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Kissimmee, FL 55+ active adult communities & homes for sale

464 homes near Kissimmee

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4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Four Seasons at Orlando
$200Ks - $700Ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Tohoqua Reserve
$300Ks - $400Ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
4 rating (4 reviews) High Vista at Ridgewood L...
$200Ks - $300Ks
High Vista at Ridgewood L..., Davenport, FL
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 homes
5 rating (2 reviews) Palms at Serenoa
$300Ks - $400Ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
3.8 rating (5 reviews) Traditions at Lake Ruby
$200Ks - $400Ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
5 rating (1 reviews) Esplanade at Highland Ran...
$300Ks - $600Ks
Esplanade at Highland Ran..., Clermont, FL
Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes
5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
Lake Henry Estates
$200Ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Gatherings of Lake Nona
$300Ks - $400Ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
Vienna Square
$200Ks - $300Ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Carlsberg Estates on Lake...
$200Ks - $300Ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Enclave at VillageWalk
$1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Serenity Reserve
$500Ks - $600Ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
Spring Lake Towers
$100Ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
The Wellington
$100Ks - $200Ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Poinsettia Heights
$100Ks - $200Ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Oakview
$100Ks - $200Ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Preserve at Lakeside Land...
$300Ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
VillageWalk at Lake Nona 11846 NAUTICA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$425,000

3 beds

|

3 baths

|

1,810 sq ft

|

Townhouse

11846 NAUTICA DR, ORLANDO, FL, 32827
Kings Ridge 3412 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$365,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

3412 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Summit Greens 793 HAWKS BLF, CLERMONT, FL, 34711, Clermont, FL 34711
$480,000

2 beds

|

3 baths

|

2,209 sq ft

|

House

793 HAWKS BLF, CLERMONT, FL, 34711
Community: Summit Greens
Heritage Hills 3210 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711
$276,500

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3210 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
Del Webb Oasis 13846 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$689,000

2 beds

|

3 baths

|

2,108 sq ft

|

House

13846 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Palms at Serenoa 3449 TWIN FLOWER CT, CLERMONT, FL, 34714, Clermont, FL 34714
$355,000

2 beds

|

2 baths

|

1,627 sq ft

|

House

3449 TWIN FLOWER CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
Esplanade at Highland Ranch 1038 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$635,000

3 beds

|

3 baths

|

2,287 sq ft

|

House

1038 TIMBERVALE TRL, CLERMONT, FL, 34715
Del Webb Orlando 613 CANTABRIA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,900

2 beds

|

2 baths

|

1,831 sq ft

|

House

613 CANTABRIA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Orlando 710 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$434,900

2 beds

|

2 baths

|

2,080 sq ft

|

House

710 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Del Webb Orlando 536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,900

3 beds

|

2 baths

|

1,508 sq ft

|

House

536 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Orlando 336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$429,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

336 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
VillageWalk at Lake Nona 11731 EAGLE RAY LN, ORLANDO, FL, 32827, Orlando, FL 32827
$685,000

3 beds

|

2 baths

|

2,005 sq ft

|

House

11731 EAGLE RAY LN, ORLANDO, FL, 32827
Twin Lakes 5037 FALLGLO WAY, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$539,900

3 beds

|

3 baths

|

2,208 sq ft

|

House

5037 FALLGLO WAY, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Traditions at Lake Ruby 3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$399,900

4 beds

|

3 baths

|

2,320 sq ft

|

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Solivita 469 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,000

3 beds

|

4 baths

|

2,616 sq ft

|

House

469 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Lake Ashton 4025 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$575,000

4 beds

|

3 baths

|

2,923 sq ft

|

House

4025 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Lake Ashton 5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$284,900

2 beds

|

2 baths

|

1,319 sq ft

|

House

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Lake Ashton 4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

3 beds

|

2 baths

|

1,756 sq ft

|

House

4168 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Solivita 572 SIENNA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$284,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

572 SIENNA DR, POINCIANA, FL, 34759
Community: Solivita
Traditions at Lake Ruby 2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$310,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884
Traditions at Lake Ruby 3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$388,900

4 beds

|

3 baths

|

2,404 sq ft

|

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Esplanade at Highland Ranch 1023 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$529,995

3 beds

|

3 baths

|

2,287 sq ft

|

House

1023 TIMBERVALE TRL, CLERMONT, FL, 34715
Palms at Serenoa 3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714
$335,000

2 beds

|

2 baths

|

1,646 sq ft

|

Villa

3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
Lake Henry Estates 488 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$259,000

2 beds

|

2 baths

|

1,626 sq ft

|

House

488 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Del Webb Orlando 333 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$354,900

2 beds

|

2 baths

|

1,655 sq ft

|

House

333 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Lake Ashton 4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$300,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4063 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Four Seasons at Orlando 2116 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$695,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

2116 LIMESTONE TRL, KISSIMMEE, FL, 34747
Heritage Hills 3788 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3788 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Tohoqua Reserve 2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$429,000

4 beds

|

2 baths

|

2,054 sq ft

|

House

2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Del Webb Sunbridge 2458 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$402,900

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2458 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Four Seasons at Orlando 7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$729,500

3 beds

|

3 baths

|

2,754 sq ft

|

House

7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Solivita 699 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$440,000

2 beds

|

2 baths

|

2,211 sq ft

|

House

699 VILLA PARK RD, POINCIANA, FL, 34759
Community: Solivita
Lake Henry Estates 514 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$217,000

2 beds

|

2 baths

|

1,279 sq ft

|

House

514 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Kings Ridge 2225 ELVERSON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

1,892 sq ft

|

House

2225 ELVERSON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Del Webb Orlando 210 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$415,000

3 beds

|

3 baths

|

2,004 sq ft

|

House

210 TOMELLOSO WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Sunbridge 2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$665,000

4 beds

|

3 baths

|

2,761 sq ft

|

House

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
VillageWalk at Lake Nona 12232 PESCARA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$454,900

3 beds

|

2 baths

|

1,708 sq ft

|

Villa

12232 PESCARA LN, ORLANDO, FL, 32827
Solivita 217 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$455,000

3 beds

|

3 baths

|

2,319 sq ft

|

House

217 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 307 MONTEREY ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,900

2 beds

|

2 baths

|

1,629 sq ft

|

House

307 MONTEREY ST, POINCIANA, FL, 34759
Community: Solivita
Esplanade at Highland Ranch 1343 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$635,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

1343 ZEEK RIDGE ST, CLERMONT, FL, 34715

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