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

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FEATURED
Active 7650 Comrow St 105, KISSIMMEE

$389,999

WINDSOR HILLS, VENTURA AT WINDSOR HILLS

7650 Comrow St 105, KISSIMMEE

3 Beds 2 Baths 1,410 SqFt Residential Condominium MLS® # S5157519
FEATURED
Active 8070 Unwind Way 5416, KISSIMMEE

$377,900

▼ $71,100 SUNSET WALK HOTEL, EMBASSY SUITES

8070 Unwind Way 5416, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5141228
FEATURED
Active 8081 Knee Deep Rd, KISSIMMEE

$377,000

▼ $22,999 MARGARITAVILLE RESORT

8081 Knee Deep Rd, KISSIMMEE

2 Beds 2 Baths 1,188 SqFt Residential Single Family Residence MLS® # S5151963
FEATURED
Active 5134 Adelaide Dr, KISSIMMEE

$375,000

COMPASS BAY

5134 Adelaide Dr, KISSIMMEE

4 Beds 4 Baths 1,782 SqFt Residential Townhouse MLS® # S5156970
FEATURED
Active 2920 Sunset Lakes Blvd, KISSIMMEE

$375,000

SUNSET LAKES

2920 Sunset Lakes Blvd, KISSIMMEE

3 Beds 2 Baths 1,399 SqFt Residential Single Family Residence MLS® # S5158175
FEATURED
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
FEATURED
Active 8061 Vacation Ave 2508, KISSIMMEE

$349,000

▼ $50,999 SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 2508, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5144118
FEATURED
Active 2821 Almaton Loop 203, KISSIMMEE

$346,000

▼ $3,900 WINDSOR HILLS, VENTURA AT WINDSOR HILLS

2821 Almaton Loop 203, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Residential Condominium MLS® # S5147977
FEATURED
Active 2916 On The Rocks Pt, KISSIMMEE

$344,999

▼ $15,000 MARGARITAVILLE, ROLLING OAKS

2916 On The Rocks Pt, KISSIMMEE

3 Beds 3 Baths 1,545 SqFt Residential Townhouse MLS® # S5149980
FEATURED
Active 8061 Vacation Ave 2510, KISSIMMEE

$340,000

▼ $5,000 SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 2510, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5144575
FEATURED
Active 3083 Yellow Lantana Ln, KISSIMMEE

$339,000

▼ $31,000 ENCANTADA

3083 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,340 SqFt Residential Townhouse MLS® # S5116892
FEATURED
Active 3151 Sunset Walk Dr 1108, KISSIMMEE

$327,999

▼ $2,000 EMBASSY SUITES, SUNSET WALK HOTEL

3151 Sunset Walk Dr 1108, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5132617
FEATURED
Active 3222 Cupid Pl, KISSIMMEE

$319,500

▼ $12,500 WEST LUCAYA VILLAGE

3222 Cupid Pl, KISSIMMEE

4 Beds 3 Baths 1,694 SqFt Residential Townhouse MLS® # S5141535
FEATURED
Active 3240 Cupid Pl, KISSIMMEE

$315,000

▲ $35,050 WEST LUCAYA VILLAGE

3240 Cupid Pl, KISSIMMEE

4 Beds 3 Baths 1,694 SqFt Residential Townhouse MLS® # S5152792
FEATURED
Active 2200 San Zanobi Dr 108, KISSIMMEE

$310,000

VENETIAN BAY

2200 San Zanobi Dr 108, KISSIMMEE

4 Beds 3 Baths 1,470 SqFt Residential Condominium MLS® # S5102991
Active 1390 Remick Ct, KISSIMMEE

$400,000

REUNION VILLAGE PH 4 & 5

1390 Remick Ct, KISSIMMEE

3 Beds 2 Baths 1,570 SqFt Residential Single Family Residence MLS® # O6441425
Active 331 Ashburton Way, KISSIMMEE

$400,000

▼ $25,000 POINCIANA VILLAGE 2 NBHD 3

331 Ashburton Way, KISSIMMEE

4 Beds 3 Baths 2,679 SqFt Residential Single Family Residence MLS® # O6431564
Active 1933 Howard Mesa Dr, KISSIMMEE

$400,000

▼ $10,990 KINDRED PH 3B 3C & 3D

1933 Howard Mesa Dr, KISSIMMEE

3 Beds 2 Baths 1,504 SqFt Residential Single Family Residence MLS® # O6437474
Active 2556 Renshaw St, KISSIMMEE

$400,000

▼ $5,000 WINDSOR HILLS PH 2

2556 Renshaw St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Residential Townhouse MLS® # O6393304
Active 2713 Wortham Ln, KISSIMMEE

