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.
1599 homes listed between $300,000 and $500,000 are for sale or pending in Kissimmee, FL today across 653 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: Kindred Ph 3B 3C & 3D (23), Westview (22), Knightsbridge 50S (21). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Kissimmee: the listings
1,281 active listings match today (47% of Kissimmee inventory), median asking $380,000, $211/sq ft, median 41 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Kissimmee
The most expensive $300k–$500k homes in Kissimmee
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 2694 La Isla Court | $499,999 | 2,317 | Emerald Island Resort |
| 5683 Nevis Terrace | $499,999 | 2,296 | Esplanade At Westview |
| 1791 Smarts Rule Street | $499,990 | 2,500 | Tohoqua |
| 2466 Relaxing Lane | $499,990 | 2,151 | Tohoqua |
| 2353 Crescent Moon Street | $499,990 | 3,438 | — |
| 2967 Penelope Loop | $499,990 | 1,914 | — |
| 4613 Formby Court | $499,900 | 2,317 | Lake Berkley Resort |
| 2821 Scenic Lane | $499,900 | 2,538 | North Shore Village |
| 1889 Rustic Falls Drive | $499,900 | 3,099 | Kindred |
| 3087 Juliet Drive | $499,900 | 2,168 | Storey Lake |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 1281 | 100% |
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 |
|---|---|---|---|---|
| Kindred Ph 3B 3C & 3D | 23 | 20 | $404,645 | $327,000 |
| Westview | 22 | 22 | $364,687 | $305,000 |
| Knightsbridge 50S | 21 | 20 | $412,756 | $357,990 |
| Kindred | 21 | 16 | $359,990 | $341,990 |
| Evergreen Park | 17 | 17 | $319,990 | $309,990 |
| Fish Lake Cove | 16 | 16 | $345,990 | $341,990 |
| Poinciana Village 5 Nbhd 1 | 16 | 2 | $336,450 | $310,000 |
| Westview 45S Gc | 16 | 16 | $321,040 | $306,420 |
| Regal Oaks At Old Town | 16 | 0 | $318,750 | $300,000 |
| Westview 50S Gc | 15 | 15 | $411,280 | $310,050 |
| Poinciana Village 2 Nbhd 3 | 15 | 1 | $349,900 | $300,000 |
| West Lucaya Village | 15 | 0 | $318,000 | $307,000 |
| Magic Village | 12 | 0 | $417,000 | $385,000 |
| Soleil At Westside | 12 | 1 | $334,500 | $309,900 |
| Storey Lake Ph 3 | 11 | 0 | $474,900 | $435,000 |
| Paradise Palms Resort Ph 2 | 11 | 0 | $378,000 | $319,999 |
| Kindred Ph 2C & 2D | 10 | 0 | $406,944 | $360,000 |
| Westview Pod B Neighborhood 2A & 2B Ph 1 | 10 | 3 | $367,445 | $315,000 |
| Poinciana Village 2 Nbhd 1 | 10 | 1 | $324,995 | $300,000 |
| Solara Resort | 9 | 0 | $469,980 | $389,900 |
| Solara Resort Vacation Villas Rep | 9 | 0 | $455,000 | $434,900 |
| Windsor At Westside Ph 3 | 9 | 0 | $445,000 | $399,900 |
| Windsor At Westside Ph 2B | 9 | 0 | $409,000 | $388,000 |
| Bvl Unit 3 | 9 | 0 | $359,950 | $309,000 |
| Paradise Palms Resort Ph 1 | 9 | 0 | $339,000 | $309,000 |
| Trafalgar Village Ph 3 | 8 | 5 | $464,945 | $380,000 |
| Kindred Ph 2A | 8 | 7 | $451,270 | $398,990 |
| Summerville Resort | 8 | 0 | $446,000 | $418,000 |
| Tohoqua Ph 2 | 8 | 1 | $414,995 | $399,000 |
| Encantada Ph 1 | 8 | 0 | $389,000 | $310,000 |
| Bellavida Ph 1 | 8 | 0 | $341,500 | $304,900 |
