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55+ Homes for Sale in Kissimmee

by Ryan Erisman | Updated: February 7, 2024

Located just south of Orlando, Kissimmee is consistently listed among the best places to retire.

To get a better sense of what the real estate market is like in Kissimmee, take a look at some of the 55+ homes currently on the market below.

Also, two of our featured communities are in Kissimmee, and both are worth a closer look:

Solivita is an award-winning retirement community in Central Florida’s attraction zone. No matter where you live within this lush gated 55-plus community in Kissimmee, you can easily walk, bike or drive your golf cart to indoor and outdoor dining venues, state-of-the-art spa and fitness complexes, pickleball or tennis courts, and other facilities for sports and games.

With two stunning championship golf courses, intimate neighborhood centers, softball field, miles of green space for walking and biking, and too many classes and clubs to count, you will have many ways to enjoy the Solivita life.

Home prices start in the $200k's.

Learn More About Solivita

Four Seasons at Orlando is a gated community of 557 single-family homes located in Kissimmee, Florida, just south of Orlando. Amenities here include a 14,000-square-foot clubhouse with a state-of-the-art fitness center and an arts and crafts room, as well as an outdoor swimming pool, pickleball courts, and access to the 18-hole Mystic Dunes Golf Club. 

There are 7 floorplans that range in size from 1,428 to 2,328 square feet. Prices start in the $400k’s.

