Search Kissimmee Real Estate Listings, $200,000 - $300,000

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Active 5356 Diplomat Ct 102, KISSIMMEE

$299,000

▼ $6,000 LUCAYA VILLAGE PH 2

5356 Diplomat Ct 102, KISSIMMEE

3 Beds 2 Baths 1,300 SqFt Residential Townhouse MLS® # O6446384
Active 8401 Crystal Cove Loop, KISSIMMEE

$299,000

EMERALD ISLAND RESORT PH 2

8401 Crystal Cove Loop, KISSIMMEE

4 Beds 4 Baths 1,645 SqFt Residential Townhouse MLS® # O6382485
Active 4457 Ochos Rios Pl, KISSIMMEE

$299,000

▼ $31,000 ESPLANADE AT WESTVIEW

4457 Ochos Rios Pl, KISSIMMEE

2 Beds 2 Baths 1,483 SqFt Residential Single Family Residence MLS® # O6417711
New
Active 8103 Coconut Palm Way 103, KISSIMMEE

$299,000

WINDSOR PALMS / WYNDHAM PALMS

8103 Coconut Palm Way 103, KISSIMMEE

3 Beds 2 Baths 1,268 SqFt Residential Condominium MLS® # O6442058
Active 4442 Maple Chase Tr, KISSIMMEE

$299,000

▼ $16,000 MAPLE CHASE AT CYPRESS WOODS

4442 Maple Chase Tr, KISSIMMEE

3 Beds 2 Baths 1,876 SqFt Residential Single Family Residence MLS® # O6390414
Active 3151 Sunset Walk Dr 411, KISSIMMEE

$299,000

▼ $10,999 SUNSET WALK HOTEL CONDO PH 1

3151 Sunset Walk Dr 411, KISSIMMEE

1 Bed 1 Bath 501 SqFt Residential Condo - Hotel MLS® # S5142031
Active 2372 Pebble Brook Rd, KISSIMMEE

$299,000

▼ $9,000 PLANTATION

2372 Pebble Brook Rd, KISSIMMEE

3 Beds 2 Baths 1,342 SqFt Residential Single Family Residence MLS® # O6441446
Active 8401 Amelia Tr, KISSIMMEE

$299,000

HAPPY TRAILS UNITS 1 & 2 UNREC

8401 Amelia Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6426570
Active Sioux Tr, KISSIMMEE

$299,000

HAPPY TRAILS UNIT 04

Sioux Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6422199
Active 7601 Acklins Rd, KISSIMMEE

