165 total properties
Did you mean the neighborhood Winter Park?
View 1401 PELHAM ROAD Winter Park, FL MLS# O6452727
$650,000
3

Beds

2.0

Baths

1,594

Sq.Ft.

1401 PELHAM ROAD

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 603 CARNATION DRIVE Winter Park, FL MLS# TB8561386
  • Recently Listed with Virtual Tour
1 of 12
$399,900
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
  • 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 624 DUNRAVEN DRIVE Winter Park, FL MLS# O6443159
$620,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

624 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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
$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
$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
$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
$220,000
2

Beds

2.0

Baths

1,281

Sq.Ft.

4786 TANGERINE AVENUE 4786

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2640 BEVERLY AVENUE Winter Park, FL MLS# TB8559088
$305,000
3

Beds

1.0

Baths

1,216

Sq.Ft.

2640 BEVERLY AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 148 OAK GROVE RD Winter Park, FL MLS# O6450470
  • 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
$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
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 700 MELROSE AVENUE M23 Winter Park, FL MLS# O6447242
  • Adult Community with Virtual Tour
1 of 29
OPEN HOUSE: Sunday 11/15 1:00 PM - 4:00 PM
$289,000
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE M23

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 4882 TANGERINE AVENUE 4882 Winter Park, FL MLS# O6448605
$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
$519,900
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 640 N PARK AVENUE 3 Winter Park, FL MLS# O6446483
$745,000
2

Beds

1.1

Baths

897

Sq.Ft.

640 N PARK AVENUE 3

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
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
View 518 GILBERT ROAD Winter Park, FL MLS# O6442915
  • Virtual Tour
1 of 48
$639,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

518 GILBERT ROAD

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC

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

357

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

PriceCount
$0 - 100K4
$100K - 200K32
$200K - 300K23
$300K - 400K18
$400K - 500K32
$500K - 600K24
$600K - 700K26
$700K - 800K18
$800K - 900K17
$900K - 1M12
$1M - Max151

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family210
Townhouse25
Condo80
Commercial15
Rental96
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 11/11/2026)

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 11/12/2026.