284 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 1401 GREEN COVE ROAD Winter Park, FL MLS# O6358093
  • Virtual Tour
1 of 57
$2,900,000
3

Beds

4.3

Baths

5,483

Sq.Ft.

1401 GREEN COVE ROAD

Winter Park, FL

Courtesy of ANCHOR REAL ESTATE
View 3425 FORSYTH ROAD Winter Park, FL MLS# S5142219
  • Virtual Tour
1 of 40
$2,800,000
16,437

Sq.Ft.

3425 FORSYTH ROAD

Winter Park, FL

Courtesy of REMAX PREMIER PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 2012 LOCH BERRY ROAD Winter Park, FL MLS# O6381093
  • Recently Listed with Virtual Tour
1 of 10
$2,699,000
5

Beds

4.1

Baths

3,800

Sq.Ft.

2012 LOCH BERRY ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 147 S INTERLACHEN AVENUE 202 Winter Park, FL MLS# L4959060
  • Recently Listed with Virtual Tour
1 of 31
$2,695,000
3

Beds

4.1

Baths

3,272

Sq.Ft.

147 S INTERLACHEN AVENUE 202

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 426 WORTHINGTON DRIVE Winter Park, FL MLS# O6360737
  • New Construction with Virtual Tour
1 of 15
$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 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 2812 MULFORD AVENUE Winter Park, FL MLS# O6354293
  • New Construction
1 of 4
$2,495,000
5

Beds

5.1

Baths

3,656

Sq.Ft.

2812 MULFORD AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2015 N PARK AVENUE Winter Park, FL MLS# O6372603
  • Recently Listed with Virtual Tour
1 of 62
$2,495,000
5

Beds

4.1

Baths

3,963

Sq.Ft.

2015 N PARK AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2361 MULBRY DRIVE Winter Park, FL MLS# O6364508
  • New Construction
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 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6381552
  • Recently Listed
1 of 4
OPEN HOUSE: Thursday 2/19 4:00 PM - 6:00 PM
$2,395,000
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1760 LEGION DRIVE Winter Park, FL MLS# O6383603
  • Recently Listed with Virtual Tour
1 of 66
OPEN HOUSE: Saturday 2/21 11:00 AM - 2:00 PM
$2,395,000
4

Beds

5.1

Baths

4,392

Sq.Ft.

1760 LEGION DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2503 VERSAILLES AVENUE Winter Park, FL MLS# O6365961
$2,350,000
5

Beds

5.0

Baths

4,026

Sq.Ft.

2503 VERSAILLES AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1624 BARCELONA WAY Winter Park, FL MLS# O6362124
  • Virtual Tour
1 of 62
$2,315,000
3

Beds

3.0

Baths

3,828

Sq.Ft.

1624 BARCELONA WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2299 VIA TUSCANY Winter Park, FL MLS# O6355858
  • Virtual Tour
1 of 60
OPEN HOUSE: Saturday 2/21 1:00 PM - 3:00 PM
$2,295,000
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
OPEN HOUSE: Sunday 2/22 1:00 PM - 3:00 PM
$2,295,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361377
  • Virtual Tour
1 of 41
$2,249,900
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
$2,249,900
Studio

Beds

0.0

Baths

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 311 E MORSE BOULEVARD 2 - 5 Winter Park, FL MLS# O6370558
  • Adult Community with Virtual Tour
1 of 32
$2,100,000
2

Beds

2.0

Baths

1,900

Sq.Ft.

311 E MORSE BOULEVARD 2 - 5

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

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

321

Estimated median home price

$695,500
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 7
$100K - 200K 36
$200K - 300K 32
$300K - 400K 20
$400K - 500K 26
$500K - 600K 18
$600K - 700K 23
$700K - 800K 20
$800K - 900K 7
$900K - 1M 7
$1M - Max 125

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 181
Townhouse 18
Condo 86
Commercial 5
Rental 88
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 2/19/2026)

Information deemed reliable but not guaranteed.

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 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 2/20/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 2/20/2026.

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 2/20/2026.