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

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Active 2907 Summer Green Tr, KISSIMMEE

$449,900

MARBELLA PH 2

2907 Summer Green Tr, KISSIMMEE

4 Beds 3 Baths 2,344 SqFt Residential Single Family Residence MLS® # TB8511167
Active 3251 Pinewood Ct, KISSIMMEE

$449,900

PLEASANT HILL LAKES UNIT 08

3251 Pinewood Ct, KISSIMMEE

3 Beds 2 Baths 2,404 SqFt Residential Single Family Residence MLS® # O6427499
Active 3251 Secret Lake Dr 1214, KISSIMMEE

$449,900

▲ $5,000 AMBAR RESIDENCES

3251 Secret Lake Dr 1214, KISSIMMEE

1 Bed 1 Bath 656 SqFt Residential Condo - Hotel MLS® # O6353437
Active Barn St, KISSIMMEE

$449,900

▼ $146,099 MARYDIA

Barn St, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5143269
Active 7667 Otterspool St, KISSIMMEE

$449,000

WINDSOR HILLS PH 2

7667 Otterspool St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Residential Townhouse MLS® # S5151169
Active 3197 Pequod Pl, KISSIMMEE

$449,000

▼ $16,000 STOREY LAKE PH 1B-2A

3197 Pequod Pl, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6442811
Active 3982 Blossom Dew Dr, KISSIMMEE

$449,000

ORANGEBRANCH BAY

3982 Blossom Dew Dr, KISSIMMEE

4 Beds 3 Baths 2,579 SqFt Residential Single Family Residence MLS® # O6420101
Active 1877 Summer Serenity Dr, KISSIMMEE

$449,000

▼ $14,000 TOHOQUA PH 4A

1877 Summer Serenity Dr, KISSIMMEE

4 Beds 3 Baths 2,776 SqFt Residential Single Family Residence MLS® # O6354995
Active 2631 E Lake Pointe Dr, KISSIMMEE

$449,000

EAST LAKE PRESERVE PH 3

2631 E Lake Pointe Dr, KISSIMMEE

4 Beds 3 Baths 2,463 SqFt Residential Single Family Residence MLS® # O6443939
Active 4258 Twisted Twig Bnd, KISSIMMEE

$449,000

STOREY CREEK

4258 Twisted Twig Bnd, KISSIMMEE

5 Beds 3 Baths 2,388 SqFt Residential Single Family Residence MLS® # S5152122
Active 3061 Rockefeller Way, KISSIMMEE

$449,000

MAGIC VILLAGE RESORT 2

3061 Rockefeller Way, KISSIMMEE

3 Beds 4 Baths 2,195 SqFt Residential Townhouse MLS® # O6424190
Active 7952 Formosa Valley Pl, KISSIMMEE

$449,000

▼ $6,000 FORMOSA VALLEY

7952 Formosa Valley Pl, KISSIMMEE

4 Beds 5 Baths 2,112 SqFt Residential Townhouse MLS® # O6427425
Active 2936 Slough Creek Dr, KISSIMMEE

$449,000

▼ $55,990 CREEKSIDE

2936 Slough Creek Dr, KISSIMMEE

5 Beds 3 Baths 2,748 SqFt Residential Single Family Residence MLS® # S5134409
Active 4466 Great Harbor Ln, KISSIMMEE

$449,000

BASS LAKE ESTATES

4466 Great Harbor Ln, KISSIMMEE

3 Beds 2 Baths 1,486 SqFt Residential Single Family Residence MLS® # S5156101
Active 3119 Rockefeller Way, KISSIMMEE

$449,000

MAGIC VILLAGE RESORT 2

3119 Rockefeller Way, KISSIMMEE

3 Beds 4 Baths 2,195 SqFt Residential Townhouse MLS® # O6385107
Active 8932 Sydney Ave, KISSIMMEE

$449,000

WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE

8932 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # O6412966
Active 7455 Brooklyn Dr, KISSIMMEE

