260 total properties
View 259 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6419225
$439,000
3

Beds

2.0

Baths

1,248

Sq.Ft.

259 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
$925,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • Virtual Tour
1 of 31
$494,999
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
  • Virtual Tour
1 of 30
$549,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View JESSICA COURT Winter Park, FL MLS# O6419256
  • Virtual Tour
1 of 11
$449,000
0.0

Baths

JESSICA COURT

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
$925,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

Courtesy of ORLANDO HOMES GROUP LLC
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$235,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,775,000
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
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 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1836 WHITEHALL DRIVE Winter Park, FL MLS# O6416158
  • New Construction with Virtual Tour
1 of 70
$2,995,000
5

Beds

6.1

Baths

4,168

Sq.Ft.

1836 WHITEHALL DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
$1,377,500
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 10/10 2:00 PM - 4:00 PM
$2,050,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Virtual Tour
1 of 9
$1,595,000
0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY 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 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • New Construction with Virtual Tour
1 of 38
$1,369,000
5

Beds

4.0

Baths

2,446

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Virtual Tour
1 of 23
$242,400
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Weichert's are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

© 2026 Georgia MLS. All rights reserved

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 10/10/2026.

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 10/10/2026.