355 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Virtual Tour
1 of 28
$370,000
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,590,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
$549,900
3

Beds

2.1

Baths

1,709

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
  • Virtual Tour
1 of 38
$368,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 1754 TAYLOR AVENUE Winter Park, FL MLS# O6421927
  • New Construction with Virtual Tour
1 of 18
$2,569,999
5

Beds

4.1

Baths

3,670

Sq.Ft.

1754 TAYLOR AVENUE

Winter Park, FL

View 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Virtual Tour
1 of 20
$2,200,000
Studio

Beds

0.0

Baths

1415 GROVE TERRACE

Winter Park, FL

View 1823 SUNSET DRIVE Winter Park, FL MLS# O6421690
  • New Construction with Virtual Tour
1 of 14
$2,549,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

1823 SUNSET DRIVE

Winter Park, FL

View 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Virtual Tour
1 of 10
$1,600,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

250 KILLARNEY

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
$190,000
1

Beds

1.0

Baths

658

Sq.Ft.

1250 S DENNING DRIVE 109

Winter Park, FL

View 1695 LEE ROAD B108 Winter Park, FL MLS# O6422568
  • Virtual Tour
1 of 15
$88,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
  • Virtual Tour
1 of 48
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

View 341 E READING WAY Winter Park, FL MLS# O6420387
$1,565,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$778,999
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1000 S SEMORAN BOULEVARD 306 Winter Park, FL MLS# R4911525
$138,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 306

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 404 Winter Park, FL MLS# R4911526
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 404

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 408 Winter Park, FL MLS# R4911527
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 408

Winter Park, FL

View 1695 LEE ROAD A116 Winter Park, FL MLS# O6420863
  • Virtual Tour
1 of 18
$135,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A116

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1180 VIA LUGANO Winter Park, FL MLS# O6413198
  • Virtual Tour
1 of 67
$4,900,000
5

Beds

5.1

Baths

4,961

Sq.Ft.

1180 VIA LUGANO

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2041 JEWELL AVENUE Winter Park, FL MLS# O6420660
  • Virtual Tour
1 of 30
$439,900
3

Beds

1.0

Baths

1,508

Sq.Ft.

2041 JEWELL AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
$424,400
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

Winter Park, FL

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

$725,000
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 38
$200K - 300K 22
$300K - 400K 15
$400K - 500K 36
$500K - 600K 26
$600K - 700K 35
$700K - 800K 11
$800K - 900K 10
$900K - 1M 10
$1M - Max 149

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 216
Townhouse 21
Condo 76
Commercial 9
Rental 77
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/6/2026)

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

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/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 9/6/2026.