107 total properties
Did you mean the neighborhood Winter Park?
View 1095 W MORSE BOULEVARD 101 Winter Park, FL MLS# O6365507
$56,028
5,282

Sq.Ft.

1095 W MORSE BOULEVARD 101

Winter Park, FL

Courtesy of DEBORAH E GARSON PA
View 1976 W FAIRBANKS AVENUE Winter Park, FL MLS# O6323896
$42,140
1,925

Sq.Ft.

1976 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of DIDOMENICO REALTY GROUP
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
  • Virtual Tour
1 of 10
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7507 ALOMA AVENUE 1B Winter Park, FL MLS# O6353862
$33,840
1,353

Sq.Ft.

7507 ALOMA AVENUE 1B

Winter Park, FL

Courtesy of MUSA REALTY COMPANY INC
View 2250 LEE ROAD 206 Winter Park, FL MLS# O6363122
  • Virtual Tour
1 of 36
$29,943
17,600

Sq.Ft.

2250 LEE ROAD 206

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
View 7507 ALOMA AVENUE 3B Winter Park, FL MLS# O6353856
$28,800
1,444

Sq.Ft.

7507 ALOMA AVENUE 3B

Winter Park, FL

Courtesy of MUSA REALTY COMPANY INC
View 1221 RICHMOND ROAD Winter Park, FL MLS# O6365952
$19,000
5

Beds

5.1

Baths

5,164

Sq.Ft.

1221 RICHMOND ROAD

Winter Park, FL

Courtesy of LA ROSA REALTY LLC
View 1860 VIA CONTESSA Winter Park, FL MLS# O6348816
  • Virtual Tour
1 of 90
$16,550
8

Beds

6.0

Baths

7,000

Sq.Ft.

1860 VIA CONTESSA

Winter Park, FL

Courtesy of SIERRA REALTY GROUP LLC
View 1436 MINNESOTA AVENUE Winter Park, FL MLS# O6359449
$15,588
805

Sq.Ft.

1436 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 2220 VIA TUSCANY Winter Park, FL MLS# O6367319
  • Recently Listed with Virtual Tour
1 of 48
$10,950
4

Beds

3.0

Baths

2,918

Sq.Ft.

2220 VIA TUSCANY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2020 VENETIAN WAY Winter Park, FL MLS# O6324414
  • Virtual Tour
1 of 38
$8,990
4

Beds

3.1

Baths

4,188

Sq.Ft.

2020 VENETIAN WAY

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 1530 VIA TUSCANY Winter Park, FL MLS# O6348216
  • Virtual Tour
1 of 25
$8,900
4

Beds

3.1

Baths

3,341

Sq.Ft.

1530 VIA TUSCANY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1442 PALM AVENUE Winter Park, FL MLS# O6354314
$8,900
4

Beds

5.0

Baths

3,611

Sq.Ft.

1442 PALM AVENUE

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 1350 LYNDALE BOULEVARD Winter Park, FL MLS# O6361248
$8,500
4

Beds

3.2

Baths

3,478

Sq.Ft.

1350 LYNDALE BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 300 KILLARNEY DRIVE Winter Park, FL MLS# O6361584
$8,500
4

Beds

3.0

Baths

2,476

Sq.Ft.

300 KILLARNEY DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1400 S PENNSYLVANIA AVENUE Winter Park, FL MLS# TB8452820
  • Adult Community with Virtual Tour
1 of 8
$7,000
4

Beds

3.0

Baths

2,310

Sq.Ft.

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of JACK KELLER INC
View 519 PARK NORTH COURT Winter Park, FL MLS# O6365855
$7,000
4

Beds

3.2

Baths

3,302

Sq.Ft.

519 PARK NORTH COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1701 PALMER AVENUE Winter Park, FL MLS# O6351918
  • Virtual Tour
1 of 38
$5,400
4

Beds

3.0

Baths

2,841

Sq.Ft.

1701 PALMER AVENUE

Winter Park, FL

Courtesy of TRUST EQUITY GROUP LLC
View 1580 OAKHURST AVENUE Winter Park, FL MLS# O6361638
$4,950
4

Beds

2.1

Baths

2,406

Sq.Ft.

1580 OAKHURST AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 104 S INTERLACHEN AVENUE 114 Winter Park, FL MLS# O6360008
$4,850
2

Beds

2.0

Baths

1,143

Sq.Ft.

104 S INTERLACHEN AVENUE 114

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

289

Estimated median home price

$665,000
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 6
$100K - 200K 39
$200K - 300K 21
$300K - 400K 17
$400K - 500K 26
$500K - 600K 22
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 101

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 166
Townhouse 20
Condo 74
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/1/2026)

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 1/2/2026.