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Kissimmee, FL 55+ active adult communities & homes for sale - Page 3

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 4064 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$449,900

3 beds

|

2 baths

|

2,354 sq ft

|

House

4064 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Heritage Hills 3640 SOLANA CIR 11B, CLERMONT, FL, 34711, Clermont, FL 34711
$275,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3640 SOLANA CIR 11B, CLERMONT, FL, 34711
Community: Heritage Hills
Cindy Certified
13356 PEACEFUL MELODY DR, WINTER GARDEN,..., Winter Garden, FL 34787
$684,990

4 beds

|

3 baths

|

2,235 sq ft

|

House

13356 PEACEFUL MELODY DR, WINTER GARDEN,...
Twin Lakes 2891 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772
$345,390

2 beds

|

2 baths

|

1,321 sq ft

|

Villa

2891 MIDSWEET AVE, ST CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 2774 BUCKEYE LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$335,910

2 beds

|

2 baths

|

1,321 sq ft

|

Villa

2774 BUCKEYE LN, ST CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Esplanade at McKinnon Groves 11397 BOURBON ROSE CIR, WINTER GARDEN, F..., Winter Garden, FL 34787
$840,000

4 beds

|

4 baths

|

2,717 sq ft

|

House

11397 BOURBON ROSE CIR, WINTER GARDEN, F...
Esplanade at McKinnon Groves 11232 CARDING MILL LN, WINTER GARDEN, FL..., Winter Garden, FL 34787
$690,000

3 beds

|

3 baths

|

1,843 sq ft

|

House

11232 CARDING MILL LN, WINTER GARDEN, FL...
Kings Ridge 3613 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

2 beds

|

2 baths

|

1,441 sq ft

|

House

3613 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
Lake Ashton 4039 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$369,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

4039 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
Twin Lakes 5094 SUNFALLS AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772
$512,900

2 beds

|

3 baths

|

2,107 sq ft

|

House

5094 SUNFALLS AVE, 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.
Solivita 195 CASAVISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$450,000

2 beds

|

2 baths

|

1,982 sq ft

|

House

195 CASAVISTA DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 885 PACIFIC RIDGE RD, POINCIANA, FL, 347..., Poinciana, FL 34759
$364,000

2 beds

|

2 baths

|

1,975 sq ft

|

House

885 PACIFIC RIDGE RD, POINCIANA, FL, 347...
Community: Solivita
Cindy Certified
3292 WINDBEAM CT, WINTER GARDEN, FL, 347..., Winter Garden, FL 34787
$899,000

3 beds

|

4 baths

|

2,872 sq ft

|

House

3292 WINDBEAM CT, WINTER GARDEN, FL, 347...
Carlsberg Estates on Lake Suzanne 452 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$399,000

3 beds

|

2 baths

|

1,979 sq ft

|

House

452 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Heritage Hills 2819 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$485,000

3 beds

|

2 baths

|

2,194 sq ft

|

House

2819 MAYPORT ST, CLERMONT, FL, 34711
Community: Heritage Hills
Kings Ridge 2109 GRAFTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$369,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

2109 GRAFTON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Summit Greens 1176 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

1176 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Four Seasons at Orlando 1900 ESTUARY LN, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$575,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

1900 ESTUARY LN, KISSIMMEE, FL, 34747
Cindy Certified
350 RUSTIC RAIL DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$275,000

3 beds

|

2 baths

|

1,540 sq ft

|

House

350 RUSTIC RAIL DR, LAKE WALES, FL, 3385...
Kings Ridge 3810 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$435,000

3 beds

|

2 baths

|

1,996 sq ft

|

House

3810 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
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
823 ANDREW ST, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$345,190

4 beds

|

3 baths

|

2,061 sq ft

|

House

823 ANDREW ST, WINTER HAVEN, FL, 33881
Del Webb Oasis 15193 AQUA SOL LN, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$459,900

3 beds

|

2 baths

|

1,579 sq ft

|

Villa

15193 AQUA SOL LN, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Solivita 601 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$234,000

2 beds

|

2 baths

|

1,258 sq ft

|

House

601 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
1112 FOX PATH, DAVENPORT, FL, 33837, Davenport, FL 33837
$272,500

3 beds

|

2 baths

|

1,725 sq ft

|

House

1112 FOX PATH, DAVENPORT, FL, 33837
Twin Lakes 4922 CATALPA DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$389,900

3 beds

|

2 baths

|

1,456 sq ft

|

House

4922 CATALPA DR, ST CLOUD, FL, 34772
Community: Twin Lakes
Cindy Certified
5339 HAVEN VIEW DR, CLERMONT, FL, 34714, Clermont, FL 34714
$410,490

2 beds

|

2 baths

|

1,779 sq ft

|

House

5339 HAVEN VIEW DR, CLERMONT, FL, 34714
Solivita 801 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$509,000

3 beds

|

2 baths

|

2,719 sq ft

|

House

801 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Traditions at Lake Ruby 4075 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$344,900

2 beds

|

2 baths

|

1,888 sq ft

|

House

4075 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Heritage Hills 3628 SOLANA CIR D, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3628 SOLANA CIR D, CLERMONT, FL, 34711
Community: Heritage Hills
Solivita 575 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$759,000

3 beds

|

3 baths

|

2,843 sq ft

|

House

575 SAN RAPHAEL ST, POINCIANA, 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 2506 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$262,500

2 beds

|

2 baths

|

1,261 sq ft

|

Villa

2506 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Tohoqua Reserve 2706 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$347,900

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

2706 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Lake Henry Estates 656 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$250,000

2 beds

|

2 baths

|

1,681 sq ft

|

House

656 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Cindy Certified
1050 MICHELANGELO LN, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$335,000

3 beds

|

2 baths

|

1,659 sq ft

|

House

1050 MICHELANGELO LN, WINTER HAVEN, FL, ...
Lake Ashton 3608 BLACKMOOR LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$649,900

2 beds

|

2 baths

|

1,795 sq ft

|

House

3608 BLACKMOOR LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Solivita 145 PALAZZO LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$220,000

2 beds

|

2 baths

|

1,102 sq ft

|

House

145 PALAZZO LN, POINCIANA, FL, 34759
Community: Solivita
Twin Lakes 2491 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$269,900

2 beds

|

2 baths

|

1,464 sq ft

|

Halfplex

2491 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
Kings Ridge 3635 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

2 beds

|

2 baths

|

1,661 sq ft

|

House

3635 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 313 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$274,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

313 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Del Webb Orlando 125 LA CRESTA CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$499,900

4 beds

|

4 baths

|

2,837 sq ft

|

House

125 LA CRESTA CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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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