52 total properties
Did you mean the neighborhood Winter Park?
View 1261 MICHIGAN AVENUE Winter Park, FL MLS# O6450090
  • Recently Listed
1 of 42
OPEN HOUSE: Sunday 11/8 12:00 PM - 2:00 PM
$650,000
3

Beds

2.1

Baths

1,798

Sq.Ft.

1261 MICHIGAN AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 257 LINCOLNSHIRE ROAD Winter Park, FL MLS# O6453656
  • Recently Listed with Virtual Tour
1 of 34
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1401 PELHAM ROAD Winter Park, FL MLS# O6452727
$650,000
3

Beds

2.0

Baths

1,594

Sq.Ft.

1401 PELHAM ROAD

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 624 DUNRAVEN DRIVE Winter Park, FL MLS# O6443159
$620,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

624 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
$509,999
3

Beds

2.0

Baths

1,460

Sq.Ft.

808 DENSMORE DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 346 ELKHORN COURT Winter Park, FL MLS# O6449383
$575,000
4

Beds

2.0

Baths

1,891

Sq.Ft.

346 ELKHORN COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449858
  • Recently Listed with Virtual Tour
1 of 30
$575,000
3

Beds

2.0

Baths

1,804

Sq.Ft.

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449843
  • Recently Listed with Virtual Tour
1 of 30
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 731 BONGART ROAD Winter Park, FL MLS# O6448911
$519,900
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 518 GILBERT ROAD Winter Park, FL MLS# O6442915
  • Virtual Tour
1 of 48
$649,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

518 GILBERT ROAD

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 510 FITZWALTER DRIVE Winter Park, FL MLS# O6448189
$530,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

510 FITZWALTER DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2322 WOODCREST DRIVE Winter Park, FL MLS# O6445796
$650,000
4

Beds

2.0

Baths

1,650

Sq.Ft.

2322 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 112 BELL PLACE Winter Park, FL MLS# O6446595
  • Virtual Tour
1 of 31
$575,000
3

Beds

2.0

Baths

2,253

Sq.Ft.

112 BELL PLACE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 250 CAROLINA AVENUE 202 Winter Park, FL MLS# O6442686
$649,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

250 CAROLINA AVENUE 202

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6442348
$637,500
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 822 SYMONDS AVENUE Winter Park, FL MLS# O6441180
$599,999
0.0

Baths

822 SYMONDS AVENUE

Winter Park, FL

Courtesy of NEWBERRY REALTY & DEV GRP INC.
View 2260 COLDSTREAM DRIVE Winter Park, FL MLS# O6437438
$675,000
4

Beds

2.0

Baths

1,509

Sq.Ft.

2260 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2825 Mulford Avenue Winter Park, FL MLS# 1230644
$629,000
2

Beds

2.0

Baths

1,249

Sq.Ft.

2825 Mulford Avenue

Winter Park, FL

View 2825 MULFORD AVENUE Winter Park, FL MLS# O6439045
$629,000
2

Beds

2.0

Baths

1,249

Sq.Ft.

2825 MULFORD AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 508 BRECHIN DRIVE Winter Park, FL MLS# O6439220
$599,000
3

Beds

2.0

Baths

1,783

Sq.Ft.

508 BRECHIN DRIVE

Winter Park, FL

Courtesy of MTL 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

361

Estimated median home price

$825,000
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

PriceCount
$0 - 100K4
$100K - 200K32
$200K - 300K21
$300K - 400K16
$400K - 500K31
$500K - 600K26
$600K - 700K32
$700K - 800K16
$800K - 900K17
$900K - 1M13
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family216
Townhouse23
Condo77
Commercial15
Rental88
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 11/2/2026)

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 11/2/2026.

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 11/2/2026.