$298,999

▼ $1 CRESTWYND BAY

7601 Acklins Rd, KISSIMMEE

3 Beds 3 Baths 1,595 SqFt Residential Townhouse MLS® # S5152952
Active 3151 Sunset Walk Dr 1209, KISSIMMEE

$298,999

EMBASSY SUITES, SUNSET WALK HOTEL

3151 Sunset Walk Dr 1209, KISSIMMEE

1 Bed 1 Bath 734 SqFt Residential Condo - Hotel MLS® # S5146573
Active 2903 Edenshire Way 102, KISSIMMEE

$298,990

▼ $21,010 LUCAYA VILLAGE PH 2

2903 Edenshire Way 102, KISSIMMEE

3 Beds 2 Baths 1,300 SqFt Residential Townhouse MLS® # S5153738
Active 4558 Ada Ln, KISSIMMEE

$298,900

BELLAVIDA PH 01

4558 Ada Ln, KISSIMMEE

3 Beds 3 Baths 1,295 SqFt Residential Townhouse MLS® # O6382558
Active 664 Madrid Dr, KISSIMMEE

$298,500

▼ $500 POINCIANA VILLAGE 1 NBHD 3 WEST

664 Madrid Dr, KISSIMMEE

3 Beds 3 Baths 2,110 SqFt Residential Single Family Residence MLS® # S5155420
Active 3202 Guana Way, KISSIMMEE

$298,000

WEST LUCAYA VILLAGE

3202 Guana Way, KISSIMMEE

3 Beds 2 Baths 1,300 SqFt Residential Townhouse MLS® # S5153508
Active 2831 Oakwater Dr 2831, KISSIMMEE

$298,000

▼ $2,000 OAKWATER CONDO PH 20-23

2831 Oakwater Dr 2831, KISSIMMEE

3 Beds 2 Baths 1,427 SqFt Residential Condominium MLS® # O6398829
Active 7519 Bliss Way 7519, KISSIMMEE

$298,000

▼ $1,000 OAKWATER PH 02-6 CONDO

7519 Bliss Way 7519, KISSIMMEE

3 Beds 2 Baths 1,255 SqFt Residential Condominium MLS® # O6388497
Active 2256 Portrait St, KISSIMMEE

$297,500

▼ $7,500 WESTVIEW POD A PHASE 1A PB 200 PG 38-44 LOT 14

2256 Portrait St, KISSIMMEE

3 Beds 3 Baths 1,407 SqFt Residential Townhouse MLS® # P4939367
Active 9033 Wildflower Ln, KISSIMMEE

$297,000

MURANO AT WESTSIDE PH 2

9033 Wildflower Ln, KISSIMMEE

3 Beds 3 Baths 1,530 SqFt Residential Townhouse MLS® # O6434728
Active 230 Bay Dr, KISSIMMEE

$296,000

SOLIVITA PH 01

230 Bay Dr, KISSIMMEE

2 Beds 2 Baths 1,489 SqFt Residential Single Family Residence MLS® # S5151874
Active 2316 Palm Tree Dr, KISSIMMEE

$296,000

▲ $14,000 SOLIVITA PH 05F

2316 Palm Tree Dr, KISSIMMEE

2 Beds 2 Baths 1,539 SqFt Residential Villa MLS® # S5152555
Active 2451 Varenna Loop, KISSIMMEE

$295,000

▼ $10,000 TAPESTRY PH 5

2451 Varenna Loop, KISSIMMEE

3 Beds 3 Baths 1,603 SqFt Residential Single Family Residence MLS® # S5149050
Active 3013 Bonfire Beach Dr 201, KISSIMMEE

$295,000

RUNAWAY BEACH CLUB CONDO

3013 Bonfire Beach Dr 201, KISSIMMEE

3 Beds 2 Baths 1,444 SqFt Residential Condominium MLS® # S5150377
Active 1147 Doncaster Ct, KISSIMMEE

$295,000

▼ $5,000 POINCIANA VILLAGE 2 NBHD 1

1147 Doncaster Ct, KISSIMMEE

4 Beds 2 Baths 1,758 SqFt Residential Single Family Residence MLS® # O6422439
Active 2724 Coupe St, KISSIMMEE

$295,000

REGAL OAKS AT OLD TOWN

2724 Coupe St, KISSIMMEE

4 Beds 3 Baths 1,440 SqFt Residential Townhouse MLS® # O6423375
Active 4812 Coral Castle Dr, KISSIMMEE

$295,000

FIESTA KEY PH 2

4812 Coral Castle Dr, KISSIMMEE

3 Beds 3 Baths 1,762 SqFt Residential Townhouse MLS® # W7889115
Active 8927 Shine Dr, KISSIMMEE

$295,000

WEST LUCAYA VILLAGE

8927 Shine Dr, KISSIMMEE

3 Beds 2 Baths 1,300 SqFt Residential Townhouse MLS® # S5155518
Active 5266 Paradise Cay Cir, KISSIMMEE

$295,000

▼ $3,000 PARADISE CAY

5266 Paradise Cay Cir, KISSIMMEE

3 Beds 3 Baths 1,595 SqFt Residential Townhouse MLS® # O6430817
Active 165 Citrine Loop, KISSIMMEE

$295,000

▼ $29,000 STEPPING STONE POD A PH 2

165 Citrine Loop, KISSIMMEE

3 Beds 2 Baths 1,510 SqFt Residential Single Family Residence MLS® # S5126819
Active 3150 Paradox Cir 305, KISSIMMEE

$295,000

THE TERRACES AT STOREY LAKE CONDO 2 PH 14

3150 Paradox Cir 305, KISSIMMEE

2 Beds 2 Baths 1,126 SqFt Residential Condominium MLS® # O6399517
Active 762 Toulon Dr, KISSIMMEE

$295,000

▼ $4,000 POINCIANA VILLAGE 5 NBHD 1

762 Toulon Dr, KISSIMMEE

4 Beds 2 Baths 1,818 SqFt Residential Single Family Residence MLS® # O6421714
Active 7505 Mourning Dove Cir 302, KISSIMMEE