Learn More About Four Seasons at Orlando
532 CASANOVA COURT KISSIMMEE FL 34759
New Listing - 17 hours on site
1 / 42
$265,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,507
SQFT
532 CASANOVA COURT
KISSIMMEE, FL 34759
SOLIVITA PH 03B Subdivision
1390 HARBOR RIDGE DRIVE KISSIMMEE FL 34759
New Listing - 2 days on site
1 / 14
$359,990
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,703
SQFT
1390 HARBOR RIDGE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 7D Subdivision
619 TAPATIO LANE KISSIMMEE FL 34759
New Listing - 4 days on site
1 / 50
$629,000
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
2,881
SQFT
619 TAPATIO LANE
KISSIMMEE, FL 34759
SOLIVITA PH 07C Subdivision
1855 FLORA PASS PLACE KISSIMMEE FL 34747
New Listing - 4 days on site
1 / 20
$375,000
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,437
SQFT
1855 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
684 GRAND CANAL DRIVE KISSIMMEE FL 34759
New Listing - 7 days on site
1 / 27
$229,900
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,387
SQFT
684 GRAND CANAL DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 03B Subdivision
2376 PALM TREE DRIVE KISSIMMEE FL 34759
New Listing - 7 days on site
1 / 41
$304,900
Residential For Sale
Active
2
BEDS
2
TOTAL BATHS
1,539
SQFT
2376 PALM TREE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 5F Subdivision
149 ACADIA DRIVE KISSIMMEE FL 34759
New Listing - a week on site
1 / 24
$225,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,240
SQFT
149 ACADIA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 04B Subdivision
428 BEL AIR WAY KISSIMMEE FL 34759
New Listing - 2 weeks on site
1 / 42
$550,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,023
SQFT
428 BEL AIR WAY
KISSIMMEE, FL 34759
SOLIVITA PH 7G UN 2 Subdivision
433 VIA ABRUZZI STREET KISSIMMEE FL 34759
New Listing - 2 weeks on site
1 / 65
$620,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,400
SQFT
433 VIA ABRUZZI STREET
KISSIMMEE, FL 34759
SOLIVITA PH 5-B A Subdivision
1598 WHITEWOOD COURT KISSIMMEE FL 34747
Open House Sat, May 17, 4 PM UTC
1 / 32
$535,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,063
SQFT
1598 WHITEWOOD COURT
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3B & 4A Subdivision
817 GRAND CANAL DRIVE KISSIMMEE FL 34759
New Listing - 3 weeks on site
1 / 43
$264,900
Single Family Residence For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,507
SQFT
817 GRAND CANAL DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 03B Subdivision
2225 SEAGRASS POINT 470 KISSIMMEE FL 34747
New Listing - 3 weeks on site
1 / 41
$501,952
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
2,118
SQFT
2225 SEAGRASS POINT 470
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
1825 PELICAN HILL WAY KISSIMMEE FL 34759
New Listing - 4 weeks on site
1 / 35
$284,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,515
SQFT
1825 PELICAN HILL WAY
KISSIMMEE, FL 34759
SOLIVITA PH 7D Subdivision
271 FALLING WATERS DRIVE KISSIMMEE FL 34759
New Listing - 4 weeks on site
1 / 47
$396,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,326
SQFT
271 FALLING WATERS DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 01 Subdivision
1948 MOLISE DRIVE KISSIMMEE FL 34759
New Listing - 4 weeks on site
1 / 59
$419,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,849
SQFT
1948 MOLISE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 5E-S Subdivision
469 SORRENTO ROAD KISSIMMEE FL 34759
1 / 53
$535,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,616
SQFT
469 SORRENTO ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 06B Subdivision
611 SAN RAPHAEL STREET KISSIMMEE FL 34759
1 / 47
$625,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,430
SQFT
611 SAN RAPHAEL STREET
KISSIMMEE, FL 34759
SOLIVITA PH 51 Subdivision
134 MELODY LN KISSIMMEE FL 34759
1 / 47
$305,000
Single Family Residence For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,574
SQFT
134 MELODY LN
KISSIMMEE, FL 34759
SOLIVITA PH 02D Subdivision
151 BELL TOWER XING W KISSIMMEE FL 34759
1 / 52
$255,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,356
SQFT
151 BELL TOWER XING W
KISSIMMEE, FL 34759
SOLIVITA - PHASE IIB Subdivision
3775 VIA MAZZINI COURT KISSIMMEE FL 34759
1 / 52
$549,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,495
SQFT
3775 VIA MAZZINI COURT
KISSIMMEE, FL 34759
SOLIVITA PH 5H UN 1 Subdivision
1671 KEY BAY TRAIL KISSIMMEE FL 34747
Price Change - 3 days ago
1 / 32
$359,900
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,557
SQFT
1671 KEY BAY TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
2192 SEAGRASS POINT 427 KISSIMMEE FL 34747
Price Change - 4 weeks ago
1 / 19
$486,606
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
2,029
SQFT
2192 SEAGRASS POINT 427
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
2168 SEAGRASS POINT 424 KISSIMMEE FL 34747
Price Change - 4 weeks ago
1 / 15
$474,162
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,969
SQFT
2168 SEAGRASS POINT 424
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
1001 PLANTATION DRIVE D5 KISSIMMEE FL 34741
1 / 27
$149,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
800
SQFT
1001 PLANTATION DRIVE D5
KISSIMMEE, FL 34741
HERITAGE HOUSE CONDOS Subdivision
722 PORTOFINO DRIVE KISSIMMEE FL 34759
Price Change - 3 hours ago
1 / 61
$340,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,229
SQFT
722 PORTOFINO DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 04C SEC 02 Subdivision
555 PRESIDO PARK PLACE KISSIMMEE FL 34759
1 / 44
$310,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,610
SQFT
555 PRESIDO PARK PLACE
KISSIMMEE, FL 34759
SOLIVITA PH 07D Subdivision
7928 HANSON BAY PLACE KISSIMMEE FL 34747
Price Change - 3 weeks ago
1 / 86
$590,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,066
SQFT
7928 HANSON BAY PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 1 Subdivision
2087 FLORA PASS PLACE KISSIMMEE FL 34747
1 / 94
$499,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,778
SQFT
2087 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
187 INDIAN WELLS AVENUE KISSIMMEE FL 34759
1 / 56
$400,000
Single Family Residence For Sale
Pending
2
BEDS
3
TOTAL BATHS
2,343
SQFT
187 INDIAN WELLS AVENUE
KISSIMMEE, FL 34759
SOLIVITA PH 07B2 Subdivision
4311 VIA CAVOUR COURT KISSIMMEE FL 34759
1 / 60
$479,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,003
SQFT
4311 VIA CAVOUR COURT
KISSIMMEE, FL 34759
