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Kissimmee, FL 55+ active adult communities & homes for sale - Page 11

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
Lake Ashton 1061 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$449,900

3 beds

|

2 baths

|

2,069 sq ft

|

House

1061 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Gatherings of Lake Nona 7557 LAUREATE BLVD 6407, ORLANDO, FL, 32..., Orlando, FL 32827
$515,000

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7557 LAUREATE BLVD 6407, ORLANDO, FL, 32...
Solivita 674 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$240,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

674 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
Heritage Hills 3572 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$369,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3572 KINLEY BROOKE LN, CLERMONT, FL, 347...
Community: Heritage Hills
Kings Ridge 4065 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$369,000

2 beds

|

2 baths

|

1,997 sq ft

|

House

4065 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Lakehaven 15512 PEACEFUL PINES ALY, CLERMONT, FL, ..., Clermont, FL 34714
$399,990

3 beds

|

3 baths

|

1,652 sq ft

|

Townhouse

15512 PEACEFUL PINES ALY, CLERMONT, FL, ...
Community: Del Webb Lakehaven
Cindy Certified
436 HENNEPIN LOOP, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$319,500

3 beds

|

2 baths

|

1,427 sq ft

|

House

436 HENNEPIN LOOP, LAKE WALES, FL, 33898
Palms at Serenoa 17718 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

17718 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Solivita 157 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$310,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

157 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 518 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$341,000

2 beds

|

2 baths

|

1,491 sq ft

|

House

518 DAVINCI PASS, KISSIMMEE, 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.
Twin Lakes 2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$525,000

3 beds

|

3 baths

|

2,362 sq ft

|

House

2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
Gatherings of Lake Nona 7505 LAUREATE BLVD 2206, ORLANDO, FL, 32..., Orlando, FL 32827
$420,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7505 LAUREATE BLVD 2206, ORLANDO, FL, 32...
VillageWalk at Lake Nona 12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$899,000

5 beds

|

4 baths

|

4,036 sq ft

|

House

12077 ULETA LN, ORLANDO, FL, 32827
Gatherings of Lake Nona 7521 LAUREATE BLVD 5307, ORLANDO, FL, 32..., Orlando, FL 32827
$475,000

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7521 LAUREATE BLVD 5307, ORLANDO, FL, 32...
Del Webb Sunbridge 6261 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$499,900

2 beds

|

2 baths

|

1,919 sq ft

|

House

6261 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
Gatherings of Lake Nona 7505 LAUREATE BLVD 2208, ORLANDO, FL, 32..., Orlando, FL 32827
$320,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7505 LAUREATE BLVD 2208, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Traditions at Lake Ruby 3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$310,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Cindy Certified
2621 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3..., St Cloud, FL 34771
$366,326

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

2621 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3...
Del Webb Sunbridge 2617 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3..., St Cloud, FL 34771
$368,726

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

2617 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3...
Community: Del Webb Sunbridge
Cindy Certified
3447 CURRENT AVE, WINTER GARDEN, FL, 347..., Winter Garden, FL 34787
$699,999

4 beds

|

4 baths

|

2,741 sq ft

|

House

3447 CURRENT AVE, WINTER GARDEN, FL, 347...
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.
Cindy Certified
545 VICEROY CT, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$315,000

3 beds

|

2 baths

|

2,035 sq ft

|

House

545 VICEROY CT, KISSIMMEE, FL, 34758
Kings Ridge 3916 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$469,000

3 beds

|

2 baths

|

2,147 sq ft

|

House

3916 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 2265 CALVERT CT, CLERMONT, FL, 34711, Clermont, FL 34711
$429,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

2265 CALVERT CT, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 380 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$249,900

3 beds

|

2 baths

|

1,786 sq ft

|

House

380 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Summit Greens 3003 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$349,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

3003 PINNACLE CT, CLERMONT, FL, 34711
Community: Summit Greens
Esplanade at Westview 4457 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$299,000

2 beds

|

2 baths

|

1,483 sq ft

|

House

4457 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Esplanade at Westview 4463 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$360,000

2 beds

|

2 baths

|

1,677 sq ft

|

House

4463 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Esplanade at Westview 4451 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$350,000

3 beds

|

3 baths

|

1,709 sq ft

|

House

4451 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Twin Lakes 5027 E FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$379,000

3 beds

|

2 baths

|

1,456 sq ft

|

House

5027 E FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
Solivita 1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$314,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
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.
Cindy Certified
4614 CORAL HARBOUR RD, KISSIMMEE, FL, 34..., Kissimmee, FL 34758
$421,230

4 beds

|

3 baths

|

2,366 sq ft

|

House

4614 CORAL HARBOUR RD, KISSIMMEE, FL, 34...
Cindy Certified
864 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$560,000

4 beds

|

2 baths

|

2,236 sq ft

|

House

864 VINEYARD RIDGE RD, MINNEOLA, FL, 347...
Cindy Certified
920 CAMBRIDGE DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33881
$270,000

4 beds

|

2 baths

|

1,846 sq ft

|

House

920 CAMBRIDGE DR, WINTER HAVEN, FL, 3388...
Spring Lake Towers 700 MIRROR TER 506, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$119,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 506, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Kings Ridge 3786 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$339,000

3 beds

|

2 baths

|

1,639 sq ft

|

House

3786 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Twin Lakes 2724 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$509,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

2724 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Tohoqua Reserve 1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$339,000

3 beds

|

2 baths

|

1,701 sq ft

|

House

1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
High Vista at Ridgewood Lakes 215 FITZGERALD LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$314,900

2 beds

|

2 baths

|

1,760 sq ft

|

House

215 FITZGERALD LN, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
1539 ASPEN AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$325,000

4 beds

|

2 baths

|

1,850 sq ft

|

House

1539 ASPEN AVE, DAVENPORT, FL, 33837
Del Webb Lakehaven 6902 CREEK FALLS ALY, CLERMONT, FL, 3471..., Clermont, FL 34714
$464,990

3 beds

|

2 baths

|

1,715 sq ft

|

House

6902 CREEK FALLS ALY, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
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.

Frequently Asked Questions


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