132 total properties
Did you mean the neighborhood Winter Park?
View 200 ST ANDREWS BOULEVARD 906 Winter Park, FL MLS# O6453614
$175,000
1

Beds

1.0

Baths

727

Sq.Ft.

200 ST ANDREWS BOULEVARD 906

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3027 AARON BUR AVENUE L1 Winter Park, FL MLS# TB8562681
  • Recently Listed with Virtual Tour
1 of 30
$169,999
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BUR AVENUE L1

Winter Park, FL

Courtesy of HOMESMART
View 257 LINCOLNSHIRE ROAD Winter Park, FL MLS# O6453656
  • Recently Listed with Virtual Tour
1 of 34
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 7463 CANFORD COURT 15 Winter Park, FL MLS# O6452947
$270,000
3

Beds

2.1

Baths

1,580

Sq.Ft.

7463 CANFORD COURT 15

Winter Park, FL

Courtesy of EXP REALTY LLC
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 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
OPEN HOUSE: Saturday 10/31 11:00 AM - 2:00 PM
$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 239 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6445496
$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 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
$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 1399 ALOMA AVENUE Winter Park, FL MLS# O6449858
  • Recently Listed with Virtual Tour
1 of 30
$575,000
3

Beds

2.0

Baths

1,804

Sq.Ft.

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449843
  • Recently Listed with Virtual Tour
1 of 30
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1320 BUCKINGHAM ROAD Winter Park, FL MLS# TB8557402
$449,000
3

Beds

2.0

Baths

1,388

Sq.Ft.

1320 BUCKINGHAM ROAD

Winter Park, FL

Courtesy of PALLADIUM INVESTMENTS INC
View 4882 TANGERINE AVENUE 4882 Winter Park, FL MLS# O6448605
  • Recently Listed with Virtual Tour
1 of 28
$185,000
2

Beds

1.1

Baths

1,281

Sq.Ft.

4882 TANGERINE AVENUE 4882

Winter Park, FL

Courtesy of SIMPLYSOLD REAL ESTATE PREMIER
View 731 BONGART ROAD Winter Park, FL MLS# O6448911
  • Recently Listed
1 of 51
$519,900
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 1500 GAY ROAD 26-C Winter Park, FL MLS# O6448226
$255,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 26-C

Winter Park, FL

Courtesy of SOTERA LIVING

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

355

Estimated median home price

$799,000
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

PriceCount
$0 - 100K3
$100K - 200K34
$200K - 300K20
$300K - 400K16
$400K - 500K32
$500K - 600K25
$600K - 700K35
$700K - 800K16
$800K - 900K15
$900K - 1M13
$1M - Max146

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family211
Townhouse22
Condo76
Commercial15
Rental87
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 10/29/2026)

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 10/30/2026.