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Kissimmee, FL 55+ active adult communities & homes for sale - Page 15

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
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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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.
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) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
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
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
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
Del Webb Lakehaven
$400ks - $800ks
Del Webb Lakehaven, Clermont, FL
New Construction | 55+ age-restricted | Built 2026 - present
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.
5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 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
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
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
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.
Enclave at VillageWalk
$700ks - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 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
Solivita 305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$474,900

3 beds

|

3 baths

|

2,454 sq ft

|

House

305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
Lake Ashton 4632 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,900

3 beds

|

2 baths

|

2,354 sq ft

|

House

4632 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Solivita 308 BEACON AVE, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$310,000

2 beds

|

2 baths

|

2,038 sq ft

|

House

308 BEACON AVE, KISSIMMEE, FL, 34759
Community: Solivita
Lake Ashton 4360 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$369,900

3 beds

|

2 baths

|

2,265 sq ft

|

House

4360 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
Lake Henry Estates 422 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844
$284,900

3 beds

|

2 baths

|

1,793 sq ft

|

House

422 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
Solivita 684 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$519,000

3 beds

|

3 baths

|

2,363 sq ft

|

House

684 SAN AUGUSTO DR, POINCIANA, FL, 34759
Community: Solivita
Heritage Hills 3464 EMBERS LN, CLERMONT, FL, 34711, Clermont, FL 34711
$435,000

3 beds

|

3 baths

|

2,032 sq ft

|

House

3464 EMBERS LN, CLERMONT, FL, 34711
Community: Heritage Hills
Lake Ashton 6308 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$444,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Esplanade at Highland Ranch 1284 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$399,000

2 beds

|

2 baths

|

1,722 sq ft

|

House

1284 ZEEK RIDGE ST, CLERMONT, FL, 34715
Del Webb Sunbridge 2745 NATURE VIEW RD, ST CLOUD, FL, 34771, St Cloud, FL 34771
$829,000

3 beds

|

4 baths

|

2,806 sq ft

|

House

2745 NATURE VIEW RD, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
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 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$390,500

3 beds

|

2 baths

|

2,027 sq ft

|

House

4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Lake Ashton 4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$334,800

3 beds

|

2 baths

|

1,918 sq ft

|

House

4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Solivita 699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$430,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

699 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
VillageWalk at Lake Nona 8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827
$474,900

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
Solivita 2472 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$289,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2472 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Heritage Hills 3550 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711
$275,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3550 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Twin Lakes 4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$450,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
Cindy Certified
1349 SUGARWOOD ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

1349 SUGARWOOD ST, DAVENPORT, FL, 33837
Lake Ashton 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$335,000

2 beds

|

2 baths

|

1,677 sq ft

|

House

5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
VillageWalk at Lake Nona 11932 LORENZA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

11932 LORENZA LN, 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.
Solivita 1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$340,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475...
Community: Solivita
VillageWalk at Lake Nona 7991 ESTA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$850,000

4 beds

|

5 baths

|

3,454 sq ft

|

House

7991 ESTA LN, ORLANDO, FL, 32827
Solivita 806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$409,900

3 beds

|

3 baths

|

2,011 sq ft

|

House

806 EBB TIDE LN, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
6528 ROVER WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$429,000

3 beds

|

2 baths

|

1,881 sq ft

|

House

6528 ROVER WAY, ST CLOUD, FL, 34771
Cindy Certified
2015 CHICKASAW BLVD, DAVENPORT, FL, 3383..., Davenport, FL 33837
$330,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

2015 CHICKASAW BLVD, DAVENPORT, FL, 3383...
Del Webb Orlando 536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,000

3 beds

|

2 baths

|

1,508 sq ft

|

House

536 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Tohoqua Reserve 1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$479,900

3 beds

|

2 baths

|

2,056 sq ft

|

House

1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
14501 GROVE RESORT AVE # 1603, WINTER GA..., Winter Garden, FL 34787
$350,000

3 beds

|

2 baths

|

1,396 sq ft

|

Condotel

14501 GROVE RESORT AVE # 1603, WINTER GA...
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$569,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747
Twin Lakes 4921 CATALPA DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$539,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

4921 CATALPA DR, 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
5200 MYRTLELEAF CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$610,000

6 beds

|

3 baths

|

2,875 sq ft

|

House

5200 MYRTLELEAF CT, ST CLOUD, FL, 34772
Solivita 1305 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$240,000

2 beds

|

2 baths

|

1,365 sq ft

|

House

1305 LOMBARDI CT, KISSIMMEE, FL, 34759
Community: Solivita
Vienna Square 1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$248,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Four Seasons at Orlando 1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$270,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1991 KEY BAY TRL, KISSIMMEE, FL, 34747
Traditions at Lake Ruby 3923 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$253,900

3 beds

|

2 baths

|

1,719 sq ft

|

House

3923 BALDWIN LN, WINTER HAVEN, FL, 33884
Kings Ridge 4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$389,900

2 beds

|

2 baths

|

1,968 sq ft

|

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$445,000

2 beds

|

3 baths

|

2,343 sq ft

|

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
Community: Solivita
Solivita 619 TAPATIO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$523,000

5 beds

|

5 baths

|

2,881 sq ft

|

House

619 TAPATIO LN, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$514,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$205,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
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.

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