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 12

576 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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) Esplanade at Highland Ran...
$300ks - $600ks
Esplanade at Highland Ran..., Clermont, FL
Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes
Esplanade at Westview
$300ks - $700ks
Esplanade at Westview, Kissimmee, FL
New Construction | Age-targeted | Built 2025 - present | 600 homes
Westhaven at Ovation - To...
$400ks - $500ks
Westhaven at Ovation - To..., Winter Garden, FL
New Construction | Age-targeted | Built 2025 - present
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
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
Del Webb Lakehaven
$400ks - $800ks
Del Webb Lakehaven, Clermont, FL
New Construction | 55+ age-restricted | Built 2026 - present
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 (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.
Esplanade at McKinnon Gro...
$300ks - $900ks
Esplanade at McKinnon Gro..., Winter Garden, FL
New Construction | Age-targeted | Built 2024 - present | 658 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
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
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 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
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
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
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
Cindy Certified
342 RUSTIC RAIL DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$319,900

4 beds

|

2 baths

|

2,381 sq ft

|

House

342 RUSTIC RAIL DR, LAKE WALES, FL, 3385...
Twin Lakes 2388 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$294,999

2 beds

|

2 baths

|

1,351 sq ft

|

House

2388 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Four Seasons at Orlando 7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$675,000

3 beds

|

2 baths

|

1,969 sq ft

|

House

7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Kings Ridge 2282 FENTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

2 baths

|

1,896 sq ft

|

House

2282 FENTON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Gatherings of Lake Nona 7521 LAUREATE BLVD 5306, ORLANDO, FL, 32..., Orlando, FL 32827
$433,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7521 LAUREATE BLVD 5306, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Heritage Hills 4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

4052 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Vienna Square 1678 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$258,500

2 beds

|

2 baths

|

1,158 sq ft

|

House

1678 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Cindy Certified
383 LEMONGRASS RD, MINNEOLA, FL, 34715, Minneola, FL 34715
$550,000

4 beds

|

2 baths

|

2,103 sq ft

|

House

383 LEMONGRASS RD, MINNEOLA, FL, 34715
Cindy Certified
3116 NAMASTE DR, CLERMONT, FL, 34714, Clermont, FL 34714
$574,940

4 beds

|

2 baths

|

2,532 sq ft

|

House

3116 NAMASTE DR, CLERMONT, FL, 34714
Cindy Certified
2790 ADELINE AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33881
$269,900

3 beds

|

2 baths

|

1,328 sq ft

|

House

2790 ADELINE AVE, WINTER HAVEN, FL, 3388...
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 715 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$414,900

2 beds

|

2 baths

|

2,056 sq ft

|

House

715 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Sunbridge 2555 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771
$865,000

3 beds

|

4 baths

|

2,866 sq ft

|

House

2555 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
Kings Ridge 3635 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$388,800

2 beds

|

2 baths

|

1,661 sq ft

|

House

3635 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 162 TALL PINES PASS, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$315,000

2 beds

|

2 baths

|

2,038 sq ft

|

House

162 TALL PINES PASS, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 813 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$489,000

3 beds

|

3 baths

|

2,454 sq ft

|

House

813 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 113 TIVOLI TRACE CT, POINCIANA, FL, 3475..., Poinciana, FL 34759
$477,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

113 TIVOLI TRACE CT, POINCIANA, FL, 3475...
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Traditions at Lake Ruby 4020 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$405,900

4 beds

|

3 baths

|

2,282 sq ft

|

House

4020 CARTERET DR, WINTER HAVEN, FL, 3388...
Tohoqua Reserve 1823 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$394,900

3 beds

|

2 baths

|

1,579 sq ft

|

Halfplex

1823 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Lake Ashton 6261 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$565,000

3 beds

|

2 baths

|

2,512 sq ft

|

House

6261 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Lake Ashton 4432 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$235,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4432 TURNBERRY LN, LAKE WALES, FL, 33859
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.
Del Webb Sunbridge 6354 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771
$459,900

2 beds

|

2 baths

|

1,670 sq ft

|

House

6354 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
Cindy Certified
1292 SUGARWOOD ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$315,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

1292 SUGARWOOD ST, DAVENPORT, FL, 33837
Solivita 524 MURANO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$259,990

2 beds

|

2 baths

|

1,507 sq ft

|

House

524 MURANO DR, POINCIANA, FL, 34759
Community: Solivita
Cindy Certified
17896 PASSIONFLOWER CIR, CLERMONT, FL, 3..., Clermont, FL 34714
$559,900

4 beds

|

3 baths

|

2,356 sq ft

|

House

17896 PASSIONFLOWER CIR, CLERMONT, FL, 3...
Esplanade at Highland Ranch 2330 HAMILTON RIDGE RD, CLERMONT, FL, 34..., Clermont, FL 34715
$410,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

2330 HAMILTON RIDGE RD, CLERMONT, FL, 34...
Cindy Certified
3094 SANCTUARY DR, CLERMONT, FL, 34714, Clermont, FL 34714
$399,000

3 beds

|

2 baths

|

1,511 sq ft

|

House

3094 SANCTUARY DR, CLERMONT, FL, 34714
Cindy Certified
652 GROVE ST, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$370,000

4 beds

|

3 baths

|

2,080 sq ft

|

House

652 GROVE ST, WINTER HAVEN, FL, 33881
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Esplanade at Highland Ranch 1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$415,500

2 beds

|

2 baths

|

1,710 sq ft

|

House

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
Cindy Certified
1097 SANDPIPER LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881
$410,000

3 beds

|

2 baths

|

1,912 sq ft

|

House

1097 SANDPIPER LOOP, WINTER HAVEN, FL, 3...
Cindy Certified
2118 EDGEWATER CIR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33880
$399,000

4 beds

|

3 baths

|

2,763 sq ft

|

House

2118 EDGEWATER CIR, WINTER HAVEN, FL, 33...
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
13184 DENDY WAY, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$664,000

4 beds

|

3 baths

|

2,211 sq ft

|

House

13184 DENDY WAY, WINTER GARDEN, FL, 3478...
Cindy Certified
4724 BROOKSHIRE CT, LAKE WALES, FL, 3389..., Lake Wales, FL 33898
$524,900

4 beds

|

2 baths

|

2,116 sq ft

|

House

4724 BROOKSHIRE CT, LAKE WALES, FL, 3389...
Heritage Hills 3550 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711
$278,500

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3550 FAIRWATERS CT D, 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
4698 CORAL HARBOUR RD, KISSIMMEE, FL, 34..., Kissimmee, FL 34758
$429,900

4 beds

|

3 baths

|

2,394 sq ft

|

House

4698 CORAL HARBOUR RD, KISSIMMEE, FL, 34...
Gatherings of Lake Nona 7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827
$419,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Cindy Certified
326 DINNER LAKE CT, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$250,000

3 beds

|

2 baths

|

1,265 sq ft

|

House

326 DINNER LAKE CT, LAKE WALES, FL, 3385...
Oakview 1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880
$210,000

2 beds

|

2 baths

|

1,220 sq ft

|

House

1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Lake Ashton 5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$315,000

3 beds

|

2 baths

|

2,011 sq ft

|

House

5264 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Palms at Serenoa 3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714
$338,000

2 beds

|

2 baths

|

1,646 sq ft

|

House

3465 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
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
576 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: Aug 25, 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