49
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$5,500,000
1731 PINETREE ROAD 
Winter Park, FL 32789
  • Beds6
  • Baths8
  • SqFt7,6547.7k
  • Built2014
  • Lot0.68 ac.
13
Listing Provided By: KELLY PRICE COMPANY LLC
$4,995,000
1520 SUMMERLAND AVENUE 
Winter Park, FL 32789
  • Beds4
  • Baths7
  • SqFt5,9946.0k
  • Built2001
  • Lot1.30 ac.
45
Listing Provided By: KELLER WILLIAMS WINTER PARK
$4,699,000
1941 LEGION DRIVE 
Winter Park, FL 32789
  • Beds7
  • Baths10
  • SqFt10,49310.5k
  • Built2008
  • Lot2.38 ac.
49
Listing Provided By: KELLY PRICE COMPANY LLC
$4,500,000
1128 PRESERVE POINT DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths5
  • SqFt6,1796.2k
  • Built2012
  • Lot2.09 ac.
32
Listing Provided By: TREE REALTY
$4,300,000
433 E NEW ENGLAND AVENUE 
Winter Park, FL 32789
  • Beds10
  • Baths14
  • SqFt8,3258.3k
  • Built1905
  • Lot0.58 ac.
28
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$4,195,000
1821 PINETREE ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt5,0065.0k
  • Built2018
  • Lot0.64 ac.
34
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$3,879,000
1013 TEMPLE GROVE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt5,7975.8k
  • Built1979
  • Lot0.69 ac.
51
Listing Provided By: AXIOM LUXURY REAL ESTATE LLC
$3,695,000
472 HENKEL CIRCLE 
Winter Park, FL 32789
  • Beds4
  • Baths7
  • SqFt4,6864.7k
  • Built2017
  • Lot0.39 ac.
39
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$3,495,000
375 VIRGINIA DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt7,5387.5k
  • Built2004
  • Lot1.32 ac.
27
Listing Provided By: PHIL KEAN REAL ESTATE LLC
$3,485,000
668 W MORSE BOULEVARD 
Winter Park, FL 32789
  • Beds4
  • Baths6
  • SqFt5,8195.8k
  • Built2020
  • Lot0.10 ac.
45
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$3,250,000
1400 GREEN COVE ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt6,3846.4k
  • Built1995
  • Lot0.70 ac.
51
Listing Provided By: FLORIDA ONE REAL ESTATE LLC
$3,199,000
671 VIA LUGANO 
Winter Park, FL 32789
  • Beds6
  • Baths9
  • SqFt7,0487.0k
  • Built2007
  • Lot0.47 ac.
27
Listing Provided By: Kelly Price Company LLC
$3,175,000
740 PALMER AVENUE 
Winter Park, FL 32789
  • Beds5
  • Baths5
  • SqFt4,8104.8k
  • Built1955
  • Lot2.79 ac.
28
Listing Provided By: PROPERTIO
$3,100,000
275 E WEBSTER AVENUE 
Winter Park, FL 32789
  • Beds8
  • Baths8
  • SqFt6,7306.7k
  • Built1978
  • Lot0.57 ac.
49
Listing Provided By: KELLY PRICE COMPANY LLC
$2,995,000
409 GENIUS DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths8
  • SqFt7,4337.4k
  • Built2007
  • Lot0.62 ac.
51
PRICE REDUCED
Listing Provided By: BLUE CHIP INTERNATIONAL REALTY LLC
$2,950,000
1637 CHASE LANDING WAY 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt6,2726.3k
  • Built2002
  • Lot0.71 ac.
51
Listing Provided By: KELLY PRICE COMPANY LLC
$2,950,000
541 VIRGINIA DRIVE 
Winter Park, FL 32789
  • Beds4
  • Baths4
  • SqFt4,7514.8k
  • Built2008
  • Lot0.51 ac.
40
Listing Provided By: LIST NOW REALTY LLC
$2,875,000
1071 LAKEVIEW DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt5,0005.0k
  • Built2000
  • Lot0.50 ac.