SOLIVITA-PH 5H-UN 1 Subdivision
159 VENTANA DRIVE KISSIMMEE FL 34759
1 / 46
$339,500
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,813
SQFT
159 VENTANA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 02C Subdivision
1905 ESTUARY LANE KISSIMMEE FL 34747
1 / 41
$750,000
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,754
SQFT
1905 ESTUARY LANE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
2017 FLORA PASS PLACE KISSIMMEE FL 34747
Open House Sat, May 17, 4:30 PM UTC
1 / 63
$484,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,202
SQFT
2017 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
1972 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
Price Change - 3 weeks ago
1 / 36
$535,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,797
SQFT
1972 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5A Subdivision
2120 ANTILLES CLUB DRIVE 10 KISSIMMEE FL 34747
Price Change - 4 weeks ago
1 / 27
$475,593
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
2,029
SQFT
2120 ANTILLES CLUB DRIVE 10
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 1 Subdivision
196 KNOLL WOOD DRIVE KISSIMMEE FL 34759
Price Change - 3 weeks ago
1 / 60
$220,000
Single Family Residence For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,574
SQFT
196 KNOLL WOOD DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 02C Subdivision
672 SAN JOAQUIN ROAD KISSIMMEE FL 34759
1 / 69
$445,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,190
SQFT
672 SAN JOAQUIN ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 7G Subdivision
7637 SAND PIERRE COURT KISSIMMEE FL 34747
1 / 40
$455,900
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,557
SQFT
7637 SAND PIERRE COURT
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
1062 UMBRIA DRIVE KISSIMMEE FL 34759
Price Change - 6 days ago
1 / 56
$355,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,655
SQFT
1062 UMBRIA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 5C Subdivision
308 VESTRELLA DRIVE KISSIMMEE FL 34759
1 / 44
$335,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,703
SQFT
308 VESTRELLA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 7F Subdivision
181 TALL PINES PASS KISSIMMEE FL 34759
1 / 32
$309,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,813
SQFT
181 TALL PINES PASS
KISSIMMEE, FL 34759
SOLIVITA PH IIB Subdivision
1987 KEY BAY TRAIL KISSIMMEE FL 34747
Price Change - 3 weeks ago
1 / 53
$380,000
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,437
SQFT
1987 KEY BAY TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 4B Subdivision
560 PRESIDO PARK PLACE KISSIMMEE FL 34759
Price Change - 3 weeks ago
0 / 0
$285,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,658
SQFT
560 PRESIDO PARK PLACE
KISSIMMEE, FL 34759
SOLIVITA PH 7D Subdivision
2448 PALM TREE DRIVE KISSIMMEE FL 34759
Price Change - 3 weeks ago
1 / 54
$314,900
Townhouse For Sale
Active
3
BEDS
2
TOTAL BATHS
1,539
SQFT
2448 PALM TREE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 5F Subdivision
2200 SEAGRASS POINT 428 KISSIMMEE FL 34747
1 / 16
$552,835
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
2,063
SQFT
2200 SEAGRASS POINT 428
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
243 NEW RIVER DRIVE KISSIMMEE FL 34759
1 / 55
$290,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,560
SQFT
243 NEW RIVER DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 01 Subdivision
501 HERITAGE TRAIL STREET KISSIMMEE FL 34759
1 / 55
$330,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,574
SQFT
501 HERITAGE TRAIL STREET
KISSIMMEE, FL 34759
SOLIVITA PH 03B Subdivision
195 CASAVISTA DRIVE KISSIMMEE FL 34759
1 / 54
$530,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,982
SQFT
195 CASAVISTA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 1H-UN 2 Subdivision
972 LADERA RANCH ROAD KISSIMMEE FL 34759
Price Change - 3 weeks ago
1 / 34
$514,995
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,318
SQFT
972 LADERA RANCH ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 7E UN 2 Subdivision
955 LADERA RANCH ROAD KISSIMMEE FL 34759
Price Change - 4 weeks ago
1 / 50
$474,900
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,224
SQFT
955 LADERA RANCH ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 7E UN 2 Subdivision
1287 GLENDORA ROAD KISSIMMEE FL 34759
1 / 76
$325,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,339
SQFT
1287 GLENDORA ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 04C SEC 01 Subdivision
1221 GLENDORA ROAD N KISSIMMEE FL 34759
Price Change - 3 weeks ago
1 / 46
$410,000
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,325
SQFT
1221 GLENDORA ROAD N
KISSIMMEE, FL 34759
SOLIVITA PH 04C SEC 01 Subdivision
2160 ANTILLES CLUB DRIVE KISSIMMEE FL 34747
Price Change - 3 days ago
1 / 34
$408,800
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,778
SQFT
2160 ANTILLES CLUB DRIVE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 1 Subdivision
2071 LIMESTONE TRAIL KISSIMMEE FL 34747
1 / 99
$580,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,066
SQFT
2071 LIMESTONE TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
217 ANASTASIA DRIVE KISSIMMEE FL 34759
1 / 83
$339,500
Single Family Residence For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,467
SQFT
217 ANASTASIA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 01 Subdivision
350 BALBOA DRIVE KISSIMMEE FL 34759
1 / 46
$420,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,334
SQFT
350 BALBOA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 02A Subdivision
540 GRAND CANAL DRIVE KISSIMMEE FL 34759
Price Change - 2 weeks ago
1 / 35
$229,900
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,507
SQFT
540 GRAND CANAL DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 03A Subdivision
2132 ANTILLES CLUB DRIVE KISSIMMEE FL 34747
1 / 45
$449,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,770
SQFT
2132 ANTILLES CLUB DRIVE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 1 Subdivision
316 SHELBOURNE LOOP KISSIMMEE FL 34759
Real Estate Owned
1 / 36
$254,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,797
SQFT
316 SHELBOURNE LOOP
KISSIMMEE, FL 34759
SOLIVITA PH 02A Subdivision
154 RANCHO MIRAGE DRIVE KISSIMMEE FL 34759
1 / 68
$644,900
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,616
SQFT
154 RANCHO MIRAGE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 07C Subdivision

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