4 Bedroom Homes for Sale in Winter Haven, FL

Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Winter Haven listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.

328 homes with four or more bedrooms are for sale or pending in Winter Haven, FL today across 160 communities. The median asking price is $333,949, from $143,000 to $1,799,900. Listings in Winter Haven without that feature have a median of $249,900. Most listings right now: Villa Mar (14), Villamar (14), Villa Mar 40'S (10). Updated September 13, 2026 from the MLS.

Winter Haven 4-bedroom 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 4-bedroom homes listed are tabled; the rest follow.

Community	4-Bedroom Homes	New build	Median list	From
Villa Mar	14	14	$344,499	$312,999
Villamar	14	11	$302,000	$237,500
Villa Mar 40'S	10	10	$296,740	$252,990
Willowbrook North	9	9	$339,640	$284,990
Lucerne Park Reserve	9	0	$330,000	$270,000
Seasons At Annabelle Estates	8	8	$342,499	$314,999
Peace Crk Reserve	6	2	$315,500	$305,000
Lakeside Landings Ph 01	6	0	$310,000	$249,000
Willowbrook South	6	6	$295,240	$288,990
Ashton Covey	5	5	$392,175	$350,165
Harmony On Lake Eloise	5	4	$329,990	$310,000
Pinnacle Point	4	0	$367,500	$350,000
Peach Crossings	4	4	$339,900	$314,900
Squires Grove Ph 2	4	0	$339,500	$299,900
Harbor At Lake Henry	4	4	$335,007	$322,795
Harmony On Lake Eloise Phase 4	4	4	$327,240	$292,900
Lake Lucerne Ph 5	4	0	$318,500	$294,500
Villamar Ph 2	4	0	$317,450	$199,900
Villamar Phase 6 And Phase 6D	4	4	$297,445	$288,900
Carefree Cove	4	0	$220,000	$204,900
Lake Lucerne Ii	3	0	$395,000	$345,000
Harmony/Lk Eloise Ph 1	3	0	$380,000	$336,000
Jace Lndg	3	0	$339,900	$280,000
Villamar Phase 7	3	3	$325,990	$324,990
Eagle Lndg Ph Ii	3	0	$324,500	$235,000
Lakes At Lucerne Park Ph 02	3	0	$315,000	$288,999
Villamar Ph 6 & Ph 6D	3	1	$315,000	$250,000
Villamar Ph 3	3	0	$304,000	$279,000
Country Club Estates	3	0	$298,900	$290,000
Inwood	3	0	$257,999	$230,000
Jan Phyl Village	3	0	$240,000	$185,000
Magnolia Shores	2	0	$1,049,925	$699,950
Waterford Oaks	2	0	$894,950	$799,900
Hamilton Pointe	2	0	$657,000	$549,000
Hart Lake Hills Ph 01	2	0	$597,000	$495,000
Estates/Lk Florence	2	1	$477,450	$405,000
West Winter Haven	2	0	$464,500	$379,000
Cypresswood	2	0	$443,500	$425,000
Southeast Terrace	2	0	$439,500	$400,000
Gates Of Lake Region	2	0	$405,000	$400,000
Buckeye Pointe	2	0	$399,950	$369,900
Traditions Ph 02	2	0	$397,450	$395,000
Terranova Ph 04	2	0	$377,450	$375,000
Residences At Winter Haven	2	2	$372,400	$359,900
Inman Groves	2	0	$359,950	$340,000
Lake Mariam Hills Rep	2	0	$355,000	$285,000
Normandy Heights	2	0	$343,450	$337,000
Crescent Pointe	2	2	$338,495	$335,924
Villamar Ph 2A	2	0	$336,000	$305,000
Country Walk/Winter Haven Ph 2	2	0	$332,345	$314,990
Lake Smart Pointe	2	0	$330,445	$325,990
Peace Creek Reserve	2	1	$317,995	$315,990
Gardens Ph 01	2	0	$312,450	$300,000
Emily Estates	2	0	$296,200	$287,500
Dundee Station	2	0	$294,449	$293,899
Villamar Ph 5	2	0	$282,500	$280,000
Villamar Ph 4	2	0	$281,000	$233,000
Buckeye Trace	2	0	$280,000	$275,000
Revised Map Of Fernwood Add	2	0	$262,000	$179,000
Lesnick Park	1	0	$1,150,000	$1,150,000

