View 518 GILBERT ROAD Winter Park, FL MLS# O6442915
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Wednesday 10/14 4:00 PM - 6:00 PM
$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 266 N RANGER BOULEVARD Winter Park, FL MLS# O6444727
  • Recently Listed with Virtual Tour
1 of 33
$724,900
4

Beds

3.0

Baths

1,692

Sq.Ft.

266 N RANGER BOULEVARD

Winter Park, FL

Courtesy of ELITE PROPERTY REAL ESTATE LLC
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6444000
  • Recently Listed with Virtual Tour
1 of 45
$780,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
The time to sell is now! THE TIME TO SELL IS NOW!
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 433 GILBERT ROAD Winter Park, FL MLS# O6428430
  • Virtual Tour
1 of 36
$669,900
3

Beds

2.0

Baths

1,800

Sq.Ft.

433 GILBERT ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2833 PRINCE JOHN ROAD Winter Park, FL MLS# O6427246
$669,000
4

Beds

2.0

Baths

1,605

Sq.Ft.

2833 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of NETWORTH REALTY OF ORLANDO, LLC
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 410 SAINT DUNSTAN WAY Winter Park, FL MLS# O6416796
$500,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

410 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
$494,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 715 S RANGER BOULEVARD Winter Park, FL MLS# O6410899
$695,000
4

Beds

3.0

Baths

2,312

Sq.Ft.

715 S RANGER BOULEVARD

Winter Park, FL

Courtesy of DAHLIA REALTY GROUP
View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
$619,500
3

Beds

2.1

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC

About Winter Park Pines

Listings in Winter Park Pines, Orlando, FL

11

Estimated median home price

$669,000
Winter Park Pines, Orlando Real Estate

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

Homes for Sale by Price in Winter Park Pines, Orlando, FL

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K0
$400K - 500K3
$500K - 600K0
$600K - 700K5
$700K - 800K3
$800K - 900K0
$900K - 1M0
$1M - Max0

Homes for Sale by Type in Winter Park Pines, Orlando, FL

Property TypeCount
Single Family11
Townhouse0
Condo0
Commercial0
Rental2
Lots and Land0
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/14/2026)

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 10/14/2026.