355 total properties
Did you mean the neighborhood Winter Park?
View 1750 WALNUT AVENUE Winter Park, FL MLS# O6422700
  • Recently Listed with Virtual Tour
1 of 55
$2,195,000
4

Beds

4.1

Baths

3,691

Sq.Ft.

1750 WALNUT AVENUE

Winter Park, FL

View 946 ENCLAVE PLACE Winter Park, FL MLS# O6411633
  • New Construction
1 of 3
$2,175,000
5

Beds

4.1

Baths

3,989

Sq.Ft.

946 ENCLAVE PLACE

Winter Park, FL

View 2299 VIA TUSCANY Winter Park, FL MLS# O6355858
  • Virtual Tour
1 of 60
$2,150,000
4

Beds

3.1

Baths

3,986

Sq.Ft.

2299 VIA TUSCANY

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 950 ENCLAVE PLACE Winter Park, FL MLS# O6410963
  • New Construction
1 of 3
$2,125,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

950 ENCLAVE PLACE

Winter Park, FL

View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6414770
  • New Construction with Virtual Tour
1 of 76
$2,099,990
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 938 ENCLAVE PLACE Winter Park, FL MLS# O6408090
  • New Construction
1 of 7
$2,099,000
5

Beds

4.1

Baths

3,865

Sq.Ft.

938 ENCLAVE PLACE

Winter Park, FL

View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$2,095,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

View 147 S INTERLACHEN AVENUE 202 Winter Park, FL MLS# L4959060
$2,070,000
3

Beds

4.1

Baths

3,272

Sq.Ft.

147 S INTERLACHEN AVENUE 202

Winter Park, FL

View 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • New Construction
1 of 4
$2,050,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

View 2036 VIA TUSCANY Winter Park, FL MLS# O6379888
$2,000,000
3

Beds

2.0

Baths

2,148

Sq.Ft.

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2036 VIA TUSCANY Winter Park, FL MLS# O6380892
$2,000,000
Studio

Beds

0.0

Baths

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2261 MULBRY DRIVE Winter Park, FL MLS# O6410979
  • Virtual Tour
1 of 77
$1,995,000
4

Beds

3.0

Baths

3,696

Sq.Ft.

2261 MULBRY DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
  • Recently Listed with Virtual Tour
1 of 30
$1,995,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3075 N GOLDENROD ROAD Winter Park, FL MLS# O6426621
  • Recently Listed with Virtual Tour
1 of 38
$1,950,000
4,687

Sq.Ft.

3075 N GOLDENROD ROAD

Winter Park, FL

View 785 N PHELPS AVENUE Winter Park, FL MLS# O6393117
  • New Construction with Virtual Tour
1 of 41
$1,900,000
5

Beds

3.1

Baths

2,964

Sq.Ft.

785 N PHELPS AVENUE

Winter Park, FL

View 910 ENCLAVE PLACE Winter Park, FL MLS# O6406803
  • New Construction
1 of 4
$1,899,000
5

Beds

4.1

Baths

3,620

Sq.Ft.

910 ENCLAVE PLACE

Winter Park, FL

View 914 ENCLAVE PLACE Winter Park, FL MLS# O6391825
  • New Construction
1 of 3
$1,895,000
5

Beds

4.1

Baths

3,617

Sq.Ft.

914 ENCLAVE PLACE

Winter Park, FL

View 311 E MORSE BOULEVARD 1-3 Winter Park, FL MLS# O6406368
  • Adult Community with Virtual Tour
1 of 28
$1,895,000
2

Beds

2.0

Baths

2,304

Sq.Ft.

311 E MORSE BOULEVARD 1-3

Winter Park, FL

View 622 PENN PLACE Winter Park, FL MLS# TB8511228
  • Virtual Tour
1 of 26
$1,895,000
3

Beds

3.1

Baths

2,767

Sq.Ft.

622 PENN PLACE

Winter Park, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Virtual Tour
1 of 83
$1,888,888
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

Winter Park, FL

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

375

Estimated median home price

$759,000
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 8
$100K - 200K 43
$200K - 300K 24
$300K - 400K 18
$400K - 500K 31
$500K - 600K 24
$600K - 700K 31
$700K - 800K 15
$800K - 900K 14
$900K - 1M 10
$1M - Max 157

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 229
Townhouse 19
Condo 83
Commercial 11
Rental 66
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/25/2026)

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.

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 7/26/2026.

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 7/26/2026.