278 total properties
Did you mean the neighborhood Winter Park?
View 7463 CANFORD COURT 15 Winter Park, FL MLS# O6452947
  • Recently Listed
1 of 44
$270,000
3

Beds

2.1

Baths

1,580

Sq.Ft.

7463 CANFORD COURT 15

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1735 DEMETREE DRIVE Winter Park, FL MLS# O6451727
  • Recently Listed with Virtual Tour
1 of 41
$1,050,000
4

Beds

3.0

Baths

2,787

Sq.Ft.

1735 DEMETREE DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1401 PELHAM ROAD Winter Park, FL MLS# O6452727
  • Recently Listed
1 of 31
$650,000
3

Beds

2.0

Baths

1,594

Sq.Ft.

1401 PELHAM ROAD

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 603 CARNATION DRIVE Winter Park, FL MLS# TB8561386
  • Recently Listed with Virtual Tour
1 of 12
$419,900
4

Beds

2.0

Baths

1,427

Sq.Ft.

603 CARNATION DRIVE

Winter Park, FL

Courtesy of A-WARD WINNING REALTY LLC
View 506 LANDER ROAD Winter Park, FL MLS# O6451927
  • Recently Listed with Virtual Tour
1 of 28
$450,000
3

Beds

2.0

Baths

1,346

Sq.Ft.

506 LANDER ROAD

Winter Park, FL

Courtesy of DERENTHAL REALTY
View 624 DUNRAVEN DRIVE Winter Park, FL MLS# O6443159
  • Recently Listed with Virtual Tour
1 of 24
OPEN HOUSE: Sunday 11/1 12:00 PM - 2:00 PM
$620,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

624 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1030 BONITA DRIVE Winter Park, FL MLS# O6452330
  • Recently Listed with Virtual Tour
1 of 5
$1,100,000
0.0

Baths

1030 BONITA DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2330 WESTMINSTER CT. Winter Park, FL MLS# O6452380
  • Recently Listed
1 of 54
$985,000
5

Beds

3.0

Baths

3,296

Sq.Ft.

2330 WESTMINSTER CT.

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1884 JESSICA COURT Winter Park, FL MLS# O6450978
  • Recently Listed with Virtual Tour
1 of 32
$699,900
3

Beds

2.0

Baths

1,666

Sq.Ft.

1884 JESSICA COURT

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
$509,999
3

Beds

2.0

Baths

1,460

Sq.Ft.

808 DENSMORE DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 4832 TANGERINE AVENUE 4832 Winter Park, FL MLS# O6451613
  • Recently Listed with Virtual Tour
1 of 15
$188,800
2

Beds

2.0

Baths

1,058

Sq.Ft.

4832 TANGERINE AVENUE 4832

Winter Park, FL

Courtesy of STARHOMES REALTY LLC
View 2887 TEMPLE TRAIL Winter Park, FL MLS# O6450536
  • Recently Listed with Virtual Tour
1 of 86
$695,000
2

Beds

2.1

Baths

1,801

Sq.Ft.

2887 TEMPLE TRAIL

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 239 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6445496
  • Recently Listed with Virtual Tour
1 of 29
$450,000
4

Beds

2.1

Baths

1,866

Sq.Ft.

239 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 4786 TANGERINE AVENUE 4786 Winter Park, FL MLS# S5159925
  • Recently Listed with Virtual Tour
1 of 52
$220,000
2

Beds

1.1

Baths

1,281

Sq.Ft.

4786 TANGERINE AVENUE 4786

Winter Park, FL

Courtesy of EXP REALTY LLC
View 220 KILLARNEY BAY COURT 6-2 Winter Park, FL MLS# O6450663
$339,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

220 KILLARNEY BAY COURT 6-2

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1939 WOODCREST DRIVE Winter Park, FL MLS# O6449666
  • Recently Listed with Virtual Tour
1 of 58
$1,349,000
4

Beds

3.1

Baths

2,575

Sq.Ft.

1939 WOODCREST DRIVE

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 2640 BEVERLY AVENUE Winter Park, FL MLS# TB8559088
  • Recently Listed with Virtual Tour
1 of 29
$305,000
3

Beds

1.0

Baths

1,216

Sq.Ft.

2640 BEVERLY AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 346 ELKHORN COURT Winter Park, FL MLS# O6449383
  • Virtual Tour
1 of 37
$575,000
4

Beds

2.0

Baths

1,891

Sq.Ft.

346 ELKHORN COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 148 OAK GROVE RD Winter Park, FL MLS# O6450470
  • Recently Listed with Virtual Tour
1 of 41
$320,000
3

Beds

2.0

Baths

1,156

Sq.Ft.

148 OAK GROVE RD

Winter Park, FL

Courtesy of CENTRAL FLORIDA REALTY EXPERTS
View 271 S ORLANDO AVENUE Winter Park, FL MLS# O6450599
  • Recently Listed with Virtual Tour
1 of 14
$1,550,000
3,430

Sq.Ft.

271 S ORLANDO AVENUE

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC

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

352

Estimated median home price

$775,000
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 3
$100K - 200K 34
$200K - 300K 19
$300K - 400K 16
$400K - 500K 33
$500K - 600K 24
$600K - 700K 36
$700K - 800K 16
$800K - 900K 14
$900K - 1M 14
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 209
Townhouse 22
Condo 75
Commercial 15
Rental 88
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/27/2026)

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 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 10/27/2026.

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 10/27/2026.