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

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Active 8028 Dreamsicle Dr, KISSIMMEE

$399,000

ROLLING OAKS PH 5

8028 Dreamsicle Dr, KISSIMMEE

2 Beds 3 Baths 1,305 SqFt Residential Single Family Residence MLS® # O6444526
Active 4870 Lake Cecile Dr, KISSIMMEE

$399,000

▼ $15,000 LAKE CECILE PARK ADD 1

4870 Lake Cecile Dr, KISSIMMEE

4 Beds 2 Baths 2,243 SqFt Residential Single Family Residence MLS® # O6436411
Active 1021 Tourmaline Dr, KISSIMMEE

$399,000

▼ $10,999 CRYSTAL COVE RESORT

1021 Tourmaline Dr, KISSIMMEE

4 Beds 2 Baths 1,397 SqFt Residential Single Family Residence MLS® # TB8519437
Active 3151 Sunset Walk Dr 508, KISSIMMEE

$399,000

SUNSET WALK HOTEL CONDO PH 1

3151 Sunset Walk Dr 508, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condominium MLS® # O6430647
Active 3013 Mandolin Dr, KISSIMMEE

$399,000

▼ $6,000 TURNBERRY RESERVE UNIT 1

3013 Mandolin Dr, KISSIMMEE

4 Beds 2 Baths 2,148 SqFt Residential Single Family Residence MLS® # O6411560
Active 2918 Sunset Vista Blvd, KISSIMMEE

$399,000

▼ $16,000 SUNSET LAKES PH 1

2918 Sunset Vista Blvd, KISSIMMEE

4 Beds 2 Baths 1,701 SqFt Residential Single Family Residence MLS® # O6427389
Active 303 Alencon Way, KISSIMMEE

$399,000

▼ $11,000 POINCIANA VILLAGE 5 NBHD 1

303 Alencon Way, KISSIMMEE

4 Beds 2 Baths 1,872 SqFt Residential Single Family Residence MLS® # S5144839
Active 2328 Caravelle Cir, KISSIMMEE

$399,000

▼ $6,000 CORAL CAY RESORT

2328 Caravelle Cir, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # O6433617
Active 7770 Sandy Ridge Dr 113, KISSIMMEE

$399,000

SPECTRUM AT REUNION CONDO PH 3A & 3B

7770 Sandy Ridge Dr 113, KISSIMMEE

3 Beds 3 Baths 1,491 SqFt Residential Condominium MLS® # O6443351
Active 2259 Waukegan Dr, KISSIMMEE

$399,000

▼ $30,000 WATERVIEW PH 1B

2259 Waukegan Dr, KISSIMMEE

4 Beds 3 Baths 2,814 SqFt Residential Single Family Residence MLS® # S5154846
Open House
Active 5801 Portico Pl, KISSIMMEE

$399,000

▼ $6,000 WESTVIEW

5801 Portico Pl, KISSIMMEE

4 Beds 4 Baths 2,138 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 4pm
Single Family Residence MLS® # O6394755
Active 2226 Taylor Creek Ct, KISSIMMEE

$399,000

WATERVIEW PH 2B

2226 Taylor Creek Ct, KISSIMMEE

4 Beds 3 Baths 2,814 SqFt Residential Single Family Residence MLS® # O6437109
Active 131 S Roma Way, KISSIMMEE

$399,000

▼ $26,000 INDIAN POINT PH 7

131 S Roma Way, KISSIMMEE

4 Beds 3 Baths 1,740 SqFt Residential Single Family Residence MLS® # O6339572
Active 3048 Seaview Castle Dr, KISSIMMEE

$399,000

COMPASS BAY UNIT 1

3048 Seaview Castle Dr, KISSIMMEE

4 Beds 3 Baths 1,872 SqFt Residential Townhouse MLS® # O6439712
Active 2750 Big Timber Dr, KISSIMMEE

$399,000

HAMMOCK TRAILS

2750 Big Timber Dr, KISSIMMEE

5 Beds 4 Baths 2,801 SqFt Residential Single Family Residence MLS® # O6441456
Active 3511 Maple Ridge Loop, KISSIMMEE

$399,000

FOREST EDGE

3511 Maple Ridge Loop, KISSIMMEE

3 Beds 2 Baths 2,284 SqFt Residential Single Family Residence MLS® # O6430870
Active 4401 Evergreen Forest Loop, KISSIMMEE

