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Kissimmee, FL 55+ active adult communities & homes for sale - Page 10

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 4188 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$315,000

2 beds

|

2 baths

|

1,154 sq ft

|

House

4188 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Cindy Certified
1714 UPLAND LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$424,900

4 beds

|

3 baths

|

2,565 sq ft

|

House

1714 UPLAND LN, WINTER HAVEN, FL, 33884
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
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, ...
Four Seasons at Orlando 7964 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$485,000

4 beds

|

3 baths

|

2,261 sq ft

|

House

7964 HANSON BAY PL, KISSIMMEE, FL, 34747
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Sunbridge 6323 DEW DROP LOOP, ST CLOUD, FL, 34771, St Cloud, FL 34771
$579,766

2 beds

|

2 baths

|

1,949 sq ft

|

House

6323 DEW DROP LOOP, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
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
Lake Henry Estates 501 EASTLAKE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$272,900

2 beds

|

2 baths

|

1,724 sq ft

|

House

501 EASTLAKE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
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
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
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.
Summit Greens 1028 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

2,084 sq ft

|

House

1028 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
Cindy Certified
1514 HAMLIN ST, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$349,900

3 beds

|

2 baths

|

2,035 sq ft

|

House

1514 HAMLIN ST, WINTER HAVEN, FL, 33881
Cindy Certified
17089 EDGEMONT LN, CLERMONT, FL, 34714, Clermont, FL 34714
$399,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

17089 EDGEMONT LN, CLERMONT, FL, 34714
Cindy Certified
436 LEMONGRASS RD, MINNEOLA, FL, 34715, Minneola, FL 34715
$579,990

4 beds

|

3 baths

|

2,105 sq ft

|

House

436 LEMONGRASS RD, MINNEOLA, FL, 34715
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
Solivita 501 HERITAGE TRAIL ST, POINCIANA, FL, 34..., Poinciana, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HERITAGE TRAIL ST, POINCIANA, FL, 34...
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Lake Ashton 4084 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$385,000

3 beds

|

2 baths

|

2,074 sq ft

|

House

4084 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Tohoqua Reserve 2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$349,900

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Esplanade at Highland Ranch 2612 FRAZEEK CT, CLERMONT, FL, 34715, Clermont, FL 34715
$435,000

3 beds

|

3 baths

|

1,827 sq ft

|

House

2612 FRAZEEK CT, CLERMONT, FL, 34715
Solivita 278 ANASTASIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$223,000

2 beds

|

2 baths

|

1,317 sq ft

|

Halfplex

278 ANASTASIA DR, 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 2789 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$499,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

2789 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Summit Greens 2361 PRAIRIE DUNES, CLERMONT, FL, 34711, Clermont, FL 34711
$344,000

2 beds

|

2 baths

|

1,565 sq ft

|

House

2361 PRAIRIE DUNES, CLERMONT, FL, 34711
Community: Summit Greens
Cindy Certified
1932 CHICKASAW BLVD, DAVENPORT, FL, 3383..., Davenport, FL 33837
$379,900

4 beds

|

2 baths

|

1,928 sq ft

|

House

1932 CHICKASAW BLVD, DAVENPORT, FL, 3383...
Twin Lakes 5038 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$424,990

2 beds

|

2 baths

|

1,707 sq ft

|

House

5038 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
Cindy Certified
2202 WILDBERRY WAY WAY, MINNEOLA, FL, 34..., Minneola, FL 34715
$440,000

3 beds

|

2 baths

|

1,483 sq ft

|

House

2202 WILDBERRY WAY WAY, MINNEOLA, FL, 34...
Del Webb Sunbridge 2531 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$699,000

3 beds

|

4 baths

|

2,808 sq ft

|

House

2531 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Solivita 394 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$475,000

2 beds

|

3 baths

|

1,850 sq ft

|

House

394 MONTEREY ST, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
1040 CAMBRIDGE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33881
$243,500

3 beds

|

2 baths

|

1,727 sq ft

|

House

1040 CAMBRIDGE DR, WINTER HAVEN, FL, 338...
Solivita 1155 N GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$485,000

3 beds

|

2 baths

|

2,719 sq ft

|

House

1155 N GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
2146 RIDGE POINTE LN, CLERMONT, FL, 3471..., Clermont, FL 34715
$559,999

4 beds

|

3 baths

|

2,373 sq ft

|

House

2146 RIDGE POINTE LN, CLERMONT, FL, 3471...
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 2112 SAINT IVES CT, CLERMONT, FL, 34711, Clermont, FL 34711
$399,000

3 beds

|

2 baths

|

2,028 sq ft

|

House

2112 SAINT IVES CT, CLERMONT, FL, 34711
Community: Kings Ridge
Del Webb Lakehaven 6807 SUNRISE COVE DR, CLERMONT, FL, 3471..., Clermont, FL 34714
$648,810

3 beds

|

2 baths

|

1,943 sq ft

|

House

6807 SUNRISE COVE DR, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Del Webb Oasis 13175 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$755,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

13175 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
Del Webb Lakehaven 6764 SUNRISE COVE DR, CLERMONT, FL, 3471..., Clermont, FL 34714
$448,940

2 beds

|

2 baths

|

1,655 sq ft

|

House

6764 SUNRISE COVE DR, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Twin Lakes 5003 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$595,000

3 beds

|

3 baths

|

2,293 sq ft

|

House

5003 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Oasis 13361 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$859,900

4 beds

|

3 baths

|

3,172 sq ft

|

House

13361 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
Cindy Certified
2975 PARKFIELD RD, ST CLOUD, FL, 34772, St Cloud, FL 34772
$399,990

4 beds

|

3 baths

|

2,098 sq ft

|

House

2975 PARKFIELD RD, ST CLOUD, FL, 34772
Solivita 2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$296,000

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

2316 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 624 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$268,500

2 beds

|

2 baths

|

1,543 sq ft

|

House

624 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Lake Ashton 5308 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$249,900

3 beds

|

2 baths

|

1,495 sq ft

|

House

5308 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
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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