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.
539 homes listed under $300,000 are for sale or pending in Winter Haven, FL today across 249 communities. The median asking price is $234,900, from $36,950 to $299,990. Listings in Winter Haven without that feature have a median of $356,315. Most listings right now: Inwood (22), Villamar (18), Serenity At Peace Creek Th (16). Updated October 2, 2026 from the MLS.
First-time buyers: what Winter Haven costs at the entry level
348 active single-family homes, townhomes and condos at or below $300,000 — median $244,900, about $1,540/mo principal & interest at 6.95% with 5% down. Live from the MLS, refreshed nightly.
Newest homes under $300K in Winter Haven
What the payment looks like
| Purchase price | P&I at 6.95%, 5% down | P&I, 20% down | Cash to close at 5% down (est.) |
|---|---|---|---|
| $150,000 | $943 | $794 | $12,000 |
| $200,000 | $1,258 | $1,059 | $16,000 |
| $250,000 | $1,572 | $1,324 | $20,000 |
| $300,000 | $1,887 | $1,589 | $24,000 |
Estimates only; taxes, insurance, HOA and mortgage insurance are on top. Closing costs assumed at 3%.
Down-payment assistance in Polk County · First-time buyer guide
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 |
|---|---|---|---|---|
| Inwood | 22 | 0 | $209,500 | $109,900 |
| Villamar | 18 | 15 | $276,445 | $237,500 |
| Serenity At Peace Creek Th | 16 | 16 | $224,990 | $219,990 |
| Garden Grove Oaks | 13 | 0 | $159,900 | $129,900 |
| Harmony On Lake Eloise | 10 | 10 | $291,400 | $263,990 |
| Jan Phyl Village | 9 | 0 | $229,900 | $185,000 |
| Orange Manor West Coop Inc | 9 | 0 | $90,500 | $75,000 |
| Lucerne Park Reserve | 7 | 0 | $260,000 | $230,000 |
| Carefree Cove | 7 | 0 | $204,900 | $165,000 |
| Winter Haven Harbour Apts Condo | 7 | 0 | $99,900 | $78,800 |
| Villamar Ph 3 | 6 | 1 | $281,500 | $245,000 |
| West Cannon Heights | 6 | 0 | $212,000 | $150,000 |
| Villa Mar 40'S | 5 | 5 | $292,990 | $252,990 |
| Villamar Phase 6 And Phase 6D | 5 | 5 | $288,900 | $275,900 |
| Villamar Ph 5 | 5 | 1 | $280,000 | $185,000 |
| Fla Highlands Co Sub | 5 | 0 | $259,000 | $245,000 |
| Harbor At Lake Henry | 5 | 5 | $254,900 | $239,900 |
| Eagle Pond Condo | 5 | 0 | $165,000 | $160,000 |
| Lakeridge Condo | 5 | 0 | $144,900 | $98,500 |
| Country Club Estates | 4 | 0 | $292,500 | $290,000 |
| Lakeside Landings Ph 01 | 4 | 0 | $292,500 | $275,000 |
| Kensington View | 4 | 0 | $269,500 | $255,000 |
| Lake Daisy Estates | 4 | 0 | $254,900 | $215,000 |
| Cypresswood Enclave Ph 01 | 4 | 0 | $219,950 | $214,900 |
| Winter Haven Heights | 4 | 0 | $205,000 | $180,000 |
| Cypresswood | 4 | 0 | $199,000 | $190,000 |
| Lake N Golf Estates Add | 4 | 0 | $184,950 | $140,000 |
| Casa Del Sol Condo Village Ph 02 | 4 | 0 | $168,500 | $150,000 |
| Wahneta Farms | 4 | 0 | $160,249 | $92,000 |
| Brookhaven Village | 4 | 0 | $153,850 | $151,000 |
| Spring Lake Towers | 4 | 0 | $134,450 | $99,900 |
| Lakeside Ranch For Mobile Homes | 4 | 0 | $99,500 | $54,900 |
| Peace Crk Reserve | 3 | 1 | $299,000 | $247,990 |
| Dundee Station | 3 | 0 | $293,899 | $255,000 |
| Eloise Woods East Lake Mariam Unit | 3 | 0 | $290,000 | $250,000 |
| Krenson Bay | 3 | 0 | $280,000 | $272,990 |
| Peach Crossings | 3 | 3 | $279,900 | $279,900 |
| Planters Walk | 3 | 0 | $269,900 | $254,900 |
| Timber Wood | 3 | 0 | $265,000 | $229,000 |
| Queens Cove Ph 04 | 3 | 0 | $259,990 | $234,900 |