40
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,850,000
455 LAKEWOOD DRIVE 
Winter Park, FL 32789
  • Beds4
  • Baths6
  • SqFt5,0185.0k
  • Built1954
  • Lot0.62 ac.
30
Listing Provided By: MAROON REALTY GROUP LLC
$2,850,000
1295 N PARK AVENUE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt4,2934.3k
  • Built2019
  • Lot0.52 ac.
46
Listing Provided By: CENTRAL FLORIDA PRIME REAL ESTATE LLC
$2,849,000
1930 VIA VENETIA 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt6,2856.3k
  • Built2011
  • Lot0.74 ac.
32
Listing Provided By: CHARLES RUTENBERG REALTY ORLANDO
$2,750,000
511 W CANTON AVENUE 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt8,9108.9k
  • Built2013
  • Lot0.86 ac.
51
Listing Provided By: COLDWELL BANKER RESIDENTIAL RE
$2,650,000
2615 OGLESBY AVENUE 
Winter Park, FL 32789
  • Beds7
  • Baths8
  • SqFt6,7006.7k
  • Built2015
  • Lot1.13 ac.
49
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,650,000
2218 VIA TUSCANY 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt4,4234.4k
  • Built2020
  • Lot0.26 ac.
35
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,585,000
647 N PARK AVENUE #8 
Winter Park, FL 32789
  • Beds3
  • Baths5
  • SqFt3,2533.3k
  • Built2019
  • Lot0.12 ac.
31
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$2,495,000
300 S INTERLACHEN AVENUE #501 
Winter Park, FL 32789
  • Beds3
  • Baths5
  • SqFt4,0904.1k
  • Built2005
  • Lot0.00 ac.
33
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,485,000
649 N PARK AVENUE 
Winter Park, FL 32789
  • Beds3
  • Baths5
  • SqFt3,1803.2k
  • Built2018
  • Lot0.09 ac.
46
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$2,465,000
1860 SUMMERLAND AVENUE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt5,0225.0k
  • Built1992
  • Lot0.70 ac.
43
Listing Provided By: PREMIER REALTY PARTNERS INC
$2,385,000
300 S INTERLACHEN AVENUE #503 
Winter Park, FL 32789
  • Beds3
  • Baths4
  • SqFt3,3553.4k
  • Built2005
  • Lot0.40 ac.
34
Listing Provided By: KELLY PRICE COMPANY LLC
$2,385,000
1760 VIA VENETIA 
Winter Park, FL 32789
  • Beds4
  • Baths6
  • SqFt6,2426.2k
  • Built2013
  • Lot0.42 ac.
51
Listing Provided By: PHIL KEAN REAL ESTATE LLC
$2,295,000
315 E NEW ENGLAND AVENUE #28 
Winter Park, FL 32789
  • Beds3
  • Baths4
  • SqFt3,6813.7k
  • Built2008
  • Lot0.63 ac.
23
Listing Provided By: KELLY PRICE COMPANY LLC
$2,195,000
1760 W FAWSETT ROAD 
Winter Park, FL 32789
  • Beds6
  • Baths7
  • SqFt4,6374.6k
  • Built2017
  • Lot0.30 ac.
50
Listing Provided By: KELLY PRICE COMPANY LLC
$2,195,000
1560 CARDINAL COURT 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt4,6104.6k
  • Built2019
  • Lot0.34 ac.
25
Listing Provided By: COLEDEV REAL ESTATE LLC
$2,195,000
147 N VIRGINIA AVENUE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt4,5124.5k
  • Built2017
  • Lot0.08 ac.
4
NEW
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,175,000
1200 VIA LUGANO 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt5,0285.0k
  • Built2000
  • Lot0.46 ac.
8
Listing Provided By: Regal R.E. Professionals LLC
$2,144,000
125 S INTERLACHEN AVENUE #2 
Winter Park, FL 32789
  • Beds2
  • Baths5
  • SqFt3,2443.2k
  • Built2016
  • Lot0.35 ac.