37 total properties
Did you mean the neighborhood Winter Park?
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
OPEN HOUSE: Sunday 8/2 11:00 AM - 2:00 PM
$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
  • Recently Listed with Virtual Tour
1 of 30
$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

The time to sell is now! THE TIME TO SELL IS NOW!
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 311 E MORSE BOULEVARD 1-3 Winter Park, FL MLS# O6406368
  • Adult Community with Virtual Tour
1 of 28
$1,895,000
2

Beds

2.0

Baths

2,304

Sq.Ft.

311 E MORSE BOULEVARD 1-3

Winter Park, FL

View 622 PENN PLACE Winter Park, FL MLS# TB8511228
  • Virtual Tour
1 of 26
$1,895,000
3

Beds

3.1

Baths

2,767

Sq.Ft.

622 PENN PLACE

Winter Park, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6427443
  • Recently Listed with Virtual Tour
1 of 55
$1,894,400
Studio

Beds

0.0

Baths

2614 PARKLAND DRIVE

Winter Park, FL

View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Virtual Tour
1 of 83
$1,888,888
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

Winter Park, FL

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
  • Recently Listed with Virtual Tour
1 of 66
OPEN HOUSE: Sunday 8/2 1:00 PM - 3:00 PM
$1,849,900
3

Beds

2.1

Baths

2,036

Sq.Ft.

318 VITORIA AVENUE

Winter Park, FL

View 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 8/2 1:00 PM - 4:00 PM
$1,800,000
4

Beds

4.0

Baths

3,065

Sq.Ft.

723 SYMONDS AVENUE

Winter Park, FL

View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Recently Listed with Virtual Tour
1 of 54
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

Winter Park, FL

View 2625 PARK PLACE DRIVE Winter Park, FL MLS# O6413031
$1,799,000
4

Beds

4.1

Baths

3,460

Sq.Ft.

2625 PARK PLACE DRIVE

Winter Park, FL

View 621 HUNTINGTON AVENUE Winter Park, FL MLS# O6394464
$1,795,000
3

Beds

3.1

Baths

2,399

Sq.Ft.

621 HUNTINGTON AVENUE

Winter Park, FL

View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1750 CAROLLEE LANE Winter Park, FL MLS# O6391179
1 of 46
OPEN HOUSE: Sunday 8/2 12:00 PM - 2:00 PM
$1,780,000
4

Beds

3.1

Baths

3,249

Sq.Ft.

1750 CAROLLEE LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1840 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 313L SYLVAN DRIVE Winter Park, FL MLS# O6424300
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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

$732,000
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 40
$200K - 300K 22
$300K - 400K 15
$400K - 500K 33
$500K - 600K 25
$600K - 700K 31
$700K - 800K 15
$800K - 900K 12
$900K - 1M 10
$1M - Max 144

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 214
Townhouse 21
Condo 79
Commercial 10
Rental 73
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 8/2/2026)

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 8/2/2026.