Homes for Sale Under $300K in Winter Haven, FL

This page tracks every Winter Haven 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.

538 homes listed under $300,000 are for sale or pending in Winter Haven, FL today across 266 communities. The median asking price is $235,000, from $36,950 to $299,999. Listings in Winter Haven without that feature have a median of $355,000. Most listings right now: Inwood (22), Villamar (17), Harmony On Lake Eloise (13). Updated September 11, 2026 from the MLS.

Winter Haven 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
	22	0	$202,999	$109,900
	17	15	$277,900	$237,500
	13	13	$273,990	$254,900
	13	13	$219,990	$219,990
	12	0	$158,950	$129,900
	9	0	$240,000	$170,000
	8	0	$102,450	$78,800
	7	7	$288,900	$276,900
Lucerne Park Reserve	7	0	$270,000	$230,000
	7	7	$254,900	$244,900
	7	0	$95,500	$75,000
	6	6	$291,490	$252,990
	6	0	$151,000	$99,900
	5	5	$289,740	$275,900
	5	5	$284,990	$269,990
	5	1	$280,000	$185,000
	5	0	$210,000	$204,900
	5	0	$144,900	$106,000
	4	0	$279,500	$249,000
	4	1	$272,000	$245,000
	4	0	$269,450	$259,000
	4	0	$242,000	$199,000
	4	0	$219,950	$214,900
	4	0	$205,000	$180,000
	4	0	$184,950	$140,000
	4	0	$171,500	$150,000
	4	0	$167,900	$165,000
	4	0	$167,350	$152,000
	4	0	$147,532	$92,000
	4	0	$134,450	$99,900
	4	0	$99,500	$54,900
	3	0	$293,899	$265,000
	3	3	$281,990	$269,990
	3	3	$279,900	$279,900
	3	0	$269,000	$259,000
	3	0	$259,990	$234,900
	3	1	$247,990	$210,000
	3	0	$245,000	$225,000
	3	0	$244,900	$224,900
	3	0	$229,900	$224,900
	3	0	$225,000	$189,900
	3	0	$215,000	$199,000
	3	0	$215,000	$140,000
	3	0	$193,000	$190,000
	3	0	$160,000	$143,000
	3	0	$107,000	$99,000
	3	0	$74,900	$65,000
	2	0	$299,745	$299,500
	2	0	$296,750	$294,500
	2	0	$294,499	$289,000
	2	0	$294,450	$290,000
	2	2	$285,900	$284,900
	2	0	$283,449	$279,998
	2	0	$282,475	$265,000
	2	0	$280,000	$275,000
	2	2	$278,400	$263,900
	2	0	$277,500	$275,000
	2	0	$277,495	$274,990
	2	0	$274,950	$260,000
	2	0	$274,750	$250,000

Also with homes under $300K for sale

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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 Winter Haven?

As of September 11, 2026, 538 Winter Haven, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 266 communities. The count updates with every MLS refresh.

What do homes under $300K cost in Winter Haven?

The median asking price today is $235,000, with listings from $36,950 to $299,999. Winter Haven listings without that feature have a median of $355,000.

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

Inwood has the most right now (22), followed by Villamar (17), Harmony On Lake Eloise (13), Serenity At Peace Creek Th (13).

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 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 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.