Homes for Sale $300K to $500K in Kissimmee, FL

This page tracks every Kissimmee listing with an asking price between $300,000 and $500,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.

1634 homes listed between $300,000 and $500,000 are for sale or pending in Kissimmee, FL today across 658 communities. The median asking price is $380,000, from $300,000 to $499,999. Listings in Kissimmee without that feature have a median of $290,000. Most listings right now: Westview (24), Kindred Ph 3B 3C & 3D (23), Kindred (21). Updated September 11, 2026 from the MLS.

Kissimmee homes $300K–$500K by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most homes $300K–$500K listed are tabled; the rest follow.

Community	Homes $300K–$500K	New build	Median list	From
Westview	24	24	$367,624	$305,000
	23	20	$400,000	$320,000
Kindred	21	15	$359,990	$341,990
Evergreen Park	18	17	$324,990	$309,990
Regal Oaks At Old Town	18	0	$322,450	$300,000
Knightsbridge 50S	16	15	$402,256	$357,990
Poinciana Village 5 Nbhd 1	16	3	$337,000	$309,999
	16	16	$314,540	$303,420
Poinciana Village 2 Nbhd 3	15	1	$349,999	$300,000
Magic Village	14	0	$427,000	$385,000
	14	0	$329,450	$309,000
	14	0	$316,500	$307,000
Westview 50S Gc	13	13	$419,980	$310,050
Paradise Palms Resort Ph 2	12	0	$392,445	$319,999
Storey Lake Ph 3	11	0	$469,000	$435,000
Soleil At Westside	11	1	$329,000	$309,900
Poinciana Village 2 Nbhd 1	11	1	$325,000	$300,000
	10	4	$371,995	$315,000
	10	3	$337,499	$300,000
Solara Resort	9	0	$475,000	$389,900
	9	5	$475,000	$315,000
Windsor At Westside Ph 3	9	0	$445,000	$399,900
Summerville Resort	9	1	$439,900	$409,000
Windsor At Westside Ph 2B	9	0	$409,000	$388,000
Kindred Ph 2A	8	7	$458,270	$436,990
Solara Resort Vacation Villas Rep	8	0	$457,449	$434,900
Tohoqua Ph 2	8	1	$437,500	$399,000
Le Reve	8	0	$432,500	$390,000
	8	0	$414,444	$374,990
Cypress Hammock Ph 1	8	0	$387,500	$325,000
Paradise Palms Resort Ph 4	8	0	$349,945	$329,900
Poinciana Village 1 Nbhd 2	8	1	$339,450	$309,900
Bellavida Ph 1	8	0	$338,950	$304,900
Storey Lake Tr K	8	0	$333,700	$310,000
Magic Village Resort 2	7	0	$469,900	$447,900
Tohoqua	7	7	$457,400	$324,190
Storey Lake	7	0	$449,000	$308,000
Windsor Hills Ph 2	7	0	$419,000	$394,000
Tapestry	7	0	$418,900	$335,000
Tapestry Ph 5	7	0	$415,000	$310,000
Encantada Ph 1	7	0	$398,500	$310,000
	7	0	$369,900	$359,000
Paradise Palms Resort Ph 1	7	0	$365,000	$326,500
Cypress Reserve Villas	7	0	$355,000	$300,000
Fish Lake Cove	7	7	$349,990	$349,990
Storey Lake Ph 2	6	0	$461,450	$439,900
Windsor At Westside Ph 1	6	0	$420,949	$390,000
Windsor At Westside	6	0	$418,949	$405,000
Lindfields Unit 1	6	0	$382,499	$319,900
	6	0	$379,450	$329,900
Hammock Trails	6	0	$377,945	$324,000
Tohoqua Ph 1	6	0	$374,250	$329,900
Bellalago	6	0	$364,000	$310,000
	6	0	$352,445	$315,000
Hub At Westside Reserve	6	2	$349,950	$329,900
Westview 45S Aa	6	6	$333,990	$328,990
Coral Cay Resort	6	0	$329,450	$314,990
	6	0	$327,499	$305,000
	6	1	$325,000	$300,000
	6	0	$324,950	$305,000

