43 total properties
Did you mean the neighborhood Winter Park?
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6401352
  • Recently Listed with Virtual Tour
1 of 49
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 910 ENCLAVE PLACE Winter Park, FL MLS# O6406803
$1,899,000
5

Beds

4.1

Baths

3,620

Sq.Ft.

910 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • Recently Listed
1 of 4
$2,050,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 311 E MORSE BOULEVARD 1-3 Winter Park, FL MLS# O6406368
  • Recently Listed with Virtual Tour
1 of 28
$2,075,000
2

Beds

2.0

Baths

2,304

Sq.Ft.

311 E MORSE BOULEVARD 1-3

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1813 HARLAND PARK DRIVE Winter Park, FL MLS# O6403483
  • Recently Listed
1 of 59
$1,995,000
4

Beds

3.1

Baths

3,551

Sq.Ft.

1813 HARLAND PARK DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1660 WALNUT AVENUE Winter Park, FL MLS# O6395277
  • New Construction with Virtual Tour
1 of 43
$1,650,000
4

Beds

3.1

Baths

2,249

Sq.Ft.

1660 WALNUT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 106 S INTERLACHEN AVENUE 518 Winter Park, FL MLS# O6400228
$1,950,000
3

Beds

2.0

Baths

1,807

Sq.Ft.

106 S INTERLACHEN AVENUE 518

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 446 MELROSE AVENUE Winter Park, FL MLS# O6402113
  • Recently Listed with Virtual Tour
1 of 39
$1,695,000
4

Beds

2.0

Baths

2,640

Sq.Ft.

446 MELROSE AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$2,195,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1565 FOREST AVENUE Winter Park, FL MLS# O6398694
  • Virtual Tour
1 of 37
$1,650,000
4

Beds

2.0

Baths

2,163

Sq.Ft.

1565 FOREST AVENUE

Winter Park, FL

Courtesy of NORDQUIST & COMPANY INC
View 543 E LAKE SUE AVENUE Winter Park, FL MLS# O6397480
$1,875,000
4

Beds

4.1

Baths

3,657

Sq.Ft.

543 E LAKE SUE AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1636 ELIZABETHS WALK Winter Park, FL MLS# O6395638
  • Virtual Tour
1 of 31
$2,195,000
4

Beds

4.1

Baths

3,412

Sq.Ft.

1636 ELIZABETHS WALK

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1110 ALABAMA DRIVE Winter Park, FL MLS# O6395692
  • Virtual Tour
1 of 53
$1,699,000
3

Beds

3.0

Baths

2,488

Sq.Ft.

1110 ALABAMA DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1110 ALABAMA Winter Park, FL MLS# A12007407
  • Virtual Tour
1 of 25
$1,750,000
3

Beds

3.0

Baths

2,488

Sq.Ft.

1110 ALABAMA

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2305 COLDSTREAM DRIVE Winter Park, FL MLS# O6393049
  • New Construction with Virtual Tour
1 of 23
$1,825,000
5

Beds

5.1

Baths

3,655

Sq.Ft.

2305 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 621 HUNTINGTON AVENUE Winter Park, FL MLS# O6394464
$1,795,000
3

Beds

3.1

Baths

2,399

Sq.Ft.

621 HUNTINGTON AVENUE

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 872 GRANVILLE DRIVE Winter Park, FL MLS# O6391464
  • Virtual Tour
1 of 40
$2,200,000
4

Beds

3.1

Baths

3,195

Sq.Ft.

872 GRANVILLE DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 785 N PHELPS AVENUE Winter Park, FL MLS# O6393117
  • New Construction with Virtual Tour
1 of 41
$1,989,000
5

Beds

3.1

Baths

2,964

Sq.Ft.

785 N PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1750 CAROLLEE LANE Winter Park, FL MLS# O6391179
$1,890,000
4

Beds

3.1

Baths

3,249

Sq.Ft.

1750 CAROLLEE LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6391922
  • Virtual Tour
1 of 46
$1,799,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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

387

Estimated median home price

$790,000
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 3
$100K - 200K 50
$200K - 300K 22
$300K - 400K 22
$400K - 500K 29
$500K - 600K 23
$600K - 700K 27
$700K - 800K 20
$800K - 900K 16
$900K - 1M 8
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 242
Townhouse 16
Condo 88
Commercial 7
Rental 72
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/19/2026)

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 5/20/2026.