32 total properties
Did you mean the neighborhood Winter Park?
View 2228 HOWARD DRIVE Winter Park, FL MLS# O6407733
  • Recently Listed with Virtual Tour
1 of 9
$2,460,000
4

Beds

3.1

Baths

3,294

Sq.Ft.

2228 HOWARD DRIVE

Winter Park, FL

Courtesy of COLEDEV REAL ESTATE LLC
View 450 LAKEWOOD DRIVE Winter Park, FL MLS# O6403490
  • Recently Listed with 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 1630 LASBURY AVENUE Winter Park, FL MLS# O6404300
  • Recently Listed with Virtual Tour
1 of 37
$2,750,000
5

Beds

3.2

Baths

4,917

Sq.Ft.

1630 LASBURY AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 2361 MULBRY DRIVE Winter Park, FL MLS# O6396840
  • New Construction with Virtual Tour
1 of 82
OPEN HOUSE: Sunday 5/17 1:00 PM - 4:00 PM
$2,325,000
4

Beds

4.0

Baths

3,111

Sq.Ft.

2361 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$2,195,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 620 PINETREE ROAD Winter Park, FL MLS# O6397264
$2,790,000
Studio

Beds

0.0

Baths

620 PINETREE ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 800 JUANITA RAEL Winter Park, FL MLS# O6396611
  • Virtual Tour
1 of 37
$2,300,000
5

Beds

4.0

Baths

4,021

Sq.Ft.

800 JUANITA RAEL

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1636 ELIZABETHS WALK Winter Park, FL MLS# O6395638
  • Virtual Tour
1 of 31
$2,195,000
4

Beds

4.1

Baths

3,412

Sq.Ft.

1636 ELIZABETHS WALK

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1529 HOLTS GROVE CIRCLE Winter Park, FL MLS# O6395062
$2,795,000
4

Beds

4.2

Baths

4,356

Sq.Ft.

1529 HOLTS GROVE CIRCLE

Winter Park, FL

Courtesy of KGV REALTY GROUP
View 432 WORTHINGTON DRIVE Winter Park, FL MLS# O6390186
  • New Construction with Virtual Tour
1 of 17
$2,719,000
5

Beds

4.1

Baths

3,845

Sq.Ft.

432 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 872 GRANVILLE DRIVE Winter Park, FL MLS# O6391464
  • Virtual Tour
1 of 40
$2,200,000
4

Beds

3.1

Baths

3,195

Sq.Ft.

872 GRANVILLE DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1130 PARK NORTH PLACE Winter Park, FL MLS# O6392394
$2,495,000
5

Beds

3.1

Baths

4,011

Sq.Ft.

1130 PARK NORTH PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
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 541 W CANTON AVENUE Winter Park, FL MLS# O6389829
  • New Construction with Virtual Tour
1 of 51
$2,800,000
4

Beds

3.1

Baths

3,553

Sq.Ft.

541 W CANTON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 609 S PHELPS AVENUE Winter Park, FL MLS# O6388598
  • New Construction with Virtual Tour
1 of 19
$2,829,000
5

Beds

4.1

Baths

4,018

Sq.Ft.

609 S PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6389035
  • Virtual Tour
1 of 68
$2,279,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of GOLDEN GROUP REALTY LLC
View 240 N Phelps Avenue Winter Park, FL MLS# 1071436
$2,279,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N Phelps Avenue

Winter Park, FL

Brevard
View 2423 VIA SIENNA Winter Park, FL MLS# O6386867
  • Virtual Tour
1 of 44
$2,200,000
4

Beds

3.1

Baths

3,472

Sq.Ft.

2423 VIA SIENNA

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2550 VENETIAN WAY Winter Park, FL MLS# O6388219
  • Virtual Tour
1 of 65
$2,399,000
4

Beds

3.2

Baths

5,051

Sq.Ft.

2550 VENETIAN WAY

Winter Park, FL

Courtesy of PALM PROPERTIES OF CF, INC.

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

385

Estimated median home price

$800,000
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 3
$100K - 200K 50
$200K - 300K 21
$300K - 400K 21
$400K - 500K 30
$500K - 600K 23
$600K - 700K 27
$700K - 800K 18
$800K - 900K 16
$900K - 1M 8
$1M - Max 168

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 239
Townhouse 16
Condo 87
Commercial 7
Rental 72
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 5/16/2026)

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.

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 5/17/2026.