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(407) 666-8452
(407) 666-8452 Email (407) 666-8452
Lois Ann Cox, PA
REALTOR®, GRI, Gold Key Certification, LeadingRE Marketing Specialist, NHCB New Home Co Broke, REALTOR®, U.S. Military on the Move Certified Military Specialist

Winter Park, FL Real Estate Subdivision Directory

Are you considering moving to a certain Winter Park, FL subdivision? Select the subdivision from the list below and browse its real estate and homes for sale.

Click any of the Winter Park Subdivisions below to view real estate listings for sale in that respective Subdivision.

City Subdivision Listings Avg Asking Price Avg Days on Market
Winter Park Alabama Condo 1 $1,250,000 78
Winter Park Albert Lee Ridge 3 $616,633 76
Winter Park Albert Lee Ridge 1st 1 $439,000 136
Winter Park Alexander Place 1 $4,250,000 43
Winter Park Aloma 5 $538,300 177
Winter Park Aloma Park 1 $310,000 49
Winter Park Aloma Trails 2 $367,000 48
Winter Park Arrowhead Cove 1 $600,000 5
Winter Park Autumn Glen 1 $415,000 12
Winter Park Banks Colonial Estates 1 $1,200,000 106
Winter Park Brookshire Heights 1 $500,000 29
Winter Park Brookshire Heights 1st 1 $530,000 27
Winter Park Brookshire Heights 2nd 1 $630,000 39
Winter Park Canton Ave Cottages 1 1 $849,000 71
Winter Park Capens 2 $725,000 418
Winter Park Casa Aloma 2 $491,950 74
Winter Park Casa Jardin Condo 1 $799,000 7
Winter Park Cedar Ridge 1 $490,000 71
Winter Park Cedarwood Village 2 $266,950 33
Winter Park Cedarwood Village 1 8 $262,375 105
Winter Park Charmont 8 $2,047,125 72
Winter Park Chateaux Du Lac 5 $232,560 88
Winter Park Cloister Grove 1 $3,975,000 423
Winter Park Cloisters Condo 1 $1,795,000 126
Winter Park Colonies 4 $136,975 246
Winter Park Comstock Park 3 $3,011,667 96
Winter Park Conwill Estates 2 $1,485,000 43
Winter Park Coronation 1 $268,950 221
Winter Park Country Lane 2 $442,500 69
Winter Park Detmar Terrace Winter Park 1 $3,600,000 0
Winter Park Dubsdread Heights 2 $337,000 85
Winter Park Eastbrook 16 $410,550 89
Winter Park Eastgate 3 $741,333 109
Winter Park Edgewood 2 $610,000 19
Winter Park Elizabeth Heights 2 $444,450 8
Winter Park Ellno Willo 1 $3,275,000 166
Winter Park Enclave At Hawks Crest 1 $419,900 14
Winter Park Fairbanks Park 2 $849,000 131
Winter Park Fairbanks Shores 5th 1 $435,000 153
Winter Park Fairshores Place 1 $549,900 46
Winter Park Fairview Heights Rep 1 $354,999 20
Winter Park Flamingo Shores 2 $669,950 56
Winter Park Fontainebleau 2 $1,745,000 13
Winter Park Forest Hills 2 $4,092,500 208
Winter Park Four Seasons Condo 2 $197,500 61
Winter Park Fremar 2 $1,299,000 132
Winter Park Garden Acres 1 $655,000 20
Winter Park Garden Grove 1 $400,000 13
Winter Park Garden Lake Estates 8 $441,587 50
Winter Park Georgetown Estates 1 $435,000 165
Winter Park Glencoe 9 $553,931 121
Winter Park Glenmoor 2 $512,250 49
Winter Park Golfside 2 $754,950 23
Winter Park Golfside Villas Condo 5 $127,800 46
Winter Park Golfview 1 $459,900 247
Winter Park Grand Pines 2 $450,450 30
Winter Park Grayson Square 4 $405,350 41
