190 total properties
View 423 OLOLU DRIVE Winter Park, FL MLS# O6369976
  • Recently Listed with Virtual Tour
1 of 51
OPEN HOUSE: Friday 1/9 4:00 PM - 6:00 PM
$599,000
3

Beds

3.0

Baths

1,920

Sq.Ft.

423 OLOLU DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 244 OSCEOLA COURT Winter Park, FL MLS# O6372232
  • Recently Listed
1 of 34
OPEN HOUSE: Saturday 1/10 2:00 PM - 4:00 PM
$1,299,000
4

Beds

2.1

Baths

1,837

Sq.Ft.

244 OSCEOLA COURT

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 690 OSCEOLA AVENUE 503 Winter Park, FL MLS# O6372265
  • Recently Listed
1 of 50
OPEN HOUSE: Saturday 1/10 12:00 PM - 3:00 PM
$495,000
2

Beds

2.0

Baths

1,148

Sq.Ft.

690 OSCEOLA AVENUE 503

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
The time to sell is now! THE TIME TO SELL IS NOW!
View 1523 MILLER AVENUE Winter Park, FL MLS# O6371649
  • Recently Listed
1 of 6
$1,550,000
5

Beds

4.0

Baths

3,164

Sq.Ft.

1523 MILLER AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 850 JUANITA RAEL Winter Park, FL MLS# O6370568
  • Recently Listed with Virtual Tour
1 of 50
$1,425,000
4

Beds

3.0

Baths

2,306

Sq.Ft.

850 JUANITA RAEL

Winter Park, FL

Courtesy of PHIL KEAN REAL ESTATE LLC
View 1996 INDIANA AVENUE Winter Park, FL MLS# O6372229
  • Recently Listed with Virtual Tour
1 of 18
$249,900
2

Beds

1.0

Baths

818

Sq.Ft.

1996 INDIANA AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 958 DUPONT AVENUE Winter Park, FL MLS# O6371341
  • Recently Listed with Virtual Tour
1 of 27
$381,000
3

Beds

2.0

Baths

1,572

Sq.Ft.

958 DUPONT AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 311 E MORSE BOULEVARD 2 - 5 Winter Park, FL MLS# O6370558
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
$2,100,000
2

Beds

2.0

Baths

1,900

Sq.Ft.

311 E MORSE BOULEVARD 2 - 5

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 860 N DENNING DRIVE Winter Park, FL MLS# O6370723
  • Recently Listed with Virtual Tour
1 of 48
$749,900
3

Beds

2.1

Baths

1,290

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

Courtesy of OUTLET REALTY
View 2500 LEE ROAD 237 Winter Park, FL MLS# V4946519
  • Recently Listed
1 of 23
$169,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 237

Winter Park, FL

Courtesy of LPT REALTY LLC (DB)
View 2002 INDIANA AVENUE Winter Park, FL MLS# GC536284
  • Recently Listed with Virtual Tour
1 of 8
$358,000
Studio

Beds

0.0

Baths

2002 INDIANA AVENUE

Winter Park, FL

Courtesy of DAWN REALTY
View 637 N PARK AVENUE Winter Park, FL MLS# O6370317
  • Recently Listed with Virtual Tour
1 of 86
$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 1816 AZALEA AVENUE Winter Park, FL MLS# O6369603
  • Recently Listed with Virtual Tour
1 of 26
$369,900
3

Beds

2.0

Baths

1,584

Sq.Ft.

1816 AZALEA AVENUE

Winter Park, FL

Courtesy of GENSTONE REALTY
View 1841 HARLAND PARK DRIVE Winter Park, FL MLS# O6369653
  • Recently Listed with Virtual Tour
1 of 28
$1,999,000
4

Beds

3.1

Baths

3,470

Sq.Ft.

1841 HARLAND PARK DRIVE

Winter Park, FL

Courtesy of SELECTIVE REALTY GROUP LLC
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369571
  • Recently Listed with Virtual Tour
1 of 29
$489,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369600
  • Recently Listed with Virtual Tour
1 of 29
$489,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1673 MAYFIELD AVENUE Winter Park, FL MLS# O6369267
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Sunday 1/11 1:00 PM - 4:00 PM
$1,195,000
4

Beds

4.0

Baths

2,540

Sq.Ft.

1673 MAYFIELD AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Recently Listed with Virtual Tour
1 of 7
$499,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
  • Recently Listed
1 of 25
$199,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

Courtesy of HOMESMART
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Recently Listed with Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY

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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 1/9/2026.

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Data is updated as of 1/9/2026.

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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 1/9/2026.

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Data is updated as of 1/9/2026.