Also with homes $300K–$500K for sale

Poinciana Village 1 Nbhd 1 South (6)
Reunion Village Phase 4 (5)
Lake Berkley Resort (5)
(5)
Seasons (5)
Oak Island Cove (5)
Veranda Palms Ph 1C (5)
Formosa Valley (5)
Cypress Hammock Ph 2 (5)
(5)
Crystal Cove Resort (5)
Tohoqua Ph 3 (5)
Poinciana Village 1 Nbhd 1 North (5)
Spectrum At Reunion Ph 2 (5)
(5)
Heritage Run (5)
Lake Wilson Reserve (5)
Windsor Palms Twnhms Ph 3A (5)
Tohoqua Ph 5B (5)
(5)
Bellalago Ph 4P (4)
Bellalago Ph 4K (4)
Tohoqua Ph 7 (4)
Paradise Palms Resort Ph 3B (4)
Terra Verde (4)
Neptune Pointe (4)
Terra Verde Ph 2 (4)
(4)
Tapestry Ph 2 (4)
Indian Wells Unit 5 (4)
Windsor Point Ph 2 (4)
Windsor Hills Ph 4 (4)
Tohoqua Ph 5A (4)
Tohoqua Reserve (4)
Concorde Estates Ph 2A (4)
Storey Creek Ph 1 (4)
Storey Creek Ph 5 (4)
Oaks Ph 1 B2 (4)
Murano At Westside (4)
Encantada (4)
(4)
(4)
Isles Of Bellalago Ph 2 (4)
(4)
Terra Esmeralda Twnhms (4)
Tapestry Ph 4 (4)
Fieldstone At Cypress Woods West (4)
(4)
Reedy Reserve Ph 3 (4)
(3)
Pennyroyal (3)
Kindred Ph 1C (3)
(3)
Storey Lake Ph 1B-2A (3)
Cypress Reserve Ph 02 (3)
(3)
Lindfields Unit 3 (3)
Fortune Lakes (3)
(3)
Bass Lake Estates (3)
Storey Creek (3)
Tohoqua Ph 4A (3)
Paradise Palms Resort (3)
(3)
Windsor At Westside; Windsor/Westside (3)
Magic Village Rep (3)
Creekside At Boggy Creek Ph 1 (3)
East Lake Preserve Ph 3 (3)
(3)
Wyndham Palms Ph 1A (3)
Jasmine Pointe At Crescent Lakes (3)
Turnberry Reserve Unit 1 (3)
(3)
Bellalago Ph 7L (3)
Kings Point (3)
Blackstone Landing Ph 1 (3)
Seasons At Big Sky Ph 1 (3)
(3)
Brighton Lakes Ph 1 (3)
Compass Bay Unit 3 (3)
Bridgewater (3)
Isles Of Bellalago (3)
Kindred Ph 1D (3)
Hub At Westside (3)
Eagles Nest At The Oaks (3)
Compass Bay Unit 1 (3)
(3)
(3)
Casa Bella (3)
(3)
(3)
Osceola Acres (3)
(3)
Kindred Ph 1E (3)
(3)
(3)
(3)
Emerald Pointe (3)
Esplanade At Westview (3)
Cypress Cay Ph 1 (3)
(3)
Storey Creek Ph 2A (3)
Bellalago Ph 3 (3)
(3)
(3)
(3)
(3)
Reunion Grande Condo (3)
Fiesta Key (3)
(3)
Encantada Ph 02 (3)
Townhomes Of Flora Ridge Ph 2 (3)
Windsor At Westside Ph 3A (2)
(2)
Summerville Resort Rep 1 (2)
Herons Landing (2)
Reunion Village Phase 5 (2)
Windsor At Westside Ph 2A (2)
North Point Ph 2B-2C (2)
(2)
Indian Creek Ph 2 (2)
(2)
Rolling Hills Estates Unit 1 At Formosa Gardens (2)
North Shore Village (2)
Cove At Storey Lake Iii (2)
Indian Creek Ph 1 (2)
Fairlawn Manor (2)
Mill Run Unit 8 (2)
Wyndham Palms Ph 3 (2)
Emerald Island Resort Ph 5A (2)
Westside Prcl E Tuscany (2)
(2)
(2)
Tohoqua Ph 1B (2)
(2)
(2)
(2)
(2)
Gleneagles (2)
Indian Wells Unit 8 (2)
(2)
(2)
Laurel Run At Crescent Lakes (2)
Forest Edge (2)
Westview 50S (2)
Westlake Hammock Ph 2 (2)
Remington Prcl M1 (2)
(2)
Emerald Island Resort (2)
(2)
Ambar Residences (2)
Bvl Briarwood Village Tr 3 (2)
Poinciana Village 1 Nbhd 3 East (2)
Banyan Cove At Cypress Woods (2)
Storey Lake Resort (2)
(2)
Southport Bay (2)
Tohoqua Ph 4B (2)
Stonehurst At Stonefield (2)
Remington Ph 1 Tr F (2)
Mill Run Unit 3 (2)
Remington Pointe (2)
(2)
Blackstone Landing Ph 2 (2)
(2)
Lago Buendia Ph 1 (2)
Paradise Palms Residence Ph 2 (2)
(2)
(2)
(2)
Woodall & Doyles (2)
Brighton Lakes Ph 1 Prcl D (2)
Bvl Unit 7 6Th Add (2)
Spectrum At Reunion (2)
Tohoqua Ph 6 (2)
Heritage Lakes (2)
Concorde Estates Ph 1B (2)
Buenaventura Lakes Unit 02 Add 01 (2)
Kindred Ph 3A (2)
Brighton Landings Ph 1 (2)
(2)
Kindred Ph 1Fb (2)
Brighton Landings Ph 2 (2)
Eagle Bay Ph 1 (2)
(2)
Verandahs (2)
(2)
(2)
Poinciana Village 01 Neighborhood 02 (2)
Eagle Pointe (2)
(2)
(2)
Storey Creek Ph 2B (2)
(2)
Compass Bay (2)
(2)
Estancia (2)
Blackstone Landing Ph 3 (2)
Stepping Stone (2)
(2)
(2)
(2)
Doral Pointe Unit 2 (2)
Bellalago Ph 3M (2)
Doral Pointe North (2)
Emerald Lake (2)
(2)
(2)
(2)
Indian Wells Unit 7 (2)
Shannon Lakes Ph 3 (2)
Cypress Cay (2)
(2)
Orange Terrace (2)
Orange Gardens Sec 4 (2)
Margaritaville, Rolling Oaks (2)
(2)
(2)
(2)
(2)
(2)
(2)
Plantation (2)
Remington Ph 1 Tr A (2)
Bella Parc Twnhms (2)
Amber Pointe Unit 2 (2)
(2)
(2)
Poinciana Village 02 (2)
(2)
Meadow Spgs (1)
(1)
(1)
(1)
(1)
Kindred 100 Rep (1)
Indian Creek Phase Iv (1)
Cumbriam Lakes Dr (1)
Cherokee Oaks (1)
Willow Bend At Crescent Lakes (1)