$399,000

BANYAN COVE AT CYPRESS WOODS

4401 Evergreen Forest Loop, KISSIMMEE

4 Beds 3 Baths 2,847 SqFt Residential Single Family Residence MLS® # O6438643
Active 1543 Beechmont Dr, KISSIMMEE

$398,990

KINDRED PH 2A

1543 Beechmont Dr, KISSIMMEE

3 Beds 2 Baths 1,504 SqFt Residential Single Family Residence MLS® # O6442514
Active 1850 Chaucer Way, KISSIMMEE

$398,950

▼ $6,050 BRIGHTON PLACE

1850 Chaucer Way, KISSIMMEE

4 Beds 2 Baths 1,828 SqFt Residential Single Family Residence MLS® # S5151405
Active 4020 Sunny Day Way, KISSIMMEE

$398,900

▼ $10,000 TURNBERRY RESERVE UNIT 1

4020 Sunny Day Way, KISSIMMEE

4 Beds 2 Baths 2,148 SqFt Residential Single Family Residence MLS® # S5149650
Active 8572 Bay Lilly Loop, KISSIMMEE

$398,500

▼ $11,500 ENCANTADA PH 1

8572 Bay Lilly Loop, KISSIMMEE

4 Beds 3 Baths 1,650 SqFt Residential Townhouse MLS® # S5142891
Active 1994 Birnham Wood Bnd, KISSIMMEE

$398,200

STOREY CREEK PH 2B

1994 Birnham Wood Bnd, KISSIMMEE

4 Beds 3 Baths 2,115 SqFt Residential Single Family Residence MLS® # GC543205
Active 3050 Secret Lake Dr, KISSIMMEE

$398,000

▼ $7,000 ENCANTADA PH 1

3050 Secret Lake Dr, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # O6435405
New
Active 4603 Ross Lanier Ln, KISSIMMEE

$398,000

LITTLE CREEK PH 2

4603 Ross Lanier Ln, KISSIMMEE

4 Beds 3 Baths 2,387 SqFt Residential Single Family Residence MLS® # O6445171
Active 216 Aquamarine Ln, KISSIMMEE

$398,000

STEPPING STONE POD A PH 1

216 Aquamarine Ln, KISSIMMEE

5 Beds 3 Baths 2,271 SqFt Residential Single Family Residence MLS® # O6346081
Active 3878 Wood Thrush Dr, KISSIMMEE

$398,000

▼ $10,000 SPRINGLAKE VILLAGE PH 5B

3878 Wood Thrush Dr, KISSIMMEE

3 Beds 2 Baths 2,061 SqFt Residential Single Family Residence MLS® # O6396827
Active 3115 Smoke Signal Cir, KISSIMMEE

$398,000

INDIAN WELLS UNIT 5

3115 Smoke Signal Cir, KISSIMMEE

3 Beds 2 Baths 1,410 SqFt Residential Single Family Residence MLS® # O6438391
Active 144 Hidalgo Ave, KISSIMMEE

$398,000

BVL UNIT 3

144 Hidalgo Ave, KISSIMMEE

4 Beds 3 Baths 1,742 SqFt Residential Single Family Residence MLS® # S5154454
Active 2361 Andrews Valley Dr, KISSIMMEE

$397,700

▼ $6,200 BLACKSTONE LANDING PH 2

2361 Andrews Valley Dr, KISSIMMEE

5 Beds 3 Baths 2,566 SqFt Residential Single Family Residence MLS® # O6429963
Active 2925 Willow Creek Ln, KISSIMMEE

$397,500

▼ $1,500 WINDSOR POINT PH 2

2925 Willow Creek Ln, KISSIMMEE

3 Beds 2 Baths 1,797 SqFt Residential Single Family Residence MLS® # C7525014
Active 7673 Recife Dr, KISSIMMEE

$396,990

▼ $28,000 MAGIC VILLAGE

7673 Recife Dr, KISSIMMEE

3 Beds 4 Baths 2,268 SqFt Residential Townhouse MLS® # O6380610
New Open House
Active 2580 Hunley Loop, KISSIMMEE

$395,000

EAGLE BAY PH 1

2580 Hunley Loop, KISSIMMEE

4 Beds 2 Baths 1,874 SqFt Residential
Sun, Oct 4th, 2026 @ 1pm - 4pm
Single Family Residence MLS® # O6445251
Active 1562 Carey Palm Cir, KISSIMMEE

