL MLS# O6430202
$1,775,000
4

Beds

3.2

Baths

3,630

Sq.Ft.

890 N PHELPS AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2525 LAFAYETTE AVENUE Winter Park, FL MLS# O6428823
  • Recently Listed with Virtual Tour
1 of 10
$1,749,000
4

Beds

3.1

Baths

2,715

Sq.Ft.

2525 LAFAYETTE AVENUE

Winter Park, FL

View 1546 MILLER AVENUE Winter Park, FL MLS# O6428019
  • Recently Listed with Virtual Tour
1 of 36
$1,419,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1546 MILLER AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Virtual Tour
1 of 25
$1,595,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Recently Listed with Virtual Tour
1 of 49
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

Winter Park, FL

View 313L SYLVAN DRIVE Winter Park, FL MLS# O6424300
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1298 BEACHVIEW AVENUE Winter Park, FL MLS# O6417337
$1,375,000
1

Beds

1.0

Baths

1,665

Sq.Ft.

1298 BEACHVIEW AVENUE

Winter Park, FL

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

View 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Virtual Tour
1 of 10
$1,600,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

250 KILLARNEY

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
  • Virtual Tour
1 of 48
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

View 341 E READING WAY Winter Park, FL MLS# O6420387
$1,625,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

View 2625 PARK PLACE DRIVE Winter Park, FL MLS# O6413031
$1,799,000
4

Beds

4.1

Baths

3,460

Sq.Ft.

2625 PARK PLACE DRIVE

Winter Park, FL

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 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
$1,450,000
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

Winter Park, FL

View 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Virtual Tour
1 of 9
$1,595,000
Studio

Beds

0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • New Construction with Virtual Tour
1 of 38
$1,429,000
5

Beds

4.0

Baths

2,351

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 641 NORTHWOOD CIRCLE Winter Park, FL MLS# O6412554
  • Virtual Tour
1 of 41
$1,669,000
3

Beds

3.2

Baths

2,756

Sq.Ft.

641 NORTHWOOD CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
$1,800,000
4

Beds

4.0

Baths

3,065

Sq.Ft.

723 SYMONDS AVENUE

Winter Park, FL

View 1841 LAKE SPIER DRIVE Winter Park, FL MLS# O6407841
$1,595,000
3

Beds

4.0

Baths

2,467

Sq.Ft.

1841 LAKE SPIER DRIVE

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

352

Estimated median home price

$732,000
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 7
$100K - 200K 38
$200K - 300K 23
$300K - 400K 13
$400K - 500K 34
$500K - 600K 26
$600K - 700K 31
$700K - 800K 14
$800K - 900K 12
$900K - 1M 11
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 214
Townhouse 22
Condo 78
Commercial 9
Rental 71
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 8/5/2026)

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 8/5/2026.