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Kissimmee, FL 55+ active adult communities & homes for sale - Page 5

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
2165 SERENITY GARDEN DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$403,490

3 beds

|

2 baths

|

1,504 sq ft

|

House

2165 SERENITY GARDEN DR, KISSIMMEE, FL, ...
Cindy Certified
2159 SERENITY GARDEN DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$421,490

4 beds

|

2 baths

|

1,665 sq ft

|

House

2159 SERENITY GARDEN DR, KISSIMMEE, FL, ...
Cindy Certified
13184 DENDY WAY, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$649,900

4 beds

|

3 baths

|

2,211 sq ft

|

House

13184 DENDY WAY, WINTER GARDEN, FL, 3478...
Lake Ashton 6136 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$549,999

3 beds

|

3 baths

|

2,682 sq ft

|

House

6136 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Lake Henry Estates 440 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$317,000

3 beds

|

2 baths

|

1,751 sq ft

|

House

440 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Four Seasons at Orlando 7969 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$749,000

3 beds

|

3 baths

|

2,194 sq ft

|

House

7969 HANSON BAY PL, KISSIMMEE, FL, 34747
Palms at Serenoa 3456 TWIN FLOWER CT, CLERMONT, FL, 34714, Clermont, FL 34714
$369,900

2 beds

|

2 baths

|

1,627 sq ft

|

House

3456 TWIN FLOWER CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
Cindy Certified
3158 MINDFULLNESS DR, CLERMONT, FL, 3471..., Clermont, FL 34714
$591,990

4 beds

|

3 baths

|

2,692 sq ft

|

House

3158 MINDFULLNESS DR, CLERMONT, FL, 3471...
Del Webb Lakehaven 6752 SUNRISE COVE DR, CLERMONT, FL, 3471..., Clermont, FL 34714
$429,020

2 beds

|

2 baths

|

1,405 sq ft

|

House

6752 SUNRISE COVE DR, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Cindy Certified
2924 FITNESS ST, CLERMONT, FL, 34714, Clermont, FL 34714
$749,900

4 beds

|

4 baths

|

2,872 sq ft

|

House

2924 FITNESS ST, CLERMONT, FL, 34714
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
5271 HAVEN VIEW DR, CLERMONT, FL, 34714, Clermont, FL 34714
$363,490

2 beds

|

2 baths

|

1,580 sq ft

|

House

5271 HAVEN VIEW DR, CLERMONT, FL, 34714
Solivita 861 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$395,000

2 beds

|

3 baths

|

2,379 sq ft

|

House

861 BELLA VIANA RD, KISSIMMEE, FL, 34759
Community: Solivita
Del Webb Sunbridge 6100 SANDY SPRINGS CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$1,050,000

4 beds

|

4 baths

|

3,559 sq ft

|

House

6100 SANDY SPRINGS CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Palms at Serenoa 17558 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

17558 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Cindy Certified
1520 CONGAREE ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$329,000

3 beds

|

2 baths

|

1,734 sq ft

|

House

1520 CONGAREE ST, DAVENPORT, FL, 33837
Cindy Certified
6939 HIGGS ALY, ORLANDO, FL, 32827, Orlando, FL 32827
$545,000

3 beds

|

2 baths

|

1,424 sq ft

|

House

6939 HIGGS ALY, ORLANDO, FL, 32827
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Lake Ashton 4195 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$349,000

3 beds

|

2 baths

|

2,035 sq ft

|

House

4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Del Webb Oasis 13056 SANDCASTLE DR, WINTER GARDEN, FL, ..., Winter Garden, FL 34787
$699,430

2 beds

|

2 baths

|

1,889 sq ft

|

House

13056 SANDCASTLE DR, WINTER GARDEN, FL, ...
Community: Del Webb Oasis
Lake Ashton 5325 SNEAD DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$359,500

3 beds

|

2 baths

|

1,833 sq ft

|

House

5325 SNEAD DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Westhaven at Ovation - Townes Collection 14075 LOCHEND WAY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$499,900

4 beds

|

3 baths

|

2,197 sq ft

|

Townhouse

14075 LOCHEND WAY, 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.
Cindy Certified
4698 CORAL HARBOUR RD, KISSIMMEE, FL, 34..., Kissimmee, FL 34758
$415,000

4 beds

|

3 baths

|

2,394 sq ft

|

House

4698 CORAL HARBOUR RD, KISSIMMEE, FL, 34...
Del Webb Sunbridge 6117 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$599,000

3 beds

|

2 baths

|

2,084 sq ft

|

House

6117 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
Solivita 508 LAGO MATISSE ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$367,000

3 beds

|

2 baths

|

1,807 sq ft

|

House

508 LAGO MATISSE ST, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 448 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$335,000

3 beds

|

2 baths

|

2,141 sq ft

|

House

448 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 320 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$370,000

3 beds

|

2 baths

|

2,038 sq ft

|

House

320 SORRENTO RD, POINCIANA, FL, 34759
Community: Solivita
Cindy Certified
1020 CAMBRIDGE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33881
$279,900

4 beds

|

2 baths

|

1,500 sq ft

|

House

1020 CAMBRIDGE DR, WINTER HAVEN, FL, 338...
Del Webb Sunbridge 2511 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$620,000

3 beds

|

2 baths

|

2,077 sq ft

|

House

2511 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Sunbridge 2722 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771
$1,025,000

3 beds

|

4 baths

|

3,778 sq ft

|

House

2722 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Tohoqua Reserve 1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$349,990

2 beds

|

2 baths

|

1,559 sq ft

|

House

1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Lake Henry Estates 596 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$210,000

2 beds

|

2 baths

|

1,345 sq ft

|

House

596 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
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.
Kings Ridge 2113 STONEBRIDGE WAY, CLERMONT, FL, 3471..., Clermont, FL 34711
$365,000

2 beds

|

2 baths

|

1,722 sq ft

|

House

2113 STONEBRIDGE WAY, CLERMONT, FL, 3471...
Community: Kings Ridge
Twin Lakes 2344 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$347,500

2 beds

|

2 baths

|

1,464 sq ft

|

House

2344 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
VillageWalk at Lake Nona 12064 NAVALE LN, ORLANDO, FL, 32827, Orlando, FL 32827
$766,770

4 beds

|

3 baths

|

2,514 sq ft

|

House

12064 NAVALE LN, ORLANDO, FL, 32827
Cindy Certified
2259 CANYON OAK DR DR, DAVENPORT, FL, 33..., Davenport, FL 33837
$275,000

3 beds

|

2 baths

|

1,420 sq ft

|

House

2259 CANYON OAK DR DR, DAVENPORT, FL, 33...
Four Seasons at Orlando 2016 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$675,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

2016 FLORA PASS PL, KISSIMMEE, FL, 34747
Four Seasons at Orlando 1983 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$549,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

1983 LIMESTONE TRL, KISSIMMEE, FL, 34747
Cindy Certified
2929 DEERBERRY LN, CLERMONT, FL, 34714, Clermont, FL 34714
$419,000

3 beds

|

2 baths

|

1,636 sq ft

|

House

2929 DEERBERRY LN, CLERMONT, FL, 34714
High Vista at Ridgewood Lakes 140 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$335,000

2 beds

|

2 baths

|

1,774 sq ft

|

House

140 MOSS LN, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Twin Lakes 5006 E FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$392,900

3 beds

|

2 baths

|

1,456 sq ft

|

House

5006 E FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
Esplanade at Westview 4488 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$314,990

2 beds

|

2 baths

|

1,872 sq ft

|

House

4488 OCHOS RIOS PL, KISSIMMEE, FL, 34758
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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