340 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Virtual Tour
1 of 49
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

Winter Park, FL

View 786 MCINTYRE AVENUE Winter Park, FL MLS# O6424399
  • Virtual Tour
1 of 28
$625,000
3

Beds

2.1

Baths

1,934

Sq.Ft.

786 MCINTYRE AVENUE

Winter Park, FL

View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1134 WASHINGTON AVENUE 13C Winter Park, FL MLS# O6416746
$525,000
3

Beds

3.1

Baths

2,195

Sq.Ft.

1134 WASHINGTON AVENUE 13C

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
  • Virtual Tour
1 of 36
$848,900
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

View 1750 WALNUT AVENUE Winter Park, FL MLS# O6422700
  • Virtual Tour
1 of 55
$2,195,000
4

Beds

4.1

Baths

3,691

Sq.Ft.

1750 WALNUT AVENUE

Winter Park, FL

View 313L SYLVAN DRIVE Winter Park, FL MLS# O6424300
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 436 W SWOOPE AVENUE Winter Park, FL MLS# O6423105
  • Virtual Tour
1 of 59
$699,000
4

Beds

3.1

Baths

2,602

Sq.Ft.

436 W SWOOPE AVENUE

Winter Park, FL

View 4437 GLENMOOR COURT Winter Park, FL MLS# O6424511
  • Virtual Tour
1 of 32
$525,000
3

Beds

2.0

Baths

2,633

Sq.Ft.

4437 GLENMOOR COURT

Winter Park, FL

View 1477 W FAIRBANKS AVENUE Winter Park, FL MLS# O6422964
$2,500,000
6,049

Sq.Ft.

1477 W FAIRBANKS AVENUE

Winter Park, FL

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

View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
  • Virtual Tour
1 of 38
OPEN HOUSE: Sunday 9/6 11:00 AM - 3:00 AM
$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 943 FAIRWAY DRIVE Winter Park, FL MLS# O6426672
  • Recently Listed with Virtual Tour
1 of 47
$689,900
4

Beds

3.0

Baths

2,067

Sq.Ft.

943 FAIRWAY DRIVE

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

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

369

Estimated median home price

$699,000
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 41
$200K - 300K 22
$300K - 400K 14
$400K - 500K 38
$500K - 600K 31
$600K - 700K 37
$700K - 800K 11
$800K - 900K 11
$900K - 1M 10
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 225
Townhouse 24
Condo 78
Commercial 9
Rental 76
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/3/2026)

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 9/3/2026.