Where this band sits in the market

The answer block above shows how the median of this band compares with the rest of the city’s listings, which tells you whether $300,000–$500,000 is the middle of the market here or the top of it. Within the band, compare on price per square foot and year built: newer subdivisions usually price higher per foot with lower expected maintenance, older ones the reverse. Each community page carries the HOA and CDD picture, the year-built range and the sales history, so two homes at the same price can be told apart in a few minutes.

Questions to ask about any listing in this band

What are the total monthly carrying costs (taxes, insurance, HOA, CDD) and how do they compare with a similar home two communities over? What is the age of the roof, HVAC and water heater? Is the community’s HOA financially healthy (reserves, no pending assessment)? How many days has the listing been on the market and has the price moved? A local agent who works the area will know which communities in this band are trading at asking and which are negotiating.

Common questions

How many homes listed between $300,000 and $500,000 are for sale in Kissimmee?

As of September 11, 2026, 1634 Kissimmee, FL listings whose MLS record reports an asking price between $300,000 and $500,000 are active or pending, across 658 communities. The count updates with every MLS refresh.

What do homes $300K–$500K cost in Kissimmee?

The median asking price today is $380,000, with listings from $300,000 to $499,999. Kissimmee listings without that feature have a median of $290,000.

Which Kissimmee community has the most homes $300K–$500K for sale?

Westview has the most right now (24), followed by Kindred Ph 3B 3C & 3D (23), Kindred (21), Evergreen Park (18).

What is the monthly payment on a $400,000 home?

At today’s rates with 20% down, principal and interest on a $400,000 purchase runs roughly $2,000–$2,300 a month before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator turns them into one monthly figure.

Keep exploring Kissimmee

Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Kissimmee, FL whose MLS record reports an asking price between $300,000 and $500,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.