43 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
  • Recently Listed with Virtual Tour
1 of 46
$1,249,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 7/11 11:00 AM - 2:00 PM
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 321 SYLVAN BOULEVARD Winter Park, FL MLS# O6417674
$1,395,000
3

Beds

2.1

Baths

2,821

Sq.Ft.

321 SYLVAN BOULEVARD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
  • Recently Listed with Virtual Tour
1 of 31
$1,275,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
$1,550,000
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

Winter Park, FL

View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • New Construction with Virtual Tour
1 of 38
$1,429,000
5

Beds

4.0

Baths

2,351

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 1600 ALABAMA DRIVE 402 Winter Park, FL MLS# O6413153
$1,250,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

1600 ALABAMA DRIVE 402

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1321 FAIRVIEW AVENUE Winter Park, FL MLS# O6412568
$1,200,000
Studio

Beds

0.0

Baths

1321 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 1077 MINNESOTA AVENUE Winter Park, FL MLS# O6411722
$1,395,000
4

Beds

4.0

Baths

3,046

Sq.Ft.

1077 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6410178
$1,450,000
Studio

Beds

0.0

Baths

120 BROADVIEW AVENUE

Winter Park, FL

View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6409860
$1,450,000
3

Beds

2.0

Baths

1,747

Sq.Ft.

120 BROADVIEW AVENUE

Winter Park, FL

View 1347 CHAPMAN CIRCLE Winter Park, FL MLS# O6408189
$1,395,000
4

Beds

3.1

Baths

2,922

Sq.Ft.

1347 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 266 W LYMAN AVENUE Winter Park, FL MLS# O6406526
$1,375,000
3

Beds

3.0

Baths

2,000

Sq.Ft.

266 W LYMAN AVENUE

Winter Park, FL

Courtesy of MAROON REALTY GROUP LLC
View 2465 BANCHORY ROAD Winter Park, FL MLS# O6403997
$1,295,000
4

Beds

5.0

Baths

3,971

Sq.Ft.

2465 BANCHORY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View Address not provided Winter Park, FL MLS# O6406381
  • New Construction with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

View 1600 S PENNSYLVANIA AVENUE Winter Park, FL MLS# NS1088189
$1,200,000
3

Beds

2.0

Baths

2,158

Sq.Ft.

1600 S PENNSYLVANIA AVENUE

Winter Park, FL

View 1600 S PENNSYLVANIA AVENUE Winter Park, FL MLS# NS1088189
$1,200,000
3

Beds

2.0

Baths

2,158

Sq.Ft.

1600 S PENNSYLVANIA AVENUE

Winter Park, FL

View 1581 MAGNOLIA AVE Winter Park, FL MLS# O6396118
  • Virtual Tour
1 of 75
$1,495,000
4

Beds

4.0

Baths

2,756

Sq.Ft.

1581 MAGNOLIA AVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1660 WALNUT AVENUE Winter Park, FL MLS# O6395277
  • New Construction with Virtual Tour
1 of 43
$1,569,000
4

Beds

3.1

Baths

2,249

Sq.Ft.

1660 WALNUT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 420 OHIO STREET Winter Park, FL MLS# O6399541
  • New Construction with Virtual Tour
1 of 8
$1,360,000
5

Beds

5.1

Baths

3,735

Sq.Ft.

420 OHIO STREET

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

389

Estimated median home price

$750,000
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 44
$200K - 300K 28
$300K - 400K 17
$400K - 500K 32
$500K - 600K 27
$600K - 700K 34
$700K - 800K 17
$800K - 900K 12
$900K - 1M 9
$1M - Max 165

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 249
Townhouse 17
Condo 89
Commercial 7
Rental 68
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/7/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 7/7/2026.