105 total properties
Did you mean the neighborhood Winter Park?
View 3651 N GOLDENROD ROAD 106 Winter Park, FL MLS# O6369311
  • Recently Listed with Virtual Tour
1 of 18
$1,550
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD 106

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
View 1565 MICHIGAN AVENUE Winter Park, FL MLS# O6360479
  • Virtual Tour
1 of 12
$1,575
2

Beds

1.0

Baths

900

Sq.Ft.

1565 MICHIGAN AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 851 MILES AVENUE 21 Winter Park, FL MLS# O6340720
  • Virtual Tour
1 of 33
$1,595
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 21

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Park, FL MLS# O6326689
  • Virtual Tour
1 of 13
$1,597
2

Beds

2.1

Baths

1,031

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of THE REALTY FACTOR INC
View 3651 N GOLDENROD ROAD D201 Winter Park, FL MLS# O6361625
$1,625
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D201

Winter Park, FL

Courtesy of VESTI LLC
View Address not provided Winter Park, FL MLS# O6367750
  • Recently Listed with Virtual Tour
1 of 24
$1,695
3

Beds

2.0

Baths

1,149

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 3057 AARON BURR AVENUE 1 Winter Park, FL MLS# O6340903
$1,700
2

Beds

2.0

Baths

1,066

Sq.Ft.

3057 AARON BURR AVENUE 1

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6368525
  • Recently Listed with Virtual Tour
1 of 12
$1,700
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 7429 DANIEL WEBSTER DRIVE 14 (#C) Winter Park, FL MLS# O6332527
$1,740
2

Beds

2.0

Baths

1,036

Sq.Ft.

7429 DANIEL WEBSTER DRIVE 14 (#C)

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 7412 WOODBURN COURT 23 Winter Park, FL MLS# O6353923
$1,750
2

Beds

2.1

Baths

1,031

Sq.Ft.

7412 WOODBURN COURT 23

Winter Park, FL

Courtesy of POWERHOUSE BROKERS INT'L
View 151 N ORLANDO AVENUE 226 Winter Park, FL MLS# O6364336
$1,750
2

Beds

1.0

Baths

768

Sq.Ft.

151 N ORLANDO AVENUE 226

Winter Park, FL

Courtesy of LOKATION
View 650 TRINIDAD COURT 650 Winter Park, FL MLS# O6364866
$1,750
2

Beds

2.0

Baths

1,120

Sq.Ft.

650 TRINIDAD COURT 650

Winter Park, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 918 GLORIOSA AVENUE Winter Park, FL MLS# O6356312
  • Virtual Tour
1 of 13
$1,795
2

Beds

2.0

Baths

1,232

Sq.Ft.

918 GLORIOSA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 200 SAINT ANDREWS BOULEVARD 1803 Winter Park, FL MLS# O6371317
  • Recently Listed with Virtual Tour
1 of 32
$1,795
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1803

Winter Park, FL

Courtesy of WILSON MANAGEMENT GROUP
View 616 MONTEGO BAY COURT S Winter Park, FL MLS# S5137961
$1,800
2

Beds

2.0

Baths

1,037

Sq.Ft.

616 MONTEGO BAY COURT S

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 654 TRINIDAD CT 654 Winter Park, FL MLS# S5140107
  • Virtual Tour
1 of 7
$1,800
2

Beds

2.0

Baths

1,120

Sq.Ft.

654 TRINIDAD CT 654

Winter Park, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 1500 GAY ROAD 3B Winter Park, FL MLS# O6333528
  • Virtual Tour
1 of 15
$1,850
2

Beds

2.0

Baths

1,100

Sq.Ft.

1500 GAY ROAD 3B

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 7337 CEDAR CREEK COURT 75 Winter Park, FL MLS# O6349617
$1,895
2

Beds

2.1

Baths

1,031

Sq.Ft.

7337 CEDAR CREEK COURT 75

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 200 SAINT ANDREWS BOULEVARD 2903 Winter Park, FL MLS# O6357483
$1,895
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2903

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 250 CAROLINA AVENUE 307 Winter Park, FL MLS# O6365311
$1,950
1

Beds

2.0

Baths

1,153

Sq.Ft.

250 CAROLINA AVENUE 307

Winter Park, FL

Courtesy of VERANDA PARK REALTY LLC

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

267

Estimated median home price

$679,000
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 34
$200K - 300K 20
$300K - 400K 15
$400K - 500K 23
$500K - 600K 20
$600K - 700K 21
$700K - 800K 22
$800K - 900K 4
$900K - 1M 10
$1M - Max 93

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 155
Townhouse 18
Condo 66
Commercial 5
Rental 102
Lots and Land 18
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/6/2026)

Information deemed reliable but not guaranteed.

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 1/7/2026.