282 total properties
Did you mean the neighborhood Winter Park?
View 2743 MERRIE OAKS ROAD Winter Park, FL MLS# O6361079
$439,000
3

Beds

2.0

Baths

1,661

Sq.Ft.

2743 MERRIE OAKS ROAD

Winter Park, FL

Courtesy of ONE45 REALTY LLC
View 1213 LINDENWOOD LANE Winter Park, FL MLS# O6362048
  • Virtual Tour
1 of 29
OPEN HOUSE: Sunday 1/18 2:00 PM - 4:00 PM
$750,000
4

Beds

2.0

Baths

2,505

Sq.Ft.

1213 LINDENWOOD LANE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 315 E NEW ENGLAND AVENUE 7 Winter Park, FL MLS# O6335422
$1,675,000
2

Beds

2.0

Baths

1,609

Sq.Ft.

315 E NEW ENGLAND AVENUE 7

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 870 CARVER STREET Winter Park, FL MLS# O6360210
  • New Construction with Virtual Tour
1 of 53
$975,000
3

Beds

3.0

Baths

1,875

Sq.Ft.

870 CARVER STREET

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6359841
  • Virtual Tour
1 of 33
$499,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 422 S RANGER BOULEVARD Winter Park, FL MLS# O6359171
$509,900
4

Beds

2.0

Baths

1,680

Sq.Ft.

422 S RANGER BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 763 Overspin Drive Winter Park, FL MLS# 256173
$699,000
Studio

Beds

0.0

Baths

763 Overspin Drive

Winter Park, FL

View 1786 N SEMORAN BOULEVARD Winter Park, FL MLS# A4671024
$200,000
3,212

Sq.Ft.

1786 N SEMORAN BOULEVARD

Winter Park, FL

Courtesy of BHHS EWM REALTY
View 102 BELL PLACE Winter Park, FL MLS# O6354345
  • New Construction with Virtual Tour
1 of 51
$1,499,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of INVESTOR'S REAL ESTATE LLC
View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6358847
  • New Construction
1 of 58
$2,350,000
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6353495
$2,295,000
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6357615
  • New Construction with Virtual Tour
1 of 50
OPEN HOUSE: Saturday 1/17 12:00 PM - 3:00 PM
$1,375,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 7480 WOODBURN COURT 39 Winter Park, FL MLS# O6356871
$199,999
3

Beds

2.1

Baths

1,151

Sq.Ft.

7480 WOODBURN COURT 39

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1401 GREEN COVE ROAD Winter Park, FL MLS# O6358093
  • Virtual Tour
1 of 58
OPEN HOUSE: Saturday 1/17 11:00 AM - 1:00 PM
$2,900,000
3

Beds

4.3

Baths

5,483

Sq.Ft.

1401 GREEN COVE ROAD

Winter Park, FL

Courtesy of ANCHOR REAL ESTATE
View 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6360088
  • New Construction with Virtual Tour
1 of 48
OPEN HOUSE: Saturday 1/17 1:00 PM - 3:00 PM
$2,295,000
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

Courtesy of THE AGENCY ORLANDO
View 2299 VIA TUSCANY Winter Park, FL MLS# O6355858
  • Virtual Tour
1 of 60
$2,345,000
4

Beds

3.1

Baths

3,986

Sq.Ft.

2299 VIA TUSCANY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1751 GLENCOE ROAD Winter Park, FL MLS# O6339739
  • New Construction with Virtual Tour
1 of 45
OPEN HOUSE: Saturday 1/17 1:00 PM - 3:00 PM
$3,745,000
5

Beds

5.2

Baths

4,520

Sq.Ft.

1751 GLENCOE ROAD

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$698,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1324 INDIANA AVENUE Winter Park, FL MLS# O6357852
  • Virtual Tour
1 of 21
$745,000
4

Beds

2.1

Baths

1,692

Sq.Ft.

1324 INDIANA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 609 GALLERY DRIVE B204 Winter Park, FL MLS# O6357629
$275,000
2

Beds

2.0

Baths

893

Sq.Ft.

609 GALLERY DRIVE B204

Winter Park, FL

Courtesy of A2Z REALTY GROUP

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

280

Estimated median home price

$670,000
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 6
$100K - 200K 34
$200K - 300K 25
$300K - 400K 15
$400K - 500K 25
$500K - 600K 17
$600K - 700K 26
$700K - 800K 19
$800K - 900K 4
$900K - 1M 10
$1M - Max 99

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 157
Townhouse 20
Condo 73
Commercial 6
Rental 101
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/16/2026)

Information deemed reliable but not guaranteed.

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 1/16/2026.

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 1/16/2026.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 1/16/2026.

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 1/16/2026.