129 total properties
Did you mean the neighborhood Winter Park?
View 720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6281659
$550,000
3

Beds

2.0

Baths

1,115

Sq.Ft.

720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6344260
$549,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of PRESTIGE PROPERTY SHOP LLC
View 100 S INTERLACHEN AVENUE 410F Winter Park, FL MLS# O6303353
$549,000
2

Beds

1.0

Baths

901

Sq.Ft.

100 S INTERLACHEN AVENUE 410F

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2412 MIDDLETON AVENUE Winter Park, FL MLS# O6356193
$549,000
3

Beds

2.0

Baths

1,340

Sq.Ft.

2412 MIDDLETON AVENUE

Winter Park, FL

Courtesy of REAL ESTATE INVESTMENTS BY BOR
View 240 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6312795
$525,000
3

Beds

2.0

Baths

1,630

Sq.Ft.

240 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1817 JESSICA COURT Winter Park, FL MLS# O6364894
$525,000
3

Beds

2.0

Baths

1,870

Sq.Ft.

1817 JESSICA COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
$520,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

346 S RANGER BOULEVARD

Winter Park, FL

Courtesy of IMPERIAL REALTY OF FLORIDA INC
View 422 S RANGER BOULEVARD Winter Park, FL MLS# O6359171
$520,000
4

Beds

2.0

Baths

1,680

Sq.Ft.

422 S RANGER BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 240 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6330690
$515,000
4

Beds

2.0

Baths

1,718

Sq.Ft.

240 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6093816
$510,000
4

Beds

3.0

Baths

1,805

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1651 N PARK AVENUE Winter Park, FL MLS# O6354776
$505,000
3

Beds

2.0

Baths

1,263

Sq.Ft.

1651 N PARK AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1116 FAIRWAY DRIVE Winter Park, FL MLS# O6265989
$499,900
3

Beds

2.0

Baths

1,738

Sq.Ft.

1116 FAIRWAY DRIVE

Winter Park, FL

Courtesy of TURN-KEY MOVES REALTY
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369571
  • Recently Listed with Virtual Tour
1 of 19
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369600
  • Recently Listed with Virtual Tour
1 of 18
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2560 Franklin Ave. Winter Park, FL MLS# F10431070
$499,000
4

Beds

2.0

Baths

1,514

Sq.Ft.

2560 Franklin Ave.

Winter Park, FL

View 3718 N Goldenrod Road Winter Park, FL MLS# A11792799
$499,000
Studio

Beds

0.0

Baths

3718 N Goldenrod Road

Winter Park, FL

Courtesy of PROCLOSE REALTY, LLC.
View 259 BLOSSOM LANE Winter Park, FL MLS# O6353902
  • Virtual Tour
1 of 24
$499,000
3

Beds

2.0

Baths

1,354

Sq.Ft.

259 BLOSSOM LANE

Winter Park, FL

Courtesy of TALENT REALTY SOLUTIONS
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6366830
$499,000
Studio

Beds

0.0

Baths

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Recently Listed with Virtual Tour
1 of 7
$499,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6359841
$499,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

301

Estimated median home price

$639,000
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 - 100K6
$100K - 200K40
$200K - 300K21
$300K - 400K19
$400K - 500K32
$500K - 600K26
$600K - 700K21
$700K - 800K22
$800K - 900K5
$900K - 1M11
$1M - Max98

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family176
Townhouse19
Condo77
Commercial5
Rental108
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 12/28/2025)

Information deemed reliable but not guaranteed.

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 12/28/2025.

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 12/28/2025.