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Kissimmee, FL 55+ active adult communities & homes for sale - Page 6

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
Esplanade at Westview 4482 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$314,990

2 beds

|

2 baths

|

1,872 sq ft

|

House

4482 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Heritage Hills 3547 FAIRWATERS CT F, CLERMONT, FL, 3471..., Clermont, FL 34711
$266,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3547 FAIRWATERS CT F, CLERMONT, FL, 3471...
Community: Heritage Hills
Summit Greens 2390 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$440,000

3 beds

|

2 baths

|

1,961 sq ft

|

House

2390 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Cindy Certified
1656 HAMLIN RIDGE RD, MINNEOLA, FL, 3471..., Minneola, FL 34715
$589,000

4 beds

|

2 baths

|

2,103 sq ft

|

House

1656 HAMLIN RIDGE RD, MINNEOLA, FL, 3471...
Cindy Certified
1069 SANDPIPER LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881
$379,999

4 beds

|

3 baths

|

2,034 sq ft

|

House

1069 SANDPIPER LOOP, WINTER HAVEN, FL, 3...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
1150 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$261,990

5 beds

|

2 baths

|

1,739 sq ft

|

House

1150 AMBER WAVES CT, LAKE WALES, FL, 338...
Solivita 542 PORTOFINO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$305,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

542 PORTOFINO DR, POINCIANA, FL, 34759
Community: Solivita
Four Seasons at Orlando 7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$695,000

3 beds

|

3 baths

|

2,754 sq ft

|

House

7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Four Seasons at Orlando 1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$349,500

2 beds

|

2 baths

|

1,437 sq ft

|

House

1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Del Webb Oasis 13360 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$595,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

13360 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
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.
Four Seasons at Orlando 2042 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$355,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

2042 KEY BAY TRL, KISSIMMEE, FL, 34747
Four Seasons at Orlando 1908 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$349,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1908 FLORA PASS PL, KISSIMMEE, FL, 34747
Solivita 1090 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$324,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

1090 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
Four Seasons at Orlando 2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$419,999

2 beds

|

2 baths

|

1,778 sq ft

|

House

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Heritage Hills 3505 BELLAND CIR F, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

2 beds

|

2 baths

|

1,503 sq ft

|

Townhouse

3505 BELLAND CIR F, CLERMONT, FL, 34711
Community: Heritage Hills
Twin Lakes 2541 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$298,500

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2541 YELLOW BRICK RD, 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
High Vista at Ridgewood Lakes 238 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$325,000

2 beds

|

2 baths

|

1,877 sq ft

|

House

238 FLEMING LN, DAVENPORT, FL, 33837
Gatherings of Lake Nona 7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827
$395,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Gatherings of Lake Nona 7545 LAUREATE BLVD 7208, ORLANDO, FL, 32..., Orlando, FL 32827
$389,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7545 LAUREATE BLVD 7208, ORLANDO, FL, 32...
Cindy Certified
3273 WHOLENESS WAY, CLERMONT, FL, 34714, Clermont, FL 34714
$551,990

4 beds

|

3 baths

|

2,199 sq ft

|

House

3273 WHOLENESS WAY, CLERMONT, FL, 34714
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 1389 LAMBARDI CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$359,900

3 beds

|

2 baths

|

1,727 sq ft

|

House

1389 LAMBARDI CT, POINCIANA, FL, 34759
Community: Solivita
Solivita 284 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$230,000

2 beds

|

2 baths

|

1,102 sq ft

|

House

284 VESTRELLA DR, POINCIANA, FL, 34759
Community: Solivita
Cindy Certified
5567 MORANT BAY PATH, KISSIMMEE, FL, 347..., Kissimmee, FL 34758
$308,290

4 beds

|

2 baths

|

1,600 sq ft

|

House

5567 MORANT BAY PATH, KISSIMMEE, FL, 347...
Cindy Certified
2637 PEACE OF MIND AVE, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$480,000

3 beds

|

2 baths

|

2,082 sq ft

|

House

2637 PEACE OF MIND AVE, KISSIMMEE, FL, 3...
Solivita 133 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$269,900

2 beds

|

2 baths

|

1,507 sq ft

|

House

133 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Del Webb Oasis 13355 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787
$899,000

3 beds

|

3 baths

|

2,710 sq ft

|

House

13355 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
VillageWalk at Lake Nona 11962 GENNARO LN, ORLANDO, FL, 32827, Orlando, FL 32827
$639,000

3 beds

|

2 baths

|

2,005 sq ft

|

House

11962 GENNARO LN, ORLANDO, FL, 32827
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Lake Ashton 4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$294,900

2 beds

|

2 baths

|

1,530 sq ft

|

House

4063 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Del Webb Orlando 333 NAVARRA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,028 sq ft

|

House

333 NAVARRA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Twin Lakes 2374 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$304,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2374 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.
Cindy Certified
1847 BUCKEYE RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$329,990

3 beds

|

2 baths

|

1,725 sq ft

|

House

1847 BUCKEYE RD, DAVENPORT, FL, 33837
Cindy Certified
120 PANDA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$340,000

4 beds

|

2 baths

|

1,851 sq ft

|

House

120 PANDA WAY, DAVENPORT, FL, 33837
Cindy Certified
17307 BAL HARBOUR DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$624,900

3 beds

|

2 baths

|

2,123 sq ft

|

House

17307 BAL HARBOUR DR, WINTER GARDEN, FL,...
Esplanade at McKinnon Groves 11234 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$415,000

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11234 SILVER TRUMPET LOOP, WINTER GARDEN...
Esplanade at McKinnon Groves 11199 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$447,118

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11199 SILVER TRUMPET LOOP, WINTER GARDEN...
Esplanade at McKinnon Groves 11202 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$437,993

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11202 SILVER TRUMPET LOOP, WINTER GARDEN...
Heritage Hills 3615 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$249,900

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3615 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Cindy Certified
4590 BROOKSHIRE PL, LAKE WALES, FL, 3389..., Lake Wales, FL 33898
$369,000

5 beds

|

3 baths

|

2,302 sq ft

|

House

4590 BROOKSHIRE PL, LAKE WALES, FL, 3389...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Palms at Serenoa 3415 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714
$397,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

3415 YELLOWTOP LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
Heritage Hills 2823 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$495,000

3 beds

|

3 baths

|

2,573 sq ft

|

House

2823 MAYPORT ST, 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.

Frequently Asked Questions


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