Homes for Sale $300K to $500K in Winter Haven, FL

This page tracks every Winter Haven 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.

327 homes listed between $300,000 and $500,000 are for sale or pending in Winter Haven, FL today across 165 communities. The median asking price is $344,999, from $300,000 to $495,000. Listings in Winter Haven without that feature have a median of $245,000. Most listings right now: Villa Mar (14), Harbor At Lake Henry (9), Ashton Covey (8). Updated September 11, 2026 from the MLS.

Winter Haven 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
	14	14	$344,499	$312,999
	9	9	$331,710	$303,900
	8	8	$372,412	$323,965
	8	8	$342,499	$314,999
	8	7	$328,900	$312,900
	7	7	$345,690	$319,990
	7	2	$315,000	$303,000
Lucerne Park Reserve	6	0	$346,400	$300,000
	6	0	$334,950	$315,000
	6	5	$323,445	$302,000
	6	6	$310,490	$303,990
	5	0	$309,900	$309,000
	4	0	$392,500	$334,950
	4	0	$367,500	$350,000
	4	4	$350,000	$350,000
	4	4	$339,900	$314,900
	4	3	$327,728	$304,016
	4	0	$317,500	$305,000
	4	4	$307,240	$305,490
	3	0	$434,900	$379,000
	3	0	$420,000	$389,000
	3	0	$395,000	$345,000
	3	0	$380,000	$336,000
	3	0	$369,900	$309,990
	3	0	$369,000	$309,900
	3	3	$359,900	$342,900
	3	0	$350,000	$329,000
	3	0	$325,990	$324,900
	3	3	$325,990	$324,990
	3	0	$319,900	$315,000
	3	0	$309,000	$304,000
	3	2	$308,000	$307,000
	2	0	$439,500	$400,000
	2	0	$405,000	$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	$377,450	$375,000
	2	2	$374,950	$359,950
	2	0	$372,450	$314,900
	2	0	$368,500	$338,000
	2	0	$364,950	$329,900
	2	0	$362,500	$360,000
	2	0	$362,450	$339,900
	2	0	$359,999	$340,000
	2	0	$359,950	$340,000
	2	0	$352,499	$315,000
	2	0	$343,450	$337,000
	2	0	$343,000	$329,000
	2	0	$337,200	$324,500
	2	0	$336,000	$305,000
	2	0	$335,000	$320,000
	2	0	$332,345	$314,990
	2	1	$322,450	$315,000
	2	1	$317,995	$315,990
	2	0	$317,500	$306,000
	2	0	$317,000	$315,000
	2	0	$315,000	$310,000
	2	2	$314,445	$301,900

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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 Winter Haven?

As of September 11, 2026, 327 Winter Haven, FL listings whose MLS record reports an asking price between $300,000 and $500,000 are active or pending, across 165 communities. The count updates with every MLS refresh.

What do homes $300K–$500K cost in Winter Haven?

The median asking price today is $344,999, with listings from $300,000 to $495,000. Winter Haven listings without that feature have a median of $245,000.

Which Winter Haven community has the most homes $300K–$500K for sale?

Villa Mar has the most right now (14), followed by Harbor At Lake Henry (9), Ashton Covey (8), Seasons At Annabelle Estates (8).

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 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 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.