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Kissimmee, FL 55+ active adult communities & homes for sale - Page 12

Living in Kissimmee

A generally small city, Kissimmee is located in Central Florida, just south of Orlando. Its proximity to Orlando’s famous amusement parks and year-long warm weather makes…

A generally small city, Kissimmee is located in Central Florida, just south of Orlando. Its proximity to Orlando’s famous amusement parks and year-long warm weather makes Kissimmee very attractive for retirees. The city’s rural area provides plenty of parks and lakes for residents to explore and get in touch with nature. It's no wonder that 55+ communities in Kissimmee have grown to be so popular!

Kissimmee Climate & Geography

Summers in Kissimmee are generally hot and humid, much like the rest of Florida, and residents can expect warm weather all year round. Cold weather is a rarity in Kissimmee, as is as snow during winter.

Recreation, Culture & Entertainment In Kissimmee 

The city is home to the Kissimmee Chain-of-Lakes, which includes some of the state’s largest fishing and recreational attractions such as kayaking, canoeing, and airboat tours. Residents also have the option to take a trip to some of the city’s popular parks such as Shingle Creek Regional Park and Boggy Creek.

Being just 30 minutes outside the city of Orlando, residents of Kissimmee can still go visit some of its grand amusement parks such as Universal Studios, Walt Disney World, and SeaWorld.

The locals of Kissimmee enjoy catching a magic show at The Great Magic Hall, or if they’re looking for more excitement, residents can go to the Kissimmee Sports Arena Rodeo to watch bull riding, barrel racing, and more.

The city also has plenty of restaurants, malls, and flea markets for residents to explore.

Kissimmee Cost of Living & Taxes

Residents of Kissimmee 55+ communities who are on a budget will appreciate the city's lower cost of living as well as Florida's tax friendly policies. Kissimmee, much like the rest of Florida, has a slightly higher cost of living than the national average, but it’s still generally cheaper than the state average. The cost of housing is also more affordable in Kissimmee than other cities in Florida, but still a bit higher than the national average.

Florida is one of the most tax-friendly states for retirees. This is due to the fact that Florida has no state income tax, no tax on Social Security, and no inheritance tax. Kissimmee does add a 1.5 percent sales tax onto the state’s 6 percent rate. 

Health Care In Kissimmee

Florida frequently scores high on Gallup’s Well-Being Index, ranking amongst the top states throughout the country.

Kissimmee is home to three medical centers and hospitals. These include Osceola Regional Medical Center, St. Regional Medical Center, and Poinciana Medical Center. Osceola Regional Medical Center is rated high performing in two procedures according to U.S News.

Frequently Asked Questions


605 homes 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) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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 (8 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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.
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 (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
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) Del Webb Oasis
$400ks - $700ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
Esplanade at McKinnon Gro...
$300ks - $900ks
Esplanade at McKinnon Gro..., Winter Garden, FL
New Construction | Age-targeted | Built 2024 - present | 658 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
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Del Webb Lakehaven
$400ks - $800ks
Del Webb Lakehaven, Clermont, FL
New Construction | 55+ age-restricted | Built 2026 - present
5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
Westhaven at Ovation - To...
$400ks - $500ks
Westhaven at Ovation - To..., Winter Garden, FL
New Construction | Age-targeted | Built 2025 - present
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
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
3.9 rating (7 reviews) Summit Greens
$300ks - $400ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 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
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Lennar at Sanctuary at We...
$300ks - $500ks
Lennar at Sanctuary at We..., Clermont, FL
New Construction | 55+ age-restricted | Built 2025 - 2026 | 203 homes
Enclave at VillageWalk
$700ks - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 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.
Serenity Reserve
$400ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Cindy Certified
286 BECKENHAM DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$302,500

4 beds

|

2 baths

|

1,811 sq ft

|

House

286 BECKENHAM DR, KISSIMMEE, FL, 34758
Cindy Certified
280 BECKENHAM DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$307,500

4 beds

|

2 baths

|

1,640 sq ft

|

House

280 BECKENHAM DR, KISSIMMEE, FL, 34758
Cindy Certified
16491 GLASSY LOCH LOOP, CLERMONT, FL, 34..., Clermont, FL 34714
$394,995

4 beds

|

2 baths

|

1,936 sq ft

|

House

16491 GLASSY LOCH LOOP, CLERMONT, FL, 34...
Del Webb Lakehaven 6838 CREEK FALLS ALY, CLERMONT, FL, 3471..., Clermont, FL 34714
$481,990

5 beds

|

3 baths

|

2,231 sq ft

|

House

6838 CREEK FALLS ALY, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Del Webb Lakehaven 6834 CREEK FALLS ALY, CLERMONT, FL, 3471..., Clermont, FL 34714
$469,990

4 beds

|

3 baths

|

1,896 sq ft

|

House

6834 CREEK FALLS ALY, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
3184 ROYAL TERN DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$286,900

3 beds

|

2 baths

|

1,725 sq ft

|

House

3184 ROYAL TERN DR, WINTER HAVEN, FL, 33...
Gatherings of Lake Nona 7521 LAUREATE BLVD 5403, ORLANDO, FL, 32..., Orlando, FL 32827
$399,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7521 LAUREATE BLVD 5403, ORLANDO, FL, 32...
Cindy Certified
2456 BATES AVE SW, WINTER HAVEN, FL, 338..., Winter Haven, FL 33880
$249,900

3 beds

|

2 baths

|

1,232 sq ft

|

House

2456 BATES AVE SW, WINTER HAVEN, FL, 338...
Twin Lakes 2748 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$439,900

3 beds

|

2 baths

|

1,863 sq ft

|

House

2748 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Esplanade at McKinnon Groves 17806 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$630,000

