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Kissimmee, FL 55+ active adult communities & homes for sale - Page 2

484 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) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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
New Kings Ridge 3721 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$250,000

3 beds

|

2 baths

|

1,794 sq ft

|

House

3721 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Four Seasons at Orlando 1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$349,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Twin Lakes 2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$559,990

3 beds

|

3 baths

|

2,365 sq ft

|

House

2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Kings Ridge 2292 EDMONTON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$349,000

2 beds

|

2 baths

|

1,554 sq ft

|

House

2292 EDMONTON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Twin Lakes 5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$425,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Sunbridge 2555 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771
$925,000

3 beds

|

4 baths

|

2,828 sq ft

|

House

2555 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
Kings Ridge 3707 FAIRFIELD DR, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

2,105 sq ft

|

House

3707 FAIRFIELD DR, CLERMONT, FL, 34711
Community: Kings Ridge
Del Webb Oasis 13545 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$428,375

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

13545 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
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
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.
Solivita 591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,..., Kissimmee, FL 34759
$390,390

2 beds

|

2 baths

|

2,078 sq ft

|

House

591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,...
Community: Solivita
Twin Lakes 4911 DRAWDY CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$565,000

3 beds

|

2 baths

|

3,122 sq ft

|

House

4911 DRAWDY CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Sunbridge 6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$494,999

3 beds

|

3 baths

|

2,077 sq ft

|

House

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7208, ORLANDO, F..., Orlando, FL 32827
$414,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7208, ORLANDO, F...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Sunbridge 2928 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$425,000

3 beds

|

3 baths

|

1,854 sq ft

|

Townhouse

2928 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Solivita 777 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$187,000

2 beds

|

2 baths

|

1,392 sq ft

|

House

777 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
Solivita 1272 BONITA CANYON DR, POINCIANA, FL, 34..., Poinciana, FL 34759
$305,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

1272 BONITA CANYON DR, POINCIANA, FL, 34...
Community: Solivita
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
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 5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$365,000

2 beds

|

2 baths

|

1,682 sq ft

|

House

5384 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
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
Solivita 113 VENICE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$300,000

3 beds

|

2 baths

|

1,813 sq ft

|

House

113 VENICE LN, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
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
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
VillageWalk at Lake Nona 12033 FORSYTHIA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$473,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

12033 FORSYTHIA DR, ORLANDO, FL, 32827
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
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 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
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
Summit Greens 1083 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$374,900

2 beds

|

2 baths

|

1,908 sq ft

|

House

1083 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Orlando 451 PALENCIA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$459,900

3 beds

|

2 baths

|

2,182 sq ft

|

House

451 PALENCIA PL, 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
New Solivita 141 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,999

3 beds

|

2 baths

|

1,786 sq ft

|

House

141 MARABELLA LOOP, POINCIANA, FL, 34759
Community: Solivita
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.
New Vienna Square 1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$229,000

2 beds

|

2 baths

|

1,329 sq ft

|

Villa

1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Traditions at Lake Ruby 3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$320,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
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...
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$625,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Lake Henry Estates 516 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$244,990

2 beds

|

2 baths

|

1,393 sq ft

|

House

516 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
New Solivita 2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$329,500

2 beds

|

2 baths

|

1,703 sq ft

|

House

2285 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita

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