Also with 4-bedroom homes for sale

Otis Heights Sub (1)
Eloise Woods West Lake Florence (1)
Waters Lake Mariam (1)
Orchid Springs Unrecorded (1)
Wyndsor At Lake Winterset (1)
Hamilton Ridge (1)
Renaissance (1)
Leisure Shores (1)
Eloise Pointe Ests Phase Two (1)
Sanctuary By The Lake Ph One (1)
Lake Jessie Or Carrs J A (1)
Pollard Shores (1)
Elbert Hills (1)
Sand Hill Lane (1)
Grey Fox Hollow Ph Three (1)
Cypresswood Plantation (1)
Orleans (1)
Harbour Estates (1)
Hanna Sub (1)
Tuscany At Winterset (1)
Hampton Cove (1)
Harrington A B Subdiviosion (1)
Lake Mariam Hills (1)
Island Lakes (1)
Ruby Lake Sub Ph Ii (1)
Lake Rochelle Estates (1)
Lake Thomas Woods Eight Add (1)
Lakewood Tr 173 (1)
Overlook Ests Ph 3 (1)
Residences Of Winter Haven (1)
Sun Rdg Village East (1)
Buckeye Rdg (1)
Ashton Covey Ph One (1)
Lake Eloise Place (1)
Terranova Phase Iv (1)
Traditions Ph 01 (1)
Nydeggers West Elbert Sub (1)
Ridge Acres Ph 02 (1)
Twin Oaks Add (1)
Summer Haven Shores (1)
Pine Terrace Rep (1)
Eloise Woods East Lake Mariam Unit (1)
Orange Hill Sub (1)
Ridge Acres Ph Ii (1)
Hamilton West Ph 02 (1)
Lakewood Community Association (1)
Fla Highlands Co Sub (1)
Reflections East Add (1)
Eagle Lndg Ph I (1)
Crossroads At Lake Region (1)
Overlook Estates East (1)
Whispering Trails Ph 01 (1)
Eloise Cove (1)
Terranova Ph Iv (1)
Lathers Grove Sub (1)
Van Duyne Shores (1)
Residences/Winter Haven (1)
Inman Grvs Ph 2 (1)
Inman Grvs Ph 1 (1)
Hamilton West Ph 01 (1)
Sutton Preserve (1)
Mandolin (1)
Fanning Sub (1)
Magnolia Preserve Ph 1 (1)
Berryhill (1)
Overlook Estates (1)
Lake Daisy Estates (1)
Lake Smart Estates (1)
Lucerne Park Reserves (1)
Peace Creek Reserve 40'S (1)
St James Xing (1)
Crescent View (1)
Coventry Cove Ph Il (1)
Squires Grove (1)
Villamar Ph 1 (1)
Bentley Place (1)
Bretton Ridge (1)
Eagle Lndg Ph Ib (1)
Spirit Lndgs (1)
Lake Link Estates (1)
Lakes/Lucerne Park Ph 4 (1)
Overlook Rdg (1)
Timber Wood (1)
Crystals Landing (1)
Jan Phyl Village Unit 03 Rep (1)
West Cannon Heights (1)
Havencrest Add (1)
Winter Haven Heights (1)
Fox Ridge Ph 01 (1)
Dugger Rep (1)
Jan Phyl Village Unit 10 (1)
Queens Cove Ph 04 (1)
Hills Lake Elbert (1)
Smart Sub (1)
Sunridge Village East (1)
Tanamora (1)
Chris Brown Cemetery Replat (1)
Lake N Golf Estates Add (1)
South College Add Rev (1)
Foxhaven (1)

What the fourth bedroom costs

The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.

Questions to ask about any four-bedroom listing

Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.

Common questions

How many homes with four or more bedrooms are for sale in Winter Haven?

As of September 13, 2026, 328 Winter Haven, FL listings whose MLS record reports four or more bedrooms are active or pending, across 160 communities. The count updates with every MLS refresh.

What do 4-bedroom homes cost in Winter Haven?

The median asking price today is $333,949, with listings from $143,000 to $1,799,900. Winter Haven listings without that feature have a median of $249,900.

Which Winter Haven community has the most 4-bedroom homes for sale?

Villa Mar has the most right now (14), followed by Villamar (14), Villa Mar 40'S (10), Willowbrook North (9).

How much more does a 4-bedroom home cost?

It depends on the city and the age of the housing stock. The answer block on this page states today’s median asking price for four-plus-bedroom homes next to the median for other listings in the same city, and each listing page shows square footage so you can compare on a per-square-foot basis.

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 four or more bedrooms. 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.