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.
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.
35
Listing Provided By: TREE REALTY
$4,350,000
433 E NEW ENGLAND AVENUE 
Winter Park, FL 32789
  • Beds10
  • Baths14
  • SqFt8,3258.3k
  • Built1905
  • Lot0.58 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.
37
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$3,595,000
375 VIRGINIA DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths5
  • 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.
47
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$3,375,000
1400 GREEN COVE ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths7
  • SqFt6,3846.4k
  • Built1995
  • Lot0.70 ac.
46
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$3,250,000
185 W FAWSETT ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt5,9365.9k
  • Built2003
  • Lot0.85 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.
51
Listing Provided By: PREMIER SOTHEBYS INTL. REALTY
$3,095,000
409 GENIUS DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths8
  • SqFt7,4337.4k
  • Built2007
  • Lot0.62 ac.
51
Listing Provided By: BLUE CHIP INTERNATIONAL REALTY LLC
$3,050,000
1637 CHASE LANDING WAY 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt6,2726.3k
  • Built2002
  • Lot0.71 ac.
40
Listing Provided By: LIST NOW REALTY LLC
$2,995,000
1071 LAKEVIEW DRIVE 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt5,0005.0k
  • Built2000
  • Lot0.50 ac.
40
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,950,000
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.
35
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$2,785,000
647 N PARK AVENUE #8 
Winter Park, FL 32789
  • Beds3
  • Baths5
  • SqFt3,2533.3k
  • Built2019
  • Lot0.12 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.
43
Listing Provided By: PREMIER REALTY PARTNERS INC
$2,500,000
300 S INTERLACHEN AVENUE #503 
Winter Park, FL 32789
  • Beds3
  • Baths4
  • SqFt3,3553.4k
  • Built2005
  • Lot0.40 ac.
51
Listing Provided By: PHIL KEAN REAL ESTATE LLC
$2,399,000
315 E NEW ENGLAND AVENUE #28 
Winter Park, FL 32789
  • Beds3
  • Baths4
  • SqFt3,6813.7k
  • Built2008
  • Lot0.63 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.
29
Listing Provided By: TRUMAN CO.
$2,249,000
2171 FORREST ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt4,5364.5k
  • Built2016
  • Lot0.26 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.
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.
20
Listing Provided By: KELLER WILLIAMS HERITAGE REALTY
$1,999,999
315 E NEW ENGLAND AVENUE #3 
Winter Park, FL 32789
  • Beds3
  • Baths4
  • SqFt3,6433.6k
  • Built2008
  • Lot0.63 ac.
19
Listing Provided By: COLONY REALTY GROUP INC.
$1,949,900
560 COUNTRY CLUB DRIVE 
Winter Park, FL 32789
  • Beds6
  • Baths7
  • SqFt4,2424.2k
  • Built2019
  • Lot0.21 ac.
34
Listing Provided By: CREEGAN PROPERTY GROUP
$1,820,000
1134 BELLA LAGO COVE 
Winter Park, FL 32792
  • Beds5
  • Baths8
  • SqFt6,9557.0k
  • Built1966
  • Lot1.23 ac.
30
Listing Provided By: TMP PREMIER REAL ESTATE LLC
$1,795,000
2229 VIA TUSCANY 
Winter Park, FL 32789
  • Beds5
  • Baths6
  • SqFt4,4234.4k
  • Built1999
  • Lot0.49 ac.
22
Listing Provided By: COLDWELL BANKER RESIDENTIAL RE
$1,750,000
2726 LAKE HOWELL LANE 
Winter Park, FL 32792
  • Beds3
  • Baths2
  • SqFt1,5521.6k
  • Built1960
  • Lot4.80 ac.
31
Listing Provided By: FANNIE HILLMAN ASSOCIATES
$1,650,000
1525 GLENCOE ROAD 
Winter Park, FL 32789
  • Beds5
  • Baths4
  • SqFt4,5544.6k
  • Built1951
  • Lot1.70 ac.
43
Listing Provided By: REGAL R.E. PROFESSIONALS LLC
$1,650,000
1544 HOLTS GROVE CIRCLE 
Winter Park, FL 32789
  • Beds4
  • Baths7
  • SqFt4,6464.6k
  • Built2011
  • Lot0.35 ac.
33
NEW
Listing Provided By: COLDWELL BANKER RESIDENTIAL RE
$1,599,900
1240 WOODMERE DRIVE 
Winter Park, FL 32789
  • Beds4
  • Baths3
  • SqFt3,3663.4k
  • Built1941
  • Lot0.31 ac.
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