359 total properties
Did you mean the neighborhood Winter Park?
View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
$899,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

Courtesy of ORLANDO HOMES GROUP LLC
View 618 BLAIRSHIRE CIRCLE Winter Park, FL MLS# O6439298
$895,000
4

Beds

3.0

Baths

1,876

Sq.Ft.

618 BLAIRSHIRE CIRCLE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1621 CHESTNUT AVENUE Winter Park, FL MLS# O6435086
  • Virtual Tour
1 of 35
$879,000
3

Beds

2.1

Baths

2,022

Sq.Ft.

1621 CHESTNUT AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445731
  • Virtual Tour
1 of 15
$850,000
4

Beds

3.0

Baths

2,301

Sq.Ft.

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445759
  • Virtual Tour
1 of 15
$850,000
0.0

Baths

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 100 S INTERLACHEN AVENUE 401 Winter Park, FL MLS# O6443942
  • Recently Listed with Virtual Tour
1 of 25
$850,000
3

Beds

2.0

Baths

1,639

Sq.Ft.

100 S INTERLACHEN AVENUE 401

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 775 MCINTYRE AVENUE 9 Winter Park, FL MLS# O6449033
$849,999
3

Beds

2.1

Baths

2,052

Sq.Ft.

775 MCINTYRE AVENUE 9

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 36
$849,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
  • Virtual Tour
1 of 42
$836,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 2345 BROOKSHIRE AVENUE Winter Park, FL MLS# O6439369
  • Virtual Tour
1 of 62
OPEN HOUSE: Sunday 10/25 1:00 PM - 3:00 PM
$825,000
3

Beds

3.0

Baths

2,488

Sq.Ft.

2345 BROOKSHIRE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1431 PALM AVENUE Winter Park, FL MLS# O6433195
  • Virtual Tour
1 of 38
$799,999
2

Beds

2.0

Baths

1,540

Sq.Ft.

1431 PALM AVENUE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1431 PALM AVENUE Winter Park, FL MLS# O6441550
  • Virtual Tour
1 of 17
$799,999
0.0

Baths

1431 PALM AVENUE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
  • Virtual Tour
1 of 68
$799,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1278 S PENNSYLVANIA AVENUE 13 Winter Park, FL MLS# O6417455
$799,000
3

Beds

2.1

Baths

1,957

Sq.Ft.

1278 S PENNSYLVANIA AVENUE 13

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
  • Virtual Tour
1 of 29
$798,000
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

Courtesy of CENTRAL TOWER PROPERTIES
View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$775,000
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Virtual Tour
1 of 38
$774,900
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1003 GOLFSIDE DRIVE Winter Park, FL MLS# O6444366
  • Virtual Tour
1 of 28
$769,900
3

Beds

3.0

Baths

2,145

Sq.Ft.

1003 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of QP HOMES REALTY 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

359

Estimated median home price

$769,900
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 34
$200K - 300K 22
$300K - 400K 19
$400K - 500K 30
$500K - 600K 27
$600K - 700K 35
$700K - 800K 18
$800K - 900K 14
$900K - 1M 14
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 212
Townhouse 22
Condo 77
Commercial 15
Rental 84
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/22/2026)

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 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 10/22/2026.

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.

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 10/22/2026.