371 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

View 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
Studio

Beds

0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

View 3373 CEDAR SPRINGS PLACE 149 Winter Park, FL MLS# O6426224
$171,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3373 CEDAR SPRINGS PLACE 149

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 230 KILLARNEY DRIVE Winter Park, FL MLS# O6415950
  • Virtual Tour
1 of 13
$1,250,000
4

Beds

1.0

Baths

1,260

Sq.Ft.

230 KILLARNEY DRIVE

Winter Park, FL

View 240 KILLARNEY DRIVE Winter Park, FL MLS# O6415977
  • Virtual Tour
1 of 13
$1,275,000
3

Beds

2.1

Baths

1,329

Sq.Ft.

240 KILLARNEY DRIVE

Winter Park, FL

View 2568 LOTAFUN AVENUE Winter Park, FL MLS# W7887744
  • Virtual Tour
1 of 25
$405,000
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 3075 N GOLDENROD ROAD Winter Park, FL MLS# O6426621
$1,950,000
4,687

Sq.Ft.

3075 N GOLDENROD ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Virtual Tour
1 of 15
OPEN HOUSE: Sunday 9/6 1:00 PM - 3:00 PM
$169,900
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

View 901 HARMON AVENUE Winter Park, FL MLS# O6425358
  • Virtual Tour
1 of 20
$650,000
2

Beds

2.0

Baths

1,277

Sq.Ft.

901 HARMON AVENUE

Winter Park, FL

View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
$1,995,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Virtual Tour
1 of 25
$1,595,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

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

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

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.