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

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Active 1721 Freeman Dr, KISSIMMEE

$359,900

▼ $10,000 OAK RUN UNIT 2

1721 Freeman Dr, KISSIMMEE

3 Beds 2 Baths 1,842 SqFt Residential Single Family Residence MLS® # O6424008
Active 1359 Isleta Loop, KISSIMMEE

$359,900

OSCEOLA VILLAGE CENTER PH 2

1359 Isleta Loop, KISSIMMEE

3 Beds 3 Baths 1,676 SqFt Residential Townhouse MLS® # O6434271
Active 4523 Alberto Cir, KISSIMMEE

$359,900

BELLAVIDA PH 1

4523 Alberto Cir, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # O6368791
Active 5782 Le Marin Way, KISSIMMEE

$359,900

▼ $9,100 WESTVIEW POD B NEIGHBORHOOD 2A & 2B PH 1

5782 Le Marin Way, KISSIMMEE

3 Beds 2 Baths 1,451 SqFt Residential Single Family Residence MLS® # O6426701
Active 2510 Hamlet Ln, KISSIMMEE

$359,900

HAMLETS

2510 Hamlet Ln, KISSIMMEE

4 Beds 3 Baths 1,929 SqFt Residential Single Family Residence MLS® # O6441105
Active 2518 Bowmer Dr, KISSIMMEE

$359,900

▼ $5,100 MILL RUN UNIT 3

2518 Bowmer Dr, KISSIMMEE

3 Beds 2 Baths 1,523 SqFt Residential Single Family Residence MLS® # S5109889
Active 632 Bittern Ct, KISSIMMEE

$359,900

▼ $10,000 POINCIANA NBRHD 05 NORTH VILLAGE 03

632 Bittern Ct, KISSIMMEE

5 Beds 3 Baths 2,530 SqFt Residential Single Family Residence MLS® # S5153815
Active 2221 Canyon Breeze Ave, KISSIMMEE

$359,900

SEDONA PH 1

2221 Canyon Breeze Ave, KISSIMMEE

3 Beds 2 Baths 1,303 SqFt Residential Single Family Residence MLS® # O6378027
Open House
Active 2546 Sage Dr, KISSIMMEE

$359,900

▼ $10,100 LAUREL RUN AT CRESCENT LAKES

2546 Sage Dr, KISSIMMEE

3 Beds 2 Baths 1,434 SqFt Residential
Sat, Oct 24th, 2026 @ 12pm - 3pm
Single Family Residence MLS® # S5144380
New
Active 1718 Margie Ct, KISSIMMEE

