Gated Communities in Winter Haven, FL: Homes for Sale

This page tracks every Winter Haven listing whose MLS record reports a gated community (manned gate, unmanned gate or security gate), by community, with live counts and asking prices, and the fee questions that come with the gate.

130 homes in gated communities are for sale or pending in Winter Haven, FL today across 78 communities. The median asking price is $309,900, from $57,900 to $1,799,900. Listings in Winter Haven without that feature have a median of $347,450. Most listings right now: Lake Ashton West Ph 01 (8), Traditions Ph 01 (6), Cypresswood (5). Updated September 9, 2026 from the MLS.

Winter Haven gated community homes 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 gated community homes listed are tabled; the rest follow.

Community	Gated Community Homes	New build	Median list	From
	8	0	$345,000	$315,000
	6	0	$309,900	$284,500
	5	0	$334,950	$190,000
	4	0	$219,950	$214,900
	4	0	$167,900	$165,000
	4	0	$97,750	$90,000
	3	0	$420,000	$300,000
	3	0	$147,500	$119,000
	2	0	$894,950	$799,900
Cypresswood Palma Ceia	2	1	$814,000	$749,000
	2	0	$597,000	$495,000
	2	0	$508,500	$452,000
	2	0	$407,500	$400,000
Valhalla	2	0	$404,250	$379,000
	2	0	$402,450	$365,000
	2	0	$397,450	$395,000
	2	0	$388,999	$355,000
	2	0	$362,500	$360,000
	2	1	$330,299	$319,532
	2	0	$312,449	$299,999
	2	0	$298,450	$269,000
	2	0	$280,000	$275,000
	2	0	$250,000	$200,000
	2	0	$222,950	$197,900
	2	0	$214,450	$199,000
	2	0	$210,000	$135,000
	2	0	$174,200	$169,900
	2	0	$142,400	$120,000
	2	0	$96,445	$57,900
	1	0	$750,000	$750,000
	1	0	$655,000	$655,000
	1	0	$634,900	$634,900
	1	0	$579,900	$579,900
	1	0	$549,500	$549,500
	1	0	$524,000	$524,000
	1	0	$519,990	$519,990
	1	0	$488,500	$488,500
	1	0	$469,000	$469,000
	1	0	$451,000	$451,000
	1	0	$449,900	$449,900
	1	0	$439,000	$439,000
	1	0	$409,000	$409,000
	1	0	$409,000	$409,000
	1	0	$405,000	$405,000
	1	0	$385,000	$385,000
	1	0	$375,000	$375,000
	1	0	$349,999	$349,999
	1	0	$349,500	$349,500
	1	0	$337,500	$337,500
	1	0	$337,000	$337,000
	1	0	$334,990	$334,990
	1	0	$325,000	$325,000
	1	0	$289,900	$289,900
	1	0	$285,000	$285,000
	1	0	$279,000	$279,000
	1	0	$275,000	$275,000
	1	0	$270,000	$270,000
	1	0	$268,520	$268,520
	1	0	$265,000	$265,000
	1	0	$253,900	$253,900

Also with gated community homes for sale: (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1), (1).

What the gate costs and what it actually does

A gate is an HOA amenity, so it shows up in dues: an unmanned keypad or transponder gate adds little; a 24-hour manned gate is a six-figure annual staffing line shared by the homeowners, and the roads behind it are usually private, which means the association, not the county, pays to repave them. Ask for the current HOA budget and reserve study, whether the roads are private, and whether a gate or road assessment is pending. The MLS field records the gate, not its staffing, so confirm which kind it is before you value it. Our true cost of ownership calculator puts HOA dues, taxes and insurance into one monthly number.

Questions to ask about any gated-community listing

Is the gate manned, and during what hours? Are the roads private, and what do the reserves look like for repaving? What are the HOA dues today and what did they run three years ago? Is there a CDD or a special assessment on the books? What are the guest-access and delivery rules? A local agent who works the community will know which gates are staffed and which associations are underfunded.

Common questions

How many homes in gated communities are for sale in Winter Haven?

As of September 9, 2026, 130 Winter Haven, FL listings whose MLS record reports a gated community are active or pending, across 78 communities. The count updates with every MLS refresh.

What do gated community homes cost in Winter Haven?

The median asking price today is $309,900, with listings from $57,900 to $1,799,900. Winter Haven listings without that feature have a median of $347,450.

Which Winter Haven community has the most gated community homes for sale?

Lake Ashton West Ph 01 has the most right now (8), followed by Traditions Ph 01 (6), Cypresswood (5), Cypresswood Enclave Ph 01 (4).

Are gated communities more expensive to own?

Usually the HOA dues are higher, because the gate, any guard staffing and the private roads behind it are paid for by the homeowners. Home prices vary by community; the table above shows the asking prices in each gated community with listings today, and the HOA figure on each community's own guide shows what the dues actually run.

Keep exploring Winter Haven

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 Winter Haven, FL whose MLS record reports a gated community. 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.