311 total properties
Did you mean the neighborhood Winter Park?
View 1117 KENWOOD AVENUE Winter Park, FL MLS# O6389970
  • Recently Listed with Virtual Tour
1 of 67
OPEN HOUSE: Sunday 3/29 12:00 PM - 2:00 PM
$3,978,900
4

Beds

4.1

Baths

4,353

Sq.Ft.

1117 KENWOOD AVENUE

Winter Park, FL

Courtesy of ROYALTY R E BOUTIQUE INC
View 1120 PALMER AVENUE Winter Park, FL MLS# O6376319
  • Virtual Tour
1 of 38
$3,800,000
3

Beds

3.1

Baths

3,413

Sq.Ft.

1120 PALMER AVENUE

Winter Park, FL

Courtesy of PHIL KEAN REAL ESTATE LLC
View 1811 ONECO AVENUE Winter Park, FL MLS# O6390054
  • Recently Listed with Virtual Tour
1 of 5
$3,795,000
5

Beds

5.1

Baths

4,508

Sq.Ft.

1811 ONECO AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 207 E KINGS WAY Winter Park, FL MLS# O6337304
  • New Construction with Virtual Tour
1 of 5
$3,650,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

207 E KINGS WAY

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1751 GLENCOE ROAD Winter Park, FL MLS# O6339739
  • New Construction with Virtual Tour
1 of 45
$3,590,000
5

Beds

5.2

Baths

4,520

Sq.Ft.

1751 GLENCOE ROAD

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6378905
  • New Construction with Virtual Tour
1 of 73
$3,549,995
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 1581 FOREST AVENUE Winter Park, FL MLS# O6382377
  • Recently Listed with Virtual Tour
1 of 52
$3,495,000
4

Beds

4.2

Baths

4,683

Sq.Ft.

1581 FOREST AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
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 1761 LEGION DRIVE Winter Park, FL MLS# O6302616
  • Virtual Tour
1 of 43
$3,295,000
5

Beds

5.1

Baths

4,955

Sq.Ft.

1761 LEGION DRIVE

Winter Park, FL

Courtesy of SCANLON REALTY GROUP LLC
View 700 PINETREE ROAD Winter Park, FL MLS# O6384717
$3,295,000
4

Beds

4.1

Baths

3,897

Sq.Ft.

700 PINETREE ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 473 FLETCHER PLACE Winter Park, FL MLS# O6357810
  • Virtual Tour
1 of 50
$3,250,000
5

Beds

5.1

Baths

4,296

Sq.Ft.

473 FLETCHER PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 948 POINCIANA LANE Winter Park, FL MLS# O6372165
  • Virtual Tour
1 of 57
OPEN HOUSE: Sunday 3/29 2:00 PM - 4:00 PM
$3,199,000
4

Beds

3.1

Baths

3,676

Sq.Ft.

948 POINCIANA LANE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1821 ENGLEWOOD ROAD Winter Park, FL MLS# O6345085
  • New Construction with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 3/28 2:00 PM - 4:00 PM
$3,135,000
5

Beds

5.1

Baths

3,863

Sq.Ft.

1821 ENGLEWOOD ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 457 E NEW ENGLAND AVENUE Winter Park, FL MLS# O6345511
$3,100,000
5

Beds

4.1

Baths

3,896

Sq.Ft.

457 E NEW ENGLAND AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 151 OAKWOOD WAY Winter Park, FL MLS# O6380037
$3,055,000
4

Beds

4.1

Baths

4,129

Sq.Ft.

151 OAKWOOD WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 670 WILLIAMS DRIVE Winter Park, FL MLS# O6376953
  • Virtual Tour
1 of 64
$2,995,000
5

Beds

4.1

Baths

4,091

Sq.Ft.

670 WILLIAMS DRIVE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 611 WILLIAMS DRIVE Winter Park, FL MLS# O6387016
  • Virtual Tour
1 of 46
$2,995,000
5

Beds

4.1

Baths

4,686

Sq.Ft.

611 WILLIAMS DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1494 WESTCHESTER AVENUE Winter Park, FL MLS# O6363530
  • New Construction with Virtual Tour
1 of 16
$2,990,000
5

Beds

4.1

Baths

3,711

Sq.Ft.

1494 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1401 GREEN COVE ROAD Winter Park, FL MLS# O6358093
  • Virtual Tour
1 of 57
$2,900,000
3

Beds

4.3

Baths

5,483

Sq.Ft.

1401 GREEN COVE ROAD

Winter Park, FL

Courtesy of ANCHOR REAL ESTATE
View 609 S PHELPS AVENUE Winter Park, FL MLS# O6388598
  • Recently Listed with Virtual Tour
1 of 18
$2,829,000
5

Beds

4.1

Baths

4,018

Sq.Ft.

609 S PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL 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

328

Estimated median home price

$762,500
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 46
$200K - 300K 21
$300K - 400K 16
$400K - 500K 29
$500K - 600K 15
$600K - 700K 22
$700K - 800K 17
$800K - 900K 10
$900K - 1M 9
$1M - Max 139

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 192
Townhouse 19
Condo 83
Commercial 3
Rental 86
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 3/24/2026)

Information deemed reliable but not guaranteed.

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 3/25/2026.

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 3/25/2026.

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 3/25/2026.

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 3/25/2026.