Homes for Sale Under $300K in Kissimmee, FL
This page tracks every Kissimmee listing with an asking price under $300,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.
936 homes listed under $300,000 are for sale or pending in Kissimmee, FL today across 383 communities. The median asking price is $246,000, from $40,000 to $299,999. Listings in Kissimmee without that feature have a median of $420,000. Most listings right now: Poinciana Village 2 Nbhd 1 (22), Poinciana Village 5 Nbhd 1 (20), West Lucaya Village (17). Updated November 11, 2026 from the MLS.
First-time buyers: what Kissimmee costs at the entry level
758 active single-family homes, townhomes and condos at or below $300,000 — median $249,900, about $1,608/mo principal & interest at 7.18% with 5% down. Live from the MLS, refreshed nightly.
Newest homes under $300K in Kissimmee
What the payment looks like
| Purchase price | P&I at 7.18%, 5% down | P&I, 20% down | Cash to close at 5% down (est.) |
|---|---|---|---|
| $150,000 | $965 | $813 | $12,000 |
| $200,000 | $1,287 | $1,084 | $16,000 |
| $250,000 | $1,609 | $1,355 | $20,000 |
| $300,000 | $1,931 | $1,626 | $24,000 |
Estimates only; taxes, insurance, HOA and mortgage insurance are on top. Closing costs assumed at 3%.
Down-payment assistance in Osceola County · First-time buyer guide
Kissimmee homes under $300K 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 under $300K listed are tabled; the rest follow.
| Community | Homes Under $300K | New build | Median list | From |
|---|---|---|---|---|
| Poinciana Village 2 Nbhd 1 | 22 | 1 | $265,000 | $189,990 |
| Poinciana Village 5 Nbhd 1 | 20 | 0 | $274,950 | $138,700 |
| West Lucaya Village | 17 | 0 | $279,990 | $249,500 |
| Villas Del Sol At Kissimmee Condo | 16 | 0 | $186,250 | $164,000 |
| Poinciana Village 1 Nbhd 2 | 14 | 0 | $264,450 | $225,000 |
| Emerald Island Resort Ph 2 | 13 | 0 | $245,000 | $190,000 |
| Meridian Palms Comm Condo | 13 | 0 | $49,500 | $41,000 |
| Regal Oaks At Old Town | 11 | 1 | $276,000 | $235,000 |
| Poinciana Village 1 Nbhd 1 South | 11 | 0 | $255,000 | $199,000 |
| Fiesta Key | 11 | 0 | $249,999 | $195,000 |
| Venetian Bay Village Condo Ph 1 | 11 | 0 | $245,000 | $195,000 |
| Lake Berkley Resort Villas Ph 2 | 11 | 0 | $235,000 | $199,900 |
| Blossom Park Villas Condo | 11 | 1 | $175,000 | $130,000 |
| Poinciana Village 2 Nbhd 3 | 10 | 0 | $275,750 | $199,000 |
| Poinciana Nbrhd 05 North Village 03 | 10 | 0 | $241,000 | $113,999 |
| Poinciana Nbrhd 05 Village 07 | 10 | 0 | $238,775 | $214,900 |
| Tuscany Preserve Ph 03 | 10 | 5 | $204,000 | $179,900 |
| Parkway Palms Resort Maingate Condo | 10 | 0 | $132,450 | $116,000 |
| Greenpoint Essential Hotel Condo | 10 | 0 | $58,450 | $49,000 |
| Broadmoor | 9 | 0 | $249,900 | $149,999 |
| Poinciana Nbrhd 02 Village 08 | 8 | 1 | $269,450 | $215,000 |
| Poinciana Village 1 Nbhd 1 North | 8 | 0 | $246,500 | $210,000 |
| Legacy Dunes Condo | 8 | 0 | $215,000 | $185,000 |