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,780,000 158
Winter Park Greenview At Winter Pines 1 $830,000 145
Winter Park H Vanwies 2 $899,000 120
Winter Park Hamilton Place 1 $1,295,000 130
Winter Park Henkel 1 $1,079,000 91
Winter Park Hidden Oaks Condo 8 $193,538 125
Winter Park Horton Aaron 1 $1,800,000 89
Winter Park Howell Branch Woods 2 $414,995 58
Winter Park Howell Estates 1st 1 $460,000 213
Winter Park Howell Estates Rep 1 $450,000 5
Winter Park Hyde Park 1 $449,000 39
Winter Park J Kronenberger 2 $4,587,500 104
Winter Park Justamere Camp Rep 2 $2,354,450 20
Winter Park Karolina On Killarney 3 $922,666 134
Winter Park Kawilla Crest 1 $639,000 47
Winter Park Kenilworth Shores 12 $1,820,791 63
Winter Park Killarney Bay Condo 1 $475,000 208
Winter Park Killarney Circle 3 $624,633 420
Winter Park Killarney Estates 6 $1,554,167 60
Winter Park Killarney Point 1 $689,000 87
Winter Park Kings Cove 1 $599,900 61
Winter Park Knowles Manor North Condo 1 $424,400 59
Winter Park Lake Ann Estates 2 $805,000 14
Winter Park Lake Bell Terrace 2 $622,500 104
Winter Park Lake Florence Preserve 2 $1,412,450 79
Winter Park Lake Forest Park 3 $2,186,000 81
Winter Park Lake Killarney Condo 3 $274,999 244
Winter Park Lake Killarney Condominium Assn Inc. 1 $199,900 68
Winter Park Lake Killarney Shores 1 $1,389,500 308
Winter Park Lake Knowles Terrace 7 $1,293,857 53
Winter Park Lake Knowles Terrace 2nd 2 $1,489,500 20
Winter Park Lake Maitland 1 $4,750,000 29
Winter Park Lake Monte 1 $998,000 95
Winter Park Lake Sylvan Shores 1 $2,200,000 46
Winter Park Lake Virginia 1 $999,000 200
Winter Park Lake Waunatta Wods 1 $599,000 21
Winter Park Lake Waunatta Woods 2 $559,000 40
Winter Park Lakeside Estates 2 $1,110,000 51
Winter Park Lakeside Manor 5 $190,240 201
Winter Park Lakeview Terrace 3 $1,026,333 21
Winter Park Lancelot/winter Park 2 $172,400 15
Winter Park Landings At Hawks Crest 3 $743,332 85
Winter Park Landmark Winter Park Condo 1 $2,350,000 69
Winter Park Laurel Spgs 1 $389,500 135
Winter Park Lawndale 5 $1,248,740 94
Winter Park Lazy Oaks Condo 3 $279,967 69
Winter Park Lords 1 $1,050,000 668
Winter Park Lost Creek 1 $685,000 157
Winter Park Lugano Terrace 1 $2,195,000 286
Winter Park Mack Peter Rev 1 $650,000 35
Winter Park Magnolia Gardens 2 $694,450 45
Winter Park Maitland Shores 1st 1 $3,500,000 81
Winter Park Maitland Shores First 2 $4,175,000 35
Winter Park Mc Intyre Place Condo 1 $635,000 6
Winter Park Mead Garden 1 $190,000 50
Winter Park Mead Garden Condominium 1 $245,000 0
Winter Park Meadows At Hawks Crest 5 $770,000 69
Winter Park Metzingers 1 $574,900 173
Winter Park Mondrian/winter Park Twnhms 1 $1,339,000 43
Winter Park Morse & Pennsylvania Twnhms 1 $2,800,000 61
Winter Park Morseland 2 $910,500 70
Winter Park New England Bldg 1 $425,000 106
Winter Park None 5 $1,709,000 77
Winter Park Northwood Terrace 2 $1,747,000 38
Winter Park Not On The List 1 $490,000 71
Winter Park Oakcrest-516 3 $366,667 58
Winter Park Olympia Heights 1 $340,000 4
