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

32 communities near Kissimmee

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4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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
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 (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Esplanade at Westview
$300ks - $700ks
Esplanade at Westview, Kissimmee, FL
New Construction | Age-targeted | Built 2025 - present | 600 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.
3.8 rating (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
Westhaven at Ovation - To...
$400ks - $500ks
Westhaven at Ovation - To..., Winter Garden, FL
New Construction | Age-targeted | Built 2025 - present
Del Webb Lakehaven
$400ks - $800ks
Del Webb Lakehaven, Clermont, FL
New Construction | 55+ age-restricted | Built 2026 - present
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
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
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 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.
5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
5 rating (1 reviews) Del Webb Oasis
$400ks - $700ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
Esplanade at McKinnon Gro...
$300ks - $900ks
Esplanade at McKinnon Gro..., Winter Garden, FL
New Construction | Age-targeted | Built 2024 - present | 658 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Enclave at VillageWalk
$700ks - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Serenity Reserve
$400ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 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.
Lennar at Sanctuary at We...
$300ks - $500ks
Lennar at Sanctuary at We..., Clermont, FL
New Construction | 55+ age-restricted | Built 2025 - 2026 | 203 homes
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Esplanade at Highland Ranch 2612 FRAZEEK CT, CLERMONT, FL, 34715, Clermont, FL 34715
$450,000

3 beds

|

3 baths

|

1,827 sq ft

|

House

2612 FRAZEEK CT, CLERMONT, FL, 34715
Solivita 373 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$349,900

2 beds

|

2 baths

|

1,658 sq ft

|

House

373 VESTRELLA DR, POINCIANA, FL, 34759
Community: Solivita
Twin Lakes 2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$550,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Sunbridge 2743 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771
$679,900

3 beds

|

3 baths

|

2,321 sq ft

|

House

2743 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 280 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$378,900

2 beds

|

2 baths

|

2,105 sq ft

|

House

280 INDIAN WELLS AVE, KISSIMMEE, FL, 347...
Community: Solivita
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
New Summit Greens 794 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$360,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

794 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
New Four Seasons at Orlando 1647 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$325,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1647 KEY BAY TRL, KISSIMMEE, FL, 34747
New Twin Lakes 5023 SUNFALLS AVE, ST CLOUD, FL, 34769, St Cloud, FL 34769
$450,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

5023 SUNFALLS AVE, ST CLOUD, FL, 34769
Community: Twin Lakes
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 Twin Lakes 5095 TWIN LAKES BLVD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$509,530

3 beds

|

2 baths

|

2,084 sq ft

|

House

5095 TWIN LAKES BLVD, ST CLOUD, FL, 3477...
Community: Twin Lakes
New Gatherings of Lake Nona 7521 LAUREATE BLVD 5208, ORLANDO, FL, 32..., Orlando, FL 32827
$419,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7521 LAUREATE BLVD 5208, ORLANDO, FL, 32...
New Tohoqua Reserve 1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$435,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
New Lake Ashton 4188 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$325,000

3 beds

|

2 baths

|

1,154 sq ft

|

House

4188 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
New Traditions at Lake Ruby 3973 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$385,000

4 beds

|

3 baths

|

2,225 sq ft

|

House

3973 BEDFORD AVE, WINTER HAVEN, FL, 3388...
New Twin Lakes 2733 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$525,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2733 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Traditions at Lake Ruby 4132 MARTINDALE LOOP, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$399,900

4 beds

|

3 baths

|

1,894 sq ft

|

House

4132 MARTINDALE LOOP, WINTER HAVEN, FL, ...
New Solivita 856 PACIFIC RIDGE RD, POINCIANA, FL, 347..., Poinciana, FL 34759
$457,000

3 beds

|

2 baths

|

1,730 sq ft

|

House

856 PACIFIC RIDGE RD, POINCIANA, FL, 347...
Community: Solivita
New Solivita 354 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$264,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

354 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
New Four Seasons at Orlando 7964 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$489,000

4 beds

|

3 baths

|

2,261 sq ft

|

House

7964 HANSON BAY PL, KISSIMMEE, FL, 34747
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 Twin Lakes 2867 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772
$339,420

2 beds

|

2 baths

|

1,321 sq ft

|

Villa

2867 MIDSWEET AVE, ST CLOUD, FL, 34772
Community: Twin Lakes
New Del Webb Sunbridge 6323 DEW DROP LOOP, ST CLOUD, FL, 34771, St Cloud, FL 34771
$611,776

2 beds

|

2 baths

|

1,949 sq ft

|

House

6323 DEW DROP LOOP, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
New Spring Lake Towers 700 MIRROR TER 511, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$149,900

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 511, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
New Lake Ashton 4052 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$409,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

4052 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
New Lake Henry Estates 501 EASTLAKE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$279,000

2 beds

|

2 baths

|

1,724 sq ft

|

House

501 EASTLAKE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
New Esplanade at Highland Ranch 2594 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$395,000

2 beds

|

2 baths

|

1,732 sq ft

|

House

2594 STARGRASS CIR, CLERMONT, FL, 34715
New Solivita 915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$569,000

4 beds

|

3 baths

|

3,110 sq ft

|

House

915 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Twin Lakes 5167 GARDENROW DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$348,440

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

5167 GARDENROW DR, ST CLOUD, FL, 34772
Community: Twin Lakes
Vienna Square 2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$280,000

3 beds

|

2 baths

|

1,935 sq ft

|

House

2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Summit Greens 1028 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$390,000

3 beds

|

2 baths

|

2,084 sq ft

|

House

1028 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
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.
Tohoqua Reserve 1845 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$344,400

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

1845 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Four Seasons at Orlando 2185 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$565,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

2185 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Esplanade at Westview 4342 ST THOMAS WAY, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$228,240

2 beds

|

2 baths

|

1,562 sq ft

|

Townhouse

4342 ST THOMAS WAY, KISSIMMEE, FL, 34758
VillageWalk at Lake Nona 11740 ASTILBE DR, ORLANDO, FL, 32827, Orlando, FL 32827
$428,000

2 beds

|

2 baths

|

1,680 sq ft

|

Halfplex

11740 ASTILBE DR, ORLANDO, FL, 32827
Kings Ridge 2067 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$300,000

2 beds

|

2 baths

|

1,273 sq ft

|

House

2067 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
Twin Lakes 2447 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$305,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2447 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
Palms at Serenoa 3899 WINGED ELM CT, CLERMONT, FL, 34714, Clermont, FL 34714
$465,000

4 beds

|

2 baths

|

2,069 sq ft

|

House

3899 WINGED ELM CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
Lake Ashton 4084 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$395,000

3 beds

|

2 baths

|

2,074 sq ft

|

House

4084 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Tohoqua Reserve 2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$349,900

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Heritage Hills 3601 SOLANA CIR A, CLERMONT, FL, 34711, Clermont, FL 34711
$299,899

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3601 SOLANA CIR A, 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.

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