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Kissimmee, FL 55+ active adult communities & homes for sale - Page 4

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
High Vista at Ridgewood Lakes 201 PRATHER DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,900

3 beds

|

2 baths

|

1,910 sq ft

|

House

201 PRATHER DR, DAVENPORT, FL, 33837
Kings Ridge 3805 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$295,000

2 beds

|

2 baths

|

1,091 sq ft

|

House

3805 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Del Webb Sunbridge 2984 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771
$365,000

2 beds

|

2 baths

|

1,584 sq ft

|

House

2984 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
Solivita 245 AMELIA ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$279,900

3 beds

|

2 baths

|

1,821 sq ft

|

House

245 AMELIA ST, POINCIANA, FL, 34759
Community: Solivita
Cindy Certified
2938 SCARLETT DR, ST CLOUD, FL, 33331, St Cloud, FL 33331
$430,000

4 beds

|

3 baths

|

1,854 sq ft

|

House

2938 SCARLETT DR, ST CLOUD, FL, 33331
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Westhaven at Ovation - Townes Collection 13953 EASDALE ALY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$499,900

3 beds

|

3 baths

|

1,770 sq ft

|

Townhouse

13953 EASDALE ALY, WINTER GARDEN, FL, 34...
Gatherings of Lake Nona 7545 LAUREATE BLVD 7201, ORLANDO, FL, 32..., Orlando, FL 32827
$344,900

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7545 LAUREATE BLVD 7201, ORLANDO, FL, 32...
Solivita 192 CASAVISTA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$769,000

3 beds

|

3 baths

|

3,135 sq ft

|

House

192 CASAVISTA DR, POINCIANA, FL, 34759
Community: Solivita
Cindy Certified
151 BRIDGER TRAIL CT, MINNEOLA, FL, 3471..., Minneola, FL 34715
$450,000

5 beds

|

3 baths

|

2,080 sq ft

|

House

151 BRIDGER TRAIL CT, MINNEOLA, FL, 3471...
Solivita 884 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$264,900

2 beds

|

2 baths

|

1,507 sq ft

|

House

884 GRAND CANAL 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.
Summit Greens 803 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

803 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
Cindy Certified
5728 PORTICO PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$304,420

3 beds

|

2 baths

|

1,424 sq ft

|

House

5728 PORTICO PL, KISSIMMEE, FL, 34758
Traditions at Lake Ruby 3541 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$345,000

3 beds

|

3 baths

|

2,006 sq ft

|

House

3541 RALEIGH DR, WINTER HAVEN, FL, 33884
Cindy Certified
3164 NAMASTE DR, CLERMONT, FL, 34714, Clermont, FL 34714
$579,949

4 beds

|

2 baths

|

2,532 sq ft

|

House

3164 NAMASTE DR, CLERMONT, FL, 34714
Palms at Serenoa 3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714
$290,000

2 beds

|

2 baths

|

1,646 sq ft

|

House

3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
Del Webb Oasis 13418 PRINCESS ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$415,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

13418 PRINCESS ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
3019 SANCTUARY DR, CLERMONT, FL, 34714, Clermont, FL 34714
$499,999

4 beds

|

2 baths

|

1,983 sq ft

|

House

3019 SANCTUARY DR, CLERMONT, FL, 34714
Cindy Certified
2938 SCARLETT DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$430,000

4 beds

|

3 baths

|

1,854 sq ft

|

House

2938 SCARLETT DR, ST CLOUD, FL, 34772
Cindy Certified
6072 BALANCE WAY, CLERMONT, FL, 34714, Clermont, FL 34714
$449,990

4 beds

|

3 baths

|

1,823 sq ft

|

House

6072 BALANCE WAY, CLERMONT, FL, 34714
Cindy Certified
6183 GREY HERON DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$339,999

5 beds

|

4 baths

|

1,872 sq ft

|

House

6183 GREY HERON DR, WINTER HAVEN, FL, 33...
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 2723 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$308,000

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

2723 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Heritage Hills 2862 CAPTIVA ST, CLERMONT, FL, 34711, Clermont, FL 34711
$544,900

4 beds

|

3 baths

|

2,562 sq ft

|

House

2862 CAPTIVA ST, CLERMONT, FL, 34711
Community: Heritage Hills
Solivita 148 RANCHO MIRAGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$639,000

3 beds

|

4 baths

|

2,580 sq ft

|

House

148 RANCHO MIRAGE DR, POINCIANA, FL, 347...
Community: Solivita
Cindy Certified
862 BALLANTYNE DR, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$350,000

4 beds

|

2 baths

|

1,928 sq ft

|

House

862 BALLANTYNE DR, LAKE WALES, FL, 33898
Cindy Certified
448 PANDA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$310,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

448 PANDA PL, DAVENPORT, FL, 33837
Twin Lakes 2788 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$585,000

3 beds

|

3 baths

|

2,335 sq ft

|

House

2788 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Palms at Serenoa 3482 SPARKLEBERRY CT, CLERMONT, FL, 3471..., Clermont, FL 34714
$420,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

3482 SPARKLEBERRY CT, CLERMONT, FL, 3471...
Community: Palms at Serenoa
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
High Vista at Ridgewood Lakes 409 ROYAL PALM DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$337,000

3 beds

|

2 baths

|

1,788 sq ft

|

House

409 ROYAL PALM DR, DAVENPORT, FL, 33837
Solivita 2358 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$290,000

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

2358 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
Four Seasons at Orlando 1646 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$345,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1646 KEY BAY TRL, 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.
Cindy Certified
2919 SUNSTAR DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$410,000

4 beds

|

2 baths

|

1,840 sq ft

|

House

2919 SUNSTAR DR, ST CLOUD, FL, 34772
Solivita 157 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$400,000

3 beds

|

2 baths

|

2,038 sq ft

|

House

157 SORRENTO RD, POINCIANA, FL, 34759
Community: Solivita
Esplanade at Westview 5683 NEVIS TER, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$499,999

3 beds

|

3 baths

|

2,296 sq ft

|

House

5683 NEVIS TER, KISSIMMEE, FL, 34758
Solivita 513 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$255,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

513 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
High Vista at Ridgewood Lakes 801 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$299,500

3 beds

|

2 baths

|

1,754 sq ft

|

House

801 HIGH VISTA DR, DAVENPORT, FL, 33837
Cindy Certified
1874 FLOURISH AVE, KISSIMMEE, FL, 34744, Kissimmee, FL 34744
$475,000

4 beds

|

3 baths

|

2,151 sq ft

|

House

1874 FLOURISH AVE, KISSIMMEE, FL, 34744
Esplanade at Highland Ranch 1279 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$675,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

1279 ZEEK RIDGE ST, CLERMONT, FL, 34715
Solivita 3443 FALLBROOK DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$285,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

3443 FALLBROOK DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Kings Ridge 3821 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$395,000

2 beds

|

2 baths

|

1,792 sq ft

|

House

3821 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Heritage Hills 3541 BELLAND CIR C, CLERMONT, FL, 34711, Clermont, FL 34711
$255,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3541 BELLAND CIR C, 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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