| Villas At Somerset The | 8 | 0 | $196,450 | $164,900 |
| Terra Verde Villas Ph 2 | 7 | 0 | $275,000 | $219,900 |
| Crestwynd Bay | 7 | 0 | $252,000 | $220,000 |
| Poinciana Nbrhd 06 Village 07 | 7 | 0 | $249,990 | $205,000 |
| Poinciana Nbrhd 02 West Village 07 | 7 | 2 | $239,990 | $200,000 |
| Villas At Seven Dwarfs Lane Condo | 7 | 0 | $215,000 | $205,000 |
| Coopersmith Village At Poinciana | 7 | 0 | $167,999 | $139,900 |
| Poinciana Village 02 Neighborhood 01 | 6 | 0 | $276,375 | $249,900 |
| Poinciana Nbrhd 04 Village 07 | 6 | 0 | $251,750 | $240,000 |
| Venetian Bay Village Condo Ph 2 | 6 | 0 | $203,500 | $193,900 |
| Fiesta Key Ph 2 | 5 | 0 | $292,500 | $279,900 |
| Remington Ph 1 Tr A | 5 | 0 | $289,000 | $269,900 |
| Encantada Ph 1 | 5 | 0 | $274,900 | $258,000 |
| Poinciana Nbrhd 03 Village 03 | 5 | 0 | $239,900 | $219,000 |
| Poinciana Village 1 Nbhd 3 South | 5 | 0 | $239,900 | $224,500 |
| Villas At Secret Lake Condo | 5 | 0 | $223,000 | $176,000 |
| Sweetwater Club Condo | 5 | 0 | $215,000 | $201,900 |
| Runaway Beach Club Condo | 5 | 0 | $215,000 | $145,000 |
| Gables At Lakeside Condo | 5 | 0 | $184,900 | $129,900 |
| Westview 45S Aa | 4 | 4 | $299,990 | $299,990 |
| Lucaya Village Ph 2 | 4 | 0 | $288,500 | $274,990 |
| Embassy Suites, Sunset Walk Hotel | 4 | 0 | $284,500 | $179,000 |
| Sunset Walk Hotel, Embassy Suites | 4 | 0 | $275,000 | $199,900 |
| Paradise Cay | 4 | 0 | $268,000 | $260,000 |
| Poinciana Village 1 Nbhd 3 West | 4 | 0 | $264,900 | $236,000 |
| Pine Island Villas At Bvl | 4 | 0 | $254,950 | $245,900 |
| Encantada Ph 2 | 4 | 0 | $254,500 | $214,000 |
| Venetian Bay Village Condo Ph 3 | 4 | 0 | $244,950 | $215,000 |
| Trafalgar Village Ph 1 | 4 | 0 | $244,949 | $238,000 |
| Eric Estates | 4 | 0 | $229,950 | $170,000 |
| Blossom Park Villas A Condo | 4 | 0 | $222,000 | $158,900 |
| Seven Eagles Condo | 4 | 0 | $221,944 | $174,999 |
| Bellalago Pod G Twnhms | 4 | 0 | $219,995 | $179,000 |
| Royal Palm Bay Condo | 4 | 0 | $216,700 | $210,000 |
| Villas At Shadow Bay The | 4 | 0 | $184,945 | $139,900 |
| Arbors Of Sendera | 4 | 0 | $157,990 | $155,000 |
| Legacy Grand East Gate Condo | 4 | 0 | $87,000 | $85,000 |
Also with homes under $300K for sale
- Maingate Hotel Condo (4)
- Reunion Grande Condo (3)
- Rolling Oaks Ph 7 (3)
- Amber Pointe Unit 2 (3)
- Bellavida Ph 1 (3)
- Lucaya Village Ph 1 (3)
- Terra Verde Villas Ph 1 (3)
- The Terraces At Storey Lake Condo 1 Ph 4 (3)
- Vlgs At Mango Key Ph 1A The (3)
- Coral Cay Resort (3)
- Club Cortile (3)
- Sun Lake Condo (3)
- Solivita Ph 03B (3)
- Westview Pod A Ph 1B & 2 (3)
- Sunset Walk Hotel Condo Ph 1 (3)
- Summerfield Twnhms (3)
- Flora Ridge Condo Ph 8 Bldg 11 (3)
- Villas At Estancia Condo (3)
- Emerald Lake (3)
- Wyndham Palms Condo Ph 2 (3)
- Robert Bass Add (3)
- Villas At Somerset (3)
- Palm Villas Condo (3)
- Caribe Cove Condo Ph 2 (3)
- Villas At Laguna Bay Condo (3)
- Shadow Bay Villas (3)
- Bella Vista Condo (3)
- Terra Condo (3)