Winter Park Olympia Heights Annex 1 $499,000 11
Winter Park Orange Grove 1 $2,569,999 48
Winter Park Orange Terrace 1 $459,900 60
Winter Park Orangewood Park 2 $617,500 57
Winter Park Orwin Manor Westminster 3 $815,667 73
Winter Park Osceola Heights 1 $1,199,000 165
Winter Park Osceola Or Lakeview Deed 1 $1,775,000 18
Winter Park Osceola Shores 2 $2,150,000 76
Winter Park Park Grove 3 $4,414,667 16
Winter Park Park Hill 1 $3,500,000 84
Winter Park Park Manor First 1 $1,500,000 31
Winter Park Park North 1 $2,200,000 152
Winter Park Park Pointe Rep 1 $1,000,050 22
Winter Park Park West Condo 2 $724,500 53
Winter Park Parklando 1 $1,049,000 137
Winter Park Parklando #3 1 $1,649,000 174
Winter Park Parklando 03 1 $1,893,000 29
Winter Park Parkview Village 4 $153,125 121
Winter Park Parkview Village Condo 1 $150,000 352
Winter Park Pennsylvania Place Rep 1 $1,895,000 96
Winter Park Pervis Survey For R E 1 $1,799,999 197
Winter Park Phillips Circle Rep 3 $534,667 150
Winter Park Pines 1 $439,900 47
Winter Park Preserve At Hawks Crest 1 $770,000 11
Winter Park Quarters At Winter Park Condo 2 $550,000 48
Winter Park Ridge High 1 $284,000 4
Winter Park Ridge High 1st 2 $374,500 6
Winter Park Robert Dhu Macdonald Park 1 $7,250,000 197
Winter Park Sandlewood Creek 1 $285,000 1
Winter Park Seville Park 4 $598,500 20
Winter Park Sharon Place 1 $1,800,000 1
Winter Park Sicilian Shores 1 $2,689,000 138
Winter Park Slovak Village 1 $235,000 63
Winter Park South Interlachen Place 2 $3,522,500 26
Winter Park South Lakemont Shores 3 $1,399,333 122
Winter Park Stansbury Estates 2 $388,500 53
Winter Park Stratford A Winter Park Condo 5 $183,640 86
Winter Park Stratford Winter Park 1 $144,000 190
Winter Park Suburban Homes 1 $535,000 117
Winter Park Suburban Homes First 1 $370,000 47
Winter Park Swoope Park 2 $697,000 130
Winter Park Sylvan Heights 3 $1,726,667 168
Winter Park Sylvan Lake Shores 3 $2,495,000 83
Winter Park Sylvan Park 2 $3,625,000 59
Winter Park Talman Mews 1 $1,450,000 27
Winter Park Tanglewood 1 $562,000 1090
Winter Park Tantum 3 $1,097,667 55
Winter Park Temple Estates 1 $2,385,000 162
Winter Park Temple Terrace 1 $950,000 162
Winter Park Temple Terrace Annex 1 $299,900 12
Winter Park Temple Trail Village 1 $575,000 14
Winter Park Terrazo Del Sol 1 $499,000 161
Winter Park The Enclave Winter Park 10 $1,966,300 114
Winter Park Timberlane Shores 2 $2,520,000 64
Winter Park Town Of Winter Park 1 $2,695,000 80
Winter Park Townhomes/harper Place 1 $540,000 127
Winter Park Trinity Bay 2 $437,450 77
Winter Park Trotters Rep 2 $685,000 77
Winter Park Tuscany Terrace 2 $1,595,000 138
Winter Park Twin Acres 1 $1,675,000 160
Winter Park Unrecorded Plat 1 $540,000 26
Winter Park Urban Green 12 1 $550,000 83
Winter Park Via Lago/hanging Moss Condo 1 $335,000 40
Winter Park Vilasa Twnhms 1 $1,399,000 68
Winter Park Villa View Park 2 $2,120,000 92
Winter Park Village Green 2 $494,000 69
Winter Park Village Winterset Inc 1 $989,500 96
Winter Park Villas Of Aragon Condo 1 $510,000 26
Winter Park Villas Of Casselberry 3 $369,967 86