$395,000

▼ $10,000 SOLARA RESIDENCE

1562 Carey Palm Cir, KISSIMMEE

3 Beds 4 Baths 1,962 SqFt Residential Townhouse MLS® # O6427089
Active 105 Cupola Loop, KISSIMMEE

$395,000

▼ $4,000 SOLIVITA PH 02D

105 Cupola Loop, KISSIMMEE

2 Beds 2 Baths 2,066 SqFt Residential Single Family Residence MLS® # S5155611
Active 8055 King Palm Cir, KISSIMMEE

$395,000

WYNDHAM PALMS PH 1A

8055 King Palm Cir, KISSIMMEE

4 Beds 2 Baths 1,567 SqFt Residential Single Family Residence MLS® # O6414590
Active 1709 Golfview Dr, KISSIMMEE

$395,000

OVEROAKS REP 1

1709 Golfview Dr, KISSIMMEE

3 Beds 2 Baths 2,302 SqFt Residential Single Family Residence MLS® # S5154295
Active 4211 Little Owl Ln, KISSIMMEE

$395,000

▼ $4,900 STOREY CREEK PH 3B & 4

4211 Little Owl Ln, KISSIMMEE

4 Beds 2 Baths 1,854 SqFt Residential Single Family Residence MLS® # S5121596
Active 2121 Blackstone Landing Dr, KISSIMMEE

$395,000

BLACKSTONE LANDING PH 1

2121 Blackstone Landing Dr, KISSIMMEE

4 Beds 4 Baths 2,948 SqFt Residential Single Family Residence MLS® # S5153093
Active 637 Eagle Pointe S, KISSIMMEE

$395,000

EAGLE POINTE PH 4

637 Eagle Pointe S, KISSIMMEE

4 Beds 3 Baths 2,319 SqFt Residential Single Family Residence MLS® # O6444266
Active 406 E Drury Ave, KISSIMMEE

$395,000

NEPTUNE REPLAT

406 E Drury Ave, KISSIMMEE

3 Beds 2 Baths 1,895 SqFt Residential Single Family Residence MLS® # S5158179
Active 8887 Geneve Ct, KISSIMMEE

$395,000

▼ $4,000 WINDSOR AT WESTSIDE PH 2B

8887 Geneve Ct, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # O6295445
Open House
Active 2425 Ashecroft Dr, KISSIMMEE

$395,000

REMINGTON PRCL K PH 2

2425 Ashecroft Dr, KISSIMMEE

4 Beds 3 Baths 1,803 SqFt Residential
Sun, Oct 4th, 2026 @ 1am - 6pm
Single Family Residence MLS® # S5157991
Active 861 Bella Viana Rd, KISSIMMEE

$395,000

▼ $20,000 SOLIVITA PH 7B2

861 Bella Viana Rd, KISSIMMEE

2 Beds 3 Baths 2,379 SqFt Residential Single Family Residence MLS® # S5156512
Active 1776 Fulfillment Dr, KISSIMMEE

$395,000

TOHOQUA PH 1

1776 Fulfillment Dr, KISSIMMEE

3 Beds 3 Baths 1,620 SqFt Residential Townhouse MLS® # S5148323
Active 1718 Golfview Dr, KISSIMMEE

$395,000

▼ $14,000 OVEROAKS REP 1

1718 Golfview Dr, KISSIMMEE

3 Beds 2 Baths 1,538 SqFt Residential Single Family Residence MLS® # S5155173
Active 7683 Fitzclarence St, KISSIMMEE

$395,000

▼ $4,000 WINDSOR HILLS PH 02

7683 Fitzclarence St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Residential Townhouse MLS® # O6421663
Active 1937 Howard Mesa Dr, KISSIMMEE

$395,000

▼ $5,000 KINDRED PH 3B 3C & 3D

1937 Howard Mesa Dr, KISSIMMEE

3 Beds 2 Baths 1,504 SqFt Residential Single Family Residence MLS® # O6437465
Active 2609 Mill Run Blvd, KISSIMMEE

$394,990

MILL RUN UNIT 5

2609 Mill Run Blvd, KISSIMMEE

3 Beds 2 Baths 1,280 SqFt Residential Single Family Residence MLS® # S5150924