- Mona Lisa At Celebration Condo Hotel (3)
- Bella Parc Twnhms (2)
- Villa Sol Twnhms Village 6 (2)
- Murano At Westside Ph 2 (2)
- The Terraces At Storey Lake Condo 2 Ph 6 (2)
- Tapestry Ph 5 (2)
- Storey Lake Tr K (2)
- Doral Pointe North (2)
- Windsor Hills, Ventura At Windsor Hills (2)
- Oakwater (2)
- Donegan Twnhms (2)
- Bellavida Ph 01 (2)
- Amber Pointe (2)
- Cypress Lakes Twnhms Ph 2 Unit 1 (2)
- Solivita Ph 05F (2)
- Solivita Ph 04C Sec 02 (2)
- The Terraces At Storey Lake Condo 1 Ph 2 (2)
- Sunset Walk Hotel Condo Ph 2-5 (2)
- Regal Oaks (2)
- Heritage Key Villas Ph 1 & 2 (2)
- Oakwater Condo Ph 7-10 (2)
- Ventura At Windsor Hills Condo Ph 3 (2)
- Pineridge Estates Unit 2 (2)
- Poinciana Village 01 Neighborhood 01 South (2)
- Paradise Cove (2)
- Oakwater Condo Ph 20-23 (2)
- Emerald Island Resort Replat (2)
- Solivita Ph Iib (2)
- Poinciana Nbrhd 02 East Village 07 (2)
- Emerald Island Residence Ph 2 (2)
- Lake Berkley Resort Villas (2)
- Poinciana Nbrhd 02 Village 03 (2)
- Solivita Ph 01 (2)
- Las Palmas Villas (2)
- Windsor Oaks (2)
- Solivita Ph 5D (2)
- Flora Ridge Condo Ph 6 Bldg 13 (2)
- Villas At Reunion Square Condo Ph 1 (2)
- Caribe Cove Condo Ph 3 (2)
- Grand Palms Condo 4 Ph 2 (2)
- Coral Estates (2)
- Raintree Park Ph 2 (2)
- Wyndham Palms Condo Ph 7 (2)
- Bvl Unit 3 (2)
- Poinciana Village 01 Neighborhood 03 West (2)
- Windsor Palms Condo Ph 10 (2)
- Fantasyworld Club Villas Unit 1 (2)
- Westview 27 Villas (2)
- Cottons Village (2)
- Villas At Shadow Bay (2)
- Marydia (2)
- Jazsam Twnhms (2)
- Fantasyworld Club Villas Unit 3 (2)
- Wyndham Palms Condo Ph 6 (2)
- Grand Palms (2)
- Rio Hills Twnhs (2)
- Rio Hills Townhouses (2)
- Villas At Seven Dwarfs Lane (2)
- Caribe Cove Condo Ph 4 (2)
- Club Cortile Condo Ph 11 (2)
- Lake Marion Golf Resort Ph 02 (2)
- Columbia Arms Condo (2)
- Marbrisa Villas (2)
- Villas At Island Club Ph 9 (2)
- Grand Palms Condo 1 (2)
- Spring Meadow Ph 1 (2)
- Campbell Heights (2)
- Cascade At Kissimmee Condo (2)
- Lake Marion Golf Residence Condo (2)
- Legacy Grand (2)
- Maingate Hotel (2)
- Villas At Reunion Square Condo Ph 5 (1)
- Margaritaville, Rolling Oaks (1)
- Rolling Oaks Ph 5 (1)
- Poinciana Nbrhd 5 Village 7 (1)
- Villas At Reunion Square Condo Ph 4 (1)
- Twnhomes Flora Ridge P2 (1)
- Soho/Lakeside Ph 1 Bldg 4 (1)
- Kindred Ph 1E (1)
- Heritage Run (1)
- Cypress Lakes Ph 6 (1)
- Tapestry Ph 4 (1)
- Emerald Pointe (1)
- Oakwater Condo Ph 11-14 (1)
- Oakwater Condo Ph 15-19 (1)
- Kindred Ph 3B 3C & 3D (1)
- Westview 45S Gc (1)
- Maple Chase At Cypress Woods (1)
- Cypress Hammock Ph 1 (1)
- Windsor Palms / Wyndham Palms (1)
- The Terraces At Storey Lake Condo 2 Ph 13 (1)
- Compass Bay Unit 3 (1)
- Cypress Lakes Twnhms Pii U1 (1)
- Esplanade At Westview (1)
- Poinciana Village 02 (1)
- C A Carsons Add (1)
- The Terraces At Storey Lake Condo 3 Ph 12 (1)
- Stepping Stone Pod A Ph 2 (1)
- Eagle Bay Ph I J1 (1)
- Tapestry Ph 2 (1)
- The Terraces At Storey Lake Condo 1 Ph 3 (1)
