29 total properties
Did you mean the neighborhood Winter Park?
View 2718 EASTERN PARKWAY Winter Park, FL MLS# O6453504
  • Recently Listed with Virtual Tour
1 of 41
OPEN HOUSE: Sunday 11/15 1:00 PM - 4:00 PM
$2,450,000
4

Beds

4.1

Baths

3,308

Sq.Ft.

2718 EASTERN PARKWAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1663 N PARK AVENUE Winter Park, FL MLS# O6453687
  • Recently Listed with Virtual Tour
1 of 51
OPEN HOUSE: Sunday 11/15 1:00 PM - 3:00 PM
$2,750,000
4

Beds

5.0

Baths

3,640

Sq.Ft.

1663 N PARK AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1441 PALM AVENUE Winter Park, FL MLS# O6452896
  • Recently Listed with Virtual Tour
1 of 16
$2,449,000
5

Beds

4.1

Baths

3,391

Sq.Ft.

1441 PALM AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1681 WOODLAND AVENUE Winter Park, FL MLS# O6449440
  • New Construction with Virtual Tour
1 of 17
$2,629,000
5

Beds

4.1

Baths

3,682

Sq.Ft.

1681 WOODLAND AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1760 OAKHURST AVENUE Winter Park, FL MLS# O6441988
  • New Construction with Virtual Tour
1 of 41
OPEN HOUSE: Saturday 11/14 12:00 PM - 4:00 PM
$2,500,000
5

Beds

4.1

Baths

3,700

Sq.Ft.

1760 OAKHURST AVENUE

Winter Park, FL

Courtesy of SIERRA REALTY GROUP LLC
View 304 SANTIAGO DRIVE Winter Park, FL MLS# O6447782
  • Virtual Tour
1 of 58
$2,195,000
5

Beds

4.1

Baths

4,213

Sq.Ft.

304 SANTIAGO DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 918 ENCLAVE PLACE Winter Park, FL MLS# O6439116
  • New Construction
1 of 8
$2,125,000
5

Beds

4.1

Baths

3,713

Sq.Ft.

918 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6440974
  • Virtual Tour
1 of 39
$2,400,000
0.0

Baths

120 BROADVIEW AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1271 PALMER AVENUE Winter Park, FL MLS# O6441038
  • Virtual Tour
1 of 61
$2,125,000
4

Beds

4.1

Baths

2,850

Sq.Ft.

1271 PALMER AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1803 Barker Drive Winter Park, FL MLS# 1087618
$2,190,000
4

Beds

3.0

Baths

3,463

Sq.Ft.

1803 Barker Drive

Winter Park, FL

Brevard
View 1803 BARKER DRIVE Winter Park, FL MLS# O6442064
  • Virtual Tour
1 of 45
$2,190,000
4

Beds

3.0

Baths

3,463

Sq.Ft.

1803 BARKER DRIVE

Winter Park, FL

Courtesy of DENOVO REALTY
View 311 E MORSE BOULEVARD 1-5 Winter Park, FL MLS# O6441437
  • Adult Community with Virtual Tour
1 of 63
$2,475,000
3

Beds

3.0

Baths

2,316

Sq.Ft.

311 E MORSE BOULEVARD 1-5

Winter Park, FL

Courtesy of COLLADO REAL ESTATE
View 1773 WALNUT AVENUE Winter Park, FL MLS# O6437159
  • New Construction with Virtual Tour
1 of 25
$2,725,000
5

Beds

4.1

Baths

3,784

Sq.Ft.

1773 WALNUT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 200 S INTERLACHEN AVENUE 350 Winter Park, FL MLS# O6438596
$2,350,000
3

Beds

3.1

Baths

3,110

Sq.Ft.

200 S INTERLACHEN AVENUE 350

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 609 S PHELPS AVENUE Winter Park, FL MLS# O6388598
  • New Construction with Virtual Tour
1 of 18
$2,800,000
5

Beds

4.1

Baths

4,018

Sq.Ft.

609 S PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 648 WORTHINGTON DRIVE Winter Park, FL MLS# O6430279
  • New Construction with Virtual Tour
1 of 5
$2,700,000
5

Beds

4.1

Baths

3,588

Sq.Ft.

648 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 645 PANSY AVENUE Winter Park, FL MLS# O6428967
  • Virtual Tour
1 of 60
$2,390,000
4

Beds

4.1

Baths

3,661

Sq.Ft.

645 PANSY AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1477 W FAIRBANKS AVENUE Winter Park, FL MLS# O6422964
$2,400,000
6,049

Sq.Ft.

1477 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1754 TAYLOR AVENUE Winter Park, FL MLS# O6421927
  • New Construction with Virtual Tour
1 of 18
$2,569,999
5

Beds

4.1

Baths

3,670

Sq.Ft.

1754 TAYLOR AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 660 W MORSE BOULEVARD Winter Park, FL MLS# O6419377
$2,695,000
3

Beds

3.1

Baths

3,286

Sq.Ft.

660 W MORSE BOULEVARD

Winter Park, FL

Courtesy of COMPASS FLORIDA 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

357

Estimated median home price

$849,000
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 4
$100K - 200K 32
$200K - 300K 24
$300K - 400K 17
$400K - 500K 31
$500K - 600K 23
$600K - 700K 26
$700K - 800K 18
$800K - 900K 17
$900K - 1M 12
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 211
Townhouse 25
Condo 79
Commercial 15
Rental 98
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/12/2026)

Information deemed reliable but not guaranteed.

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.

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 11/12/2026.