91 total properties
Did you mean the neighborhood Winter Park?
View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6350734
$2,500
3

Beds

1.1

Baths

1,351

Sq.Ft.

1622 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
View Address not provided Winter Park, FL MLS# O6379158
  • Recently Listed
1 of 2
$2,500
Studio

Beds

0.0

Baths

Address not provided

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1826 PINEVIEW CIRCLE Winter Park, FL MLS# O6373874
  • Virtual Tour
1 of 14
$2,495
3

Beds

2.0

Baths

1,222

Sq.Ft.

1826 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1256 MICHIGAN AVENUE Winter Park, FL MLS# O6379767
  • Recently Listed with Virtual Tour
1 of 27
$2,450
2

Beds

2.0

Baths

1,050

Sq.Ft.

1256 MICHIGAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1812 PINEVIEW CIRCLE Winter Park, FL MLS# O6379940
  • Recently Listed with Virtual Tour
1 of 21
$2,375
3

Beds

2.0

Baths

1,238

Sq.Ft.

1812 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 2886 CAREW AVENUE Winter Park, FL MLS# O6331998
  • Virtual Tour
1 of 29
$2,350
4

Beds

2.1

Baths

1,701

Sq.Ft.

2886 CAREW AVENUE

Winter Park, FL

Courtesy of THE TEAM REAL ESTATE GROUP INC
View 1148 PARK GREEN PLACE Winter Park, FL MLS# O6352263
$2,350
3

Beds

2.0

Baths

1,282

Sq.Ft.

1148 PARK GREEN PLACE

Winter Park, FL

Courtesy of DON ASHER & ASSOCIATES, INC.
View 2113 Shadow View Circel 2113 Winter Park, FL MLS# A11741510
$2,300
3

Beds

2.1

Baths

1,583

Sq.Ft.

2113 Shadow View Circel 2113

Winter Park, FL

Courtesy of REALTY ICONIC, LLC.
View 1250 S DENNING DRIVE 112 Winter Park, FL MLS# O6377101
  • Recently Listed with Virtual Tour
1 of 23
$2,150
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 112

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 148 OAK GROVE ROAD Winter Park, FL MLS# O6361640
  • Virtual Tour
1 of 20
$2,095
3

Beds

2.0

Baths

1,156

Sq.Ft.

148 OAK GROVE ROAD

Winter Park, FL

Courtesy of THE CAVALIERI PROPERTY MANAGEMENT LLC
View 2011 CORNELL AVENUE Winter Park, FL MLS# O6329429
  • Virtual Tour
1 of 15
$2,000
2

Beds

1.1

Baths

1,091

Sq.Ft.

2011 CORNELL AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 200 SAINT ANDREWS BOULEVARD 1805 Winter Park, FL MLS# O6372204
$2,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1805

Winter Park, FL

Courtesy of LIVE MVRK LLC
View Address not provided Winter Park, FL MLS# TB8444168
$1,949
3

Beds

2.0

Baths

1,136

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TAH FLORIDA LLC
View 7473 BELLE RIVER COURT 16 Winter Park, FL MLS# O6349869
$1,895
3

Beds

2.1

Baths

1,151

Sq.Ft.

7473 BELLE RIVER COURT 16

Winter Park, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 250 CAROLINA AVENUE 307 Winter Park, FL MLS# O6365311
$1,895
1

Beds

2.0

Baths

1,153

Sq.Ft.

250 CAROLINA AVENUE 307

Winter Park, FL

Courtesy of VERANDA PARK REALTY LLC
View 1500 GAY ROAD 3B Winter Park, FL MLS# O6333528
  • Virtual Tour
1 of 15
$1,850
2

Beds

2.0

Baths

1,100

Sq.Ft.

1500 GAY ROAD 3B

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 200 SAINT ANDREWS BOULEVARD 2903 Winter Park, FL MLS# O6357483
$1,850
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2903

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 685 Grenadine Ct. Winter Park, FL MLS# A11952398
  • Recently Listed with Virtual Tour
1 of 20
$1,850
3

Beds

2.0

Baths

1,350

Sq.Ft.

685 Grenadine Ct.

Winter Park, FL

Courtesy of SYNERGY INTERNATIONAL REALTY, INC.
View 627 GRENADINE COURT S Winter Park, FL MLS# O6378462
  • Recently Listed with Virtual Tour
1 of 43
$1,795
2

Beds

2.0

Baths

1,037

Sq.Ft.

627 GRENADINE COURT S

Winter Park, FL

Courtesy of RE REALTY
View 7412 WOODBURN COURT 23 Winter Park, FL MLS# O6353923
$1,750
2

Beds

2.1

Baths

1,031

Sq.Ft.

7412 WOODBURN COURT 23

Winter Park, FL

Courtesy of POWERHOUSE BROKERS INT'L

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

295

Estimated median home price

$695,000
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 7
$100K - 200K 34
$200K - 300K 29
$300K - 400K 15
$400K - 500K 25
$500K - 600K 17
$600K - 700K 25
$700K - 800K 18
$800K - 900K 5
$900K - 1M 8
$1M - Max 112

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 165
Townhouse 17
Condo 78
Commercial 6
Rental 90
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/5/2026)

Information deemed reliable but not guaranteed.

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 2/5/2026.