- Eagles Nest At The Oaks (1)
- Villas At Reunion Square; A Condo Ph 3 (1)
- Silver Lake Estates Unit 2 (1)
- Country Green Ph 1 Unit 2 (1)
- Town & Country Estates Unit 1 (1)
- Tohoqua Ph 1 (1)
- Shenandoah (1)
- Peppertree At Cyp Wds U1 (1)
- Caribe Cove Ph 05 Condo (1)
- Buenaventura Lakes Unit 11 Add 02 (1)
- Poinciana Nbrhd 5 North Vill 3 (1)
- Orange Gardens Sec 3 (1)
- Plantation (1)
- Cypress Lake Ph 1 (1)
- Storey Creek Ph 2A (1)
- Eagle Bay Ph 1 (1)
- Osceola Village Center Ph 2 (1)
- Soleil At Westside (1)
- Solivita Ph 02D (1)
- Bvl Unit 11 1St Add (1)
- I M Mabbetts Add (1)
- Lucaya Village (1)
- The Terraces At Storey Lake Condo 2 Ph 14 (1)
- Poinciana Village 05 Neighborhood 01 (1)
- Heatherstone At Crescent Lakes (1)
- Shingle Creek Village Terrace (1)
- Westview Pod A Phase 3 (1)
- Terraces At Reunion Condo Ph 8 (1)
- Poinciana Sub Nbrhd 5 Vil 7 (1)
- Villas At Reunion Square Condo Ph 3 (1)
- Spectrum/Reunion (1)
- Bvl Unit 2 (1)
- The Terraces At Storey Lake Condo No 2 Ph13 (1)
- Solivita Ph 7D (1)
- Villas At Island Club Ph 10 (1)
- Storey Lake Condo (1)
- Cypress Cay Ph 1 (1)
- Cane Island Condo (1)
- Ventura At Windsor Hills Condo Ph 6 (1)
- Storey Lake Condo 3 Ph 11 (1)
- Poinciana Village 5 Nbhd 1 (1)
- Poinciana Nbrhd 3 Village 3 (1)
- Westview Ph 1B & 2 Pod A (1)
- Windsor Hills P1 (1)
- Heritage Crossing Condo Ph 12 (1)
- Flora Ridge Condo Ph 3 Bldg 6 (1)
- Poinciana Village 01 Neighborhood 02 (1)
- Wyndham Palms Condo (1)
- Oaks At Cypress Woods The (1)
- Peppertree At Cypress Woods Unit 1 (1)
- Regency Pointe (1)
- Windsor Hills (1)
- Flora Ridge Ph 5 Condo (1)
- Championsgate Condo Ph 6 (1)
- Four Seasons At Orlando Ph 4B (1)
- Indian Ridge Villas Ph 2 (1)
- Westview South (1)
- Poinciana Nbrhd 6 Vill 7 (1)
- The Terraces At Storey Lake Condo 1 Ph 1 (1)
- The Terraces At Storey Lake Condo 2 Ph 15 (1)
- Cummings Rockwell (1)
- The Terraces At Storey Lake Condo No 1 Ph 2 (1)
- Woodall & Doyle (1)
- Harbor Town (1)
- Heritage Crossing Condo Ph 2 (1)
- Reedy Reserve Ph 3 (1)
- Villas At Estancia (1)
- Poinciana Subdivision Nbrhd 1 Vil 3 (1)
- Majors Lane Twnhs (1)
- Villages At Mango Key Ph 01A (1)
- Sunset Walk Hotel Condo (1)
- Lake Deer Estates (1)
- Poinciana Nbrhd 03 South Village 07 (1)
- Sun Pointe (1)
- Murano At Westside (1)
- Orange Gardens Sec 4 (1)
- Poinciana Vlg 2 Nbhd 1 (1)
- Emerald Island Resort Rep (1)
- Poinciana Neighborhood 2 Village 8 (1)
- Poinciana Villages (1)
- Compass Bay Unit 2 (1)
- Benita Park (1)
- Ventura At Windsor Hills Condo Ph 7 (1)
- Compass Bay Unit 02 (1)
- Solivita Ph 04B (1)
- Solivita Ph 04C Sec 01 (1)
- Poinciana Sub Village 1 Nbrhd 2 (1)
- Flora Ridge A Condo Ph 1 (1)
- Ventura At Windsor Hills Condo Ph 2 (1)
- Canterbury Terrace (1)
- Fantasyworld Club Villas Unit 2 (1)
- Overlook Reserve Ph 2 (1)
- Poinciana Sub Nbrhd 05 Village 07 (1)
- Villas At Island Club Ph 2 Bldg V (1)
- Windmill Point Unit 4B (1)
- Poinciana Village 2 Nbhd 3 (1)
