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

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

27 communities near Kissimmee

Sort by:

Relevance

Relevance

4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Four Seasons at Orlando
$300Ks - $700Ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Tohoqua Reserve
$300Ks - $400Ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 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.
3.9 rating (7 reviews) Summit Greens
$300Ks - $500Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 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
5 rating (2 reviews) Palms at Serenoa
$300Ks - $500Ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
3.8 rating (5 reviews) Traditions at Lake Ruby
$200Ks - $400Ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 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
5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
Lake Henry Estates
$100Ks - $200Ks
Lake Henry Estates, Haines City, FL
Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes
Gatherings of Lake Nona
$300Ks - $400Ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
Vienna Square
$100Ks - $300Ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Carlsberg Estates on Lake...
$200Ks - $300Ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 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
$1Ms - $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
Serenity Reserve
$500Ks - $600Ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
Spring Lake Towers
$100Ks - $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
Poinsettia Heights
$100Ks - $200Ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Oakview
$200Ks - $200Ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Preserve at Lakeside Land...
$300Ks - $300Ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
New Kings Ridge 3516 CHAPEL HILL BLVD, CLERMONT, FL, 347..., Clermont, FL 34711
$429,990

3 beds

|

2 baths

|

1,846 sq ft

|

House

3516 CHAPEL HILL BLVD, CLERMONT, FL, 347...
Community: Kings Ridge
New Lake Ashton 2204 ASHTON PALMS DR # 2204, LAKE WALES,..., Lake Wales, FL 33859
$250,000

3 beds

|

2 baths

|

1,362 sq ft

|

Condo

2204 ASHTON PALMS DR # 2204, LAKE WALES,...
Community: Lake Ashton
Four Seasons at Orlando 7632 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$349,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

7632 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Palms at Serenoa 17581 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714
$344,900

2 beds

|

2 baths

|

1,627 sq ft

|

Villa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347...
Community: Palms at Serenoa
Solivita 972 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$475,000

3 beds

|

3 baths

|

2,318 sq ft

|

House

972 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Four Seasons at Orlando 2116 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$695,000

2 beds

|

3 baths

|

2,360 sq ft

|

House

2116 LIMESTONE TRL, KISSIMMEE, FL, 34747
New Kings Ridge 3707 FAIRFIELD DR, CLERMONT, FL, 34711, Clermont, FL 34711
$419,000

3 beds

|

2 baths

|

2,105 sq ft

|

House

3707 FAIRFIELD DR, CLERMONT, FL, 34711
Community: Kings Ridge
Del Webb Orlando 409 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$419,990

3 beds

|

2 baths

|

2,009 sq ft

|

House

409 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Twin Lakes 2772 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$499,900

3 beds

|

2 baths

|

1,863 sq ft

|

House

2772 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Twin Lakes 2621 REDBLUSH TER, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$477,900

3 beds

|

3 baths

|

1,982 sq ft

|

House

2621 REDBLUSH TER, SAINT CLOUD, FL, 3477...
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.
New Spring Lake Towers 700 MIRROR TER 505, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$139,400

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 505, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Traditions at Lake Ruby 3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$285,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

3365 RALEIGH DR, WINTER HAVEN, FL, 33884
Four Seasons at Orlando 1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$360,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1991 KEY BAY TRL, KISSIMMEE, FL, 34747
New Palms at Serenoa 17613 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714
$335,000

2 beds

|

2 baths

|

1,627 sq ft

|

House

17613 SUMMERSWEET WAY, CLERMONT, FL, 347...
Community: Palms at Serenoa
New Palms at Serenoa 17590 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$478,000

4 beds

|

2 baths

|

2,034 sq ft

|

House

17590 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
New Del Webb Orlando 508 ZAMORA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$414,900

3 beds

|

2 baths

|

1,962 sq ft

|

House

508 ZAMORA WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Solivita 113 VENICE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$306,000

3 beds

|

2 baths

|

1,813 sq ft

|

House

113 VENICE LN, KISSIMMEE, FL, 34759
Community: Solivita
Palms at Serenoa 17571 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$400,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

17571 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
VillageWalk at Lake Nona 12021 JEWEL FISH LN, ORLANDO, FL, 32827, Orlando, FL 32827
$749,000

4 beds

|

4 baths

|

2,667 sq ft

|

House

12021 JEWEL FISH LN, ORLANDO, FL, 32827
High Vista at Ridgewood Lakes 205 CUNNINGHAM DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,502 sq ft

|

House

205 CUNNINGHAM DR, 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.
Traditions at Lake Ruby 2919 WOODWARD LN, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$350,000

3 beds

|

2 baths

|

1,649 sq ft

|

House

2919 WOODWARD LN, WINTER HAVEN, FL, 3388...
Twin Lakes 2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$304,900

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Del Webb Sunbridge 6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$450,000

3 beds

|

3 baths

|

1,738 sq ft

|

Townhouse

6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Solivita 836 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$253,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

836 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Twin Lakes 2454 DREAM HOME CT, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$777,900

3 beds

|

3 baths

|

2,208 sq ft

|

House

2454 DREAM HOME CT, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Want to learn more about 55+ communities in Kissimmee? 55places can help!
Questions? Call us: (689) 215-8956
Twin Lakes 2458 DREAM HOME CT, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$961,900

3 beds

|

3 baths

|

2,966 sq ft

|

House

2458 DREAM HOME CT, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Kings Ridge 2096 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$294,500

2 beds

|

2 baths

|

1,170 sq ft

|

House

2096 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
Traditions at Lake Ruby 3023 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$240,000

2 beds

|

2 baths

|

1,385 sq ft

|

Townhouse

3023 CANEEL ST, WINTER HAVEN, FL, 33884
Traditions at Lake Ruby 2825 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$233,000

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

2825 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Solivita 3432 FALLBROOK DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$312,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

3432 FALLBROOK DR, 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.
Lake Ashton 4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$424,000

3 beds

|

2 baths

|

2,027 sq ft

|

House

4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Solivita 543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$439,000

2 beds

|

3 baths

|

2,235 sq ft

|

House

543 VIA VITALE CT, KISSIMMEE, FL, 34759
Community: Solivita
New Del Webb Sunbridge 2479 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771
$575,000

4 beds

|

2 baths

|

2,054 sq ft

|

House

2479 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
New Palms at Serenoa 17418 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$415,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

17418 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
New Lake Ashton 5461 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$419,900

3 beds

|

2 baths

|

2,041 sq ft

|

House

5461 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
Solivita 428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$425,000

2 beds

|

2 baths

|

2,023 sq ft

|

House

428 BEL AIR WAY, KISSIMMEE, FL, 34759
Community: Solivita
New Lake Ashton 1069 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$375,000

2 beds

|

2 baths

|

1,688 sq ft

|

House

1069 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Esplanade at Highland Ranch 1339 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$630,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

1339 ZEEK RIDGE ST, CLERMONT, FL, 34715
Twin Lakes 5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$425,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
New Lake Henry Estates 488 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$279,000

2 beds

|

2 baths

|

1,386 sq ft

|

House

488 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates

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
27 communities near Kissimmee
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.
© 2025 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: Nov 07, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top