Winter Park Virginia Heights 1 $995,000 81
Winter Park Virginia Heights Rep 2 $1,325,000 89
Winter Park Virginia Hgts Rep 1 $810,000 75
Winter Park Vistas At Lake Howell 2 $325,000 78
Winter Park Waterbridge 1 $660,000 8
Winter Park Waterfall Cove 4 $121,725 114
Winter Park Waterfall Cove At Winter Park 1 $205,000 539
Winter Park Waterfall Cove At Winter Park Condominium D107 1 $180,000 20
Winter Park Waterfall Cove Of Winter Park 1 $88,999 49
Winter Park Waterfall Cove/winter Park 1 $108,000 139
Winter Park Waters Edge At Hawks Crest 1 $1,350,000 0
Winter Park Whispering Waters/phillips Circle Rep 1 $1,825,000 109
Winter Park Whisperwood Condo 4 $209,450 102
Winter Park Windsong Elizabeths Walk 43/81 1 $1,450,000 74
Winter Park Windsong-preserve Point 1 $8,950,000 323
Winter Park Windward Square 5 $282,300 72
Winter Park Winflor Court Pt Rep 1 $3,995,000 132
Winter Park Winter Park 5 $2,718,800 126
Winter Park Winter Park Estates 5 $493,000 67
Winter Park Winter Park Gardens Condo 1 $350,000 95
Winter Park Winter Park Oasis 1 $1,599,000 78
Winter Park Winter Park Pines 9 $634,756 139
Winter Park Winter Park Pines Merrie Oaks 4 $486,225 83
Winter Park Winter Park Pines Patio Homes 2 $309,493 80
Winter Park Winter Park Pines Rep 4 $563,350 72
Winter Park Winter Park Residential 1 $1,849,900 69
Winter Park Winter Park Rev 1 $1,770,000 147
Winter Park Winter Park Village 7 $1,282,500 73
Winter Park Winter Park Villas Condo 1 $199,900 5
Winter Park Winter Park Woods Condo 2 $104,700 170
Winter Park Winter Woods 1 $375,000 47
Winter Park Woodcrest 3 $393,300 46
Winter Park Woodmere Terrace Rep 1 $4,900,000 49
Winter Park Wrenwood 1 $362,000 34
Winter Park Wrenwood Condo 2 $180,000 76
Winter Park Wrenwood Heights 2 $417,500 69
Lois Ann Cox, PA
Lois Ann Cox, PA Cell: (407) 666-8452 Work Phone: (407) 532-0333 Direct Phone: (407) 532-0333 Cell Phone: (407) 666-8452 Email Me
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 08/25/2026. The listing information on this page last changed on 08/25/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 08/25/2026 12:05:08 AM EST) or GAMLS (last updated Mon 08/24/2026 11:15:12 PM EST) or Stellar MLS (last updated Mon 08/24/2026 11:58:52 PM EST) or SPC MLS (last updated Mon 08/24/2026 11:21:16 PM EST) or Martin MLS (last updated Mon 08/24/2026 11:38:15 PM EST) or Indian River MLS (last updated Mon 08/24/2026 11:30:08 PM EST) or Daytona MLS (last updated Mon 08/24/2026 11:36:42 PM EST) or Northeast Florida MLS (last updated Mon 08/24/2026 11:58:54 PM EST) or Beaches MLS (last updated Mon 08/24/2026 11:55:34 PM EST) or BORMLS (last updated Mon 08/24/2026 11:16:35 PM EST) or Scout MLS (Golden Isles) (last updated Mon 08/24/2026 7:06:31 AM EST) or Amelia/Nassau MLS (last updated Mon 08/24/2026 11:25:13 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 08/24/2026 11:42:31 PM EST) or NFLMLS (last updated Mon 08/24/2026 9:04:48 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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