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.
318 homes listed between $300,000 and $500,000 are for sale or pending in Winter Haven, FL today across 164 communities. The median asking price is $349,450, from $300,000 to $499,900. Listings in Winter Haven without that feature have a median of $239,999. Most listings right now: Villa Mar (13), Villamar (10), Seasons At Annabelle Estates (9). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Winter Haven: the listings
263 active listings match today (36% of Winter Haven inventory), median asking $349,900, $173/sq ft, median 47 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Winter Haven
The most expensive $300k–$500k homes in Winter Haven
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 100 Alachua Drive | $499,900 | 2,002 | — |
| 44 Brevard Drive | $495,500 | 2,269 | — |
| 154 2Nd Street #Unit 7 | $495,000 | 1,640 | polk county |
| 3158 Beauchamp Court | $484,900 | 2,552 | — |
| 1818 6Th Street | $479,000 | 2,006 | — |
| 4123 Island Lakes Drive | $470,000 | 1,990 | — |
| 315 Lanceolate Drive | $469,000 | 2,153 | — |
| 405 Valley Court | $465,000 | 2,463 | — |
| 1814 Sandhill Lane | $462,000 | 2,550 | — |
| 900 Lake Martha Drive | $460,000 | 3,408 | — |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 263 | 100% |
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 |
|---|---|---|---|---|
| Villa Mar | 13 | 13 | $346,890 | $309,999 |
| Villamar | 10 | 9 | $328,995 | $312,900 |
| Seasons At Annabelle Estates | 9 | 9 | $339,999 | $309,999 |
| Ashton Covey | 8 | 8 | $372,412 | $323,965 |
| Lake Ashton West Ph 01 | 8 | 0 | $334,950 | $315,000 |
| Harbor At Lake Henry | 7 | 7 | $335,560 | $320,480 |
| Peace Crk Reserve | 7 | 2 | $315,000 | $303,000 |
| Willowbrook North | 6 | 6 | $350,652 | $309,990 |
| Harmony On Lake Eloise | 6 | 6 | $347,945 | $302,000 |
| Villamar Phase 7 | 5 | 5 | $325,990 | $309,990 |
| Traditions Ph 01 | 5 | 0 | $309,900 | $309,000 |
| Traditions Ph 02 | 4 | 0 | $372,500 | $349,001 |
| Lucerne Park Reserve | 4 | 0 | $367,950 | $300,000 |
| Pinnacle Point | 4 | 0 | $364,500 | $340,000 |
| 38Th Street Subdivision | 4 | 4 | $350,000 | $350,000 |
| Peach Crossings | 4 | 4 | $339,900 | $314,900 |
| Crescent Pointe | 4 | 3 | $327,728 | $304,016 |
| Cypresswood | 3 | 0 | $425,000 | $355,000 |
| Lake Ashton West Ph Ii South | 3 | 0 | $422,999 | $355,000 |
| Island Lakes | 3 | 0 | $410,000 | $379,000 |
| Lake Lucerne Ii | 3 | 0 | $395,000 | $345,000 |
| Harmony/Lk Eloise Ph 1 | 3 | 0 | $380,000 | $336,000 |
| Buckeye Pointe | 3 | 0 | $369,900 | $309,990 |
| Residences At Winter Haven | 3 | 3 | $359,900 | $342,900 |
| Ridge Acres Ph 02 | 3 | 0 | $350,000 | $349,900 |
| Squires Grove Ph 2 | 3 | 0 | $350,000 | $329,000 |
| Fla Highlands Co Sub | 3 | 0 | $340,000 | $309,000 |
| Inman Grvs Ph 2 | 3 | 0 | $340,000 | $329,999 |
| Harmony On Lake Eloise Phase 4 | 3 | 3 | $333,990 | $329,990 |
| Lake Smart Pointe | 3 | 0 | $325,990 | $324,900 |
| Lakeside Landings Ph 01 | 3 | 0 | $319,900 | $300,000 |
| Villamar Ph 2 | 3 | 0 | $319,900 | $300,000 |
| Villamar Ph 4 | 3 | 0 | $309,900 | $300,000 |
| Eloise Woods Lake Mariam Unit | 2 | 0 | $497,700 | $495,500 |
| Southeast Terrace | 2 | 0 | $439,500 | $400,000 |
| Winterset Gardens 1St Add | 2 | 0 | $424,950 | $399,900 |
| Lake Mariam Hills Rep | 2 | 0 | $407,499 | $399,999 |
| Overlook Estates East | 2 | 0 | $389,950 | $370,000 |
| Buckeye Rdg | 2 | 0 | $387,499 | $360,000 |
| Terranova Ph 04 | 2 | 0 | $374,950 | $370,000 |
| Lake Lucerne Ph 5 | 2 | 0 | $368,500 | $338,000 |
| Lake Elbert Heights Unit 01 02 Rep | 2 | 0 | $364,950 | $329,900 |
| Jace Lndg | 2 | 0 | $362,450 | $339,900 |
| Inman Groves | 2 | 0 | $359,950 | $340,000 |
| Estates/Lk Florence | 2 | 0 | $355,000 | $335,000 |
| Villamar Ph 2A | 2 | 0 | $336,000 | $305,000 |
| Eagle Lndg Ph Ii | 2 | 0 | $334,750 | $324,500 |
