208 total properties
Did you mean the neighborhood Winter Park?
View 100 S INTERLACHEN AVENUE 401 Winter Park, FL MLS# O6443942
  • Recently Listed with Virtual Tour
1 of 25
$850,000
3

Beds

2.0

Baths

1,639

Sq.Ft.

100 S INTERLACHEN AVENUE 401

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1871 BRYAN AVENUE Winter Park, FL MLS# O6446584
  • Recently Listed with Virtual Tour
1 of 31
$599,000
0.0

Baths

1871 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 3032 ANTIQUE OAKS CIRCLE 145 Winter Park, FL MLS# O6446981
  • Recently Listed with Virtual Tour
1 of 15
$139,999
1

Beds

1.0

Baths

749

Sq.Ft.

3032 ANTIQUE OAKS CIRCLE 145

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2332 SHERBROOKE ROAD Winter Park, FL MLS# O6447371
$549,000
4

Beds

3.0

Baths

1,842

Sq.Ft.

2332 SHERBROOKE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 712 BAFFIE AVENUE Winter Park, FL MLS# O6445837
  • Recently Listed with Virtual Tour
1 of 14
$439,900
3

Beds

1.0

Baths

1,304

Sq.Ft.

712 BAFFIE AVENUE

Winter Park, FL

Courtesy of RP INVESTMENT REALTY LLC
View 3416 ARBUTUS LANE Winter Park, FL MLS# O6445692
  • Recently Listed with Virtual Tour
1 of 20
$379,900
4

Beds

3.0

Baths

1,421

Sq.Ft.

3416 ARBUTUS LANE

Winter Park, FL

Courtesy of GPS REALTY GROUP
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445731
$850,000
4

Beds

3.0

Baths

2,301

Sq.Ft.

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445759
  • Recently Listed with Virtual Tour
1 of 15
$850,000
0.0

Baths

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 200 SAINT ANDREWS BOULEVARD 704 Winter Park, FL MLS# O6445691
  • Recently Listed with Virtual Tour
1 of 40
$159,000
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 704

Winter Park, FL

Courtesy of EXP REALTY LLC
View 266 N RANGER BOULEVARD Winter Park, FL MLS# O6444727
  • Recently Listed with Virtual Tour
1 of 33
$724,900
4

Beds

3.0

Baths

1,692

Sq.Ft.

266 N RANGER BOULEVARD

Winter Park, FL

Courtesy of ELITE PROPERTY REAL ESTATE LLC
View 1250 S DENNING DRIVE 119 Winter Park, FL MLS# O6444618
  • Recently Listed with Virtual Tour
1 of 31
$265,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 119

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1003 GOLFSIDE DRIVE Winter Park, FL MLS# O6444366
  • Recently Listed with Virtual Tour
1 of 28
$769,900
3

Beds

3.0

Baths

2,145

Sq.Ft.

1003 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of QP HOMES REALTY LLC
View 2818 AMBERGATE ROAD Winter Park, FL MLS# O6444112
  • Recently Listed
1 of 30
$429,900
3

Beds

2.0

Baths

1,398

Sq.Ft.

2818 AMBERGATE ROAD

Winter Park, FL

Courtesy of MARK SPAIN REAL ESTATE
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6444000
  • Recently Listed with Virtual Tour
1 of 45
$780,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
View 1660 ORANGE AVENUE Winter Park, FL MLS# L4965340
  • Recently Listed with Virtual Tour
1 of 61
$479,900
3

Beds

2.0

Baths

1,614

Sq.Ft.

1660 ORANGE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 450 N LAKEMONT AVE Winter Park, FL MLS# O6445021
  • Recently Listed with Virtual Tour
1 of 25
$200,000

450 N LAKEMONT AVE

Winter Park, FL

Courtesy of DOVER INTERNATIONAL CO., INC.
View 173 SCOTTSDALE SQUARE 173 Winter Park, FL MLS# S5158339
  • Recently Listed with Virtual Tour
1 of 13
$100,000
1

Beds

1.0

Baths

785

Sq.Ft.

173 SCOTTSDALE SQUARE 173

Winter Park, FL

Courtesy of AXEN REALTY LLC
View 188 SANDLEWOOD 1 Winter Park, FL MLS# O6445407
  • Recently Listed with Virtual Tour
1 of 25
$290,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

188 SANDLEWOOD 1

Winter Park, FL

Courtesy of NOELKE REALTY
View 192 BALFOUR DRIVE 2 Winter Park, FL MLS# O6443731
  • Recently Listed with Virtual Tour
1 of 52
$319,000
2

Beds

2.0

Baths

1,287

Sq.Ft.

192 BALFOUR DRIVE 2

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8551269
  • Recently Listed with Virtual Tour
1 of 24
$140,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT 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

369

Estimated median home price

$745,000
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 - 100K2
$100K - 200K38
$200K - 300K25
$300K - 400K20
$400K - 500K33
$500K - 600K25
$600K - 700K37
$700K - 800K18
$800K - 900K12
$900K - 1M16
$1M - Max143

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family216
Townhouse20
Condo82
Commercial14
Rental93
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 10/14/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Weichert's are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

© 2026 Georgia MLS. All rights reserved

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 10/14/2026.

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 10/14/2026.