Search Kissimmee Real Estate Listings, $400,000 - $500,000

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FEATURED
Active 2694 La Isla Ct, KISSIMMEE

$499,999

▼ $15,001 EMERALD ISLAND RESORT

2694 La Isla Ct, KISSIMMEE

5 Beds 3 Baths 2,317 SqFt Residential Single Family Residence MLS® # S5149891
FEATURED
Active 8965 Cuban Palm Rd, KISSIMMEE

$469,000

▼ $10,000 PARADISE PALMS RESORT

8965 Cuban Palm Rd, KISSIMMEE

6 Beds 5 Baths 3,291 SqFt Residential Single Family Residence MLS® # S5147422
FEATURED
Active 1909 Majorca Dr, KISSIMMEE

$424,999

▼ $10,000 WINDSOR AT WESTSIDE

1909 Majorca Dr, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # S5149758
FEATURED
Active 3015 Yellow Lantana Ln, KISSIMMEE

$418,999

ENCANTADA

3015 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # S5126724
FEATURED
Active 2427 Dubai St, KISSIMMEE

$408,000

▼ $16,000 WINDSOR AT WESTSIDE

2427 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # S5123971
FEATURED
Active 1356 Centre Court Ridge Dr 303, KISSIMMEE

$404,000

▼ $6,000 REUNION RESORT, CENTRE COURT RIDGE

1356 Centre Court Ridge Dr 303, KISSIMMEE

3 Beds 3 Baths 1,590 SqFt Residential Condominium MLS® # S5153768
Active 3052 Gatsby St, KISSIMMEE

$500,000

STOREY LAKE PH 2

3052 Gatsby St, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6367814
Active 1711 Windward Oaks Ct, KISSIMMEE

$500,000

▼ $25,000 BELLALAGO

1711 Windward Oaks Ct, KISSIMMEE

5 Beds 5 Baths 3,189 SqFt Residential Single Family Residence MLS® # O6433747
Active 3092 Rockefeller Way, KISSIMMEE

$500,000

MAGIC VILLAGE RESORT 2

3092 Rockefeller Way, KISSIMMEE

4 Beds 6 Baths 2,356 SqFt Residential Townhouse MLS® # O6368277
Active 2606 Royal Fern Pl, KISSIMMEE

$500,000

▼ $30,000 DAHLIA RESERVE AT CRESCENT LAKES

2606 Royal Fern Pl, KISSIMMEE

6 Beds 4 Baths 2,658 SqFt Residential Single Family Residence MLS® # O6391472
Active 1672 Tropical Palms Cir, KISSIMMEE

$500,000

SOLARA RESIDENCE VACATION VILLAS

1672 Tropical Palms Cir, KISSIMMEE

6 Beds 5 Baths 2,294 SqFt Residential Townhouse MLS® # O6429663
Active 1733 Bridgets Ct, KISSIMMEE

$500,000

M3 AT KISSIMMEE BAY

1733 Bridgets Ct, KISSIMMEE

4 Beds 3 Baths 2,665 SqFt Residential Single Family Residence MLS® # O6428985
Active 2510 Amati Dr, KISSIMMEE

$500,000

TAPESTRY

2510 Amati Dr, KISSIMMEE

3 Beds 3 Baths 2,132 SqFt Residential Single Family Residence MLS® # O6437788
Active 8912 Rhodes St, KISSIMMEE

$500,000

▲ $10,000 WINDSOR AT WESTSIDE PH 1

8912 Rhodes St, KISSIMMEE

7 Beds 6 Baths 3,314 SqFt Residential Single Family Residence MLS® # S5148044
Active 3016 Camino Real Dr S, KISSIMMEE

$500,000

▼ $10,000 VILLA SOL PH 2 VILLAGE 3

3016 Camino Real Dr S, KISSIMMEE

4 Beds 2 Baths 2,074 SqFt Residential Single Family Residence MLS® # O6437303
New
Active 2963 Sera Bella Way, KISSIMMEE

$500,000

SERA BELLA

2963 Sera Bella Way, KISSIMMEE

3 Beds 3 Baths 2,416 SqFt Residential Single Family Residence MLS® # S5158839
Open House
Active 5683 Nevis Ter, KISSIMMEE