| Poinciana Village 1 Nbhd 2 | 8 | 1 | $338,995 | $309,900 |
| Poinciana Nbrhd 06 Village 07 | 8 | 2 | $332,500 | $310,000 |
| Cypress Hammock Ph 2 | 7 | 0 | $469,900 | $362,500 |
| Storey Lake Ph 2 | 7 | 0 | $460,000 | $439,900 |
| Magic Village Resort 2 | 7 | 0 | $459,000 | $447,900 |
| Tohoqua | 7 | 6 | $457,400 | $324,190 |
| Le Reve | 7 | 0 | $436,000 | $406,000 |
| Tapestry | 7 | 0 | $418,900 | $335,000 |
| Windsor Hills Ph 2 | 7 | 0 | $414,900 | $394,000 |
| Hammock Trails | 7 | 0 | $399,000 | $323,990 |
| Tohoqua Ph 1 | 7 | 0 | $384,500 | $314,900 |
| Cypress Hammock Ph 1 | 7 | 0 | $375,000 | $325,000 |
| Paradise Palms Resort Ph 4 | 7 | 0 | $359,990 | $329,900 |
| Storey Lake Tr K | 7 | 0 | $332,000 | $319,900 |
| Westview 45S Aa | 7 | 7 | $324,990 | $323,990 |
| Oak Island Cove | 6 | 0 | $464,450 | $365,000 |
| Lake Berkley Resort | 6 | 0 | $459,450 | $429,000 |
| Formosa Valley | 6 | 0 | $444,495 | $438,900 |
| Storey Lake | 6 | 0 | $439,900 | $308,000 |
| Reunion Village Ph 4 & 5 | 6 | 1 | $416,400 | $391,900 |
| Lindfields Unit 1 | 6 | 0 | $382,499 | $317,500 |
| Tapestry Ph 5 | 6 | 0 | $374,950 | $310,000 |
| Sunset Walk Hotel Condo Ph 1 | 6 | 0 | $374,450 | $329,900 |
| Bellalago | 6 | 0 | $359,000 | $310,000 |
| Tohoqua Ph 5A | 6 | 1 | $348,450 | $308,000 |
| Hub At Westside Reserve | 6 | 2 | $337,500 | $329,900 |
| Poinciana Village 1 Nbhd 1 South | 6 | 0 | $314,000 | $309,000 |
| Reunion Village Phase 4 | 5 | 4 | $478,900 | $418,000 |
| Cove At Storey Lake 4 | 5 | 0 | $469,000 | $459,990 |
Also with homes $300K–$500K for sale
- Seasons (5)
- Paradise Palms Resort Ph 3B (5)
- Bellalago Ph 4K (5)
- Windsor At Westside (5)
- Crystal Cove Resort (5)
- Windsor At Westside Ph 1 (5)
- Storey Creek Ph 3B & 4 (5)
- Tohoqua Ph 3 (5)
- Hub At Westside (5)
- Poinciana Village 1 Nbhd 1 North (5)
- Spectrum At Reunion Ph 2 (5)
- Bvl Unit 2 (5)
- Poinciana Nbrhd 05 North Village 03 (5)
- Reunion Grande Condo (5)
- Poinciana Village 1 Nbhd 3 West (5)
- Poinciana Nbrhd 05 Village 07 (5)
- Summer Flowers Twnhms (5)
- Coral Cay Resort (5)
- Lucaya Village Ph 2 (5)
- Poinciana Nbrhd 02 West Village 07 (5)
- Woods At Kings Crest The Ph 1 (4)
- Tohoqua Ph 7 (4)
- Bellalago Ph 4P (4)
- Neptune Pointe (4)
- Shingle Creek Reserve At The Oaks Ph 3 & 4 (4)
- Terra Verde Ph 2 (4)
- Indian Wells Unit 5 (4)
- Tohoqua Ph 4A (4)
- Tapestry Ph 2 (4)
- Windsor Point Ph 2 (4)
- Compass Bay Unit 3 (4)
- Stepping Stone Pod A Ph 1 (4)
- Eagle Lake Ph 3 (4)
- Oaks Ph 1 B2 (4)
- Encantada (4)
- Storey Creek Ph 1 (4)
- Storey Creek Ph 5 (4)
- Bridgewater (4)
- Terra Verde Villas Ph 1 (4)
- Sedona Ph 1 (4)
- Isles Of Bellalago Ph 2 (4)
- Murano At Westside (4)
- Kindred Ph 1D (4)
- Coralwood (4)
- Compass Bay Unit 1 (4)
- Sunset Walk Hotel, Embassy Suites (4)
- Indian Wells Unit 7 (4)
- Fieldstone At Cypress Woods West (4)
- Poinciana Nbrhd 04 Village 07 (4)
- Tapestry Ph 4 (4)
- Ventura At Windsor Hills Condo Ph 3 (4)
- Tohoqua Ph 5B (4)
- Heritage Run (4)
- Terra Verde Villas Ph 2 (4)
- Lake Wilson Reserve (4)
