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Kissimmee, FL 55+ active adult communities & homes for sale - Page 2

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
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
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
Del Webb Orlando 336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$424,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

336 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Traditions at Lake Ruby 4035 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$249,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

4035 CARTERET DR, WINTER HAVEN, FL, 3388...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
5369 TEMPEST WAY, CLERMONT, FL, 34714, Clermont, FL 34714
$283,490

2 beds

|

2 baths

|

1,421 sq ft

|

Villa

5369 TEMPEST WAY, CLERMONT, FL, 34714
Cindy Certified
2676 GIARDINO LOOP, KISSIMMEE, FL, 34741, Kissimmee, FL 34741
$349,000

3 beds

|

3 baths

|

1,700 sq ft

|

Townhouse

2676 GIARDINO LOOP, KISSIMMEE, FL, 34741
Esplanade at Highland Ranch 1334 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$554,900

3 beds

|

3 baths

|

2,084 sq ft

|

House

1334 ZEEK RIDGE ST, CLERMONT, FL, 34715
Cindy Certified
3101 ROYAL TERN DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$279,990

4 beds

|

2 baths

|

1,851 sq ft

|

House

3101 ROYAL TERN DR, WINTER HAVEN, FL, 33...
Solivita 513 HEARTWELL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$275,000

2 beds

|

2 baths

|

1,488 sq ft

|

House

513 HEARTWELL 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.
Cindy Certified
1154 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$247,990

4 beds

|

2 baths

|

1,560 sq ft

|

House

1154 AMBER WAVES CT, LAKE WALES, FL, 338...
Palms at Serenoa 17766 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$414,777

3 beds

|

2 baths

|

1,722 sq ft

|

House

17766 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Heritage Hills 3493 EMBERS LN, CLERMONT, FL, 34711, Clermont, FL 34711
$395,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3493 EMBERS LN, CLERMONT, FL, 34711
Community: Heritage Hills
Cindy Certified
1733 FELICITY LN, KISSIMMEE, FL, 34744, Kissimmee, FL 34744
$419,900

4 beds

|

3 baths

|

2,030 sq ft

|

House

1733 FELICITY LN, KISSIMMEE, FL, 34744
Cindy Certified
4540 GLIDING WAVE ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$560,000

3 beds

|

2 baths

|

2,144 sq ft

|

House

4540 GLIDING WAVE ST, WINTER GARDEN, FL,...
Esplanade at Westview 4494 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$319,990

2 beds

|

2 baths

|

1,713 sq ft

|

House

4494 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Carlsberg Estates on Lake Suzanne 483 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$248,000

3 beds

|

2 baths

|

1,510 sq ft

|

House

483 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Cindy Certified
593 KISTLER CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$499,900

4 beds

|

2 baths

|

2,065 sq ft

|

House

593 KISTLER CIR, CLERMONT, FL, 34715
Solivita 169 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$345,000

2 beds

|

2 baths

|

1,673 sq ft

|

House

169 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Solivita 566 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$265,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

566 VINEYARD WAY, 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.
Del Webb Orlando 475 PALENCIA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$414,900

3 beds

|

2 baths

|

2,042 sq ft

|

House

475 PALENCIA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lake Ashton 1321 OAKMONT DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$424,900

3 beds

|

2 baths

|

2,312 sq ft

|

House

1321 OAKMONT DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Cindy Certified
2913 BLUESTEM LN, CLERMONT, FL, 34714, Clermont, FL 34714
$439,900

4 beds

|

2 baths

|

1,801 sq ft

|

House

2913 BLUESTEM LN, CLERMONT, FL, 34714
Cindy Certified
2578 AUTUMN PEACE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34744
$469,500

3 beds

|

2 baths

|

2,056 sq ft

|

House

2578 AUTUMN PEACE DR, KISSIMMEE, FL, 347...
Cindy Certified
469 NOVA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$320,000

3 beds

|

2 baths

|

1,694 sq ft

|

House

469 NOVA DR, DAVENPORT, FL, 33837
Del Webb Lakehaven 15555 PEACEFUL PINES ALY, CLERMONT, FL, ..., Clermont, FL 34714
$511,590

4 beds

|

3 baths

|

2,341 sq ft

|

House

15555 PEACEFUL PINES ALY, CLERMONT, FL, ...
Community: Del Webb Lakehaven
Del Webb Sunbridge 2496 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$500,000

2 beds

|

2 baths

|

1,670 sq ft

|

House

2496 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
High Vista at Ridgewood Lakes 217 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$324,750

2 beds

|

2 baths

|

1,790 sq ft

|

House

217 FLEMING LN, DAVENPORT, FL, 33837
Cindy Certified
2441 OAKWOOD LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$339,000

3 beds

|

2 baths

|

1,420 sq ft

|

House

2441 OAKWOOD LN, DAVENPORT, FL, 33837
Solivita 4108 VIA TOLEDO CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$500,000

3 beds

|

3 baths

|

2,310 sq ft

|

House

4108 VIA TOLEDO CT, 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.
Solivita 501 PALERMO BLVD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$520,000

3 beds

|

3 baths

|

2,580 sq ft

|

House

501 PALERMO BLVD, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
6283 RED HERRING DR, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881
$275,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

6283 RED HERRING DR, WINTER HAVEN, FL, 3...
Cindy Certified
416 LEMONGRASS RD, MINNEOLA, FL, 34715, Minneola, FL 34715
$564,990

4 beds

|

2 baths

|

2,103 sq ft

|

House

416 LEMONGRASS RD, MINNEOLA, FL, 34715
Del Webb Sunbridge 2361 DAISY TREE RD, ST CLOUD, FL, 34771, St Cloud, FL 34771
$459,900

2 beds

|

2 baths

|

1,650 sq ft

|

House

2361 DAISY TREE RD, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Lake Ashton 5281 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$279,900

3 beds

|

2 baths

|

1,495 sq ft

|

House

5281 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Del Webb Oasis 15066 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$967,500

3 beds

|

4 baths

|

2,955 sq ft

|

House

15066 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
Lake Ashton 4047 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

3 beds

|

2 baths

|

1,905 sq ft

|

House

4047 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Henry Estates 430 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844
$332,900

2 beds

|

2 baths

|

1,650 sq ft

|

House

430 HARBOURVIEW DR, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Vienna Square 1631 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$190,500

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1631 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Lake Ashton 4028 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$330,000

2 beds

|

2 baths

|

1,784 sq ft

|

House

4028 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
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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