not an image

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

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

29 communities 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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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 (7 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
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
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
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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
Westhaven at Ovation - To...
$400ks - $500ks
Westhaven at Ovation - To..., Winter Garden, FL
New Construction | Age-targeted | Built 2025 - present
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
3.9 rating (7 reviews) Summit Greens
$300ks - $400ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Lake Henry Estates
$100ks - $300ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 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
5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 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.
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Enclave at VillageWalk
$700ks - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Serenity Reserve
$400ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 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
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
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Solivita 373 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$349,900

2 beds

|

2 baths

|

1,658 sq ft

|

House

373 VESTRELLA DR, POINCIANA, FL, 34759
Community: Solivita
Twin Lakes 2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$550,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Sunbridge 2743 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771
$679,900

3 beds

|

3 baths

|

2,321 sq ft

|

House

2743 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Solivita 280 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$379,900

2 beds

|

2 baths

|

2,105 sq ft

|

House

280 INDIAN WELLS AVE, KISSIMMEE, FL, 347...
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Del Webb Sunbridge 2732 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771
$350,000

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2732 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
Carlsberg Estates on Lake Suzanne 364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$284,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
New Solivita 2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$287,500

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

2316 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
New Kings Ridge 3515 CHESSINGTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$449,900

2 beds

|

2 baths

|

2,010 sq ft

|

House

3515 CHESSINGTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
New Solivita 624 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$279,900

2 beds

|

2 baths

|

1,543 sq ft

|

House

624 GRAND CANAL 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.
New Del Webb Orlando 389 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$359,900

2 beds

|

2 baths

|

1,668 sq ft

|

House

389 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Solivita 1144 VIA GALUPPI ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$365,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

1144 VIA GALUPPI ST, KISSIMMEE, FL, 3475...
Community: Solivita
New VillageWalk at Lake Nona 12236 PESCARA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$449,900

3 beds

|

2 baths

|

1,708 sq ft

|

Halfplex

12236 PESCARA LN, ORLANDO, FL, 32827
New Lake Ashton 4227 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,900

3 beds

|

2 baths

|

1,847 sq ft

|

House

4227 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Lake Ashton 5308 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$255,000

3 beds

|

2 baths

|

1,495 sq ft

|

House

5308 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
New Lake Ashton 1061 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$449,900

3 beds

|

2 baths

|

2,069 sq ft

|

House

1061 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Oakview 1525 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$200,000

2 beds

|

2 baths

|

1,333 sq ft

|

Villa

1525 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
New Gatherings of Lake Nona 7557 LAUREATE BLVD 6407, ORLANDO, FL, 32..., Orlando, FL 32827
$575,000

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7557 LAUREATE BLVD 6407, ORLANDO, FL, 32...
New Solivita 674 VINEYARD WAY 6747, POINCIANA, FL, 34..., Poinciana, FL 34759
$280,000

2 beds

|

2 baths

|

1,387 sq ft

|

House

674 VINEYARD WAY 6747, POINCIANA, FL, 34...
Community: Solivita
New Heritage Hills 3572 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3572 KINLEY BROOKE LN, CLERMONT, FL, 347...
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.
New Heritage Hills 3648 SOLANA CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$279,899

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3648 SOLANA CIR, CLERMONT, FL, 34711
Community: Heritage Hills
New Kings Ridge 4065 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$378,000

2 beds

|

2 baths

|

1,997 sq ft

|

House

4065 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
New Solivita 106 PRIMA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$419,000

2 beds

|

3 baths

|

2,357 sq ft

|

House

106 PRIMA DR, POINCIANA, FL, 34759
Community: Solivita
New Palms at Serenoa 17718 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

2 beds

|

2 baths

|

1,822 sq ft

|

House

17718 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
New Solivita 157 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$320,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

157 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
New Solivita 518 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$346,000

2 beds

|

2 baths

|

1,491 sq ft

|

House

518 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
New Lake Ashton 5337 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$355,000

3 beds

|

2 baths

|

1,833 sq ft

|

House

5337 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Twin Lakes 2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$549,700

3 beds

|

3 baths

|

2,362 sq ft

|

House

2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
New Del Webb Sunbridge 2542 CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$329,000

2 beds

|

2 baths

|

1,584 sq ft

|

House

2542 CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
New Vienna Square 1674 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$242,000

2 beds

|

2 baths

|

1,350 sq ft

|

Villa

1674 LINZ CT, WINTER HAVEN, FL, 33884
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.
New Gatherings of Lake Nona 7505 LAUREATE BLVD 2206, ORLANDO, FL, 32..., Orlando, FL 32827
$420,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7505 LAUREATE BLVD 2206, ORLANDO, FL, 32...
New VillageWalk at Lake Nona 12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$919,000

5 beds

|

4 baths

|

4,036 sq ft

|

House

12077 ULETA LN, ORLANDO, FL, 32827
New Gatherings of Lake Nona 7521 LAUREATE BLVD 5307, ORLANDO, FL, 32..., Orlando, FL 32827
$524,900

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7521 LAUREATE BLVD 5307, ORLANDO, FL, 32...
New Del Webb Sunbridge 6261 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$540,000

2 beds

|

2 baths

|

1,919 sq ft

|

House

6261 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
New Solivita 218 BAY DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$465,000

3 beds

|

2 baths

|

1,842 sq ft

|

House

218 BAY DR, KISSIMMEE, FL, 34759
Community: Solivita
New Tohoqua Reserve 1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$450,000

3 beds

|

3 baths

|

2,175 sq ft

|

House

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
New Kings Ridge 3916 PAYTON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$519,000

3 beds

|

3 baths

|

2,722 sq ft

|

House

3916 PAYTON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Gatherings of Lake Nona 7505 LAUREATE BLVD 2208, ORLANDO, FL, 32..., Orlando, FL 32827
$349,900

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7505 LAUREATE BLVD 2208, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Traditions at Lake Ruby 3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$320,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Del Webb Sunbridge 2617 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3..., St Cloud, FL 34771
$387,176

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

2617 HAMMOCK HARBOR AVE, ST CLOUD, FL, 3...
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.

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 [email protected]. 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
29 communities
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: Jun 29, 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