- Windsor Palms Twnhms Ph 3A (4)
- Storey Lake Ph 1B-2A (3)
- Cypress Reserve Ph 02 (3)
- Lindfields Unit 3 (3)
- Bellalago Ph 5J Sec 3 (3)
- Hilliard Ridg (3)
- Kindred Ph 1C (3)
- East Lake Preserve Ph 3 (3)
- Bass Lake Estates (3)
- Windsor At Westside; Windsor/Westside (3)
- Magic Village Rep (3)
- Kindred Ph 3A (3)
- Wyndham Palms Ph 1A (3)
- Windsor Hills Ph 4 (3)
- Eagle Pointe Ph 2 (3)
- Jasmine Pointe At Crescent Lakes (3)
- Sedona Ph 2 (3)
- Tohoqua Reserve (3)
- Banyan Cove At Cypress Woods (3)
- Blackstone Landing Ph 2 (3)
- Eagle Bay Ph 1 (3)
- Seasons At Big Sky Ph 1 (3)
- Brighton Lakes Ph 1 (3)
- Concorde Estates Ph 2A (3)
- Cypress Reserve Villas (3)
- Kindred Ph 1E (3)
- Indian Ridge Villas Ph 1 (3)
- Compass Bay Unit 5 (3)
- Eagle Lake Ph 4B (3)
- The Terraces At Storey Lake Condo 3 Ph 12 (3)
- Osceola Acres (3)
- Esplanade At Westview (3)
- Osceola Village Center Ph 2 (3)
- Montego Bay (3)
- Casa Bella (3)
- Terra Esmeralda Twnhms (3)
- Wilderness Ph 3 The (3)
- Bellalago Ph 3 (3)
- Eagle Pointe (3)
- Emerald Pointe (3)
- Cypress Cay Ph 1 (3)
- Blackstone Landing Ph 3 (3)
- Overlook Reserve Ph 1 (3)
- Fiesta Key (3)
- Encantada Ph 02 (3)
- Poinciana Nbrhd 02 Village 08 (3)
- Reedy Reserve Ph 3 (3)
- North Shore Village (2)
- Pennyroyal (2)
- Windsor At Westside Ph 3A (2)
- Summerville Resort Rep 1 (2)
- Herons Landing (2)
- Villa Sol Ph 2 Village 3 (2)
- Seasons At Big Sky Ph 2 (2)
- Reunion Village Phase 5 (2)
- Windsor At Westside Ph 2A (2)
- North Point Ph 2B-2C (2)
- Indian Creek Ph 2 (2)
- Villa Sol Ph 1 Village 5 (2)
- Veranda Palms Ph 1C (2)
- Indian Creek Ph 1 (2)
- Cove At Storey Lake Iii (2)
- Marbella Ph 2 (2)
- Wyndham Palms Ph 3 (2)
- Storey Creek Ph 6 (2)
- Emerald Island Resort Ph 5A (2)
- Indian Ridge Villas Ph 4 (2)
- Brighton Lakes Ph 2 Prcl J (2)
- Tohoqua Ph 1B (2)
- Indian Wells Unit 8 (2)
- Windsor/Westside-Ph 3 (2)
- Poinciana Village 01 Neighborhood 02 (2)
- Bvl Unit 9 5Th Add (2)
- Overlook Reserve Ph 2 (2)
- Osprey Ridge (2)
- Westview Pod B Neighborhood 5 Ph 1 (2)
- Gleneagles (2)
- Laurel Run At Crescent Lakes (2)
- Forest Edge (2)
- Cumbrian Lakes Resort Ph 2 (2)
- Storey Creek (2)
- Westlake Hammock Ph 2 (2)
- Mill Run Unit 8 (2)
- Waterview Ph 1B (2)
- Bellalago Ph 7L (2)
- Cumbrian Lakes Resort Ph 3 (2)
- Emerald Island Resort (2)
- Ambar Residences (2)
- Bvl Briarwood Village Tr 3 (2)
- Poinciana Village 1 Nbhd 3 East (2)
- Turnberry Reserve Unit 1 (2)
- Paradise Palms Resort (2)
- Overoaks Rep 1 (2)
- Tohoqua Ph 4B (2)
- Southport Bay (2)
- Storey Creek Ph 2A (2)
- Remington Prcl M1 (2)
- Blackstone Landing Ph 1 (2)
- Waterview Ph 3B (2)
- Lago Buendia Ph 1 (2)
- Kindred Ph 1A & 1B (2)
- Eagle Lake Ph 2A (2)
- Brighton Lakes Ph 1 Prcl D (2)
- Bvl Unit 7 6Th Add (2)
- Spectrum At Reunion (2)
- Eagles Nest At The Oaks (2)
- Woodall & Doyles (2)
- Concorde Estates Ph 1 (2)
- Buenaventura Lakes Unit 02 Add 01 (2)
- Poinciana Nbrhd 03 Village 03 (2)
- Kindred Ph 1Fb (2)
- The Terraces At Storey Lake Condo 2 Ph 6 (2)
- Isles Of Bellalago (2)
- Renee Terrace Sec 4 (2)