$359,900

MARGIE COURT

1718 Margie Ct, KISSIMMEE

3 Beds 2 Baths 1,217 SqFt Residential Single Family Residence MLS® # O6446903
Active 3008 Seaview Castle Dr, KISSIMMEE

$359,900

▼ $9,100 COMPASS BAY UNIT 1

3008 Seaview Castle Dr, KISSIMMEE

3 Beds 3 Baths 1,882 SqFt Residential Townhouse MLS® # S5139706
Active 2312 Brook Marsh Loop, KISSIMMEE

$359,900

LAKE WILSON

2312 Brook Marsh Loop, KISSIMMEE

3 Beds 3 Baths 1,780 SqFt Residential Townhouse MLS® # O6423525
Active 4502 Philadelphia Cir, KISSIMMEE

$359,900

▼ $29,100 LIBERTY VILLAGE PH 2

4502 Philadelphia Cir, KISSIMMEE

4 Beds 2 Baths 1,950 SqFt Residential Single Family Residence MLS® # O6423270
Active 2542 Camphorwood Cir, KISSIMMEE

$359,900

OAK HOLLOW PH 3

2542 Camphorwood Cir, KISSIMMEE

3 Beds 2 Baths 1,406 SqFt Residential Single Family Residence MLS® # S5136753
Active 3131 Paradox Cir 108, KISSIMMEE

$359,800

▼ $10,000 THE TERRACES AT STOREY LAKE CONDO NO 2 PH 7

3131 Paradox Cir 108, KISSIMMEE

3 Beds 2 Baths 1,329 SqFt Residential Condominium MLS® # S5146717
Active 1910 Goblet Cove St, KISSIMMEE

$359,000

▼ $6,000 BELLALAGO

1910 Goblet Cove St, KISSIMMEE

3 Beds 2 Baths 1,768 SqFt Residential Single Family Residence MLS® # S5154724
Active 4039 Navigator Way, KISSIMMEE

$359,000

▼ $36,000 BELLA ISLE / ISLES OF BELLALAGO

4039 Navigator Way, KISSIMMEE

4 Beds 3 Baths 2,123 SqFt Residential Single Family Residence MLS® # P4936335
Active 3151 Sunset Walk Dr 1214, KISSIMMEE

$359,000

▼ $40,000 SUNSET WALK HOTEL, EMBASSY SUITES

3151 Sunset Walk Dr 1214, KISSIMMEE

2 Beds 2 Baths 1,163 SqFt Residential Condo - Hotel MLS® # S5141552
Active 1211 Lehigh St, KISSIMMEE

$359,000

▼ $5,900 JOHNSTON PARK REP

1211 Lehigh St, KISSIMMEE

3 Beds 2 Baths 1,685 SqFt Residential Single Family Residence MLS® # S5147242
Active 2927 Sentence St, KISSIMMEE

$359,000

▼ $10,000 STOREY LAKE TRACK K

2927 Sentence St, KISSIMMEE

3 Beds 3 Baths 2,016 SqFt Residential Townhouse MLS® # O6436064
Active 1608 Mohegan Blvd, KISSIMMEE

$359,000

HERITAGE RUN

1608 Mohegan Blvd, KISSIMMEE

3 Beds 3 Baths 2,016 SqFt Residential Townhouse MLS® # O6431298
New
Active 4858 Kingston Cir, KISSIMMEE

$359,000

MONTEGO BAY

4858 Kingston Cir, KISSIMMEE

3 Beds 2 Baths 1,611 SqFt Residential Single Family Residence MLS® # S5158748
Active 657 Mckinley Ct, KISSIMMEE

$359,000

▼ $20,000 POINCIANA VILLAGE 1 NBHD 1 SOUTH

657 Mckinley Ct, KISSIMMEE

3 Beds 2 Baths 1,122 SqFt Residential Single Family Residence MLS® # O6313270
Active 3505 Forest Park Dr, KISSIMMEE

$359,000

▼ $10,000 BELLALAGO

3505 Forest Park Dr, KISSIMMEE

3 Beds 2 Baths 2,053 SqFt Residential Single Family Residence MLS® # O6429562
Active 2345 Southbury, KISSIMMEE

$359,000

▼ $10,000 TOHOQUA PHASE 1

2345 Southbury, KISSIMMEE

3 Beds 3 Baths 1,553 SqFt Residential Townhouse MLS® # S5151680
Active Plaza Dr Nw, KISSIMMEE

$359,000

BVL BOGGY CREEK PLAZA PH 2

Plaza Dr Nw, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # K4903700
Active 1502 Jadewood Way, KISSIMMEE

