Search Kissimmee Real Estate Listings, $300,000 - $400,000

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Active 2700 Camaro Dr, KISSIMMEE

$309,900

▼ $10,000 REGAL OAKS AT OLD TOWN

2700 Camaro Dr, KISSIMMEE

4 Beds 4 Baths 1,852 SqFt Residential Townhouse MLS® # O6434044
Active 1177 Seaside Mist Tr, KISSIMMEE

$309,900

SOLEIL AT WESTSIDE

1177 Seaside Mist Tr, KISSIMMEE

3 Beds 3 Baths 1,460 SqFt Residential Townhouse MLS® # S5153645
Active 136 Pompano Beach Dr, KISSIMMEE

$309,900

TERRA VERDE VILLAS PH 1

136 Pompano Beach Dr, KISSIMMEE

3 Beds 3 Baths 1,286 SqFt Residential Townhouse MLS® # O6408419
Active 17 S Flag Ct, KISSIMMEE

$309,900

POINCIANA VILLAGE 1 NBHD 3 SOUTH

17 S Flag Ct, KISSIMMEE

3 Beds 2 Baths 1,500 SqFt Residential Single Family Residence MLS® # O6418950
Active 2446 Temple Grove Ln, KISSIMMEE

$309,900

DONEGAN TWNHMS

2446 Temple Grove Ln, KISSIMMEE

3 Beds 3 Baths 1,423 SqFt Residential Townhouse MLS® # S5152136
Open House
Active 566 Oak Branch Cir, KISSIMMEE

$309,900

OAKS AT CYPRESS WOODS REP THE

566 Oak Branch Cir, KISSIMMEE

4 Beds 3 Baths 1,854 SqFt Residential
Sun, Oct 4th, 2026 @ 11am - 2pm
Single Family Residence MLS® # S5155434
Active 3206 Gold Ln, KISSIMMEE

