35 total properties
Did you mean the neighborhood Winter Park?
View 785 N PHELPS AVENUE Winter Park, FL MLS# O6393117
  • Recently Listed with Virtual Tour
1 of 41
$2,049,000
5

Beds

3.1

Baths

2,964

Sq.Ft.

785 N PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1570 PALMER AVENUE Winter Park, FL MLS# O6383529
  • Recently Listed with Virtual Tour
1 of 39
$1,690,000
4

Beds

3.1

Baths

3,048

Sq.Ft.

1570 PALMER AVENUE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 1750 CAROLLEE LANE Winter Park, FL MLS# O6391179
  • Recently Listed
1 of 47
$1,995,000
4

Beds

3.1

Baths

3,249

Sq.Ft.

1750 CAROLLEE LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6391922
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Sunday 3/29 2:00 PM - 4:00 PM
$1,899,500
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6392409
  • Recently Listed with Virtual Tour
1 of 61
$1,699,000
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 906 ENCLAVE PLACE Winter Park, FL MLS# O6383092
  • Recently Listed
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
  • Recently Listed with 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
  • Recently Listed
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
  • Recently Listed with Virtual Tour
1 of 57
$1,970,000
5

Beds

4.1

Baths

4,363

Sq.Ft.

1177 KENWOOD AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 501 HENKEL CIRCLE Winter Park, FL MLS# O6389996
$1,825,000
5

Beds

4.1

Baths

3,746

Sq.Ft.

501 HENKEL CIRCLE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1560 WOODLAND AVENUE Winter Park, FL MLS# O6389070
  • Recently Listed with Virtual Tour
1 of 88
$1,850,000
5

Beds

4.1

Baths

3,851

Sq.Ft.

1560 WOODLAND AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP
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 1521 CHESTNUT AVENUE Winter Park, FL MLS# A4685113
  • Recently Listed with Virtual Tour
1 of 57
$1,899,900
4

Beds

3.0

Baths

2,842

Sq.Ft.

1521 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2423 VIA SIENNA Winter Park, FL MLS# O6386867
  • Recently Listed with 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 61
OPEN HOUSE: Saturday 3/28 1:00 PM - 3:00 PM
$1,795,000
5

Beds

3.1

Baths

3,304

Sq.Ft.

2501 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 629 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6386610
  • New Construction with Virtual Tour
1 of 46
$1,695,000
4

Beds

3.1

Baths

3,031

Sq.Ft.

629 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of CLASSIC HOMES
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
$1,950,000
4

Beds

4.0

Baths

2,810

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1810 HOLLYWOOD AVENUE Winter Park, FL MLS# O6377320
  • New Construction with Virtual Tour
1 of 10
$1,689,000
4

Beds

3.1

Baths

2,604

Sq.Ft.

1810 HOLLYWOOD AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC

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

328

Estimated median home price

$762,500
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 4
$100K - 200K 46
$200K - 300K 21
$300K - 400K 16
$400K - 500K 29
$500K - 600K 15
$600K - 700K 22
$700K - 800K 17
$800K - 900K 10
$900K - 1M 9
$1M - Max 139

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 192
Townhouse 19
Condo 83
Commercial 3
Rental 86
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 3/24/2026)

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 3/26/2026.