2 beds

|

2 baths

|

1,843 sq ft

|

House

17806 SEDONA ST, WINTER GARDEN, FL, 3478...
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 3497 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$255,000

2 beds

|

2 baths

|

1,499 sq ft

|

House

3497 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
Esplanade at McKinnon Groves 11221 CARDING MILL LN, WINTER GARDEN, FL..., Winter Garden, FL 34787
$750,000

3 beds

|

3 baths

|

2,085 sq ft

|

House

11221 CARDING MILL LN, WINTER GARDEN, FL...
Westhaven at Ovation - Townes Collection 12830 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$471,000

3 beds

|

3 baths

|

1,857 sq ft

|

Townhouse

12830 SUNSET WALK DR, WINTER GARDEN, FL,...
Cindy Certified
2950 SUNSTAR DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$417,500

3 beds

|

2 baths

|

1,680 sq ft

|

House

2950 SUNSTAR DR, ST CLOUD, FL, 34772
Cindy Certified
2919 PARKFIELD RD, ST CLOUD, FL, 34772, St Cloud, FL 34772
$359,900

3 beds

|

2 baths

|

1,712 sq ft

|

House

2919 PARKFIELD RD, ST CLOUD, FL, 34772
Cindy Certified
1113 CITRUS LANDINGS BLVD, DAVENPORT, FL..., Davenport, FL 33837
$360,000

3 beds

|

2 baths

|

1,970 sq ft

|

House

1113 CITRUS LANDINGS BLVD, DAVENPORT, FL...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Kings Ridge 3605 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$316,500

3 beds

|

2 baths

|

1,572 sq ft

|

House

3605 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
Westhaven at Ovation - Townes Collection 12792 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$580,000

4 beds

|

3 baths

|

1,930 sq ft

|

Townhouse

12792 SUNSET WALK DR, WINTER GARDEN, FL,...
Del Webb Orlando 212 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$403,900

3 beds

|

2 baths

|

1,568 sq ft

|

House

212 GRANADA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Westhaven at Ovation - Townes Collection 13861 EASDALE ALY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$499,000

4 beds

|

3 baths

|

2,031 sq ft

|

Townhouse

13861 EASDALE ALY, WINTER GARDEN, FL, 34...
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.
Westhaven at Ovation - Townes Collection 12808 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$539,000

4 beds

|

3 baths

|

1,897 sq ft

|

Townhouse

12808 SUNSET WALK DR, WINTER GARDEN, FL,...
VillageWalk at Lake Nona 11800 ZELKOVA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$715,000

3 beds

|

2 baths

|

2,005 sq ft

|

House

11800 ZELKOVA LN, ORLANDO, FL, 32827
Cindy Certified
365 JYOTI DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$330,000

4 beds

|

2 baths

|

1,821 sq ft

|

House

365 JYOTI DR, DAVENPORT, FL, 33837
Cindy Certified
988 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$469,900

4 beds

|

2 baths

|

2,215 sq ft

|

House

988 VINEYARD RIDGE RD, MINNEOLA, FL, 347...
Cindy Certified
1013 SADIE RIDGE RD, CLERMONT, FL, 34715, Clermont, FL 34715
$444,500

4 beds

|

2 baths

|

1,846 sq ft

|

House

1013 SADIE RIDGE RD, CLERMONT, FL, 34715
Del Webb Oasis 15806 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$444,900

2 beds

|

2 baths

|

1,574 sq ft

|

Halfplex

15806 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Cindy Certified
357 NOVA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$320,000

3 beds

|

2 baths

|

1,593 sq ft

|

House

357 NOVA DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Orlando 418 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$346,500

3 beds

|

2 baths

|

1,713 sq ft

|

House

418 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Cindy Certified
412 NE AVE, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$260,000

3 beds

|

2 baths

|

1,451 sq ft

|

House

412 NE AVE, WINTER HAVEN, FL, 33881
Spring Lake Towers 700 MIRROR TER 507, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$164,900

2 beds

|

2 baths

|

1,351 sq ft

|

Condo

700 MIRROR TER 507, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
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 5312 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$334,900

3 beds

|

2 baths

|

1,700 sq ft

|

House

5312 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Twin Lakes 2740 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$589,900

3 beds

|

3 baths

|

2,208 sq ft

|

House

2740 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Heritage Hills 4056 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$367,900

3 beds

|

2 baths

|

1,857 sq ft

|

House

4056 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Del Webb Sunbridge 2691 RIVER CREEK LN, ST. CLOUD, FL, 3477..., St. Cloud, FL 34771
$629,999

4 beds

|

5 baths

|

2,866 sq ft

|

House

2691 RIVER CREEK LN, ST. CLOUD, FL, 3477...
Community: Del Webb Sunbridge
High Vista at Ridgewood Lakes 223 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$289,990

3 beds

|

2 baths

|

1,774 sq ft

|

House

223 RIDGE VIEW DR, DAVENPORT, FL, 33837
Traditions at Lake Ruby 4130 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$309,900

2 beds

|

2 baths

|

1,819 sq ft

|

House

4130 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Palms at Serenoa 17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$374,900

3 beds

|

2 baths

|

1,621 sq ft

|

House

17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Solivita 184 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$324,900

2 beds

|

2 baths

|

1,574 sq ft

|

House

184 VENTANA DR, 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 2764 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$610,500

3 beds

|

3 baths

|

2,208 sq ft

|

House

2764 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Kings Ridge 4215 GREENWICH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$348,000

2 beds

|

2 baths

|

2,000 sq ft

|

House

4215 GREENWICH CT, 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.

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