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Kissimmee, FL 55+ active adult communities & homes for sale - Page 7

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
Tohoqua Reserve 2756 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$310,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

2756 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Del Webb Oasis 15000 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$849,990

3 beds

|

4 baths

|

2,861 sq ft

|

House

15000 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$369,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Gatherings of Lake Nona 7545 LAUREATE BLVD 7404, ORLANDO, FL, 32..., Orlando, FL 32827
$414,990

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32...
Gatherings of Lake Nona 7545 LAUREATE BLVD 7408, ORLANDO, FL, 32..., Orlando, FL 32827
$389,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7545 LAUREATE BLVD 7408, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Kings Ridge 2525 NEW CASTLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

2 beds

|

3 baths

|

1,715 sq ft

|

House

2525 NEW CASTLE CT, CLERMONT, FL, 34711
Community: Kings Ridge
High Vista at Ridgewood Lakes 347 ROYAL PALM DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$245,000

2 beds

|

2 baths

|

1,395 sq ft

|

House

347 ROYAL PALM DR, DAVENPORT, FL, 33837
Esplanade at Highland Ranch 1197 ESPERANZA RIDGE RD, CLERMONT, FL, 3..., Clermont, FL 34715
$620,000

3 beds

|

3 baths

|

2,333 sq ft

|

House

1197 ESPERANZA RIDGE RD, CLERMONT, FL, 3...
Solivita 896 BARCELONA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$333,000

2 beds

|

3 baths

|

1,935 sq ft

|

House

896 BARCELONA DR, POINCIANA, FL, 34759
Community: Solivita
Del Webb Orlando 442 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$424,900

3 beds

|

3 baths

|

2,581 sq ft

|

House

442 DEL SOL AVE, 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.
Cindy Certified
2524 RAPOLLO DR, KISSIMMEE, FL, 34741, Kissimmee, FL 34741
$414,990

3 beds

|

2 baths

|

1,706 sq ft

|

House

2524 RAPOLLO DR, KISSIMMEE, FL, 34741
Solivita 205 BELL TOWER XING, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$254,500

2 beds

|

2 baths

|

1,405 sq ft

|

House

205 BELL TOWER XING, KISSIMMEE, FL, 3475...
Community: Solivita
Del Webb Oasis 15084 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$899,999

3 beds

|

3 baths

|

2,270 sq ft

|

House

15084 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
Cindy Certified
12523 GOLD HONEYSUCKLE ST, WINTER GARDEN..., Winter Garden, FL 34787
$844,990

4 beds

|

3 baths

|

2,552 sq ft

|

House

12523 GOLD HONEYSUCKLE ST, WINTER GARDEN...
Cindy Certified
870 BALLANTYNE DR, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$315,000

4 beds

|

2 baths

|

1,822 sq ft

|

House

870 BALLANTYNE DR, LAKE WALES, FL, 33898
Solivita 364 ACADIA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$250,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 ACADIA DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
495 TAFT DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$285,990

3 beds

|

2 baths

|

1,405 sq ft

|

House

495 TAFT DR, DAVENPORT, FL, 33837
Palms at Serenoa 17782 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$439,000

4 beds

|

2 baths

|

2,034 sq ft

|

House

17782 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Cindy Certified
3277 WHOLENESS WAY, CLERMONT, FL, 34714, Clermont, FL 34714
$610,490

4 beds

|

4 baths

|

2,911 sq ft

|

House

3277 WHOLENESS WAY, CLERMONT, FL, 34714
High Vista at Ridgewood Lakes 919 ASHTON DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$349,900

3 beds

|

2 baths

|

2,081 sq ft

|

House

919 ASHTON DR, DAVENPORT, FL, 33837
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
17932 PASSIONFLOWER CIR, CLERMONT, FL, 3..., Clermont, FL 34714
$519,900

4 beds

|

3 baths

|

2,356 sq ft

|

House

17932 PASSIONFLOWER CIR, CLERMONT, FL, 3...
Solivita 778 IRVINE RANCH RD, POINCIANA, FL, 3475..., Poinciana, FL 34759
$525,000

4 beds

|

3 baths

|

2,326 sq ft

|

House

778 IRVINE RANCH RD, POINCIANA, FL, 3475...
Community: Solivita
Heritage Hills 3650 LIMESTONE ST, CLERMONT, FL, 34711, Clermont, FL 34711
$384,000

3 beds

|

2 baths

|

1,677 sq ft

|

House

3650 LIMESTONE ST, CLERMONT, FL, 34711
Community: Heritage Hills
Gatherings of Lake Nona 7517 LAUREATE BLVD 4303, ORLANDO, FL, 32..., Orlando, FL 32827
$309,900

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7517 LAUREATE BLVD 4303, ORLANDO, FL, 32...
Twin Lakes 5013 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$549,900

3 beds

|

3 baths

|

3,114 sq ft

|

House

5013 VANTAGE CT, ST CLOUD, FL, 34772
Community: Twin Lakes
Kings Ridge 4224 SNOWDON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$292,000

2 beds

|

2 baths

|

1,170 sq ft

|

House

4224 SNOWDON ST, CLERMONT, FL, 34711
Community: Kings Ridge
Preserve at Lakeside Landings 5852 MARSH LANDING DR, WINTER HAVEN, FL,..., Winter Haven, FL 33881
$325,000

4 beds

|

2 baths

|

2,091 sq ft

|

House

5852 MARSH LANDING DR, WINTER HAVEN, FL,...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Heritage Hills 3516 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$420,000

3 beds

|

2 baths

|

1,879 sq ft

|

House

3516 KINLEY BROOKE LN, CLERMONT, FL, 347...
Community: Heritage Hills
Gatherings of Lake Nona 7505 LAUREATE BLVD 2407, ORLANDO, FL, 32..., Orlando, FL 32827
$550,000

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7505 LAUREATE BLVD 2407, ORLANDO, FL, 32...
Solivita 105 CUPOLA LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$395,000

2 beds

|

2 baths

|

2,066 sq ft

|

House

105 CUPOLA LOOP, 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.
Gatherings of Lake Nona 7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827
$359,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...
Solivita 1055 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$279,000

3 beds

|

2 baths

|

1,590 sq ft

|

House

1055 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
Cindy Certified
3052 NAMASTE DR, CLERMONT, FL, 34714, Clermont, FL 34714
$887,000

74 beds

|

3 baths

|

2,199 sq ft

|

House

3052 NAMASTE DR, CLERMONT, FL, 34714
Esplanade at Highland Ranch 908 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$633,000

3 beds

|

3 baths

|

2,396 sq ft

|

House

908 BRAEWOOD DR, CLERMONT, FL, 34715
Esplanade at Highland Ranch 2666 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$525,000

2 beds

|

2 baths

|

2,172 sq ft

|

House

2666 STARGRASS CIR, CLERMONT, FL, 34715
Del Webb Orlando 478 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$394,900

3 beds

|

2 baths

|

2,030 sq ft

|

House

478 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lake Ashton 4231 COCONUT DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$539,900

3 beds

|

3 baths

|

2,338 sq ft

|

House

4231 COCONUT DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Esplanade at Westview 4493 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$313,990

2 beds

|

2 baths

|

1,553 sq ft

|

House

4493 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
VillageWalk at Lake Nona 11951 FIORE DR, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

2 baths

|

1,554 sq ft

|

Halfplex

11951 FIORE DR, ORLANDO, FL, 32827
Esplanade at Westview 4464 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$314,990

2 beds

|

2 baths

|

1,872 sq ft

|

House

4464 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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