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.
314 homes with four or more bedrooms are for sale or pending in Winter Haven, FL today across 152 communities. The median asking price is $339,000, from $143,000 to $1,399,900. Listings in Winter Haven without that feature have a median of $249,832. Most listings right now: Villamar (16), Villa Mar (13), Seasons At Annabelle Estates (8). Updated October 2, 2026 from the MLS.
Live 4-bedroom homes in Winter Haven: the listings
246 active listings match today (34% of Winter Haven inventory), median asking $342,983, $163/sq ft, median 52 days on market. Photo cards link to the listing; refreshed nightly.
Newest 4-bedroom homes in Winter Haven
The most expensive 4-bedroom homes in Winter Haven
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 3640 Crump Road | $1,399,900 | 3,309 | — |
| 250 Brigham Road | $1,195,000 | 3,235 | — |
| 1200 W Lake Otis Drive | $1,150,000 | 6,100 | — |
| 694 Lake Otis Drive | $949,000 | 3,483 | — |
| 2510 Cypress Gardens Boulevard | $865,000 | 3,482 | — |
| 25 Lakewood Causeway | $849,900 | 4,108 | — |
| 9469 Waterford Oaks Drive | $789,900 | 3,648 | — |
| 328 Hamilton Shores Drive | $765,000 | 3,812 | — |
| 9513 Waterford Oaks Boulevard | $750,000 | 3,611 | — |
| 1016 S Lake Mariam Drive | $750,000 | 3,694 | — |
4-Bedroom Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 57 | 23% |
| $300K–$500K | 158 | 64% |
| $500K–$750K | 21 | 9% |
| $750K–$1M | 7 | 3% |
| $1M+ | 3 | 1% |
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 |
|---|---|---|---|---|
| Villamar | 16 | 12 | $320,000 | $237,500 |
| Villa Mar | 13 | 13 | $346,890 | $309,999 |
| Seasons At Annabelle Estates | 8 | 8 | $347,499 | $319,999 |
| Willowbrook North | 7 | 7 | $344,990 | $289,990 |
| Peace Crk Reserve | 7 | 2 | $315,000 | $299,000 |
| Lucerne Park Reserve | 7 | 0 | $300,000 | $260,000 |
| Villa Mar 40'S | 7 | 7 | $293,990 | $252,990 |
| Ashton Covey | 5 | 5 | $392,175 | $350,165 |
| Villamar Phase 7 | 5 | 5 | $325,990 | $309,990 |
| Lakeside Landings Ph 01 | 5 | 0 | $300,000 | $295,000 |
| Waterford Oaks | 4 | 0 | $769,950 | $725,000 |
| Harmony On Lake Eloise | 4 | 4 | $366,490 | $339,900 |
| Pinnacle Point | 4 | 0 | $364,500 | $340,000 |
| Peach Crossings | 4 | 4 | $339,900 | $314,900 |
| Lake Lucerne Ph 5 | 4 | 0 | $318,500 | $279,900 |
| Villamar Ph 2 | 4 | 0 | $309,950 | $199,900 |
| Villamar Phase 6 And Phase 6D | 4 | 4 | $299,945 | $288,900 |
| Carefree Cove | 4 | 0 | $207,450 | $195,000 |
| Magnolia Shores | 3 | 0 | $649,900 | $425,000 |
| Lake Lucerne Ii | 3 | 0 | $395,000 | $345,000 |
| Harmony/Lk Eloise Ph 1 | 3 | 0 | $380,000 | $336,000 |
| Ridge Acres Ph 02 | 3 | 0 | $350,000 | $349,900 |
| Squires Grove Ph 2 | 3 | 0 | $350,000 | $329,000 |
| Inman Grvs Ph 2 | 3 | 0 | $340,000 | $329,999 |
| Jace Lndg | 3 | 0 | $339,900 | $280,000 |
| Harbor At Lake Henry | 3 | 3 | $338,305 | $322,795 |
| Eagle Lndg Ph Ii | 3 | 0 | $324,500 | $235,000 |
| Lakes At Lucerne Park Ph 02 | 3 | 0 | $315,000 | $280,000 |
| Villamar Ph 6 & Ph 6D | 3 | 1 | $315,000 | $250,000 |
| Fla Highlands Co Sub | 3 | 0 | $309,000 | $245,000 |
| Willowbrook South | 3 | 3 | $301,900 | $294,490 |
| Villamar Ph 3 | 3 | 0 | $295,000 | $278,000 |
| Country Club Estates | 3 | 0 | $290,000 | $290,000 |
| Inwood | 3 | 0 | $257,999 | $210,000 |
| Jan Phyl Village | 3 | 0 | $219,000 | $185,000 |
| Hamilton Pointe | 2 | 0 | $649,000 | $533,000 |
| West Winter Haven | 2 | 0 | $464,500 | $379,000 |
| Estates/Lk Florence | 2 | 1 | $462,250 | $375,000 |
| Cypresswood | 2 | 0 | $443,500 | $425,000 |
| Southeast Terrace | 2 | 0 | $439,500 | $400,000 |
| Winterset Gardens 1St Add | 2 | 0 | $424,950 | $399,900 |
| Buckeye Pointe | 2 | 0 | $399,950 | $369,900 |
| Traditions Ph 02 | 2 | 0 | $397,450 | $395,000 |
| Buckeye Rdg | 2 | 0 | $387,499 | $360,000 |
| Terranova Ph 04 | 2 | 0 | $374,950 | $370,000 |
| Residences At Winter Haven | 2 | 2 | $372,400 | $359,900 |
