60 total properties
Did you mean the neighborhood Winter Park?
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

View 300 CAROLINA AVENUE 402C Winter Park, FL MLS# O6410016
$710,000
3

Beds

2.0

Baths

1,350

Sq.Ft.

300 CAROLINA AVENUE 402C

Winter Park, FL

View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6409849
$650,000
3

Beds

2.0

Baths

1,467

Sq.Ft.

1009 LAKE BELL DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6410167
$650,000
Studio

Beds

0.0

Baths

1009 LAKE BELL DRIVE

Winter Park, FL

View 2418 EUSTON ROAD Winter Park, FL MLS# O6409323
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1 of 34
$659,998
3

Beds

2.1

Baths

2,048

Sq.Ft.

2418 EUSTON ROAD

Winter Park, FL

Courtesy of TOLARIS REALTY GROUP LLC
View 715 S RANGER BOULEVARD Winter Park, FL MLS# O6410899
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1 of 48
OPEN HOUSE: Sunday 8/30 11:00 AM - 2:00 PM
$695,000
4

Beds

3.0

Baths

2,312

Sq.Ft.

715 S RANGER BOULEVARD

Winter Park, FL

View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
$599,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
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1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

View 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
$799,000
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
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1 of 36
$630,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
$614,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
$695,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

View 1977 DUNDEE DRIVE Winter Park, FL MLS# O6341378
$695,500
1,656

Sq.Ft.

1977 DUNDEE DRIVE

Winter Park, FL

View 744 CORNWALL ROAD Winter Park, FL MLS# O6332168
$630,000
4

Beds

2.0

Baths

1,968

Sq.Ft.

744 CORNWALL ROAD

Winter Park, FL

View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
$640,000
3

Beds

2.1

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 770 W WEBSTER AVENUE Winter Park, FL MLS# O6323574
$725,000
4

Beds

2.0

Baths

1,008

Sq.Ft.

770 W WEBSTER AVENUE

Winter Park, FL

View 770 W WEBSTER AVENUE REAR LOT Winter Park, FL MLS# O6323647
$725,000
Studio

Beds

0.0

Baths

770 W WEBSTER AVENUE REAR LOT

Winter Park, FL

View 3377 FORSYTH ROAD Winter Park, FL MLS# O6173998
$725,000
4,104

Sq.Ft.

3377 FORSYTH ROAD

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

376

Estimated median home price

$697,250
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 - 200K41
$200K - 300K22
$300K - 400K15
$400K - 500K36
$500K - 600K33
$600K - 700K39
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max150

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse22
Condo81
Commercial9
Rental80
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 8/25/2026)

Information deemed reliable but not guaranteed.

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 8/25/2026.