309 total properties
Did you mean the neighborhood Winter Park?
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
$1,275,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
$195,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 313 SYLVAN DRIVE Winter Park, FL MLS# O6407606
  • New Construction with Virtual Tour
1 of 10
$5,500,000
4

Beds

4.1

Baths

4,775

Sq.Ft.

313 SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
1 of 37
OPEN HOUSE: Sunday 7/19 12:00 PM - 2:00 PM
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

View 1836 WHITEHALL DRIVE Winter Park, FL MLS# O6416158
  • New Construction with Virtual Tour
1 of 70
$3,500,000
5

Beds

6.1

Baths

4,168

Sq.Ft.

1836 WHITEHALL DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 39
OPEN HOUSE: Sunday 7/19 11:00 AM - 2:00 PM
$2,250,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Virtual Tour
1 of 38
$849,900
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

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

Courtesy of BAY HILL REALTY LLC
View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
$775,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

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 231 CHELTON CIRCLE Winter Park, FL MLS# O6414890
  • Virtual Tour
1 of 67
$4,950,000
4

Beds

5.2

Baths

5,550

Sq.Ft.

231 CHELTON CIRCLE

Winter Park, FL

View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Virtual Tour
1 of 83
$1,888,888
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

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 413 W MORSE BOULEVARD Winter Park, FL MLS# O6412134
$2,695,000
3

Beds

3.1

Baths

3,048

Sq.Ft.

413 W MORSE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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 2240 VENETIAN WAY Winter Park, FL MLS# O6413398
  • Virtual Tour
1 of 27
$3,500,000
4

Beds

3.1

Baths

4,036

Sq.Ft.

2240 VENETIAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2831 MULFORD AVENUE Winter Park, FL MLS# O6414319
  • Virtual Tour
1 of 28
$695,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

2831 MULFORD AVENUE

Winter Park, FL

View 230 E ROCKWOOD WAY Winter Park, FL MLS# O6412857
  • Virtual Tour
1 of 59
$2,189,000
5

Beds

4.0

Baths

3,374

Sq.Ft.

230 E ROCKWOOD WAY

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

Price Count
$0 - 100K 8
$100K - 200K 38
$200K - 300K 13
$300K - 400K 14
$400K - 500K 18
$500K - 600K 22
$600K - 700K 23
$700K - 800K 8
$800K - 900K 10
$900K - 1M 7
$1M - Max 120

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 167
Townhouse 12
Condo 68
Commercial 7
Rental 67
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/18/2026)

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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 7/19/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 7/19/2026.