237 total properties
Did you mean the neighborhood Winter Park?
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
  • Virtual Tour
1 of 26
$159,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 232

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
  • Virtual Tour
1 of 42
$800,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
The time to sell is now! THE TIME TO SELL IS NOW!
View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6404564
  • Virtual Tour
1 of 67
$1,750,000
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$180,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

Courtesy of M L VAZ REALTY INC
View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
$154,500
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Virtual Tour
1 of 27
$535,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
  • Virtual Tour
1 of 8
$849,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$495,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

View 1581 MAGNOLIA AVE Winter Park, FL MLS# O6396118
  • Virtual Tour
1 of 75
$1,495,000
4

Beds

4.0

Baths

2,756

Sq.Ft.

1581 MAGNOLIA AVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Virtual Tour
1 of 26
$240,000
3

Beds

3.0

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Virtual Tour
1 of 41
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
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 420 OHIO STREET Winter Park, FL MLS# O6399541
  • New Construction with Virtual Tour
1 of 8
$1,360,000
5

Beds

5.1

Baths

3,735

Sq.Ft.

420 OHIO STREET

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6402984
$1,185,999
6

Beds

4.0

Baths

2,282

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6402961
  • Virtual Tour
1 of 52
$1,150,000
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
$194,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

View 2111 MALLARD CIRCLE Winter Park, FL MLS# O6401350
  • Virtual Tour
1 of 28
$1,199,000
4

Beds

3.0

Baths

2,667

Sq.Ft.

2111 MALLARD CIRCLE

Winter Park, FL

View 363 N PHELPS AVENUE Winter Park, FL MLS# O6401811
  • Virtual Tour
1 of 36
$1,249,000
4

Beds

3.0

Baths

2,871

Sq.Ft.

363 N PHELPS AVENUE

Winter Park, FL

View 2838 WRIGHT AVENUE Winter Park, FL MLS# O6399931
  • New Construction with Virtual Tour
1 of 10
$2,399,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

2838 WRIGHT AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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

273

Estimated median home price

$695,000
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 5
$100K - 200K 40
$200K - 300K 17
$300K - 400K 14
$400K - 500K 24
$500K - 600K 19
$600K - 700K 22
$700K - 800K 12
$800K - 900K 8
$900K - 1M 4
$1M - Max 108

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 158
Townhouse 10
Condo 70
Commercial 7
Rental 73
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/12/2026)

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 7/12/2026.

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 7/12/2026.