$359,000

▲ $9,000 KINDRED PH 2C & 2D PB 30 PGS 74-80 LOT 323

1502 Jadewood Way, KISSIMMEE

4 Beds 2 Baths 1,846 SqFt Residential Single Family Residence MLS® # O6233314
Active 3020 Palermo Rose Way, KISSIMMEE

$359,000

CONCORDE ESTATES PH 1

3020 Palermo Rose Way, KISSIMMEE

3 Beds 2 Baths 1,899 SqFt Residential Single Family Residence MLS® # S5157719
Active 721 Mabbette St, KISSIMMEE

$358,990

MATHEWS ADD

721 Mabbette St, KISSIMMEE

3 Beds 2 Baths 1,027 SqFt Residential Single Family Residence MLS® # S5141765
Active 8966 Sugar Palm Rd, KISSIMMEE

$358,000

▼ $1,000 PARADISE PALMS RESORT PH 3B

8966 Sugar Palm Rd, KISSIMMEE

4 Beds 3 Baths 1,902 SqFt Residential Townhouse MLS® # O6439700
Active 2239 Rita Ln, KISSIMMEE

$357,990

FISH LAKE

2239 Rita Ln, KISSIMMEE

3 Beds 3 Baths 1,489 SqFt Residential Townhouse MLS® # O6441527
Active 1851 Southbury Dr, KISSIMMEE

$357,990

KINDRED

1851 Southbury Dr, KISSIMMEE

3 Beds 3 Baths 1,551 SqFt Residential Townhouse MLS® # O6440756
Active 7629 Danube Rd, KISSIMMEE

$357,000

LAKE WILSON RESERVE

7629 Danube Rd, KISSIMMEE

3 Beds 3 Baths 1,797 SqFt Residential Townhouse MLS® # G5104815
Active 4811 Pliny Ct, KISSIMMEE

$356,000

WINDWARD CAY UNIT 2

4811 Pliny Ct, KISSIMMEE

3 Beds 2 Baths 1,570 SqFt Residential Single Family Residence MLS® # R4911702
Active 4720 Vero Beach Pl, KISSIMMEE

$355,499

▼ $7,000 TERRA VERDE VILLAS PH 2

4720 Vero Beach Pl, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # TB8497348
Active 1320 Oak Grove Ct, KISSIMMEE

$355,000

▼ $5,000 OAK GROVE

1320 Oak Grove Ct, KISSIMMEE

3 Beds 2 Baths 1,229 SqFt Residential Single Family Residence MLS® # O6441949
Active 2511 Bright Jewel St, KISSIMMEE

$355,000

▼ $5,000 CYPRESS CAY PH 2

2511 Bright Jewel St, KISSIMMEE

3 Beds 3 Baths 1,683 SqFt Residential Townhouse MLS® # S5148888
Active 1346 Isleta Loop, KISSIMMEE

$355,000

OSCEOLA VILLAGE CENTER PB 32 PGS 60-64 LOT 138

1346 Isleta Loop, KISSIMMEE

3 Beds 3 Baths 1,673 SqFt Residential Townhouse MLS® # S5157188
New
Active 4580 Gadwall Dr, KISSIMMEE

$355,000

OSPREY RIDGE

4580 Gadwall Dr, KISSIMMEE

3 Beds 2 Baths 1,651 SqFt Residential Single Family Residence MLS® # O6445593
Active 1708 Casuarina Ln, KISSIMMEE

$355,000

▼ $5,000 OAKBROOK ESTATES

1708 Casuarina Ln, KISSIMMEE

3 Beds 2 Baths 1,502 SqFt Residential Single Family Residence MLS® # S5155638
Active 907 Hacienda Cir, KISSIMMEE

$355,000

ESTANCIA

907 Hacienda Cir, KISSIMMEE

3 Beds 2 Baths 1,822 SqFt Residential Single Family Residence MLS® # O6421949
New
Active 5109 Killarney Way, KISSIMMEE

$355,000

COMPASS BAY UNIT 4

5109 Killarney Way, KISSIMMEE

4 Beds 4 Baths 1,637 SqFt Residential Townhouse MLS® # O6445953
Active 3037 Beach Palm Ave, KISSIMMEE

$355,000

PARADISE PALMS RESORT PH 2

3037 Beach Palm Ave, KISSIMMEE

4 Beds 3 Baths 1,902 SqFt Residential Townhouse MLS® # O6438535
Active 2581 Marshfield Preserve Way, KISSIMMEE

$355,000

CONCORDE ESTATES PH 2B

2581 Marshfield Preserve Way, KISSIMMEE

3 Beds 2 Baths 2,235 SqFt Residential Single Family Residence MLS® # A4694287
Active 1691 Key Bay Tr, KISSIMMEE

$355,000

FOUR SEASONS AT ORLANDO PH 3B

1691 Key Bay Tr, KISSIMMEE

2 Beds 2 Baths 1,557 SqFt Residential Villa MLS® # S5149880
Active 1001 La Mirada Ct, KISSIMMEE

$355,000

▼ $8,000 LAGO BUENDIA PH 1

1001 La Mirada Ct, KISSIMMEE

4 Beds 3 Baths 1,626 SqFt Residential Townhouse MLS® # O6391089
Active 4475 Casablanca Ave, KISSIMMEE

$355,000

CASA BELLA

4475 Casablanca Ave, KISSIMMEE

3 Beds 2 Baths 1,541 SqFt Residential Single Family Residence MLS® # S5156268
Active 2042 Key Bay Tr, KISSIMMEE

$355,000

FOUR SEASONS AT ORLANDO PH 4B

2042 Key Bay Tr, KISSIMMEE

2 Beds 2 Baths 1,557 SqFt Residential Villa MLS® # O6438140