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.

995 homes listed under $300,000 are for sale or pending in Kissimmee, FL today across 409 communities. The median asking price is $245,000, from $800 to $299,999. Listings in Kissimmee without that feature have a median of $429,000. Most listings right now: Poinciana Village 5 Nbhd 1 (29), Poinciana Village 2 Nbhd 1 (23), Poinciana Nbrhd 05 North Village 03 (16). Updated September 11, 2026 from the MLS.

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 5 Nbhd 1	29	0	$265,000	$146,000
Poinciana Village 2 Nbhd 1	23	0	$275,000	$140,000
	16	0	$242,500	$129,999
Regal Oaks At Old Town	15	0	$276,000	$240,000
	15	0	$233,000	$219,000
Blossom Park Villas Condo	15	1	$175,000	$149,990
	14	0	$275,499	$260,000
Poinciana Village 1 Nbhd 1 South	14	0	$273,388	$204,900
Poinciana Village 1 Nbhd 2	13	0	$275,000	$225,000
Fiesta Key	13	0	$254,000	$206,500
	12	2	$264,495	$219,900
	12	0	$244,950	$204,900
Poinciana Village 1 Nbhd 1 North	11	0	$259,000	$220,000
	11	0	$242,500	$214,900
Villas Del Sol At Kissimmee Condo	11	0	$179,900	$164,000
Greenpoint Essential Hotel Condo	11	0	$65,000	$55,000
Meridian Palms Comm Condo	11	0	$49,500	$41,000
	10	4	$254,995	$200,000
Runaway Beach Club Condo	10	0	$240,000	$155,000
Villas At Seven Dwarfs Lane Condo	10	0	$226,250	$210,000
Legacy Dunes Condo	10	0	$217,500	$176,950
	10	0	$199,000	$164,900
Parkway Palms Resort Maingate Condo	10	0	$134,950	$120,000
Poinciana Village 2 Nbhd 3	9	0	$276,500	$220,000
Emerald Island Resort Ph 2	9	0	$249,000	$239,000
	9	0	$245,000	$199,000
Crestwynd Bay	8	0	$265,000	$235,000
	8	0	$246,500	$199,999
	8	1	$244,950	$190,000
Westview 27 Villas	8	8	$227,615	$221,490
Coopersmith Village At Poinciana	8	0	$178,499	$145,000
Villas At Estancia Condo	7	0	$250,000	$205,000
Broadmoor	7	0	$199,900	$149,999
Fiesta Key Ph 2	6	0	$294,500	$269,990
Poinciana Village 02 Neighborhood 01	6	0	$287,450	$216,900
Paradise Cay	6	0	$274,995	$269,000
	6	1	$267,500	$219,000
	6	0	$254,950	$185,000
Encantada Ph 2	6	0	$250,000	$225,000
Sweetwater Club Condo	6	0	$206,994	$189,900
	5	0	$279,900	$229,900
Club Cortile	5	0	$265,000	$259,000
Palm Villas Condo	5	0	$212,900	$189,900
Marbrisa Villas	5	0	$190,000	$179,000
Arbors Of Sendera	5	0	$158,990	$139,990
Coral Cay Resort	4	0	$285,250	$263,190
Bellavida Ph 1	4	0	$284,950	$265,000
	4	0	$275,000	$199,900
Bellalago Pod G Twnhms	4	0	$272,447	$209,990
Poinciana Village 01 Neighborhood 03 West	4	0	$267,950	$197,500
	4	0	$244,450	$230,000
	4	0	$242,500	$220,000
Eric Estates	4	0	$237,500	$170,000
	4	0	$222,450	$219,000
Country Cove Villas	4	0	$214,500	$205,000
Villas At Shadow Bay The	4	0	$184,945	$159,900
Gables At Lakeside Condo	4	0	$177,500	$134,900
	4	0	$63,900	$63,900
Remington Ph 1 Tr A	3	0	$299,900	$275,000
Encantada Ph 1	3	0	$299,000	$265,900

