299 total properties
Did you mean the neighborhood Winter Park?
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 623 SAINT JOHNS COURT 623 Winter Park, FL MLS# O6362363
$200,000
2

Beds

2.0

Baths

1,120

Sq.Ft.

623 SAINT JOHNS COURT 623

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 1494 WESTCHESTER AVENUE Winter Park, FL MLS# O6363530
  • New Construction with Virtual Tour
1 of 16
$2,990,000
5

Beds

4.1

Baths

3,711

Sq.Ft.

1494 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1134 WASHINGTON AVENUE 13 Winter Park, FL MLS# O6362206
$675,000
3

Beds

3.1

Baths

2,083

Sq.Ft.

1134 WASHINGTON AVENUE 13

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2632 MANDAN TRAIL Winter Park, FL MLS# O6362577
  • Virtual Tour
1 of 30
$799,900
4

Beds

2.1

Baths

2,441

Sq.Ft.

2632 MANDAN TRAIL

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1807 YORKSHIRE DRIVE Winter Park, FL MLS# TB8451098
  • New Construction
1 of 3
$1,450,000
4

Beds

4.1

Baths

3,565

Sq.Ft.

1807 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of WEEKLEY HOMES REALTY COMPANY
View 311 E MORSE BOULEVARD 6-3 Winter Park, FL MLS# O6362964
  • Adult Community with Virtual Tour
1 of 36
$329,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1909 EDWIN BOULEVARD Winter Park, FL MLS# O6362682
  • Virtual Tour
1 of 11
$440,000
3

Beds

2.0

Baths

1,355

Sq.Ft.

1909 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 714 DENTON ROAD Winter Park, FL MLS# O6362464
  • Virtual Tour
1 of 32
$449,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

714 DENTON ROAD

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 1695 LEE ROAD E211 Winter Park, FL MLS# L4957574
  • Virtual Tour
1 of 24
$129,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E211

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY SMART 1
View 1802 ARBOR PARK DRIVE Winter Park, FL MLS# TB8450994
$895,000
3

Beds

3.0

Baths

1,808

Sq.Ft.

1802 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of FLORIDA EXECUTIVE REALTY
View 240 E Lake Sue Ave Winter Park, FL MLS# F10537698
  • Virtual Tour
1 of 15
$1,107,750
2

Beds

2.0

Baths

1,329

Sq.Ft.

240 E Lake Sue Ave

Winter Park, FL

View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5138926
$145,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 1624 BARCELONA WAY Winter Park, FL MLS# O6362124
  • Virtual Tour
1 of 61
$2,350,000
3

Beds

3.0

Baths

3,828

Sq.Ft.

1624 BARCELONA WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3651 N GOLDENROD ROAD E102 Winter Park, FL MLS# O6362614
$168,150
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD E102

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361377
  • Virtual Tour
1 of 41
$2,350,000
5

Beds

4.0

Baths

3,948

Sq.Ft.

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361935
$2,350,000
Studio

Beds

0.0

Baths

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2722 EASTERN PARKWAY Winter Park, FL MLS# O6360734
  • New Construction with Virtual Tour
1 of 14
$2,289,000
5

Beds

4.1

Baths

3,334

Sq.Ft.

2722 EASTERN PARKWAY

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1251 ARLINGTON PLACE Winter Park, FL MLS# O6358201
  • Virtual Tour
1 of 43
$845,000
3

Beds

3.1

Baths

2,116

Sq.Ft.

1251 ARLINGTON PLACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1630 CHESTNUT AVENUE Winter Park, FL MLS# O6360357
  • Virtual Tour
1 of 58
$1,750,000
3

Beds

4.1

Baths

3,164

Sq.Ft.

1630 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE

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

299

Estimated median home price

$649,000
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 7
$100K - 200K 40
$200K - 300K 21
$300K - 400K 18
$400K - 500K 30
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 174
Townhouse 19
Condo 78
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 12/25/2025)

Information deemed reliable but not guaranteed.

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Data is updated as of 12/25/2025.

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.

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Data is updated as of 12/25/2025.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 12/25/2025.

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 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 12/25/2025.