$400,000

REMINGTON PH 1 TR E

2713 Wortham Ln, KISSIMMEE

4 Beds 2 Baths 1,433 SqFt Residential Single Family Residence MLS® # S5152871
Active 1090 Boardwalk Pl, KISSIMMEE

$400,000

SOLEIL AT WESTSIDE

1090 Boardwalk Pl, KISSIMMEE

3 Beds 3 Baths 2,206 SqFt Residential Single Family Residence MLS® # O6432294
Active 1254 Wispy Cypress Dr, KISSIMMEE

$400,000

CYPRESS HAMMOCK PH 1

1254 Wispy Cypress Dr, KISSIMMEE

3 Beds 3 Baths 1,917 SqFt Residential Townhouse MLS® # S5152481
Active 2600 Shortleaf, KISSIMMEE

$400,000

▼ $14,000 PLEASANT HILL LAKES

2600 Shortleaf, KISSIMMEE

4 Beds 2 Baths 1,959 SqFt Residential Single Family Residence MLS® # L4961677
Active 2986 Sun Pointe Ct, KISSIMMEE

$400,000

▲ $100,000 SUN POINTE

2986 Sun Pointe Ct, KISSIMMEE

8 Beds 5 Baths 2,196 SqFt Residential Single Family Residence MLS® # S5146240
Active 7833 Turkey Oak Ln, KISSIMMEE

$400,000

INDIAN RIDGE VILLAS PH 4

7833 Turkey Oak Ln, KISSIMMEE

4 Beds 2 Baths 1,601 SqFt Residential Single Family Residence MLS® # G5117711
Active 2615 Palisade Blvd, KISSIMMEE

$400,000

▼ $10,000 TAPESTRY PH 2

2615 Palisade Blvd, KISSIMMEE

4 Beds 3 Baths 2,320 SqFt Residential Single Family Residence MLS® # O6383132
Active 2114 The Oaks Blvd, KISSIMMEE

$400,000

▼ $4,000 OAKS PH 1 B-2

2114 The Oaks Blvd, KISSIMMEE

3 Beds 2 Baths 2,609 SqFt Residential Single Family Residence MLS® # C7525948
Active 1921 Howard Mesa Dr, KISSIMMEE

$400,000

KINDRED PH 3B 3C & 3D

1921 Howard Mesa Dr, KISSIMMEE

3 Beds 2 Baths 1,504 SqFt Residential Single Family Residence MLS® # O6443048
Active 4706 Cumbrian Lakes Dr, KISSIMMEE

$400,000

▼ $10,000 CUMBRIAN LAKES RESORT PH 2

4706 Cumbrian Lakes Dr, KISSIMMEE

4 Beds 3 Baths 1,902 SqFt Residential Single Family Residence MLS® # O6418381
Open House
Active 1924 Turtle Dove Ln, KISSIMMEE

$399,999

▼ $15,001 STOREY CREEK PH 5

1924 Turtle Dove Ln, KISSIMMEE

4 Beds 2 Baths 1,843 SqFt Residential
Sun, Oct 4th, 2026 @ 2pm - 5pm
Single Family Residence MLS® # TB8545183
Active E Lake Shore Blvd, KISSIMMEE

$399,999

FLORIDA FRUIT BELT SALES

E Lake Shore Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6431655
Active 2092 Cross Prairie Pkwy, KISSIMMEE

