Call us at (689) 215-8956 to learn more about active adult communities in Kissimmee

Kissimmee, FL 55+ active adult communities & homes for sale - Page 9

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

Sort by:

Relevance

Relevance

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
Del Webb Sunbridge 2865 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771
$859,000

4 beds

|

4 baths

|

2,854 sq ft

|

House

2865 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
Cindy Certified
5119 BUTTONSAGE DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$509,956

4 beds

|

2 baths

|

1,893 sq ft

|

House

5119 BUTTONSAGE DR, ST CLOUD, FL, 34772
Cindy Certified
2380 VOLUNTEER AVE, KISSIMMEE, FL, 34744, Kissimmee, FL 34744
$389,000

3 beds

|

2 baths

|

2,068 sq ft

|

House

2380 VOLUNTEER AVE, KISSIMMEE, FL, 34744
Cindy Certified
2844 ARMSTRONG AVE, CLERMONT, FL, 34714, Clermont, FL 34714
$589,760

4 beds

|

3 baths

|

2,214 sq ft

|

House

2844 ARMSTRONG AVE, CLERMONT, FL, 34714
Cindy Certified
5123 BUTTONSAGE DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$540,132

4 beds

|

3 baths

|

2,174 sq ft

|

House

5123 BUTTONSAGE DR, ST CLOUD, FL, 34772
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
5127 BUTTONSAGE DR, ST CLOUD, FL, 34772, St Cloud, FL 34772
$504,013

3 beds

|

2 baths

|

1,742 sq ft

|

House

5127 BUTTONSAGE DR, ST CLOUD, FL, 34772
Cindy Certified
761 GREENWAY BLVD, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$273,900

5 beds

|

2 baths

|

1,708 sq ft

|

House

761 GREENWAY BLVD, LAKE WALES, FL, 33859
Lake Henry Estates 472 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$240,000

2 beds

|

2 baths

|

1,117 sq ft

|

House

472 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Cindy Certified
6430 ROVER WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$484,990

3 beds

|

2 baths

|

1,608 sq ft

|

House

6430 ROVER WAY, ST CLOUD, FL, 34771
Cindy Certified
1055 SUGARWOOD ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$319,900

4 beds

|

3 baths

|

2,248 sq ft

|

House

1055 SUGARWOOD ST, 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.
Solivita 159 CASAVISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$419,500

2 beds

|

2 baths

|

1,771 sq ft

|

House

159 CASAVISTA DR, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
5279 HAVEN VIEW DR, CLERMONT, FL, 34714, Clermont, FL 34714
$469,990

4 beds

|

3 baths

|

2,366 sq ft

|

House

5279 HAVEN VIEW DR, CLERMONT, FL, 34714
VillageWalk at Lake Nona 11731 EAGLE RAY LN, ORLANDO, FL, 32827, Orlando, FL 32827
$630,000

3 beds

|

2 baths

|

2,005 sq ft

|

House

11731 EAGLE RAY LN, ORLANDO, FL, 32827
Kings Ridge 4334 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

2 beds

|

2 baths

|

1,989 sq ft

|

House

4334 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 1940 FARMINGTON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$397,000

2 beds

|

3 baths

|

1,722 sq ft

|

House

1940 FARMINGTON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 230 BAY DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$296,000

2 beds

|

2 baths

|

1,489 sq ft

|

House

230 BAY DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Cindy Certified
2821 PLYMOUTH PL, KISSIMMEE, FL, 34741, Kissimmee, FL 34741
$370,000

3 beds

|

3 baths

|

1,838 sq ft

|

Villa

2821 PLYMOUTH PL, KISSIMMEE, FL, 34741
Twin Lakes 2516 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$275,000

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2516 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 2720 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$399,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

2720 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Cindy Certified
2410 RELAXING LN, KISSIMMEE, FL, 34744, Kissimmee, FL 34744
$489,990

