98 total properties
Did you mean the neighborhood Winter Park?
View 685 Grenadine Ct. Winter Park, FL MLS# A11952398
  • Recently Listed with Virtual Tour
1 of 20
$1,850
3

Beds

2.0

Baths

1,350

Sq.Ft.

685 Grenadine Ct.

Winter Park, FL

Courtesy of SYNERGY INTERNATIONAL REALTY, INC.
View 311 E MORSE BOULEVARD 1-5 Winter Park, FL MLS# O6376059
  • Recently Listed
1 of 52
$11,500
3

Beds

3.0

Baths

2,462

Sq.Ft.

311 E MORSE BOULEVARD 1-5

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 651 TRINIDAD COURT S Winter Park, FL MLS# O6376073
  • Recently Listed with Virtual Tour
1 of 21
$1,450
1

Beds

1.0

Baths

759

Sq.Ft.

651 TRINIDAD COURT S

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1000 S SEMORAN BOULEVARD 116 Winter Park, FL MLS# O6376263
  • Recently Listed with Virtual Tour
1 of 28
$1,600
2

Beds

2.0

Baths

1,072

Sq.Ft.

1000 S SEMORAN BOULEVARD 116

Winter Park, FL

Courtesy of SPACES & STYLES GROUP
View 2905 ANTIQUE OAKS CIRCLE 4 Winter Park, FL MLS# O6376272
  • Recently Listed with Virtual Tour
1 of 27
$1,370
1

Beds

1.0

Baths

749

Sq.Ft.

2905 ANTIQUE OAKS CIRCLE 4

Winter Park, FL

Courtesy of EXIT REAL ESTATE RESULTS
View 2992 CHANTILLY AVENUE Winter Park, FL MLS# O6375763
  • Recently Listed with Virtual Tour
1 of 39
$2,880
3

Beds

2.0

Baths

1,496

Sq.Ft.

2992 CHANTILLY AVENUE

Winter Park, FL

Courtesy of LEMUEL PROPERTY MANAGEMENT LLC
View 2818 SALISBURY BOULEVARD Winter Park, FL MLS# O6375344
$2,100
3

Beds

1.0

Baths

1,167

Sq.Ft.

2818 SALISBURY BOULEVARD

Winter Park, FL

Courtesy of ZEMBALA GROUP
View 7425 WYNNEWOOD SQUARE 176 Winter Park, FL MLS# O6375456
  • Recently Listed with Virtual Tour
1 of 26
$1,700
2

Beds

2.1

Baths

1,031

Sq.Ft.

7425 WYNNEWOOD SQUARE 176

Winter Park, FL

Courtesy of ZAID ROYALE REALTY PLLC
View Address not provided Winter Park, FL MLS# O6375024
$2,650
2

Beds

1.0

Baths

1,000

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of LOMBARDI LEMAY REALTY
View 3266 OAK LAKE PLACE 140 Winter Park, FL MLS# O6375695
  • Recently Listed with Virtual Tour
1 of 13
$1,700
2

Beds

2.1

Baths

1,031

Sq.Ft.

3266 OAK LAKE PLACE 140

Winter Park, FL

Courtesy of LET'S OWN FL, LLC
View 900 S KENTUCKY AVENUE Winter Park, FL MLS# O6374630
  • Recently Listed with Virtual Tour
1 of 15
$3,500
3

Beds

2.0

Baths

1,508

Sq.Ft.

900 S KENTUCKY AVENUE

Winter Park, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
View 1826 PINEVIEW CIRCLE Winter Park, FL MLS# O6373874
  • Recently Listed with Virtual Tour
1 of 14
$2,495
3

Beds

2.0

Baths

1,222

Sq.Ft.

1826 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 3651 N GOLDENROD ROAD E103 Winter Park, FL MLS# O6373934
  • Recently Listed with Virtual Tour
1 of 7
$1,325
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD E103

Winter Park, FL

Courtesy of AMERICAN REALTY EXPERTS
View 3651 N GOLDENROD ROAD C205 Winter Park, FL MLS# O6373015
  • Recently Listed with Virtual Tour
1 of 11
$1,495
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C205

Winter Park, FL

Courtesy of CFRP REALTY LLC
View 1049 N KENTUCKY AVENUE Winter Park, FL MLS# O6373029
  • Recently Listed with Virtual Tour
1 of 43
$6,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

1049 N KENTUCKY AVENUE

Winter Park, FL

Courtesy of THE AGENCY FL
View 840 W CANTON AVENUE Winter Park, FL MLS# O6372874
  • Recently Listed with Virtual Tour
1 of 17
$4,000
2

Beds

2.0

Baths

1,400

Sq.Ft.

840 W CANTON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1835 EDWIN BOULEVARD Winter Park, FL MLS# O6372293
  • Recently Listed with Virtual Tour
1 of 50
$3,175
3

Beds

2.0

Baths

1,436

Sq.Ft.

1835 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 438 W SWOOPE AVENUE Winter Park, FL MLS# O6368619
  • Recently Listed with Virtual Tour
1 of 27
$4,495
3

Beds

2.1

Baths

2,317

Sq.Ft.

438 W SWOOPE AVENUE

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 2352 SMILEY AVENUE Winter Park, FL MLS# O6372791
  • Recently Listed with Virtual Tour
1 of 15
$2,700
3

Beds

2.0

Baths

1,456

Sq.Ft.

2352 SMILEY AVENUE

Winter Park, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
View 200 SAINT ANDREWS BOULEVARD 1805 Winter Park, FL MLS# O6372204
  • Recently Listed with Virtual Tour
1 of 13
$2,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1805

Winter Park, FL

Courtesy of LIVE MVRK 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

291

Estimated median home price

$650,000
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 6
$100K - 200K 35
$200K - 300K 30
$300K - 400K 16
$400K - 500K 25
$500K - 600K 18
$600K - 700K 26
$700K - 800K 17
$800K - 900K 4
$900K - 1M 9
$1M - Max 105

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 163
Townhouse 19
Condo 78
Commercial 6
Rental 101
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/26/2026)

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 1/26/2026.