279 total properties
Did you mean the neighborhood Winter Park?
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 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

The time to sell is now! THE TIME TO SELL IS NOW!
View 2305 COLDSTREAM DRIVE Winter Park, FL MLS# O6393049
  • New Construction with Virtual Tour
1 of 23
$1,825,000
5

Beds

5.1

Baths

3,655

Sq.Ft.

2305 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
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 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 7/19 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 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

Courtesy of OLDE TOWN BROKERS INC
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
  • Recently Listed
1 of 4
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6391922
  • Virtual Tour
1 of 46
$1,725,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 641 NORTHWOOD CIRCLE Winter Park, FL MLS# O6412554
  • Virtual Tour
1 of 41
$1,725,000
3

Beds

3.2

Baths

2,756

Sq.Ft.

641 NORTHWOOD CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 341 E READING WAY Winter Park, FL MLS# O6420387
  • Recently Listed
1 of 57
OPEN HOUSE: Sunday 7/19 2:00 PM - 4:00 PM
$1,695,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

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 2501 WINTER PARK ROAD Winter Park, FL MLS# O6384756
$1,649,000
5

Beds

3.1

Baths

3,304

Sq.Ft.

2501 WINTER PARK ROAD

Winter Park, FL

View 446 MELROSE AVENUE Winter Park, FL MLS# O6402113
  • Virtual Tour
1 of 39
$1,625,000
4

Beds

2.0

Baths

2,640

Sq.Ft.

446 MELROSE AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Recently Listed with Virtual Tour
1 of 10
$1,600,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

250 KILLARNEY

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 1510 MILLER AVENUE Winter Park, FL MLS# O6350503
  • New Construction with Virtual Tour
1 of 70
$1,599,900
5

Beds

4.1

Baths

3,252

Sq.Ft.

1510 MILLER 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

315

Estimated median home price

$825,000
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 6
$100K - 200K 39
$200K - 300K 17
$300K - 400K 14
$400K - 500K 23
$500K - 600K 23
$600K - 700K 23
$700K - 800K 11
$800K - 900K 13
$900K - 1M 7
$1M - Max 139

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 194
Townhouse 16
Condo 71
Commercial 7
Rental 71
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/15/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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.

Data is updated as of 7/16/2026.

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 7/16/2026.