Gated Communities in Kissimmee, FL

Looking for gated communities in Kissimmee, FL? Momentum tracks 149 Kissimmee communities with evidence of gated community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.

Kissimmee gated communities at a glance

149

Communities tracked

$378,500

Median sale price

105 days

Median days on market

1,097

Recent closings

The communities, by recent sales activity

Community	City	Median price	1-yr change	Days on mkt
STOREY LAKE PH I-2 · agent	Kissimmee	$462,000	–	166 d
WINDSOR AT WESTSIDE · agent	Kissimmee	$536,000	–	58 d
Bellalago · agent	Kissimmee	$388,000	–	72 d
Tohoqua · agent	Kissimmee	$440,000	–	74 d
WINDSOR HILLS PHASE THREE · agent	Kissimmee	$620,000	–	91 d
REUNION VILLAGE · agent	Kissimmee	$489,000	–	75 d
BELLAVIDA · agent	Kissimmee	$436,000	–	167 d
Tapestry · agent	Kissimmee	$465,000	–	72 d
WYNDHAM PALMS · agent	Kissimmee	$432,000	–	17 d
REUNION WEST · agent	Kissimmee	$675,000	–	59 d
ENCANTADA · agent	Kissimmee	$291,000	–	74 d
Westview · agent	Kissimmee	$365,000	–	32 d
Esplanade at Westview · agent	Kissimmee	$455,000	–	42 d
ISLES OF BELLALAGO · agent	Kissimmee	$372,000	–	32 d
VERANDA PALMS · agent	Kissimmee	$660,000	–	89 d
ADEN NORTH AT WESTVIEW · agent	Kissimmee	$394,000	–	166 d
REUNION WEST VLGS NORTH · agent	Kissimmee	$1.21M	–	179 d
SUNSET LAKES · agent	Kissimmee	$441,000	–	99 d
COMPASS BAY · agent	Kissimmee	$340,000	–	48 d
Fiesta Key · agent	Kissimmee	$278,000	–	125 d
REUNION WEST VILLAGE 3A · agent	Kissimmee	$912,000	–	181 d
Hub at Westside Reserve · agent	Kissimmee	$328,000	–	58 d
KISSIMMEE BAY · agent	Kissimmee	$566,000	–	96 d
TERRA VERDE · agent	Kissimmee	$455,000	–	67 d
Tohoqua Reserve · agent	Kissimmee	$414,000	–	219 d

Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.

Every other tracked gated communities in Kissimmee

What gates change about ownership

Controlled access typically comes with a manned gate, a transponder system, or both — funded through HOA dues. Expect guest-access procedures, delivery and contractor rules, and in some communities rental restrictions. Review the HOA budget for how the gate and any roving patrol are funded, and whether roads are private (the HOA maintains them — another line in the dues) or public.

Due diligence before you buy behind a gate

Request the HOA documents early: budget, reserves, rules, and the last two years of meeting minutes. Private roads, gates and common areas are owner-funded, so thin reserves become special assessments. Our buyer closing costs calculator helps you model dues and assessments into the real monthly cost.

What it costs to own here

At Osceola County’s typical combined millage of 15.23 mills, a purchase at $378,500 (the median across these Kissimmee gated communities) generates roughly $5,766 a year in property tax before exemptions — about $480 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Osceola County average about $1,735 a year ($145 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Osceola County near $2,191 (principal and interest on the typical home, tax, and insurance).

Run your exact numbers: the property tax after purchase calculator uses Osceola County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.

Demand and supply in Osceola County right now

In the most recent IRS migration data (2022-2023), Osceola County gained a net 5,703 people to relocation, with the largest inbound flows from NY, NJ, TX. Households moving IN reported average incomes of $59,276 versus $52,104 for those leaving — the income mix of demand, straight from tax filings. Population is up about 20.2% over the recent multi-year window. On the supply side, builders pulled 7,366 residential permits in Osceola County in 2025 (5,085 single-family), down 16.4% year over year — against 10,003 at the 2021 peak. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 7.3% versus its income-and-rent fundamentals.

Explore more of Kissimmee

Run the numbers in Osceola County

Common questions

How many gated communities does Kissimmee, FL have?

Momentum currently tracks 149 communities in Kissimmee with evidence of gated community living in MLS or verified amenity records. Others exist; these are the ones with active market data.

What do homes in Kissimmee gated communities cost?

The median sale price across tracked gated communities in Kissimmee is about $378,500, varying widely by community - see the table for community-level medians.

How does Momentum classify a community as one of the gated communities?

A community appears here when we find gate, guard house or controlled-access amenities reported on MLS listings or verified amenity records for the community. We do not guess from names alone. Verify any specific amenity or restriction with the association before you rely on it.

How much is home insurance in Osceola County?

Citizens Property Insurance policies in Osceola County average about $1,735 a year, per Citizens filings. Private quotes vary widely with roof age, construction and wind mitigation - a wind-mitigation inspection often unlocks meaningful credits.

What are property taxes like in Osceola County?

Typical combined millage in Osceola County is about 15.23 mills - roughly 1.52% of assessed value a year before exemptions. Florida resets assessed value to about your purchase price when you buy, then homestead exemptions and the 3% Save Our Homes cap apply.

Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.