| Squires Grove | 3 | 0 | $244,900 | $224,900 |
| Planters Walk Ph 03 | 3 | 0 | $230,000 | $225,000 |
| Orchid Springs Patio Homes | 3 | 0 | $224,900 | $220,000 |
| Winterset 01 A Condo 02 Amd | 3 | 0 | $215,000 | $199,000 |
| Tanamora | 3 | 0 | $215,000 | $140,000 |
| Foxhaven | 3 | 0 | $185,000 | $143,000 |
| Winterset 02 A Condo Ph 01 | 3 | 0 | $170,000 | $169,900 |
| Winter Ridge Condo | 3 | 0 | $135,000 | $99,900 |
| Orchid Spgs Vill 300 Barcelona | 3 | 0 | $129,500 | $95,000 |
| Imperial Harboursphases 01 & 02 | 3 | 0 | $99,000 | $99,000 |
| Orchid Spgs Vill 100 Condo | 3 | 0 | $94,900 | $65,000 |
| West Winter Haven | 2 | 2 | $299,400 | $298,900 |
| Willowbrook North | 2 | 2 | $289,990 | $289,990 |
| Lake Lucerne Ph 5 | 2 | 0 | $289,450 | $279,900 |
| Gardens Ph 01 | 2 | 0 | $286,999 | $279,000 |
| Willowbrook South | 2 | 2 | $285,195 | $275,900 |
| Buckeye Trace | 2 | 0 | $280,000 | $275,000 |
| Lakeside Lndgs Ph 3 | 2 | 0 | $278,400 | $269,900 |
| Country Walk/Winter Haven | 2 | 0 | $277,500 | $275,000 |
| Saxon Myers Rep Ph 2 | 2 | 0 | $277,000 | $255,000 |
Also with homes under $300K for sale
- Hutchinson Add (2)
- Villamar Phase 7 (2)
- Sandalwood Sub (2)
- North Lake Elbert Heights (2)
- Peace Creek Reserve 40'S (2)
- Shadow Wood (2)
- Cooper Estates (2)
- Lake Ashton West Ph 01 (2)
- Lakes/Lucerne Park Ph 4 (2)
- Florida Highland Co (2)
- Traditions Ph 01 (2)
- Cinnamon Ridge Ph 03 (2)
- Fox Ridge Ph 01 (2)
- Crystals Landing (2)
- Anna Mar (2)
- Vienna Square Ph 01 (2)
- Jan Phyl Village Unit 03 A (2)
- Villamar Ph 6 & Ph 6D (2)
- Winterset 03 A Condo Ph 01 (2)
- Queens Cove Ph 02 (2)
- Hills Lake Elbert (2)
- Traditions Ph 1 (2)
- Lake Idyll Estates (2)
- Vienna Square (2)
- Silvercrest Add (2)
- Lake Dexter Woods Ph 02 (2)
- Elbert Park Resub (2)
- Whispering Trails Ph 02 (2)
- Casarena On Lakes (2)
- Eloise Woods Lake Mariam Unit (2)
- Oakview (2)
- Foxhaven Ph 03 (2)
- Hartridge Landing (2)
- Lake Shipp Heights (2)
- Lucerne Park Fruit Assn (2)
- College Heights Or Coker & Buzbee (2)
- Eula Vista Sub (2)
- Royal Crescent Condo (2)
- Country Lake Condo Ph 01 (2)
- Havencrest Add (2)
- Village Park (2)
- Garden Villas Condo Ph 01 (2)
- Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B (2)
- Lake Kit Condo (2)
- Rosewood Manor (2)
- Imperial Villas (2)
- Fairview Village (2)
- Orchid Spgs Vill 400 San Miguel (2)
- St James Crossing (1)
- Summit East Ph 01 (1)
- Waterside Village (1)
- Crescent Pointe (1)
- Highland Harbor (1)
- Country Walk/Winter Winter Hav (1)
- Elbert Hills (1)
- Kings Pond Ph 02 (1)
- Coventry Cove Ph Il (1)
- Harmony On Lake Eloise Phase 4 (1)
- Villamar Phase 6 (1)
- Villamar Ph Four (1)
- Emily Estates (1)
- Lake Deer (1)
- Lake Mariam Hills Rep (1)
- Lakes At Lucerne Park Ph 02 (1)
- Lake Smart Estates (1)
- Jace Lndg (1)
- Spirit Lndgs (1)
- Eloise Woods Lake Roy Unit (1)
- Elbert Acres (1)
- Magnolia Preserve Ph 4 (1)
- Villamar Ph 2A (1)
- Gardens (1)
- Lake Lucerne Ph 1 (1)
- Leisure Shores (1)
- Lake Dexter Woods I (1)
- Buckeye Haven (1)
- Morningside At Winterset (1)
- Cypresswood Golf Villas Gc-2 (1)
- Idylwild Heights (1)
- Kings Pond Sub (1)
- Solis Gardens (1)
- Lake View Sub (1)
- South Lake Elbert Heights (1)
- Moores F M Sub (1)
- Kings Pond Ph 2 (1)
- Tranquility Park 2Nd Rep (1)
- Town Acres 25 (1)
- Yonnally W P Resub (1)
- Peace Creek Reserve (1)
- Berryhill (1)
- Coventry Cove Ph Ii (1)