4 beds

|

3 baths

|

2,151 sq ft

|

House

2410 RELAXING LN, KISSIMMEE, FL, 34744
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 2680 REDBLUSH TER, ST CLOUD, FL, 34772, St Cloud, FL 34772
$599,000

3 beds

|

3 baths

|

2,293 sq ft

|

House

2680 REDBLUSH TER, ST CLOUD, FL, 34772
Community: Twin Lakes
Cindy Certified
5399 WHISPERING GARDEN WAY, CLERMONT, FL..., Clermont, FL 34714
$275,990

2 beds

|

2 baths

|

1,421 sq ft

|

Villa

5399 WHISPERING GARDEN WAY, CLERMONT, FL...
Cindy Certified
2523 AVENUE E SW, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$298,900

3 beds

|

2 baths

|

1,930 sq ft

|

House

2523 AVENUE E SW, WINTER HAVEN, FL, 3388...
Kings Ridge 3604 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

2 beds

|

2 baths

|

1,377 sq ft

|

House

3604 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Cindy Certified
2519 AVENUE E SW, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$299,900

3 beds

|

2 baths

|

1,675 sq ft

|

House

2519 AVENUE E SW, WINTER HAVEN, FL, 3388...
Cindy Certified
144 WATERSIDE CIR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33880
$299,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

144 WATERSIDE CIR, WINTER HAVEN, FL, 338...
Twin Lakes 5087 TWIN LAKES BLVD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$412,500

3 beds

|

2 baths

|

1,863 sq ft

|

House

5087 TWIN LAKES BLVD, 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
Cindy Certified
2806 PLYMOUTH PL, KISSIMMEE, FL, 34741, Kissimmee, FL 34741
$367,000

3 beds

|

3 baths

|

1,838 sq ft

|

Townhouse

2806 PLYMOUTH PL, KISSIMMEE, FL, 34741
Traditions at Lake Ruby 2820 TRADITIONS BLVD, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$309,900

3 beds

|

2 baths

|

1,823 sq ft

|

House

2820 TRADITIONS BLVD, WINTER HAVEN, FL, ...
Carlsberg Estates on Lake Suzanne 4178 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$285,000

3 beds

|

3 baths

|

1,718 sq ft

|

House

4178 CANNES AVE, LAKE WALES, FL, 33859
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.
Esplanade at McKinnon Groves 17742 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$900,000

3 beds

|

3 baths

|

2,475 sq ft

|

House

17742 SEDONA ST, WINTER GARDEN, FL, 3478...
Solivita 766 CARMEL LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$399,000

3 beds

|

3 baths

|

2,320 sq ft

|

House

766 CARMEL LN, KISSIMMEE, FL, 34759
Community: Solivita
Esplanade at McKinnon Groves 11341 BOURBON ROSE CIR, WINTER GARDEN, F..., Winter Garden, FL 34787
$925,000

4 beds

|

5 baths

|

2,974 sq ft

|

House

11341 BOURBON ROSE CIR, WINTER GARDEN, F...
Esplanade at McKinnon Groves 11275 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$400,000

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11275 SILVER TRUMPET LOOP, WINTER GARDEN...
Esplanade at McKinnon Groves 11279 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$432,318

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11279 SILVER TRUMPET LOOP, WINTER GARDEN...
Summit Greens 794 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

794 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
Twin Lakes 5023 SUNFALLS AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772
$405,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

5023 SUNFALLS AVE, ST CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 5095 TWIN LAKES BLVD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$464,990

3 beds

|

2 baths

|

2,084 sq ft

|

House

5095 TWIN LAKES BLVD, 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
Gatherings of Lake Nona 7521 LAUREATE BLVD 5208, ORLANDO, FL, 32..., Orlando, FL 32827
$399,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7521 LAUREATE BLVD 5208, ORLANDO, FL, 32...
Tohoqua Reserve 1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$425,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
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


Want more information about active adult communities around Kissimmee?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Kissimmee?

Call us: (689) 215-8956
605 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top