- Shingle Creek Reserve At The Oaks Ph 7 Rep 2 (2)
- Windsor Hills, Ventura At Windsor Hills (2)
- Parsons Pond Ph 3 (2)
- Indian Wells (2)
- Tohoqua Ph 6 (2)
- Concorde Estates Ph 1B (2)
- Storey Creek Ph 2B (2)
- Compass Bay (2)
- Pineridge Estates Unit 2 (2)
- Solivita Ph 04C Sec 02 (2)
- Monterey Village Ph 1 Unit 1 (2)
- Trafalgar Village Ph 2 (2)
- Estancia (2)
- Bellalago Ph 3M (2)
- Emerald Lake (2)
- The Terraces At Storey Lake Condo 2 Ph 15 (2)
- Marisol Ph 2 (2)
- Villas At Reunion Square Condo Ph 1 (2)
- The Terraces At Storey Lake Condo 2 Ph 5 (2)
- Bermuda Bay (2)
- Shannon Lakes Ph 3 (2)
- Ham Brown Reserve-Ph 1A 1B 1C (2)
- Ventura At Windsor Hills Condo Ph 6 (2)
- Buenaventura Lakes Unit 02 Add 01 (2)
- Pinehurst At Cypress Woods (2)
- Osceola Park Estates Unit 1 (2)
- Ventura At Windsor Hills Condo Ph 7 (2)
- Sun Lake Condo (2)
- Ventura At Windsor Hills Condo Ph 1 (2)
- Bella Parc Twnhms (2)
- Westview 40S Gc (2)
- Remington Ph 1 Tr A (2)
- Paradise Palms Resort P1 (2)
- Poinciana Village 02 (2)
- Poinciana Nbrhd 5 Village 7 (2)
- Raintree At Springlake Village Ph 1A (1)
- Pleasant Hill Lakes Unit 2 (1)
- Wyndham Palms Ph 1B (1)
- Cumbrian Lakes Resort Ph 1 (1)
- Ridgewood 1 Rev (1)
- Indian Crk Ph 06 (1)
- Indian Creek Phase Iv (1)
- Cumbriam Lakes Dr (1)
- Willow Bend At Crescent Lakes (1)
- North Point Ph 1B (1)
- Preserve At Tapestry (1)
- Emerald Island Resort Ph 3 (1)
- Woodland Creek (1)
- Spectrum At Reunion Condo Ph 4A & 4B (1)
- Reunion Ph 2 Prcl 3 (1)
- Paradise Palms Resort Ph 3A (1)
- Windsor/Westside-Ph 2B (1)
- The Terraces At Storey Lake Condo 3 Ph 10 (1)
- Oaks 2 The (1)
- Veranda Palms Ph 1B (1)
- Cypress Hammock (1)
- Campbell Cove (1)
- Wyndham Pointe / Acadia Estates (1)
- Storey Creek 40S (1)
- Sunset Walk Hotel Condo Ph 2-5 (1)
- Emerald Isl Rsrt Ph5A (1)
- Rustic Acres Unit 1 (1)
- Cumbrian Lakes Resort Ph 01 (1)
- Indian Creek Ph 4 (1)
- Maria W Rao (1)
- Storey Lake Ph I-3A (1)
- Lake Berkley Resort Ph 2 (1)
- Cherokee Oaks (1)
- Storey Creek Ph 3A (1)
- Margaritaville (1)
- Wndsor/Westside-Ph 3 (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 October 2, 2026, 1599 Kissimmee, FL listings whose MLS record reports an asking price between $300,000 and $500,000 are active or pending, across 653 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?
Kindred Ph 3B 3C & 3D has the most right now (23), followed by Westview (22), Knightsbridge 50S (21), Kindred (21).
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
- All homes for sale in Kissimmee
- Kissimmee ZIP codes with prices
- Kissimmee pool homes
- Kissimmee waterfront homes
- Kissimmee golf course homes
- Kissimmee gated community homes
- Kissimmee 4-bedroom homes
- Kissimmee homes under $300K
- Homes $300K–$500K in every city
Homes $300K–$500K in nearby Osceola County cities
- St Cloud homes $300K–$500K (940 for sale)
- Reunion homes $300K–$500K (69 for sale)
- Harmony homes $300K–$500K (45 for sale)
- Celebration homes $300K–$500K (24 for sale)
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.