$309,900

▼ $5,000 WEST LUCAYA VILLAGE

3206 Gold Ln, KISSIMMEE

4 Beds 3 Baths 1,694 SqFt Residential Townhouse MLS® # O6410198
Active 1418 Sarasota Dr, KISSIMMEE

$309,900

▼ $10,000 POINCIANA NBRHD 02 WEST VILLAGE 07

1418 Sarasota Dr, KISSIMMEE

4 Beds 3 Baths 2,224 SqFt Residential Single Family Residence MLS® # O6325670
Active 703 Robin Ct, KISSIMMEE

$309,000

▼ $5,999 POINCIANA NBRHD 05 NORTH VILLAGE 03

703 Robin Ct, KISSIMMEE

4 Beds 3 Baths 2,113 SqFt Residential Single Family Residence MLS® # O6422256
Active 2905 Satire St, KISSIMMEE

$309,000

▼ $11,000 STOREY LAKE

2905 Satire St, KISSIMMEE

3 Beds 3 Baths 1,869 SqFt Residential Townhouse MLS® # O6411574
Active 666 Florida Pkwy, KISSIMMEE

$309,000

▲ $49,000 BVL UNIT 3

666 Florida Pkwy, KISSIMMEE

2 Beds 2 Baths 1,000 SqFt Residential Single Family Residence MLS® # P4937699
Active 3108 Westbrook Rd, KISSIMMEE

$309,000

▼ $20,000 CONCORDE ESTATES PH 1B

3108 Westbrook Rd, KISSIMMEE

4 Beds 2 Baths 2,041 SqFt Residential Single Family Residence MLS® # S5154674
Active 8959 Coco Palm Rd, KISSIMMEE

$309,000

▼ $30,000 PARADISE PALMS RESORT PH 1

8959 Coco Palm Rd, KISSIMMEE

4 Beds 3 Baths 1,902 SqFt Residential Townhouse MLS® # O6440602
Active 7525 Bliss Way, KISSIMMEE

$308,900

▼ $11,000 OAKWATER CONDO PH 2-6

7525 Bliss Way, KISSIMMEE

3 Beds 3 Baths 1,808 SqFt Residential Townhouse MLS® # O6345659
Active 2723 Summer Retreat Ln, KISSIMMEE

$308,000

TOHOQUA PH 5A

2723 Summer Retreat Ln, KISSIMMEE

2 Beds 2 Baths 1,559 SqFt Residential Villa MLS® # S5157687
Active 3161 Paradox Cir 304, KISSIMMEE

$308,000

STOREY LAKE

3161 Paradox Cir 304, KISSIMMEE

2 Beds 2 Baths 1,126 SqFt Residential Condominium MLS® # O6430228
Active 3575 Davenport Creek Ct, KISSIMMEE

$307,990

▼ $5,000 REEDY RESERVE PH 3

3575 Davenport Creek Ct, KISSIMMEE

3 Beds 3 Baths 1,365 SqFt Residential Townhouse MLS® # S5149729
Active 280 Beckenham Dr, KISSIMMEE

$307,500

▼ $5,000 POINCIANA VILLAGE 02

280 Beckenham Dr, KISSIMMEE

4 Beds 2 Baths 1,640 SqFt Residential Single Family Residence MLS® # C7527217
Active 3151 Paradox Cir 104, KISSIMMEE

$307,000

▲ $2,000 THE TERRACES AT STOREY LAKE CONDO 3 PH 9

3151 Paradox Cir 104, KISSIMMEE

2 Beds 2 Baths 1,126 SqFt Residential Condominium MLS® # O6384113
Active 8919 Shine Dr, KISSIMMEE

$307,000

WEST LUCAYA VILLAGE

8919 Shine Dr, KISSIMMEE

3 Beds 2 Baths 1,300 SqFt Residential Townhouse MLS® # S5140136
Active 441 Caraway Dr, KISSIMMEE

$305,000

POINCIANA NBRHD 03 SOUTH VILLAGE 07

441 Caraway Dr, KISSIMMEE

4 Beds 2 Baths 1,476 SqFt Residential Single Family Residence MLS® # S5156678
Active 23 Peterlee Ct, KISSIMMEE

$305,000

POINCIANA VLG 2 NBHD 1

23 Peterlee Ct, KISSIMMEE

4 Beds 2 Baths 1,704 SqFt Residential Single Family Residence MLS® # O6444694
Active 17 Herring Ct, KISSIMMEE

$305,000

▼ $10,000 POINCIANA NBRHD 04 VILLAGE 07

17 Herring Ct, KISSIMMEE

3 Beds 2 Baths 1,768 SqFt Residential Single Family Residence MLS® # O6333693
Active 1178 Jade East Ln, KISSIMMEE

$305,000

JADE EAST UNIT 2

1178 Jade East Ln, KISSIMMEE

3 Beds 2 Baths 1,148 SqFt Residential Townhouse MLS® # G5118255
Active 7664 Comrow St 304, KISSIMMEE

$305,000

▼ $15,000 VENTURA AT WINDSOR HILLS CONDO

7664 Comrow St 304, KISSIMMEE

3 Beds 2 Baths 1,450 SqFt Residential Condominium MLS® # O6395555
Active 1409 Hillsborough Way, KISSIMMEE

$305,000

▼ $5,000 POINCIANA NBRHD 02 WEST VILLAGE 07

1409 Hillsborough Way, KISSIMMEE

4 Beds 2 Baths 1,794 SqFt Residential Single Family Residence MLS® # O6399957
Active 153 Club Villas Ln, KISSIMMEE

$305,000

▼ $5,000 REMINGTON PH 1 TR A

153 Club Villas Ln, KISSIMMEE

2 Beds 2 Baths 1,306 SqFt Residential Townhouse MLS® # S5153772
