250 total properties
Did you mean the neighborhood Winter Park?
View 1451 LYNDALE BOULEVARD Winter Park, FL MLS# O6237975
$1,999,993
6

Beds

4.0

Baths

3,853

Sq.Ft.

1451 LYNDALE BOULEVARD

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 1540 PALM AVENUE Winter Park, FL MLS# O6345573
  • Virtual Tour
1 of 58
$1,999,000
5

Beds

3.1

Baths

3,423

Sq.Ft.

1540 PALM AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1752 CHESTNUT AVENUE Winter Park, FL MLS# O6331369
  • Virtual Tour
1 of 64
$1,995,000
4

Beds

4.1

Baths

3,314

Sq.Ft.

1752 CHESTNUT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 319 SANTIAGO DRIVE Winter Park, FL MLS# O6347294
  • Virtual Tour
1 of 44
$1,990,000
4

Beds

4.1

Baths

3,515

Sq.Ft.

319 SANTIAGO DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6301489
  • Virtual Tour
1 of 54
$1,973,450
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 633 BALMORAL ROAD Winter Park, FL MLS# O6353491
  • Virtual Tour
1 of 8
$1,875,000
4

Beds

2.1

Baths

2,674

Sq.Ft.

633 BALMORAL ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 633 BALMORAL ROAD Winter Park, FL MLS# O6353528
  • Virtual Tour
1 of 9
$1,875,000
Studio

Beds

0.0

Baths

633 BALMORAL ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 617 WORTHINGTON DRIVE Winter Park, FL MLS# O6320955
$1,770,000
5

Beds

4.1

Baths

3,533

Sq.Ft.

617 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 446 ALBERTA DRIVE Winter Park, FL MLS# O6319233
  • Virtual Tour
1 of 69
$1,750,000
4

Beds

2.1

Baths

3,263

Sq.Ft.

446 ALBERTA DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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
View 1571 LASBURY AVENUE Winter Park, FL MLS# O6345436
  • Virtual Tour
1 of 49
$1,699,999
4

Beds

3.0

Baths

2,749

Sq.Ft.

1571 LASBURY AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 141 W LAKE SUE AVENUE Winter Park, FL MLS# O6345896
$1,690,000
Studio

Beds

0.0

Baths

141 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 315 E NEW ENGLAND AVENUE 7 Winter Park, FL MLS# O6335422
$1,675,000
2

Beds

2.0

Baths

1,511

Sq.Ft.

315 E NEW ENGLAND AVENUE 7

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6367773
  • Recently Listed with Virtual Tour
1 of 7
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1166 OAKS BOULEVARD Winter Park, FL MLS# O6341707
  • Virtual Tour
1 of 44
$1,649,999
4

Beds

3.1

Baths

2,860

Sq.Ft.

1166 OAKS BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1510 MILLER AVENUE Winter Park, FL MLS# O6350503
  • New Construction with Virtual Tour
1 of 5
$1,634,900
5

Beds

4.1

Baths

3,252

Sq.Ft.

1510 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 607 ELLEN DRIVE Winter Park, FL MLS# O6354269
  • New Construction with Virtual Tour
1 of 45
$1,630,000
4

Beds

3.2

Baths

2,812

Sq.Ft.

607 ELLEN DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1450 GLENCOE ROAD Winter Park, FL MLS# O6356770
$1,625,000
4

Beds

3.0

Baths

2,785

Sq.Ft.

1450 GLENCOE ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1417 MILLER AVENUE Winter Park, FL MLS# O6271186
  • New Construction
1 of 6
$1,599,900
5

Beds

4.0

Baths

3,312

Sq.Ft.

1417 MILLER AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1270 ARLINGTON PLACE Winter Park, FL MLS# O6324320
  • Virtual Tour
1 of 55
$1,599,000
3

Beds

4.0

Baths

2,964

Sq.Ft.

1270 ARLINGTON PLACE

Winter Park, FL

Courtesy of RE/MAX 200 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

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 107
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 12/26/2025)

Information deemed reliable but not guaranteed.

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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 12/26/2025.

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.

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 12/26/2025.

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 12/26/2025.

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 12/26/2025.