View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
$750,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 637 N PARK AVENUE Winter Park, FL MLS# O6370317
$3,895,000
3

Beds

3.2

Baths

4,237

Sq.Ft.

637 N PARK AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 503 W CANTON AVENUE Winter Park, FL MLS# O6367552
$1,146,000
3

Beds

2.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 501 W CANTON AVENUE Winter Park, FL MLS# O6344716
$1,225,000
3

Beds

2.1

Baths

2,372

Sq.Ft.

501 W CANTON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6282473
$1,215,000
6

Beds

4.0

Baths

2,284

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 737 N CAPEN AVENUE Winter Park, FL MLS# O6120134
$824,900
3

Beds

2.0

Baths

1,930

Sq.Ft.

737 N CAPEN AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC

About Downtown Winter Park

Listings in Downtown Winter Park, Winter Park, FL

6

Estimated median home price

$1,180,500
Downtown Winter Park, Winter Park Real Estate

Search Downtown Winter Park, Florida Real Estate Listings & New Homes for Sale in Downtown Winter Park, FL. Find Downtown Winter Park Houses, Townhouses, Condos, & Properties for Sale at Weichert.com

Homes for Sale by Price in Downtown Winter Park, Winter Park, FL

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K0
$400K - 500K0
$500K - 600K0
$600K - 700K0
$700K - 800K1
$800K - 900K1
$900K - 1M0
$1M - Max4

Homes for Sale by Type in Downtown Winter Park, Winter Park, FL

Property TypeCount
Single Family2
Townhouse4
Condo0
Commercial0
Rental4
Lots and Land0
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/24/2026)

Information deemed reliable but not guaranteed.

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 2/24/2026.