| Summerhaven Shores | 2 | 0 | $332,500 | $320,000 |
| Villamar Ph 6 & Ph 6D | 2 | 1 | $322,450 | $315,000 |
| Peace Creek Reserve | 2 | 1 | $317,995 | $315,990 |
| Lakes At Lucerne Park Ph 02 | 2 | 0 | $317,000 | $315,000 |
| Willowbrook South | 2 | 2 | $314,445 | $301,900 |
| Plaza Sub | 2 | 0 | $309,999 | $309,999 |
| St James Xing | 2 | 0 | $307,000 | $305,000 |
| Villa Mar 40'S | 2 | 2 | $305,490 | $305,490 |
| Raingarden | 1 | 0 | $495,000 | $495,000 |
| Cypresswood Plantations | 1 | 0 | $484,900 | $484,900 |
| Village/Spirit Lake Ph 01 | 1 | 0 | $469,000 | $469,000 |
| Ruby Lake Sub Ph Ii | 1 | 0 | $465,999 | $465,999 |
| Lake Mariam Hills | 1 | 0 | $465,000 | $465,000 |
Also with homes $300K–$500K for sale
- Hutchinson Add (1)
- East El Otis Park Rep (1)
- Lake Rochelle Estates (1)
- Lake Thomas Woods Eight Add (1)
- Lake Ashton West Ph 2 South (1)
- Hart Lake Cove Ph 02 (1)
- Hendersons Ext Kenilworth Park (1)
- Overlook Ests Ph 3 (1)
- Lake Ashton West Ph Ii North (1)
- Lake Thomas Woods Eighth Add (1)
- Lake Winterset Acres Unit #2 (1)
- Residences Of Winter Haven (1)
- Sun Rdg Village East (1)
- Magnolia Shores (1)
- Ashton Covey Ph One (1)
- Linger & Nichols Sub/Winter H (1)
- Lake Lucerne Ph 1 (1)
- Overlook Estates (1)
- Lucerne Shores (1)
- Lake Eloise Place (1)
- East View Pkwy (1)
- Gates Of Lake Region (1)
- Cypress Grove Ph 02 Stage 01 (1)
- Terranova Phase Iv (1)
- Winterset 04 A Condo Ph 01 (1)
- Nydeggers West Elbert Sub (1)
- Eloise Woods (1)
- Gardens Interlochen (1)
- Lake Thomas Woods Add 03 (1)
- Winterset Gardens (1)
- Pine Terrace Rep (1)
- Valencia Wood Estates First Add (1)
- Summer Haven Shores (1)
- Eloise Woods Lake Roy Un (1)
- Terranova Ph 01 (1)
- Hamilton West Ph 02 (1)
- Twin Oaks Add (1)
- Lakewood Community Association (1)
- Lake Thomas Woods Sixth Add (1)
- West Winter Haven (1)
- Eloise Woods East Lake Mariam Unit (1)
- Eagle Lndg Ph I (1)
- Crossroads At Lake Region (1)
- Ridge Acres Ph Ii (1)
- College Estates (1)
- Hartridge Hills (1)
- Eloise Cove (1)
- Terranova Ph 03 (1)
- Audubon Place Sub (1)
- Lake Dexter Moorings (1)
- Hills/Lk Elbert (1)
- Robinson Sub (1)
- Reflections East Add (1)
- Homewood Sub (1)
- Lake Bess Country Club (1)
- Orange Hill Sub (1)
- Eagle Crest (1)
- Lesnick Park (1)
- Crystals Landing (1)
- Normandy Heights (1)
- Lathers Grove Sub (1)
- Residences/Winter Haven (1)
- Summit East Ph 02 (1)
- Winterset Park (1)
- Terranova Ph Iv (1)
- Inman Grvs Ph 1 (1)
- Van Duyne Shores (1)
- Village/Crystal Beach (1)
- Lake Thomas Woods Seventh Add (1)
- Cypresswood Mdws (1)
- Almeda Park (1)
- Carls Sub (1)
- Hamilton West Ph 01 (1)
- Gates Lake Region (1)
- Villamar Ph 6 (1)
- Harmony On Lake Eloise Phase 1 (1)
- Gardens Ph 01 (1)
- Villamar Ph 5 (1)
- Fla Hlnds (1)
- Thornhill Oaks (1)
- Mariana Heights (1)
- Lake Daisy Estates (1)
- Haven Terrace (1)
- Fanning Sub (1)
- Villamar Phase 6 And Phase 6D (1)
- Magnolia Preserve Ph 1 (1)
- Lake Deer (1)
- Lake Elbert Estates (1)
- Berryhill (1)
- Haven Place (1)
- Country Walk/Winter Haven Ph 2 (1)
- Haven Homes Sub (1)
- Villamar Ph 3 (1)
- Lake Smart Estates (1)
- Eloise Woods Lake Mariam Un (1)
- Lucerne Park Reserves (1)
- Casarena On Lakes (1)
- Carrolls Sub (1)
- Jan Phyl Village (1)
- Harmony/Lk Eloise Ph 2 (1)
- Jan Phyl Village Un #16 (1)
- Harmony On Lake Eloise Phase 2 (1)
- Emily Estates (1)
- Crescent View (1)
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?
What do homes $300K–$500K cost in Winter Haven?
Which Winter Haven community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Winter Haven
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Homes $300K–$500K in nearby Polk County cities
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- Lake Alfred homes $300K–$500K (85 for sale)
- Bartow homes $300K–$500K (80 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 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.