$499,999

ESPLANADE AT WESTVIEW

5683 Nevis Ter, KISSIMMEE

3 Beds 3 Baths 2,296 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 4pm
Single Family Residence MLS® # O6441274
Active 2466 Relaxing Ln, KISSIMMEE

$499,990

TOHOQUA PH 3

2466 Relaxing Ln, KISSIMMEE

4 Beds 3 Baths 2,151 SqFt Residential Single Family Residence MLS® # S5154219
Active 2353 Crescent Moon St, KISSIMMEE

$499,990

▼ $16,010 SEDONA PH 2

2353 Crescent Moon St, KISSIMMEE

5 Beds 4 Baths 3,438 SqFt Residential Single Family Residence MLS® # O6434813
Active 1791 Smarts Rule St, KISSIMMEE

$499,990

▼ $15,010 TOHOQUA PH 1B

1791 Smarts Rule St, KISSIMMEE

4 Beds 3 Baths 2,500 SqFt Residential Single Family Residence MLS® # S5155513
Active 2967 Penelope Loop, KISSIMMEE

$499,990

COVE AT STOREY LAKE 4

2967 Penelope Loop, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # S5142974
Active 8184 Fan Palm Way, KISSIMMEE

$499,900

▼ $30,000 WYNDHAM PALMS PH 1B

8184 Fan Palm Way, KISSIMMEE

6 Beds 4 Baths 2,368 SqFt Residential Single Family Residence MLS® # O6424807
Active 3087 Juliet Dr, KISSIMMEE

$499,900

STOREY LAKE

3087 Juliet Dr, KISSIMMEE

5 Beds 4 Baths 2,168 SqFt Residential Townhouse MLS® # O6434113
Active 1889 Rustic Falls Dr, KISSIMMEE

$499,900

KINDRED PH 1C

1889 Rustic Falls Dr, KISSIMMEE

4 Beds 4 Baths 3,099 SqFt Residential Single Family Residence MLS® # S5138827
Active 2821 Scenic Ln, KISSIMMEE

$499,900

NORTH SHORE VILLAGE

2821 Scenic Ln, KISSIMMEE

4 Beds 3 Baths 2,538 SqFt Residential Single Family Residence MLS® # O6379416
Active 3839 Golden Feather Way, KISSIMMEE

$499,900

▼ $19,000 BELLALAGO PH 4P

3839 Golden Feather Way, KISSIMMEE

4 Beds 4 Baths 3,032 SqFt Residential Single Family Residence MLS® # O6387485
Active 2207 Jessica Ln, KISSIMMEE

$499,900

WOODS AT KINGS CREST THE PH 1

2207 Jessica Ln, KISSIMMEE

4 Beds 3 Baths 1,978 SqFt Residential Single Family Residence MLS® # O6439173
Active 4613 Formby Ct, KISSIMMEE

$499,900

LAKE BERKLEY RESORT

4613 Formby Ct, KISSIMMEE

6 Beds 3 Baths 2,317 SqFt Residential Single Family Residence MLS® # O6436142
Active S Vernon Ave, KISSIMMEE

$499,900

▲ $20,000 MARIA W RAO

S Vernon Ave, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5092303
Active 4602 Cumbrian Lakes Dr, KISSIMMEE