$447,900

▼ $24,100 MAGIC VILLAGE RESORT 2

7455 Brooklyn Dr, KISSIMMEE

3 Beds 4 Baths 2,195 SqFt Residential Townhouse MLS® # O6397425
Active 7571 Sunny Dreams Lane Na, KISSIMMEE

$447,000

▼ $38,000 SUMMERVILLE RESORT

7571 Sunny Dreams Lane Na, KISSIMMEE

4 Beds 5 Baths 1,804 SqFt Residential Condominium MLS® # O6411224
Active 1974 Spring Shower Cir, KISSIMMEE

$447,000

▼ $2,000 TOHOQUA PH 5A

1974 Spring Shower Cir, KISSIMMEE

3 Beds 3 Baths 2,175 SqFt Residential Single Family Residence MLS® # O6418282
Active 2914 Blooming Alamanda Loop, KISSIMMEE

$445,900

OAK ISLAND COVE

2914 Blooming Alamanda Loop, KISSIMMEE

4 Beds 3 Baths 1,662 SqFt Residential Single Family Residence MLS® # S5154555
Active 2887 Sweetspire Cir, KISSIMMEE

$445,900

BRIGHTON LAKES PH 2 PRCL J

2887 Sweetspire Cir, KISSIMMEE

5 Beds 3 Baths 3,387 SqFt Residential Single Family Residence MLS® # S5157561
Active 4760 Goodmans Bay Dr, KISSIMMEE

$445,690

WESTVIEW

4760 Goodmans Bay Dr, KISSIMMEE

5 Beds 3 Baths 2,520 SqFt Residential Single Family Residence MLS® # W7889613
Active 4982 Windermere Ave, KISSIMMEE

$445,000

▼ $10,000 STOREY LAKE PH 3

4982 Windermere Ave, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6402327
Open House
Active 611 Abaco Ct, KISSIMMEE

$445,000

▼ $4,999 BASS LAKE ESTATES

611 Abaco Ct, KISSIMMEE

5 Beds 4 Baths 2,625 SqFt Residential
Sun, Oct 4th, 2026 @ 2pm - 5pm
Single Family Residence MLS® # O6435668
Active 3181 Brasilia Ave, KISSIMMEE

$445,000

MAGIC VILLAGE

3181 Brasilia Ave, KISSIMMEE

3 Beds 4 Baths 2,268 SqFt Residential Townhouse MLS® # O6355090
Active 1496 Brentwood Dr, KISSIMMEE

$445,000

KNIGHTSBRIDGE 50S

1496 Brentwood Dr, KISSIMMEE

3 Beds 2 Baths 1,580 SqFt Residential Single Family Residence MLS® # O6422761
Active 8942 Sydney Ave, KISSIMMEE

$445,000

▼ $13,000 WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE

8942 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6404821
Active 313 Santa Barbara Ln, KISSIMMEE

$445,000

▼ $4,900 SOLIVITA PH 07B2

313 Santa Barbara Ln, KISSIMMEE

2 Beds 3 Baths 2,343 SqFt Residential Single Family Residence MLS® # S5131195
Active 2948 Crest Dr, KISSIMMEE

$445,000

MARBELLA PH 2

2948 Crest Dr, KISSIMMEE

4 Beds 3 Baths 1,923 SqFt Residential Single Family Residence MLS® # O6409508
Active 2637 Sunrise Shores Dr, KISSIMMEE

$445,000

▼ $20,000 SUMMERVILLE RESORT

2637 Sunrise Shores Dr, KISSIMMEE

4 Beds 5 Baths 1,804 SqFt Residential Townhouse MLS® # O6374492
Active 1869 Nice Ct, KISSIMMEE

$445,000

▼ $5,000 WINDSOR AT WESTSIDE PH 2A

1869 Nice Ct, KISSIMMEE

5 Beds 4 Baths 2,492 SqFt Residential Single Family Residence MLS® # O6383451
Active 8936 Sydney Ave, KISSIMMEE

$445,000

WINDSOR AT WESTSIDE PH 3

8936 Sydney Ave, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # O6374304
Active 1100 Saint Michel Way, KISSIMMEE

$445,000

POINCIANA VILLAGE 5 NBHD 1

1100 Saint Michel Way, KISSIMMEE

6 Beds 5 Baths 4,216 SqFt Residential Single Family Residence MLS® # O6443264
Open House
Active 1508 Jenni Lee Ct, KISSIMMEE