- Concorde Estates Ph 2B (1)
- Windsor Palms, Wyndham Palms (1)
- Poinciana Nbrhd 06 South Village 03 (1)
- Solivita Ph 5F-Un 1 Rep (1)
- Caribe Cove Ph 5 (1)
- Caribe Cove Condo Ph 5 (1)
- Villas Of Emerald Lake Condo Ph 4 (1)
- Florida Palms Rep (1)
- Trafalgar Village Phase One (1)
- Raintree Park Ph 1 (1)
- Autumn Lane Twnhms Condo (1)
- Venetian Bay Villages Condo Phase 3 (1)
- Solivita Ph Vib (1)
- Poinciana Nbrhd 3 South Village 7 (1)
- Villas At Estancia; A Condo (1)
What under $300,000 buys and what to check
In this price band the differences between listings are usually age, size and condition rather than location alone, so read each listing’s year built, square footage and property type (a condo or manufactured home and a single-family home can sit at the same price with very different monthly costs). Budget the full monthly number, not the price: taxes, insurance, and HOA or CDD fees are all on each listing page, and our true cost of ownership calculator puts them into one figure. Insurance quotes on older roofs and older electrical can change which of two similar homes is actually cheaper.
Questions to ask about any listing in this band
How old is the roof, and will insurers write it? Is there a four-point inspection on file? What did the seller pay for insurance last year? In a condo, what are the dues, is there a special assessment or milestone inspection pending, and what do the reserves look like? Is the price a recent reduction, and how long has it been listed? A local agent who works the area will know which communities in this band have the fewest surprises at inspection.
Common questions
How many homes listed under $300,000 are for sale in Kissimmee?
As of November 11, 2026, 936 Kissimmee, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 383 communities. The count updates with every MLS refresh.
What do homes under $300K cost in Kissimmee?
The median asking price today is $246,000, with listings from $40,000 to $299,999. Kissimmee listings without that feature have a median of $420,000.
Which Kissimmee community has the most homes under $300K for sale?
Poinciana Village 2 Nbhd 1 has the most right now (22), followed by Poinciana Village 5 Nbhd 1 (20), West Lucaya Village (17), Villas Del Sol At Kissimmee Condo (16).
What is the monthly payment on a home under $300,000?
At today’s rates with 20% down, principal and interest on a $300,000 purchase runs in the $1,500–$1,700 a month range before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator linked above turns them into one monthly number.
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 $300K–$500K
- Homes Under $300K in every city
Homes Under $300K in nearby Osceola County cities
- St Cloud homes under $300K (156 for sale)
- Reunion homes under $300K (33 for sale)
- Celebration homes under $300K (14 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 under $300,000. 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.