Also with homes under $300K for sale

(3)
Oakwater (3)
(3)
(3)
(3)
Shingle Creek Village Terrace (3)
Emerald Lake (3)
(3)
Windsor Oaks (3)
Summerfield Twnhms (3)
Blossom Park Villas A Condo (3)
(3)
Poinciana Village 1 Nbhd 3 South (3)
Villas At Secret Lake Condo (3)
Robert Bass Add (3)
Royal Palm Bay Condo (3)
Villas At Somerset (3)
(3)
(3)
(3)
Terra Condo (3)
(3)
Essex Park Villas Condo (3)
Kissimmee Executive Park (3)
S A Robinsons (3)
Murano At Westside Ph 2 (2)
(2)
Bellavida Ph 01 (2)
(2)
Compass Bay Unit 1 (2)
Poinciana Village 1 Nbhd 3 East (2)
Amber Pointe Unit 2 (2)
(2)
Cane Island Condo (2)
(2)
Cypress Lake Ph 1 (2)
Amber Pointe (2)
Regal Oaks (2)
(2)
(2)
Poinciana Village 01 Neighborhood 02 (2)
Paradise Cove (2)
Venetian Bay Village P3 (2)
(2)
(2)
Royale Bermuda Twnhs (2)
(2)
Poinciana Village 01 Neighborhood 01 South (2)
(2)
Pine Island Villas At Bvl (2)
(2)
(2)
(2)
Villas At Island Club Ph 10 (2)
Seven Eagles Condo (2)
(2)
(2)
(2)
Marydia (2)
Jazsam Twnhms (2)
Rio Hills Townhouses (2)
(2)
(2)
Enclave The (2)
(2)
Caribbean Villas Condo Ph A-F (2)
Las Palmas Villas (2)
Villas At Seven Dwarfs Lane (2)
(2)
Villas At Laguna Bay Condo (2)
Caribe Cove (2)
(2)
Villas Del Sol At Kiss Condo (2)
Michigan Oaks (2)
(2)
Poinciana Commercenter 1 (2)
Legacy Dunes (2)
(2)
(2)
Mona Lisa At Celebration Condo Hotel (2)
Heritage House Condos (2)
(2)
Cascade At Kissimmee Condo (2)
(2)
(2)
Loveland Estates (2)
Kyngs Point (2)
Tapestry Ph 4 (1)
(1)
(1)
Soho/Lakeside Ph 1 Bldg 4 (1)
Poinciana Nbhd 1 N Vlg 1 (1)
Heritage Run (1)
Plantation (1)
(1)
(1)
(1)
(1)
(1)
Hammock Trails (1)
Maple Chase At Cypress Woods (1)
Bella Parc Twnhms (1)
(1)
(1)
(1)
Cypress Lakes Twnhms Pii U1 (1)
Poinciana Estates Sec B (1)
Westview 40S Gc (1)
(1)
Laurel Run At Crescent Lakes (1)
Poinciana Village 01 Neighborhood 01 North (1)
Lake Wilson Reserve (1)
(1)
(1)
(1)
(1)
Tapestry Ph 5 (1)
Tapestry (1)
(1)
Emerald Island Resort Rep (1)
(1)
(1)
(1)
Lindfields Unit 1 (1)
(1)
Mill Run (1)
Pebble Creek Add (1)
(1)
(1)
(1)
(1)
(1)
Pebble Creek (1)
(1)
Windsor Hills, Ventura At Windsor Hills (1)
Concorde Estates Ph 2A (1)
(1)
Mill Run Un 5 (1)
(1)
(1)
(1)
Eagle Bay Ph 1 (1)
(1)
(1)
Bellalago Pod G Townhomes (1)
(1)
(1)
(1)
Heatherstone At Crescent Lakes (1)
Poinciana Nbhd 1 S Vlg 1 (1)
(1)
Spectrum/Reunion (1)
(1)
(1)
Oaks At Cypress Woods The (1)
Storey Lake Condo (1)
Cypress Cay Ph 1 (1)
Mill Run Unit 6 (1)
(1)
(1)
(1)
(1)
(1)
(1)
(1)
Windsor Hills P1 (1)
Flora Ridge Condo Ph 3 Bldg 6 (1)
(1)
(1)
The Terraces At Storey Lake, Storey Lake (1)
(1)
(1)
(1)
(1)
(1)
(1)
(1)
Benita Park (1)
Chelsea Square 5B (1)
(1)
Woodall & Doyle (1)
Indian Wells Unit 4 (1)
(1)
Villas At Estancia (1)
Majors Lane Twnhs (1)
(1)
(1)
(1)
(1)
(1)
Emerald Island Resort Replat (1)
Concorde Estates Ph 2B (1)
(1)
(1)
Compass Bay Unit 2 (1)
Villas At Seven Dwarfs (1)
(1)
(1)
(1)
(1)
(1)
J J Keens (1)
(1)
(1)
Poinciana Nbrhd 1 North Village 1 (1)
Emerald Island Residence Ph 2 (1)
(1)
Storey Creek 40S (1)
Poinciana Village 1 Nbhd 5 (1)
Emerald Garden At Bvl (1)
Caribe Cove Resort (1)
(1)
(1)
(1)
(1)
Reedy Reserve Ph 3 (1)
Remington Pointe (1)
(1)
Reunion Ph 1 Parcel 2 (1)
Poinciana Village (1)
(1)
Poinciana Village 1 Nbd 1 North (1)
Windsor Palms, Wyndham Palms (1)
(1)
Caribe Cove Ph 5 (1)
Flora Ridge Ph 10 Condo (1)
Bvl Lakepointe Twnhms (1)
Florida Palms Rep (1)
Florida Palms (1)
Lake Berkley Resort Vill (1)
(1)
(1)
(1)
(1)
(1)
(1)
Pine Island Villas (1)
Pineridge Estates Unit 2 (1)
(1)
(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 September 11, 2026, 995 Kissimmee, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 409 communities. The count updates with every MLS refresh.

What do homes under $300K cost in Kissimmee?

The median asking price today is $245,000, with listings from $800 to $299,999. Kissimmee listings without that feature have a median of $429,000.

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

Poinciana Village 5 Nbhd 1 has the most right now (29), followed by Poinciana Village 2 Nbhd 1 (23), Poinciana Nbrhd 05 North Village 03 (16), Regal Oaks At Old Town (15).

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

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.