$499,900

▼ $10,100 CUMBRIAN LAKES RESORT PH 1

4602 Cumbrian Lakes Dr, KISSIMMEE

5 Beds 5 Baths 2,636 SqFt Residential Single Family Residence MLS® # O6412906
Active 453 Sorrento Rd, KISSIMMEE

$499,900

SOLIVITA - PHASE VIB

453 Sorrento Rd, KISSIMMEE

3 Beds 4 Baths 2,580 SqFt Residential Single Family Residence MLS® # O6408903
Active N/A, KISSIMMEE

$499,900

PENNYROYAL

N/A, KISSIMMEE

4 Beds 3 Baths 2,272 SqFt Residential Single Family Residence MLS® # S5152516
Active 2924 Boating Blvd, KISSIMMEE

$499,900

▼ $20,000 SHINGLE CREEK RESERVE AT THE OAKS PH 3 & 4

2924 Boating Blvd, KISSIMMEE

5 Beds 3 Baths 2,842 SqFt Residential Single Family Residence MLS® # S5138344
Active 3133 Riachuelo Ln, KISSIMMEE

$499,900

▼ $39,100 VILLA SOL PH 1 VILLAGE 5

3133 Riachuelo Ln, KISSIMMEE

4 Beds 3 Baths 2,351 SqFt Residential Single Family Residence MLS® # O6430008
Active 2464 White Poppy Dr, KISSIMMEE

$499,900

▼ $15,100 MURANO AT WESTSIDE

2464 White Poppy Dr, KISSIMMEE

5 Beds 4 Baths 2,845 SqFt Residential Single Family Residence MLS® # S5147622
Active 1888 Gobi Dr, KISSIMMEE

$499,900

▼ $20,000 WINDSOR AT WESTSIDE PH 2A

1888 Gobi Dr, KISSIMMEE

6 Beds 5 Baths 3,142 SqFt Residential Single Family Residence MLS® # S5154103
Active 7581 Brooklyn Dr, KISSIMMEE

$499,900

MAGIC VILLAGE RESORT 2

7581 Brooklyn Dr, KISSIMMEE

4 Beds 5 Baths 2,356 SqFt Residential Townhouse MLS® # O6439073
Active 4733 Cumbriam Lakes Dr, KISSIMMEE

$499,000

CUMBRIAM LAKES DR

4733 Cumbriam Lakes Dr, KISSIMMEE

5 Beds 4 Baths 2,876 SqFt Residential Single Family Residence MLS® # S5145397
Open House
Active 3193 Toho Ct, KISSIMMEE

$499,000

▼ $20,900 FELLS COVE UNIT 1 PH 1

3193 Toho Ct, KISSIMMEE

4 Beds 2 Baths 2,420 SqFt Residential
Sun, Oct 11th, 2026 @ 1pm - 3pm
Single Family Residence MLS® # O6350540
Active 3910 Redfin Pl, KISSIMMEE

$499,000

▼ $26,000 BELLALAGO PH 4K

3910 Redfin Pl, KISSIMMEE

4 Beds 4 Baths 2,727 SqFt Residential Single Family Residence MLS® # S5150540
New
Active 2577 Oneida Loop, KISSIMMEE

$499,000

INDIAN CRK PH 06

2577 Oneida Loop, KISSIMMEE

5 Beds 4 Baths 2,136 SqFt Residential Single Family Residence MLS® # O6443443
Active 4436 Azure Isle Way, KISSIMMEE

$499,000

▼ $11,000 NORTH POINT PH 1B

4436 Azure Isle Way, KISSIMMEE

4 Beds 3 Baths 2,251 SqFt Residential Single Family Residence MLS® # O6379702
Active 2717 Eagle Cliff Dr, KISSIMMEE

$499,000

▼ $1,000 EAGLE LAKE PH 3

2717 Eagle Cliff Dr, KISSIMMEE

4 Beds 4 Baths 3,052 SqFt Residential Single Family Residence MLS® # S5141957
Active 9029 Flamingo Key Way, KISSIMMEE

$499,000

▼ $31,000 SOLARA RESORT

9029 Flamingo Key Way, KISSIMMEE

4 Beds 4 Baths 2,472 SqFt Residential Single Family Residence MLS® # O6409063
Active 2462 Dubai St, KISSIMMEE

$499,000

WINDSOR AT WESTSIDE PH 3A

2462 Dubai St, KISSIMMEE

5 Beds 4 Baths 2,492 SqFt Residential Single Family Residence MLS® # P4939824
Active 2429 Dubai St, KISSIMMEE

$499,000

▼ $20,900 WINDSOR AT WESTSIDE PH 3

2429 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6206939
Active 5500 Willow Bend Tr, KISSIMMEE

$499,000

▼ $16,000 WILLOW BEND AT CRESCENT LAKES

5500 Willow Bend Tr, KISSIMMEE

4 Beds 3 Baths 2,847 SqFt Residential Single Family Residence MLS® # S5147335
Active 4879 Clock Tower Dr, KISSIMMEE

$499,000

STOREY LAKE

4879 Clock Tower Dr, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6432058