38 total properties
Did you mean the neighborhood Winter Park?
View 1130 PARK NORTH PLACE Winter Park, FL MLS# O6392394
$2,200,000
5

Beds

3.1

Baths

4,011

Sq.Ft.

1130 PARK NORTH PLACE

Winter Park, FL

View 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Virtual Tour
1 of 20
$2,200,000
Studio

Beds

0.0

Baths

1415 GROVE TERRACE

Winter Park, FL

View 1885 TEMPLE DRIVE Winter Park, FL MLS# O6359471
  • Virtual Tour
1 of 59
OPEN HOUSE: Saturday 8/8 2:00 PM - 4:00 PM
$2,195,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 942 ENCLAVE PLACE Winter Park, FL MLS# O6411550
  • New Construction
1 of 4
$2,195,000
5

Beds

5.0

Baths

3,831

Sq.Ft.

942 ENCLAVE PLACE

Winter Park, FL

View 1750 WALNUT AVENUE Winter Park, FL MLS# O6422700
  • Virtual Tour
1 of 55
$2,195,000
4

Beds

4.1

Baths

3,691

Sq.Ft.

1750 WALNUT AVENUE

Winter Park, FL

View 946 ENCLAVE PLACE Winter Park, FL MLS# O6411633
  • New Construction
1 of 3
$2,175,000
5

Beds

4.1

Baths

3,989

Sq.Ft.

946 ENCLAVE PLACE

Winter Park, FL

View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 8/8 10:00 AM - 1:00 PM
$2,150,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

View 950 ENCLAVE PLACE Winter Park, FL MLS# O6410963
  • New Construction
1 of 3
$2,125,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

950 ENCLAVE PLACE

Winter Park, FL

View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6428654
  • Recently Listed with Virtual Tour
1 of 59
OPEN HOUSE: Saturday 8/8 12:00 PM - 2:00 PM
$2,099,990
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

View 938 ENCLAVE PLACE Winter Park, FL MLS# O6408090
  • New Construction
1 of 7
$2,099,000
5

Beds

4.1

Baths

3,865

Sq.Ft.

938 ENCLAVE PLACE

Winter Park, FL

View 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • New Construction
1 of 4
$2,050,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$1,995,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
$1,995,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3075 N GOLDENROD ROAD Winter Park, FL MLS# O6426621
  • Recently Listed with Virtual Tour
1 of 38
$1,950,000
4,687

Sq.Ft.

3075 N GOLDENROD ROAD

Winter Park, FL

View 910 ENCLAVE PLACE Winter Park, FL MLS# O6406803
  • New Construction
1 of 4
$1,899,000
5

Beds

4.1

Baths

3,620

Sq.Ft.

910 ENCLAVE PLACE

Winter Park, FL

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

View 622 PENN PLACE Winter Park, FL MLS# TB8511228
  • Virtual Tour
1 of 26
OPEN HOUSE: Saturday 8/8 1:00 PM - 3:00 PM
$1,895,000
3

Beds

3.1

Baths

2,767

Sq.Ft.

622 PENN PLACE

Winter Park, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 721 PANSY AVENUE Winter Park, FL MLS# O6352857
  • Virtual Tour
1 of 29
$1,850,000
4

Beds

4.0

Baths

2,653

Sq.Ft.

721 PANSY AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,849,900
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

View 318 VITORIA AVENUE Winter Park, FL MLS# O6428907
  • Virtual Tour
1 of 66
OPEN HOUSE: Saturday 8/8 1:00 PM - 3:00 PM
$1,849,900
3

Beds

2.1

Baths

2,036

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

354

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 7
$100K - 200K 39
$200K - 300K 23
$300K - 400K 14
$400K - 500K 34
$500K - 600K 26
$600K - 700K 32
$700K - 800K 14
$800K - 900K 11
$900K - 1M 11
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 216
Townhouse 22
Condo 79
Commercial 9
Rental 69
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 8/6/2026)

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 8/7/2026.