178 total properties
Did you mean the neighborhood Winter Park?
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Recently Listed with Virtual Tour
1 of 17
$195,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
  • Recently Listed
1 of 29
$644,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2748 LION HEART ROAD Winter Park, FL MLS# O6379237
  • Recently Listed with Virtual Tour
1 of 49
$500,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

2748 LION HEART ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 4872 ORANGE AVENUE Winter Park, FL MLS# O6380333
  • Recently Listed with Virtual Tour
1 of 18
$375,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

4872 ORANGE AVENUE

Winter Park, FL

Courtesy of ALFA REAL ESTATE LLC
View 200 SAINT ANDREWS BOULEVARD 2302 Winter Park, FL MLS# O6377760
  • Recently Listed with Virtual Tour
1 of 18
$195,000
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2302

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 630 SAINT DUNSTAN WAY Winter Park, FL MLS# O6376860
$675,000
5

Beds

2.0

Baths

2,240

Sq.Ft.

630 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
  • Recently Listed with Virtual Tour
1 of 41
$255,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378461
  • Recently Listed with Virtual Tour
1 of 11
$630,000
Studio

Beds

0.0

Baths

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
  • Recently Listed with Virtual Tour
1 of 55
$549,900
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 620 DARCEY DRIVE Winter Park, FL MLS# O6378148
  • Recently Listed
1 of 42
$739,000
4

Beds

2.0

Baths

2,075

Sq.Ft.

620 DARCEY DRIVE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 841 W SWOOPE AVENUE Winter Park, FL MLS# O6373287
  • Recently Listed with Virtual Tour
1 of 5
$740,000
2

Beds

1.0

Baths

1,396

Sq.Ft.

841 W SWOOPE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6377279
  • Recently Listed with Virtual Tour
1 of 70
$435,000
4

Beds

2.0

Baths

1,536

Sq.Ft.

2249 MINNESOTA AVENUE

Winter Park, FL

Courtesy of MARKET CONNECT REALTY LLC
View 3315 AMBER WOOD WAY 104 Winter Park, FL MLS# O6376997
  • Recently Listed with Virtual Tour
1 of 26
$165,000
2

Beds

1.1

Baths

990

Sq.Ft.

3315 AMBER WOOD WAY 104

Winter Park, FL

Courtesy of 100% REAL ESTATE, INC
View 508 DARCEY DRIVE Winter Park, FL MLS# O6377090
  • Recently Listed
1 of 25
$580,000
3

Beds

1.1

Baths

1,295

Sq.Ft.

508 DARCEY DRIVE

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 2609 SUMMERFIELD ROAD Winter Park, FL MLS# O6377302
$899,000
5

Beds

2.0

Baths

2,554

Sq.Ft.

2609 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
  • Recently Listed with Virtual Tour
1 of 34
OPEN HOUSE: Saturday 2/7 11:00 AM - 2:00 PM
$579,999
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
  • Recently Listed with Virtual Tour
1 of 31
$509,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 326 FITZHUGH ROAD Winter Park, FL MLS# O6372053
  • Virtual Tour
1 of 45
$475,000
4

Beds

3.0

Baths

1,835

Sq.Ft.

326 FITZHUGH ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 535 N INTERLACHEN AVENUE 106 Winter Park, FL MLS# O6376040
  • Recently Listed with Virtual Tour
1 of 23
$595,000
2

Beds

2.0

Baths

970

Sq.Ft.

535 N INTERLACHEN AVENUE 106

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 681 OVERSPIN DRIVE Winter Park, FL MLS# O6376464
  • Recently Listed with Virtual Tour
1 of 64
$680,000
4

Beds

2.1

Baths

2,220

Sq.Ft.

681 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RE/MAX SELECT 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

300

Estimated median home price

$687,500
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 7
$100K - 200K 34
$200K - 300K 29
$300K - 400K 16
$400K - 500K 26
$500K - 600K 18
$600K - 700K 25
$700K - 800K 18
$800K - 900K 5
$900K - 1M 8
$1M - Max 114

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 170
Townhouse 17
Condo 78
Commercial 6
Rental 91
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/6/2026)

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 2/6/2026.

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 2/6/2026.

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 2/6/2026.