- Villamar Ph 1 (1)
- Leslie J A Sub (1)
- Eagle Landing Phase I (1)
- Tranquility Park 02 Rep (1)
- Eagle Lndg Ph I (1)
- Buckeye Ridge (1)
- Winter Haven (1)
- Wahneta Farms Resub (1)
- Queens Cove (1)
- Osprey Landings Ph 01 (1)
- Lakes/ Lucerne Park Ph 3 (1)
- West Winter Haven Replat Blks 2 To 6 (1)
- Jewett Mary B (1)
- West Lake Park (1)
- Dugger Rep (1)
- Deer Lake Terrace Sub (1)
- Lake Elbert Estates (1)
- Richmond Square Sub (1)
- Vienna Square Phase 3A (1)
- Jan Phyl Village Unit 03 Rep (1)
- Vienna Square Ph 2C (1)
- Lake Elbert Heights Unit 02 02 Rep (1)
- Queens Cove Ph 03B (1)
- Haven Grove Estates (1)
- Lake Add (1)
- Saxon-Myers Rep Ph 02 (1)
- Beverly Heights (1)
- Fox Ridge Ph 02 (1)
- Beymer Stoner Sub (1)
- Traditions Ph 2A (1)
- Eagle Lndg Ph Ii (1)
- Traditions Phase 1 (1)
- Jan Phyl Village Unit 10 (1)
- Inwood Area (1)
- Villamar Ph 4 (1)
- Crescent View (1)
- Cypresswood Patio Homes (1)
- Dinner Lake Estates (1)
- Cypresswood Villas/Green Bldg (1)
- Laha Wa Manor (1)
- Maud Meadows (1)
- Waters Edge Unit 01 A Rep 02 (1)
- Tranquility Park Sub (1)
- Squires Grove Ph 2 (1)
- Sunridge Village East (1)
- Lesnick Park (1)
- Brookhaven Village Second Add (1)
- Haven Grove Manor (1)
- Vienna Square Duplex (1)
- Orangewood Add (1)
- Coker A B Add (1)
- West Winter Haven Rep (1)
- Waters Edge Unit 1 Replat (1)
- Waters Edge Unit 01 A Rep (1)
- Villamar Ph 2 (1)
- Idyl Ridge View (1)
- Hartridge Manor (1)
- Doves Rest Add (1)
- South College (1)
- Conine Heights (1)
- Vienna Square Ph 2B (1)
- Chris Brown Cemetery Replat (1)
- North Gate Village (1)
- Parkland Village (1)
- Carls Sub (1)
- Cypresswood Golf Villas Gi-4 (1)
- Stonebridge Vls Ph 02 (1)
- Orchid Springs Village (1)
- Revised Map Of Fernwood Add (1)
- Harrington A B Sub (1)
- Haven Terrace (1)
- Cypresswood Villas/Green (1)
- Madera Park Sub (1)
- Daniels Sub (1)
- Cypresswood Villas On The Green (1)
- Cypresswood Tennis Villas (1)
- Cypresswood Tennis Vls (1)
- Florence Village (1)
- Beech Haven Estates (1)
- Park Lake 03 02 Amd (1)
- Imperial Harbours Ph 01 (1)
- Brookhaven Village First Add (1)
- Eloise Woods Lakes Miriam Un (1)
- Lake N Golf Estates (1)
- Lake Buckeye Condo (1)
- Lake Kit (1)
- The Haven (1)
- Lamplighter Village (1)
- Cypresswood Golf Villas (1)
- Orchid Spgs Village #300 (1)
- Carefree Rv Country Club (1)
- Sandy Cove Winter Haven (1)
- Kenilworth Park (1)
- Hawaiian A Condo (1)
- Orchid Spgs Vill 200 Condo (1)
- Country Lake Condo (1)
- Deerwood Or Harriben Investment Co (1)
- Bookers Sub (1)
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?
What do homes under $300K cost in Winter Haven?
Which Winter Haven community has the most homes under $300K for sale?
What is the monthly payment on a home under $300,000?
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 4-bedroom homes
- Winter Haven homes $300K–$500K
- Homes Under $300K in every city
Homes Under $300K in nearby Polk County cities
- Lakeland homes under $300K (540 for sale)
- Davenport homes under $300K (443 for sale)
- Haines City homes under $300K (306 for sale)
- Lake Wales homes under $300K (268 for sale)
- Poinciana homes under $300K (136 for sale)
- Auburndale homes under $300K (109 for sale)
- Bartow homes under $300K (74 for sale)
- Dundee homes under $300K (59 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 under $300,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.