315 total properties
Did you mean the neighborhood Winter Park?
View 1782 PINE AVENUE Winter Park, FL MLS# O6389039
  • Recently Listed
1 of 66
$4,197,000
5

Beds

6.1

Baths

4,782

Sq.Ft.

1782 PINE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 259 E CANTON AVENUE 259 Winter Park, FL MLS# O6389246
  • Recently Listed with Virtual Tour
1 of 36
$649,000
2

Beds

2.0

Baths

1,040

Sq.Ft.

259 E CANTON AVENUE 259

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2918 ANTIQUE OAKS CIRCLE 25 Winter Park, FL MLS# O6389113
  • Recently Listed with Virtual Tour
1 of 21
$189,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 25

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Park, FL MLS# S5145631
  • Recently Listed with Virtual Tour
1 of 10
$440,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • Recently Listed with Virtual Tour
1 of 9
$944,890
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6389035
  • Recently Listed with Virtual Tour
1 of 68
$2,279,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of GOLDEN GROUP REALTY LLC
View 240 N Phelps Avenue Winter Park, FL MLS# 1071436
  • Recently Listed
1 of 68
$2,279,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N Phelps Avenue

Winter Park, FL

Brevard
View 218 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6388723
  • Recently Listed with Virtual Tour
1 of 29
$635,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

218 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 3131 LOWNDES DRIVE Winter Park, FL MLS# O6388846
  • Recently Listed with Virtual Tour
1 of 24
$554,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

3131 LOWNDES DRIVE

Winter Park, FL

Courtesy of A +ROI PROPERTY
View 1705 ELIZABETHS WALK Winter Park, FL MLS# O6389723
$1,650,000
5

Beds

5.0

Baths

3,820

Sq.Ft.

1705 ELIZABETHS WALK

Winter Park, FL

Courtesy of HOMEVEST REALTY
View 4858 TANGERINE AVENUE 4858 Winter Park, FL MLS# O6388649
  • Recently Listed with Virtual Tour
1 of 25
$219,900
2

Beds

2.0

Baths

1,058

Sq.Ft.

4858 TANGERINE AVENUE 4858

Winter Park, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1521 CHESTNUT AVENUE Winter Park, FL MLS# A4685113
  • Recently Listed with Virtual Tour
1 of 57
$1,899,900
4

Beds

3.0

Baths

2,842

Sq.Ft.

1521 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 465 N PHELPS AVENUE Winter Park, FL MLS# O6388286
  • Virtual Tour
1 of 6
$849,900
Studio

Beds

0.0

Baths

465 N PHELPS AVENUE

Winter Park, FL

Courtesy of FIDICITY REALTY INC
View 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
  • Virtual Tour
1 of 44
$649,900
3

Beds

2.0

Baths

1,469

Sq.Ft.

1926 NATALEN ROAD

Winter Park, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 2423 VIA SIENNA Winter Park, FL MLS# O6386867
  • Recently Listed with Virtual Tour
1 of 44
$2,200,000
4

Beds

3.1

Baths

3,472

Sq.Ft.

2423 VIA SIENNA

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 325 N PHELPS AVENUE Winter Park, FL MLS# O6388118
  • Recently Listed with Virtual Tour
1 of 6
$795,000
Studio

Beds

0.0

Baths

325 N PHELPS AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2550 VENETIAN WAY Winter Park, FL MLS# O6388219
  • Recently Listed with Virtual Tour
1 of 65
$2,450,000
4

Beds

3.2

Baths

5,051

Sq.Ft.

2550 VENETIAN WAY

Winter Park, FL

Courtesy of PALM PROPERTIES OF CF, INC.
View 236 SCOTTSDALE SQUARE 236 Winter Park, FL MLS# O6388547
  • Recently Listed with Virtual Tour
1 of 26
$75,000
2

Beds

2.0

Baths

1,085

Sq.Ft.

236 SCOTTSDALE SQUARE 236

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
View 2040 RANDALL CIRCLE Winter Park, FL MLS# O6386920
  • Recently Listed with Virtual Tour
1 of 39
$3,450,000
5

Beds

4.2

Baths

4,636

Sq.Ft.

2040 RANDALL CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Recently Listed with Virtual Tour
1 of 39
$599,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

320

Estimated median home price

$732,400
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 41
$200K - 300K 26
$300K - 400K 18
$400K - 500K 28
$500K - 600K 15
$600K - 700K 20
$700K - 800K 20
$800K - 900K 7
$900K - 1M 9
$1M - Max 131

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 18
Condo 83
Commercial 3
Rental 85
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 3/16/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 3/17/2026.

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 3/17/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 3/17/2026.