Active 3020 Bird Of Paradise Ln, KISSIMMEE

$305,000

ENCANTADA PH 02

3020 Bird Of Paradise Ln, KISSIMMEE

2 Beds 3 Baths 1,161 SqFt Residential Townhouse MLS® # O6436878
Active 704 S Clyde Ave, KISSIMMEE

$305,000

E B WATERS & SONS ADD

704 S Clyde Ave, KISSIMMEE

3 Beds 1 Bath 1,096 SqFt Residential Single Family Residence MLS® # S5152030
Active 4779 Warrior Ln, KISSIMMEE

$304,999

▼ $5,000 INDIAN WELLS UNIT 7

4779 Warrior Ln, KISSIMMEE

2 Beds 2 Baths 1,330 SqFt Residential Single Family Residence MLS® # O6426473
Active 1816 Manitoba Ct, KISSIMMEE

$304,999

▼ $10,001 POINCIANA NBRHD 5 VILLAGE 7

1816 Manitoba Ct, KISSIMMEE

4 Beds 2 Baths 1,809 SqFt Residential Single Family Residence MLS® # L4963219
Active 638 Gull Dr, KISSIMMEE

$304,990

▼ $10,000 POINCIANA NBRHD 05 NORTH VILLAGE 03

638 Gull Dr, KISSIMMEE

4 Beds 2 Baths 1,658 SqFt Residential Single Family Residence MLS® # S5155836
Active 4717 Flagler Beach Way, KISSIMMEE

$304,900

TERRA VERDE VILLAS PH 2

4717 Flagler Beach Way, KISSIMMEE

3 Beds 3 Baths 1,286 SqFt Residential Townhouse MLS® # O6332223
Active 2739 Coupe St, KISSIMMEE

$304,900

▼ $4,500 REGAL OAKS AT OLD TOWN

2739 Coupe St, KISSIMMEE

3 Beds 3 Baths 1,435 SqFt Residential Townhouse MLS® # S5155453
Active 2706 Impala Ln 2706, KISSIMMEE

$304,900

REGAL OAKS AT OLD TOWN

2706 Impala Ln 2706, KISSIMMEE

3 Beds 3 Baths 1,435 SqFt Residential Townhouse MLS® # O6440854
Active 4564 Ada Ln, KISSIMMEE

$304,900

BELLAVIDA PH 1

4564 Ada Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Residential Townhouse MLS® # O6414668
Active 2784 Almaton Loop 301, KISSIMMEE

$304,000

▼ $4,000 VENTURA AT WINDSOR HILLS CONDO PH 1

2784 Almaton Loop 301, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Residential Condo - Hotel MLS® # O6412307
Active 2510 Hassonite St, KISSIMMEE

$303,500

▼ $5,500 AMBER POINTE

2510 Hassonite St, KISSIMMEE

3 Beds 3 Baths 1,763 SqFt Residential Townhouse MLS® # S5155371
Active 286 Beckenham Dr, KISSIMMEE

$302,500

▼ $2,500 POINCIANA VILLAGE 02

286 Beckenham Dr, KISSIMMEE

4 Beds 2 Baths 1,811 SqFt Residential Single Family Residence MLS® # C7527222
Active 1323 Congo Dr, KISSIMMEE

$300,000

▼ $9,990 POINCIANA NBRHD 02 WEST VILLAGE 07

1323 Congo Dr, KISSIMMEE

3 Beds 2 Baths 1,328 SqFt Residential Single Family Residence MLS® # O6421157
Active 1112 S Beach Cir, KISSIMMEE

$300,000

FIESTA KEY

1112 S Beach Cir, KISSIMMEE

3 Beds 3 Baths 1,468 SqFt Residential Townhouse MLS® # O6337100
Active 5483 Paradise Cay Cir, KISSIMMEE

$300,000

PARADISE CAY

5483 Paradise Cay Cir, KISSIMMEE

3 Beds 3 Baths 1,187 SqFt Residential Townhouse MLS® # O6416889
Active 1485 Isleta Loop, KISSIMMEE

$300,000

OSCEOLA VILLAGE CENTER PH 2

1485 Isleta Loop, KISSIMMEE

3 Beds 3 Baths 1,740 SqFt Residential Townhouse MLS® # S5155946
New Open House
Active 145 Hidalgo Ave, KISSIMMEE

$300,000

BVL UNIT 3 1ST ADD

145 Hidalgo Ave, KISSIMMEE

2 Beds 2 Baths 1,000 SqFt Residential
Sun, Oct 4th, 2026 @ 2pm - 5pm
Single Family Residence MLS® # O6443064
Active 1321 Dunbarton Ct, KISSIMMEE

$300,000

▼ $10,000 POINCIANA VILLAGE 2 NBHD 1

1321 Dunbarton Ct, KISSIMMEE

4 Beds 2 Baths 2,093 SqFt Residential Single Family Residence MLS® # O6312121
Active Choctaw Tr, KISSIMMEE

$300,000

Choctaw Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6078904
Active 2852 Eastham Ln, KISSIMMEE

$300,000

▼ $40,000 CYPRESS RESERVE VILLAS

2852 Eastham Ln, KISSIMMEE

3 Beds 3 Baths 1,776 SqFt Residential Townhouse MLS® # S5139025
Active 2018 Cypress Bay Blvd, KISSIMMEE

$300,000

CYPRESS LAKES TWNHMS PH 2 UNIT 1

2018 Cypress Bay Blvd, KISSIMMEE

3 Beds 3 Baths 1,824 SqFt Residential Townhouse MLS® # O6373358