44 total properties
Did you mean the neighborhood Winter Park?
View 785 N PHELPS AVENUE Winter Park, FL MLS# O6393117
  • New Construction with Virtual Tour
1 of 41
$1,989,000
5

Beds

3.1

Baths

2,964

Sq.Ft.

785 N PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1750 CAROLLEE LANE Winter Park, FL MLS# O6391179
$1,820,000
4

Beds

3.1

Baths

3,249

Sq.Ft.

1750 CAROLLEE LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6391922
  • Virtual Tour
1 of 46
$1,799,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 906 ENCLAVE PLACE Winter Park, FL MLS# O6383092
  • New Construction
1 of 5
$1,925,000
5

Beds

4.1

Baths

3,618

Sq.Ft.

906 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1181 VIA CAPRI Winter Park, FL MLS# O6391636
  • Virtual Tour
1 of 11
$1,800,000
Studio

Beds

0.0

Baths

1181 VIA CAPRI

Winter Park, FL

Courtesy of KARDOSH REALTY
View 914 ENCLAVE PLACE Winter Park, FL MLS# O6391825
  • New Construction
1 of 3
$1,895,000
5

Beds

4.1

Baths

3,617

Sq.Ft.

914 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1177 KENWOOD AVENUE Winter Park, FL MLS# O6390592
  • Virtual Tour
1 of 57
$1,800,000
5

Beds

4.1

Baths

4,363

Sq.Ft.

1177 KENWOOD AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 1705 ELIZABETHS WALK Winter Park, FL MLS# O6389723
$1,650,000
5

Beds

5.0

Baths

3,820

Sq.Ft.

1705 ELIZABETHS WALK

Winter Park, FL

Courtesy of HOMEVEST REALTY
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 2501 WINTER PARK ROAD Winter Park, FL MLS# O6384756
  • Virtual Tour
1 of 63
OPEN HOUSE: Saturday 5/30 1:00 PM - 3:00 PM
$1,649,000
5

Beds

3.1

Baths

3,304

Sq.Ft.

2501 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 318 VITORIA AVENUE Winter Park, FL MLS# O6388489
  • Virtual Tour
1 of 65
$2,200,000
3

Beds

2.1

Baths

2,433

Sq.Ft.

318 VITORIA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1760 ALABAMA DRIVE Winter Park, FL MLS# O6386409
  • Virtual Tour
1 of 45
$2,198,000
4

Beds

2.1

Baths

2,841

Sq.Ft.

1760 ALABAMA DRIVE

Winter Park, FL

Courtesy of DAILLAND REAL ESTATE
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 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6381988
  • New Construction
1 of 3
$1,949,999
4

Beds

4.0

Baths

2,810

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 147 S INTERLACHEN AVENUE 202 Winter Park, FL MLS# L4959060
$2,170,000
3

Beds

4.1

Baths

3,272

Sq.Ft.

147 S INTERLACHEN AVENUE 202

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 1903 N PARK AVENUE Winter Park, FL MLS# O6375766
  • Virtual Tour
1 of 42
$1,695,000
4

Beds

4.0

Baths

2,807

Sq.Ft.

1903 N PARK AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 640 ARJAY WAY Winter Park, FL MLS# O6372947
  • Virtual Tour
1 of 46
$1,890,000
5

Beds

3.2

Baths

3,953

Sq.Ft.

640 ARJAY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1840 ANZLE AVENUE Winter Park, FL MLS# O6374102
  • New Construction with Virtual Tour
1 of 12
$1,750,000
4

Beds

2.1

Baths

2,350

Sq.Ft.

1840 ANZLE AVENUE

Winter Park, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 1711 BARCELONA WAY Winter Park, FL MLS# O6372739
  • Virtual Tour
1 of 60
$2,100,000
5

Beds

3.0

Baths

3,669

Sq.Ft.

1711 BARCELONA WAY

Winter Park, FL

Courtesy of VOSS REALTY 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

391

Estimated median home price

$785,000
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 2
$100K - 200K 48
$200K - 300K 24
$300K - 400K 24
$400K - 500K 28
$500K - 600K 23
$600K - 700K 29
$700K - 800K 21
$800K - 900K 15
$900K - 1M 10
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 247
Townhouse 15
Condo 87
Commercial 7
Rental 75
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/26/2026)

Information deemed reliable but not guaranteed.

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 5/26/2026.