188 total properties
View 860 N DENNING DRIVE Winter Park, FL MLS# O6370723
  • Recently Listed
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 19
$499,900
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 18
$499,900
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 1/4 1:00 PM - 4:00 PM
$1,300,000
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 ROAD 222 Winter Park, FL MLS# O6368580
  • Recently Listed
1 of 25
$199,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 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
View 900 CARVER STREET Winter Park, FL MLS# O6368746
$425,000
3

Beds

2.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of LEGACY REALTY & BROKERS LLC
View 851 MILES AVENUE 13 Winter Park, FL MLS# O6368234
  • Recently Listed with Virtual Tour
1 of 24
OPEN HOUSE: Sunday 1/4 1:00 PM - 4:00 PM
$219,000
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 13

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 560 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6367721
$2,599,000
6

Beds

5.2

Baths

3,946

Sq.Ft.

560 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 300 CAROLINA AVENUE 201 Winter Park, FL MLS# O6366544
  • Recently Listed with Virtual Tour
1 of 19
$739,000
2

Beds

2.0

Baths

1,305

Sq.Ft.

300 CAROLINA AVENUE 201

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6367841
  • Recently Listed with Virtual Tour
1 of 28
$450,000
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 5

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 2361 MULBRY DRIVE Winter Park, FL MLS# O6364508
  • Recently Listed
1 of 3
$2,395,000
4

Beds

4.0

Baths

3,111

Sq.Ft.

2361 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6367773
  • Recently Listed with Virtual Tour
1 of 7
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2811 EASTERN PARKWAY Winter Park, FL MLS# O6365983
  • Recently Listed with Virtual Tour
1 of 21
OPEN HOUSE: Sunday 1/4 11:00 AM - 1:00 PM
$665,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2811 EASTERN PARKWAY

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2503 VERSAILLES AVENUE Winter Park, FL MLS# O6365961
$2,775,000
5

Beds

5.0

Baths

4,026

Sq.Ft.

2503 VERSAILLES AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC

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.

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Data is updated as of 1/4/2026.

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Data is updated as of 1/4/2026.

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Data is updated as of 1/4/2026.