334 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 925 S SEMORAN BOULEVARD 103 Winter Park, FL MLS# O6409391
$373,000
1,454

Sq.Ft.

925 S SEMORAN BOULEVARD 103

Winter Park, FL

View 7505 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6405854
$390,000
3

Beds

2.0

Baths

1,471

Sq.Ft.

7505 LAUREL SPRINGS DRIVE

Winter Park, FL

View 2718 SANDWELL DRIVE Winter Park, FL MLS# O6410283
$525,000
3

Beds

2.0

Baths

1,597

Sq.Ft.

2718 SANDWELL DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2333 WESTMINSTER COURT Winter Park, FL MLS# O6407054
$699,000
4

Beds

2.0

Baths

1,877

Sq.Ft.

2333 WESTMINSTER COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
$259,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

Winter Park, FL

View 1347 CHAPMAN CIRCLE Winter Park, FL MLS# O6408189
$1,395,000
4

Beds

3.1

Baths

2,922

Sq.Ft.

1347 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6401352
  • New Construction with Virtual Tour
1 of 49
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

View 926 ENCLAVE PLACE Winter Park, FL MLS# O6408030
  • New Construction with Virtual Tour
1 of 6
$2,235,000
5

Beds

4.1

Baths

4,150

Sq.Ft.

926 ENCLAVE PLACE

Winter Park, FL

View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

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 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • New Construction
1 of 4
$2,050,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
$695,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
$379,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

View 266 W LYMAN AVENUE Winter Park, FL MLS# O6406526
$1,375,000
3

Beds

3.0

Baths

2,000

Sq.Ft.

266 W LYMAN AVENUE

Winter Park, FL

Courtesy of MAROON REALTY GROUP LLC
View 2465 BANCHORY ROAD Winter Park, FL MLS# O6403997
$1,295,000
4

Beds

5.0

Baths

3,971

Sq.Ft.

2465 BANCHORY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Virtual Tour
1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

Courtesy of THE REAL ESTATE PRINCIPLE, INC
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 311 E MORSE BOULEVARD 1-3 Winter Park, FL MLS# O6406368
  • Adult Community with Virtual Tour
1 of 28
$1,925,000
2

Beds

2.0

Baths

2,304

Sq.Ft.

311 E MORSE BOULEVARD 1-3

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

393

Estimated median home price

$750,000
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

PriceCount
$0 - 100K4
$100K - 200K45
$200K - 300K27
$300K - 400K18
$400K - 500K31
$500K - 600K29
$600K - 700K34
$700K - 800K17
$800K - 900K12
$900K - 1M9
$1M - Max167

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family250
Townhouse17
Condo91
Commercial7
Rental71
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/5/2026)

Information deemed reliable but not guaranteed.

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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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.

Data is updated as of 7/6/2026.

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 7/6/2026.