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

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


604 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
Solivita 513 BARCELONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

513 BARCELONA DR, KISSIMMEE, FL, 34759
Community: Solivita
Twin Lakes 2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$550,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
New Lake Ashton 4029 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$599,000

3 beds

|

2 baths

|

2,330 sq ft

|

House

4029 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Twin Lakes 4918 DRAWDY CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$439,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4918 DRAWDY CT, ST CLOUD, FL, 34772
Community: Twin Lakes
New Lake Ashton 5288 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$314,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

5288 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
New
Cindy Certified
3234 MINDFULLNESS DR, CLERMONT, FL, 3471..., Clermont, FL 34714
$555,990

4 beds

|

3 baths

|

2,175 sq ft

|

House

3234 MINDFULLNESS DR, CLERMONT, FL, 3471...
New
Cindy Certified
2704 MERCY CIR, CLERMONT, FL, 34714, Clermont, FL 34714
$588,990

4 beds

|

3 baths

|

2,692 sq ft

|

House

2704 MERCY CIR, CLERMONT, FL, 34714
New Esplanade at Highland Ranch 959 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$400,000

2 beds

|

2 baths

|

1,788 sq ft

|

House

959 BRAEWOOD DR, CLERMONT, FL, 34715
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.
New
Cindy Certified
16437 FERNRIDGE ST, CLERMONT, FL, 34714, Clermont, FL 34714
$439,900

4 beds

|

3 baths

|

2,081 sq ft

|

House

16437 FERNRIDGE ST, CLERMONT, FL, 34714
New
Cindy Certified
988 CAMBRIDGE DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33881
$299,900

4 beds

|

2 baths

|

1,867 sq ft

|

House

988 CAMBRIDGE DR, WINTER HAVEN, FL, 3388...
New Del Webb Lakehaven 15559 PEACEFUL PINES ALY, CLERMONT, FL, ..., Clermont, FL 34714
$545,350

5 beds

|

3 baths

|

2,603 sq ft

|

House

15559 PEACEFUL PINES ALY, CLERMONT, FL, ...
Community: Del Webb Lakehaven
New
Cindy Certified
15302 HONEYBELL DR, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$575,000

3 beds

|

2 baths

|

1,979 sq ft

|

House

15302 HONEYBELL DR, WINTER GARDEN, FL, 3...
New Twin Lakes 5031 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$399,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

5031 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
New Twin Lakes 2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$488,500

3 beds

|

3 baths

|

2,335 sq ft

|

House

2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Twin Lakes 2457 DREAM HOME CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$380,000

2 beds

|

2 baths

|

1,346 sq ft

|

House

2457 DREAM HOME CT, ST CLOUD, FL, 34772
Community: Twin Lakes
New Solivita 637 VOLTERRA BLVD, POINCIANA, FL, 34759, Poinciana, FL 34759
$649,900

3 beds

|

3 baths

|

2,903 sq ft

|

House

637 VOLTERRA BLVD, POINCIANA, FL, 34759
Community: Solivita
New
Cindy Certified
5362 WHISPERING GARDEN WAY, CLERMONT, FL..., Clermont, FL 34714
$308,240

2 beds

|

2 baths

|

1,421 sq ft

|

Villa

5362 WHISPERING GARDEN WAY, CLERMONT, FL...
New
Cindy Certified
13345 BEEBE ALY, ORLANDO, FL, 32827, Orlando, FL 32827
$649,990

3 beds

|

2 baths

|

1,981 sq ft

|

House

13345 BEEBE ALY, ORLANDO, FL, 32827
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.
New
Cindy Certified
2579 CLEAR NIGHT AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34744
$516,100

3 beds

|

2 baths

|

1,943 sq ft

|

House

2579 CLEAR NIGHT AVE, KISSIMMEE, FL, 347...
New
Cindy Certified
5606 DENNERY BAY RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34758
$380,030

4 beds

|

3 baths

|

2,175 sq ft

|

House

5606 DENNERY BAY RD, KISSIMMEE, FL, 3475...
New
Cindy Certified
3629 MAIDENCAIN ST, CLERMONT, FL, 34714, Clermont, FL 34714
$460,000

4 beds

|

2 baths

|

1,851 sq ft

|

House

3629 MAIDENCAIN ST, CLERMONT, FL, 34714
New
Cindy Certified
414 TAFT DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$385,000

3 beds

|

2 baths

|

1,968 sq ft

|

House

414 TAFT DR, DAVENPORT, FL, 33837
New Solivita 532 PASADENA PL, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,990

2 beds

|

2 baths

|

1,548 sq ft

|

House

532 PASADENA PL, POINCIANA, FL, 34759
Community: Solivita
New Lake Ashton 4227 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

4227 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Del Webb Orlando 533 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$330,000

2 beds

|

2 baths

|

1,728 sq ft

|

House

533 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New
Cindy Certified
4046 DINNER LAKE WAY, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$360,000

4 beds

|

2 baths

|

2,752 sq ft

|

House

4046 DINNER LAKE WAY, LAKE WALES, FL, 33...
Four Seasons at Orlando 1999 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$575,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

1999 LIMESTONE TRL, KISSIMMEE, FL, 34747
Cindy Certified
4419 LINWOOD TRACE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$615,000

4 beds

|

3 baths

|

2,105 sq ft

|

House

4419 LINWOOD TRACE LN, CLERMONT, 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.
Lake Ashton 5344 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$310,000

3 beds

|

2 baths

|

1,680 sq ft

|

House

5344 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Lake Ashton 4232 DORNOCH DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$449,000

3 beds

|

2 baths

|

2,229 sq ft

|

House

4232 DORNOCH DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Solivita 4085 VIA TOLEDO CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$519,900

4 beds

|

3 baths

|

2,444 sq ft

|

House

4085 VIA TOLEDO CT, POINCIANA, FL, 34759
Community: Solivita
Solivita 124 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$310,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

124 VENTANA DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 173 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759
$249,900

2 beds

|

2 baths

|

1,317 sq ft

|

House

173 BELL TOWER XING, POINCIANA, FL, 3475...
Community: Solivita
Solivita 1120 VIA GALUPPI ST, POINCIANA, FL, 3475..., Poinciana, FL 34759
$320,000

2 beds

|

2 baths

|

1,367 sq ft

|

House

1120 VIA GALUPPI ST, POINCIANA, FL, 3475...
Community: Solivita
Del Webb Orlando 123 MAGELLAN CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$514,900

3 beds

|

3 baths

|

2,186 sq ft

|

House

123 MAGELLAN CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Solivita 219 KNOLL WOOD DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$255,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

219 KNOLL WOOD DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 180 TALL PINES PASS, POINCIANA, FL, 3475..., Poinciana, FL 34759
$249,000

2 beds

|

2 baths

|

1,595 sq ft

|

House

180 TALL PINES PASS, POINCIANA, FL, 3475...
Community: Solivita
Twin Lakes 2327 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,469 sq ft

|

Villa

2327 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
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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