$295,000

TERRACES AT REUNION CONDO PH 8

7505 Mourning Dove Cir 302, KISSIMMEE

3 Beds 2 Baths 1,354 SqFt Residential Condominium MLS® # O6438769
Active 513 Barcelona Dr, KISSIMMEE

$295,000

SOLIVITA PH 04C SEC 02

513 Barcelona Dr, KISSIMMEE

2 Beds 2 Baths 1,574 SqFt Residential Single Family Residence MLS® # O6435898
Active 3150 Paradox Cir 302, KISSIMMEE

$295,000

▲ $10,000 THE TERRACES AT STOREY LAKE CONDO 3 PH 12

3150 Paradox Cir 302, KISSIMMEE

2 Beds 2 Baths 1,186 SqFt Residential Condominium MLS® # O6368790
Active 2024 Cypress Bay Blvd, KISSIMMEE

$294,999

▼ $3,000 CYPRESS LAKES TWNHMS PH 2 UNIT 1

2024 Cypress Bay Blvd, KISSIMMEE

3 Beds 3 Baths 1,807 SqFt Residential Townhouse MLS® # S5145498
Active 539 Brentford Ct, KISSIMMEE

$294,900

▼ $5,000 POINCIANA VILLAGE 2 NBHD 3

539 Brentford Ct, KISSIMMEE

3 Beds 2 Baths 1,876 SqFt Residential Single Family Residence MLS® # TB8512665
Active 2727 Sun Key Pl, KISSIMMEE

$294,900

▼ $10,000 EMERALD ISLAND RESORT REP

2727 Sun Key Pl, KISSIMMEE

3 Beds 3 Baths 1,291 SqFt Residential Townhouse MLS® # S5144518
Active 4741 Clock Tower Dr 102, KISSIMMEE

$294,500

▼ $22,000 THE TERRACES AT STOREY LAKE CONDO 1 PH 3

4741 Clock Tower Dr 102, KISSIMMEE

2 Beds 2 Baths 1,186 SqFt Residential Condominium MLS® # O6348912
Active 4878 Coral Castle Dr, KISSIMMEE

$294,000

FIESTA KEY PH 2

4878 Coral Castle Dr, KISSIMMEE

3 Beds 3 Baths 1,762 SqFt Residential Townhouse MLS® # S5151187
Active 2968 Caribbean Soul Dr, KISSIMMEE

$294,000

▼ $5,000 ROLLING OAKS PH 7

2968 Caribbean Soul Dr, KISSIMMEE

2 Beds 3 Baths 1,394 SqFt Residential Townhouse MLS® # O6416435
Active 811 Carrousel Ln, KISSIMMEE

$293,500

▼ $1,500 POINCIANA VILLAGE 5 NBHD 1

811 Carrousel Ln, KISSIMMEE

3 Beds 2 Baths 1,536 SqFt Residential Single Family Residence MLS® # S5150738
Active 1991 Key Bay Tr, KISSIMMEE

$293,000

FOUR SEASONS AT ORLANDO PH 4B

1991 Key Bay Tr, KISSIMMEE

2 Beds 2 Baths 1,437 SqFt Residential Villa MLS® # TB8421378
Active 4729 Coral Castle Dr, KISSIMMEE

$292,900

▼ $3,000 FIESTA KEY PH 2

4729 Coral Castle Dr, KISSIMMEE

3 Beds 3 Baths 1,762 SqFt Residential Townhouse MLS® # S5148424
Active 149 Aurora Ln, KISSIMMEE

$290,999

▼ $5,000 POINCIANA VILLAGE 1 NBHD 2

149 Aurora Ln, KISSIMMEE

3 Beds 2 Baths 1,600 SqFt Residential Single Family Residence MLS® # S5155796
Open House
Active 314 Sherborne Ln, KISSIMMEE

$290,000

POINCIANA VILLAGE 1 NBHD 1 NORTH

314 Sherborne Ln, KISSIMMEE

3 Beds 2 Baths 1,646 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 3pm
Single Family Residence MLS® # S5157215
Active 7656 Whisper Way 103, KISSIMMEE

$290,000

VILLAS AT REUNION SQUARE; A CONDO PH 3

7656 Whisper Way 103, KISSIMMEE

3 Beds 3 Baths 1,630 SqFt Residential Condominium MLS® # O6440778
Active 611 Elbridge Dr, KISSIMMEE

$290,000

POINCIANA VILLAGE 2 NBHD 3

611 Elbridge Dr, KISSIMMEE

3 Beds 2 Baths 1,474 SqFt Residential Single Family Residence MLS® # O6437985
Active 157 Pompano Beach Dr, KISSIMMEE

$290,000

▼ $10,000 TERRA VERDE VILLAS PH 2

157 Pompano Beach Dr, KISSIMMEE

3 Beds 3 Baths 1,286 SqFt Residential Townhouse MLS® # S5132465