| Harmony On Lake Eloise Phase 4 | 2 | 2 | $360,900 | $292,900 |
| Inman Groves | 2 | 0 | $359,950 | $340,000 |
| Lake Mariam Hills Rep | 2 | 0 | $350,000 | $285,000 |
| Crescent Pointe | 2 | 2 | $338,495 | $335,924 |
| Villamar Ph 2A | 2 | 0 | $336,000 | $305,000 |
| Lake Smart Pointe | 2 | 0 | $330,445 | $325,990 |
| Peace Creek Reserve | 2 | 1 | $317,995 | $315,990 |
| St James Xing | 2 | 0 | $307,000 | $305,000 |
| Emily Estates | 2 | 0 | $296,200 | $287,500 |
| Dundee Station | 2 | 0 | $294,449 | $293,899 |
| Villamar Ph 4 | 2 | 0 | $290,000 | $233,000 |
| Villamar Ph 5 | 2 | 0 | $282,500 | $280,000 |
| Buckeye Trace | 2 | 0 | $280,000 | $275,000 |
| Foxhaven | 2 | 0 | $201,500 | $143,000 |
Also with 4-bedroom homes for sale
- Lesnick Park (1)
- Otis Heights Sub (1)
- Eloise Woods West Lake Florence (1)
- Waters Lake Mariam (1)
- Orchid Springs Unrecorded (1)
- Wyndsor At Lake Winterset (1)
- Hart Lake Hills Ph 01 (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)
- East View Pkwy (1)
- Elbert Hills (1)
- Sand Hill Lane (1)
- Grey Fox Hollow Ph Three (1)
- Cypresswood Plantation (1)
- Hanna Sub (1)
- Tuscany At Winterset (1)
- Hampton Cove (1)
- Harrington A B Subdiviosion (1)
- Cypresswood Plantations (1)
- Island Lakes (1)
- Ruby Lake Sub Ph Ii (1)
- Lake Mariam Hills (1)
- Hutchinson Add (1)
- East El Otis Park Rep (1)
- Lake Rochelle Estates (1)
- Lake Thomas Woods Eight Add (1)
- Hart Lake Cove Ph 02 (1)
- Overlook Ests Ph 3 (1)
- Lake Winterset Acres Unit #2 (1)
- Residences Of Winter Haven (1)
- Sun Rdg Village East (1)
- Ashton Covey Ph One (1)
- Lake Eloise Place (1)
- Gates Of Lake Region (1)
- Terranova Phase Iv (1)
- Traditions Ph 01 (1)
- Nydeggers West Elbert Sub (1)
- Pine Terrace Rep (1)
- Summer Haven Shores (1)
- Hamilton West Ph 02 (1)
- Twin Oaks Add (1)
- Lakewood Community Association (1)
- Eloise Woods East Lake Mariam Unit (1)
- Eagle Lndg Ph I (1)
- Crossroads At Lake Region (1)
- Ridge Acres Ph Ii (1)
- Overlook Estates East (1)
- College Estates (1)
- Eloise Cove (1)
- Reflections East Add (1)
- Normandy Heights (1)
- Lathers Grove Sub (1)
- Residences/Winter Haven (1)
- Inman Grvs Ph 1 (1)
- Van Duyne Shores (1)
- Hamilton West Ph 01 (1)
- Gardens Ph 01 (1)
- Haven Terrace (1)
- Fanning Sub (1)
- Magnolia Preserve Ph 1 (1)
- Berryhill (1)
- Country Walk/Winter Haven Ph 2 (1)
- Lake Smart Estates (1)
- Lucerne Park Reserves (1)
- Crescent View (1)
- Peace Creek Reserve 40'S (1)
- Summit East Ph 01 (1)
- Lake Daisy Estates (1)
- Coventry Cove Ph Il (1)
- Squires Grove (1)
- Spirit Lndgs (1)
- Lakes/Lucerne Park Ph 4 (1)
- Timber Wood (1)
- Crystals Landing (1)
- West Cannon Heights (1)
- Winter Haven Heights (1)
- Dugger Rep (1)
- Jan Phyl Village Unit 03 Rep (1)
- Havencrest Add (1)
- Jan Phyl Village Unit 10 (1)
- Queens Cove Ph 04 (1)
- Fox Ridge Ph 01 (1)
- Hills Lake Elbert (1)
- Sunridge Village East (1)
- Tanamora (1)
- Lake N Golf Estates Add (1)
- Chris Brown Cemetery Replat (1)
- Revised Map Of Fernwood Add (1)
- Wahneta Farms (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?
What do 4-bedroom homes cost in Winter Haven?
Which Winter Haven community has the most 4-bedroom homes for sale?
How much more does a 4-bedroom home cost?
Keep exploring Winter Haven
- All homes for sale in Winter Haven
- Winter Haven ZIP codes with prices
- Winter Haven pool homes
- Winter Haven waterfront homes
- Winter Haven golf course homes
- Winter Haven gated community homes
- Winter Haven homes under $300K
- Winter Haven homes $300K–$500K
- 4-Bedroom Homes in every city
4-Bedroom Homes in nearby Polk County cities
- Davenport 4-bedroom homes (1201 for sale)
- Lakeland 4-bedroom homes (474 for sale)
- Haines City 4-bedroom homes (354 for sale)
- Auburndale 4-bedroom homes (143 for sale)
- Poinciana 4-bedroom homes (107 for sale)
- Bartow 4-bedroom homes (91 for sale)
- Lake Wales 4-bedroom homes (88 for sale)
- Eagle Lake 4-bedroom homes (75 for sale)
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.