260 total properties
Did you mean the neighborhood Winter Park?
View 1754 TAYLOR AVENUE Winter Park, FL MLS# O6421927
  • Recently Listed with Virtual Tour
1 of 17
$2,569,999
5

Beds

4.1

Baths

3,670

Sq.Ft.

1754 TAYLOR AVENUE

Winter Park, FL

View 1823 SUNSET DRIVE Winter Park, FL MLS# O6421690
  • Recently Listed with Virtual Tour
1 of 14
$2,549,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

1823 SUNSET DRIVE

Winter Park, FL

View 3425 FORSYTH ROAD Winter Park, FL MLS# S5142219
  • Virtual Tour
1 of 40
$2,500,000
16,437

Sq.Ft.

3425 FORSYTH ROAD

Winter Park, FL

Courtesy of REMAX PREMIER PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 450 LAKEWOOD DRIVE Winter Park, FL MLS# O6403490
  • Virtual Tour
1 of 78
$2,500,000
5

Beds

4.2

Baths

4,572

Sq.Ft.

450 LAKEWOOD DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1477 W FAIRBANKS AVENUE Winter Park, FL MLS# O6422964
  • Recently Listed with Virtual Tour
1 of 70
$2,500,000
6,049

Sq.Ft.

1477 W FAIRBANKS AVENUE

Winter Park, FL

View 2228 HOWARD DRIVE Winter Park, FL MLS# O6407733
  • New Construction with Virtual Tour
1 of 9
$2,460,000
4

Beds

3.1

Baths

3,294

Sq.Ft.

2228 HOWARD DRIVE

Winter Park, FL

View 2838 WRIGHT AVENUE Winter Park, FL MLS# O6399931
  • New Construction with Virtual Tour
1 of 10
$2,399,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

2838 WRIGHT AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6381552
  • New Construction
1 of 61
$2,394,500
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

View 1630 ELM AVENUE Winter Park, FL MLS# O6388606
  • New Construction with Virtual Tour
1 of 15
$2,385,000
5

Beds

4.1

Baths

3,408

Sq.Ft.

1630 ELM AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 140 E MORSE BOULEVARD J Winter Park, FL MLS# O6414891
$2,350,000
3

Beds

3.0

Baths

2,143

Sq.Ft.

140 E MORSE BOULEVARD J

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1885 TEMPLE DRIVE Winter Park, FL MLS# O6359471
  • Virtual Tour
1 of 56
$2,225,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Recently Listed with Virtual Tour
1 of 20
$2,200,000
Studio

Beds

0.0

Baths

1415 GROVE TERRACE

Winter Park, FL

View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6414770
  • New Construction with Virtual Tour
1 of 76
$2,199,000
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1750 WALNUT AVENUE Winter Park, FL MLS# O6422700
  • Recently Listed with Virtual Tour
1 of 55
OPEN HOUSE: Sunday 7/12 10:00 AM - 1:00 PM
$2,195,000
4

Beds

4.1

Baths

3,691

Sq.Ft.

1750 WALNUT 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

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$2,095,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

View 147 S INTERLACHEN AVENUE 202 Winter Park, FL MLS# L4959060
$2,070,000
3

Beds

4.1

Baths

3,272

Sq.Ft.

147 S INTERLACHEN AVENUE 202

Winter Park, FL

View 2036 VIA TUSCANY Winter Park, FL MLS# O6379888
$2,000,000
3

Beds

2.0

Baths

2,148

Sq.Ft.

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2036 VIA TUSCANY Winter Park, FL MLS# O6380892
$2,000,000
Studio

Beds

0.0

Baths

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 318 VITORIA AVENUE Winter Park, FL MLS# O6388489
  • Virtual Tour
1 of 66
$1,980,000
3

Beds

2.1

Baths

2,433

Sq.Ft.

318 VITORIA AVENUE

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

268

Estimated median home price

$675,000
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 18
$300K - 400K 14
$400K - 500K 24
$500K - 600K 20
$600K - 700K 21
$700K - 800K 10
$800K - 900K 7
$900K - 1M 4
$1M - Max 105

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 151
Townhouse 10
Condo 72
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 7/11/2026)

Information deemed reliable but not guaranteed.

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.

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 7/11/2026.

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 7/11/2026.