$444,900

WOODS AT KINGS CREST THE PH 1

1508 Jenni Lee Ct, KISSIMMEE

3 Beds 3 Baths 2,077 SqFt Residential
Sun, Oct 4th, 2026 @ 12pm - 3pm
Single Family Residence MLS® # S5158025
Active 4827 Clock Tower Dr, KISSIMMEE

$444,900

STOREY LAKE

4827 Clock Tower Dr, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6340940
Active 4337 Quote St, KISSIMMEE

$444,000

▼ $10,000 COVE AT STOREY LAKE III

4337 Quote St, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6427004
Active 3539 Maple Ridge Loop, KISSIMMEE

$444,000

FOREST EDGE

3539 Maple Ridge Loop, KISSIMMEE

4 Beds 2 Baths 2,298 SqFt Residential Single Family Residence MLS® # O6386171
Open House
Active 5210 Worchester Dr, KISSIMMEE

$443,320

▲ $100 KNIGHTSBRIDGE 50S

5210 Worchester Dr, KISSIMMEE

4 Beds 3 Baths 2,584 SqFt Residential
Sun, Oct 4th, 2026 @ 9am - 5pm
Single Family Residence MLS® # O6442469
Active 2677 Rania Ln, KISSIMMEE

$440,144

▼ $3,855 HILLIARD RIDG

2677 Rania Ln, KISSIMMEE

4 Beds 2 Baths 1,723 SqFt Residential Single Family Residence MLS® # O6427175
Active 1974 Majorca Dr, KISSIMMEE

$440,000

▼ $4,900 WINDSOR AT WESTSIDE PH 1

1974 Majorca Dr, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # S5151890
Active 3215 Stratton Cir, KISSIMMEE

$440,000

▼ $10,000 SOUTH POINTE

3215 Stratton Cir, KISSIMMEE

4 Beds 3 Baths 2,432 SqFt Residential Single Family Residence MLS® # S5150428
Active 4980 Warrior Ln, KISSIMMEE

$440,000

INDIAN WELLS UNIT 5

4980 Warrior Ln, KISSIMMEE

3 Beds 2 Baths 1,330 SqFt Residential Single Family Residence MLS® # S5147417
Active 3011 Bransbury Ct, KISSIMMEE

$440,000

▼ $5,000 LINDFIELDS UNIT 1

3011 Bransbury Ct, KISSIMMEE

4 Beds 3 Baths 2,230 SqFt Residential Single Family Residence MLS® # S5113614
Active 2333 Walnut Canyon Dr, KISSIMMEE

$439,999

BLACKSTONE LANDING PH 2

2333 Walnut Canyon Dr, KISSIMMEE

4 Beds 3 Baths 2,520 SqFt Residential Single Family Residence MLS® # S5157794
Active 2830 Paynes Prairie Cir, KISSIMMEE

$439,999

▼ $10,000 HERITAGE LAKES PH 2

2830 Paynes Prairie Cir, KISSIMMEE

4 Beds 3 Baths 2,746 SqFt Residential Single Family Residence MLS® # O6434733
Active 3028 Camino Real Dr S, KISSIMMEE

$439,995

VILLA SOL PH 02 VILLAGE 03

3028 Camino Real Dr S, KISSIMMEE

4 Beds 2 Baths 2,259 SqFt Residential Single Family Residence MLS® # O6426588
Active 1732 Flourish Ave, KISSIMMEE

$439,990

▼ $10,000 TOHOQUA PH 1

1732 Flourish Ave, KISSIMMEE

4 Beds 3 Baths 2,234 SqFt Residential Single Family Residence MLS® # S5152529
New
Active 7937 Formosa Valley Pl, KISSIMMEE

$439,990

FORMOSA VALLEY

7937 Formosa Valley Pl, KISSIMMEE

4 Beds 5 Baths 2,112 SqFt Residential Townhouse MLS® # O6444927