272 total properties
Did you mean the neighborhood Winter Park?
View 1494 WESTCHESTER AVENUE Winter Park, FL MLS# O6363530
  • New Construction with Virtual Tour
1 of 16
$2,990,000
5

Beds

4.1

Baths

3,711

Sq.Ft.

1494 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 541 W CANTON AVENUE Winter Park, FL MLS# O6307816
  • New Construction with Virtual Tour
1 of 49
$2,935,000
4

Beds

3.1

Baths

3,553

Sq.Ft.

541 W CANTON AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1401 GREEN COVE ROAD Winter Park, FL MLS# O6358093
  • Virtual Tour
1 of 58
OPEN HOUSE: Sunday 12/28 2:00 PM - 4:00 PM
$2,900,000
3

Beds

4.3

Baths

5,483

Sq.Ft.

1401 GREEN COVE ROAD

Winter Park, FL

Courtesy of ANCHOR REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 2503 VERSAILLES AVENUE Winter Park, FL MLS# O6365961
  • Recently Listed with Virtual Tour
1 of 53
$2,775,000
5

Beds

5.0

Baths

4,026

Sq.Ft.

2503 VERSAILLES AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 426 WORTHINGTON DRIVE Winter Park, FL MLS# O6360737
  • New Construction with Virtual Tour
1 of 14
$2,679,000
5

Beds

4.1

Baths

3,520

Sq.Ft.

426 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 560 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6367721
$2,599,000
6

Beds

5.2

Baths

3,946

Sq.Ft.

560 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 185 SYLVAN BOULEVARD Winter Park, FL MLS# O6304627
  • New Construction with Virtual Tour
1 of 10
$2,590,000
4

Beds

4.1

Baths

3,138

Sq.Ft.

185 SYLVAN BOULEVARD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2550 VENETIAN WAY Winter Park, FL MLS# O6258445
  • Virtual Tour
1 of 34
OPEN HOUSE: Sunday 12/28 12:00 PM - 3:00 PM
$2,499,000
4

Beds

3.2

Baths

4,875

Sq.Ft.

2550 VENETIAN WAY

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2812 MULFORD AVENUE Winter Park, FL MLS# O6354293
$2,495,000
5

Beds

5.1

Baths

3,656

Sq.Ft.

2812 MULFORD AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2361 MULBRY DRIVE Winter Park, FL MLS# O6364508
  • Recently Listed
1 of 3
$2,395,000
4

Beds

4.0

Baths

3,111

Sq.Ft.

2361 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6358847
  • New Construction
1 of 58
$2,350,000
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6360088
  • New Construction with Virtual Tour
1 of 48
$2,350,000
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

Courtesy of THE AGENCY ORLANDO
View 1624 BARCELONA WAY Winter Park, FL MLS# O6362124
  • Virtual Tour
1 of 61
$2,350,000
3

Beds

3.0

Baths

3,828

Sq.Ft.

1624 BARCELONA WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361377
  • Virtual Tour
1 of 41
$2,350,000
5

Beds

4.0

Baths

3,948

Sq.Ft.

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361935
$2,350,000
Studio

Beds

0.0

Baths

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2299 VIA TUSCANY Winter Park, FL MLS# O6355858
  • Virtual Tour
1 of 60
$2,345,000
4

Beds

3.1

Baths

3,986

Sq.Ft.

2299 VIA TUSCANY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6353495
$2,295,000
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1885 TEMPLE DRIVE Winter Park, FL MLS# O6359471
  • Virtual Tour
1 of 65
$2,295,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2722 EASTERN PARKWAY Winter Park, FL MLS# O6360734
  • New Construction with Virtual Tour
1 of 14
$2,289,000
5

Beds

4.1

Baths

3,334

Sq.Ft.

2722 EASTERN PARKWAY

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2001 LAKE DRIVE Winter Park, FL MLS# O6336920
  • Virtual Tour
1 of 63
$2,165,000
5

Beds

4.0

Baths

4,798

Sq.Ft.

2001 LAKE DRIVE

Winter Park, FL

Courtesy of THE AGENCY ORLANDO

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

301

Estimated median home price

$639,000
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 40
$200K - 300K 21
$300K - 400K 19
$400K - 500K 32
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 176
Townhouse 19
Condo 77
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/28/2025)

Information deemed reliable but not guaranteed.

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Data is updated as of 12/28/2025.

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Data is updated as of 12/28/2025.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 12/28/2025.

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.

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 12/28/2025.