$399,999

TOHOQUA PH 4B

2092 Cross Prairie Pkwy, KISSIMMEE

3 Beds 3 Baths 1,826 SqFt Residential Single Family Residence MLS® # O6437999
Active 3402 Great Pond Dr, KISSIMMEE

$399,999

BELLALAGO

3402 Great Pond Dr, KISSIMMEE

4 Beds 2 Baths 1,923 SqFt Residential Single Family Residence MLS® # O6409354
Active 1827 Southfork Dr, KISSIMMEE

$399,999

▼ $15,001 KINDRED PH 3A

1827 Southfork Dr, KISSIMMEE

3 Beds 2 Baths 1,516 SqFt Residential Single Family Residence MLS® # O6443474
Active 1437 Mona Dr, KISSIMMEE

$399,999

▼ $14,901 MILL RUN UNIT 7

1437 Mona Dr, KISSIMMEE

3 Beds 3 Baths 1,705 SqFt Residential Single Family Residence MLS® # O6435299
Active 254 Amber Way, KISSIMMEE

$399,999

▼ $5,000 STEPPING STONE PH 2 POD A

254 Amber Way, KISSIMMEE

5 Beds 3 Baths 2,287 SqFt Residential Single Family Residence MLS® # S5154825
Active 1904 Howard Mesa Dr, KISSIMMEE

$399,997

▼ $13,648 KINDRED PH 3B 3C & 3D

1904 Howard Mesa Dr, KISSIMMEE

3 Beds 2 Baths 1,504 SqFt Residential Single Family Residence MLS® # O6436426
Active 2401 Volunteer Ave, KISSIMMEE

$399,990

▼ $15,010 TOHOQUA PH 2

2401 Volunteer Ave, KISSIMMEE

4 Beds 3 Baths 2,044 SqFt Residential Single Family Residence MLS® # O6408166
Active 1073 Turquoise Waves Cv, KISSIMMEE

$399,990

SOLEIL AT WESTSIDE

1073 Turquoise Waves Cv, KISSIMMEE

3 Beds 2 Baths 1,740 SqFt Residential Single Family Residence MLS® # O6337335
Active 2022 Majorca Dr, KISSIMMEE

$399,990

WINDSOR AT WESTSIDE PH 1

2022 Majorca Dr, KISSIMMEE

4 Beds 4 Baths 2,102 SqFt Residential Townhouse MLS® # O6396215
Active 8060 Dreamsicle Dr, KISSIMMEE

$399,900

▼ $25,100 ROLLING OAKS PH 5

8060 Dreamsicle Dr, KISSIMMEE

3 Beds 3 Baths 1,564 SqFt Residential Single Family Residence MLS® # W7886608
Active 1596 Cross Prairie Pkwy, KISSIMMEE

$399,900

TOHOQUA PH 2

1596 Cross Prairie Pkwy, KISSIMMEE

4 Beds 3 Baths 2,044 SqFt Residential Single Family Residence MLS® # O6435436
Active 4902 Pall Mall St E, KISSIMMEE

$399,900

▼ $8,100 TRAFALGAR VLG PH 3

4902 Pall Mall St E, KISSIMMEE

4 Beds 3 Baths 2,139 SqFt Residential Single Family Residence MLS® # S5153223
Active 461 Boxwood Ct, KISSIMMEE

$399,900

▼ $15,100 BVL UNIT 7

461 Boxwood Ct, KISSIMMEE

4 Beds 2 Baths 1,775 SqFt Residential Single Family Residence MLS® # O6346030
Active 3081 Marshfield Preserve Way, KISSIMMEE

$399,900

▼ $7,100 CONCORDE ESTATES PH 1

3081 Marshfield Preserve Way, KISSIMMEE

4 Beds 4 Baths 2,668 SqFt Residential Single Family Residence MLS® # O6381743
Active 4752 Blue Diamond St, KISSIMMEE

$399,900

▼ $20,000 CRYSTAL COVE RESORT

4752 Blue Diamond St, KISSIMMEE

3 Beds 3 Baths 2,420 SqFt Residential Single Family Residence MLS® # O6387480
Active 2300 Finwick Ct, KISSIMMEE

$399,900

SHELBY PLACE PH 2

2300 Finwick Ct, KISSIMMEE

3 Beds 2 Baths 1,642 SqFt Residential Single Family Residence MLS® # S5158099
Active 3175 Tocoa Cir, KISSIMMEE

$399,900

COMPASS BAY UNIT 3

3175 Tocoa Cir, KISSIMMEE

4 Beds 4 Baths 1,782 SqFt Residential Townhouse MLS® # O6429820