306 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6428654
  • New Construction with Virtual Tour
1 of 59
$1,999,990
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT 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 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 751 PANSY AVENUE Winter Park, FL MLS# O6432554
  • Recently Listed with Virtual Tour
1 of 44
$1,950,000
3

Beds

3.1

Baths

2,703

Sq.Ft.

751 PANSY AVENUE

Winter Park, FL

View 1420 ALOMA AVENUE Winter Park, FL MLS# O6430343
$1,949,500
3

Beds

3.1

Baths

2,422

Sq.Ft.

1420 ALOMA AVENUE

Winter Park, FL

View 1702 ARBOR PARK DRIVE Winter Park, FL MLS# O6435407
  • Recently Listed with Virtual Tour
1 of 49
$1,900,000
4

Beds

3.1

Baths

2,950

Sq.Ft.

1702 ARBOR PARK DRIVE

Winter Park, FL

View 910 ENCLAVE PLACE Winter Park, FL MLS# O6406803
  • New Construction
1 of 4
$1,899,000
5

Beds

4.1

Baths

3,620

Sq.Ft.

910 ENCLAVE PLACE

Winter Park, FL

View 914 ENCLAVE PLACE Winter Park, FL MLS# O6391825
  • New Construction
1 of 3
$1,895,000
5

Beds

4.1

Baths

3,617

Sq.Ft.

914 ENCLAVE PLACE

Winter Park, FL

View 1661 LAUREL ROAD Winter Park, FL MLS# O6435812
  • Virtual Tour
1 of 81
$1,875,000
3

Beds

3.0

Baths

3,127

Sq.Ft.

1661 LAUREL ROAD

Winter Park, FL

View 2343 VERSAILLES AVENUE Winter Park, FL MLS# O6432029
  • Recently Listed
1 of 43
$1,865,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2343 VERSAILLES AVENUE

Winter Park, FL

View 721 PANSY AVENUE Winter Park, FL MLS# O6352857
  • Virtual Tour
1 of 29
$1,850,000
4

Beds

4.0

Baths

2,653

Sq.Ft.

721 PANSY AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,849,900
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

View 1550 PALM AVENUE Winter Park, FL MLS# O6436458
  • Recently Listed
1 of 10
$1,829,000
4

Beds

3.1

Baths

2,706

Sq.Ft.

1550 PALM AVENUE

Winter Park, FL

View 311 E MORSE BOULEVARD 1-3 Winter Park, FL MLS# O6406368
  • Adult Community with Virtual Tour
1 of 28
$1,825,000
2

Beds

2.0

Baths

2,304

Sq.Ft.

311 E MORSE BOULEVARD 1-3

Winter Park, FL

View 631 WILLIAMS DRIVE Winter Park, FL MLS# O6437346
  • Virtual Tour
1 of 57
$1,824,000
4

Beds

3.1

Baths

2,972

Sq.Ft.

631 WILLIAMS DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Virtual Tour
1 of 83
$1,800,000
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

Winter Park, FL

Courtesy of SIMPLICITY: A RE BROKERAGE CO
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 1220 SHARON PLACE Winter Park, FL MLS# O6435525
  • Virtual Tour
1 of 11
$1,800,000
Studio

Beds

0.0

Baths

1220 SHARON PLACE

Winter Park, FL

View 106 S INTERLACHEN AVENUE 518 Winter Park, FL MLS# O6400228
$1,795,000
3

Beds

2.0

Baths

1,807

Sq.Ft.

106 S INTERLACHEN AVENUE 518

Winter Park, FL

View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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 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.