400 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 1600 LEGION DRIVE Winter Park, FL MLS# O6415591
  • Virtual Tour
1 of 70
$3,995,000
5

Beds

5.1

Baths

4,483

Sq.Ft.

1600 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 200 SAINT ANDREWS BLVD 3206 Winter Park, FL MLS# O6416143
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BLVD 3206

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 6/13 1:00 PM - 3:00 PM
$1,550,000
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • Recently Listed with Virtual Tour
1 of 41
OPEN HOUSE: Sunday 6/14 1:00 PM - 4:00 PM
$2,250,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Recently Listed with Virtual Tour
1 of 38
OPEN HOUSE: Saturday 6/13 11:00 AM - 1:00 PM
$879,000
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Recently Listed with Virtual Tour
1 of 9
$1,595,000
Studio

Beds

0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 1220 WOODMERE DRIVE Winter Park, FL MLS# O6415611
  • Recently Listed with Virtual Tour
1 of 44
$1,700,000
4

Beds

3.1

Baths

2,815

Sq.Ft.

1220 WOODMERE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 121 E FAWSETT ROAD Winter Park, FL MLS# O6413910
  • Recently Listed with Virtual Tour
1 of 11
$3,490,000
5

Beds

5.1

Baths

4,191

Sq.Ft.

121 E FAWSETT ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
$775,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1521 CAVENDISH RD Winter Park, FL MLS# O6415985
  • Recently Listed with Virtual Tour
1 of 22
$470,000
2

Beds

1.0

Baths

1,036

Sq.Ft.

1521 CAVENDISH RD

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 700 MELROSE AVENUE K25 Winter Park, FL MLS# O6414821
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Sunday 6/14 2:00 PM - 4:00 PM
$245,000
1

Beds

1.0

Baths

787

Sq.Ft.

700 MELROSE AVENUE K25

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • Recently Listed with Virtual Tour
1 of 38
OPEN HOUSE: Saturday 6/13 11:00 AM - 3:00 PM
$1,429,000
5

Beds

4.0

Baths

2,351

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Recently Listed with Virtual Tour
1 of 24
$259,999
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

Courtesy of REALTY OF RIVERVIEW LLC
View 231 CHELTON CIRCLE Winter Park, FL MLS# O6414890
  • Recently Listed with Virtual Tour
1 of 67
$4,950,000
4

Beds

5.2

Baths

5,550

Sq.Ft.

231 CHELTON CIRCLE

Winter Park, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
View 1221 RICHMOND ROAD Winter Park, FL MLS# O6407648
  • Recently Listed
1 of 48
$4,995,000
5

Beds

5.1

Baths

5,164

Sq.Ft.

1221 RICHMOND ROAD

Winter Park, FL

Courtesy of LA ROSA REALTY HORIZONS LLC
View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Recently Listed with Virtual Tour
1 of 83
$2,188,888
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

Winter Park, FL

Courtesy of SIMPLICITY: A RE BROKERAGE CO
View 650 DOUGLAS AVENUE Winter Park, FL MLS# O6414807
$550,000
3

Beds

2.0

Baths

1,280

Sq.Ft.

650 DOUGLAS AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
  • Recently Listed with Virtual Tour
1 of 29
$519,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 413 W MORSE BOULEVARD Winter Park, FL MLS# O6412134
  • Recently Listed with Virtual Tour
1 of 28
$2,695,000
3

Beds

3.1

Baths

3,048

Sq.Ft.

413 W MORSE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
  • Recently Listed with Virtual Tour
1 of 26
OPEN HOUSE: Sunday 6/14 12:00 PM - 2:00 PM
$550,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

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

400

Estimated median home price

$797,500
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 2
$100K - 200K 43
$200K - 300K 23
$300K - 400K 23
$400K - 500K 28
$500K - 600K 29
$600K - 700K 30
$700K - 800K 23
$800K - 900K 14
$900K - 1M 9
$1M - Max 176

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 266
Townhouse 15
Condo 83
Commercial 7
Rental 70
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/13/2026)

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.

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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.

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 6/13/2026.

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 6/13/2026.

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 6/13/2026.