Homes for Sale Under $300K in Winter Garden, FL
This page tracks every Winter Garden 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.
115 homes listed under $300,000 are for sale or pending in Winter Garden, FL today across 51 communities. The median asking price is $220,000, from $1,695 to $299,900. Listings in Winter Garden without that feature have a median of $639,999. Most listings right now: Southern Pines Condo (13), Grove Residence & Spa Hotel Condo Ii (13), Grove Residence & Spa Hotel Condo 3 (9). Updated September 11, 2026 from the MLS.
Winter Garden homes under $300K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Homes Under $300K | New build | Median list | From |
|---|---|---|---|---|
| 13 | 0 | $275,000 | $212,000 | |
| Grove Residence & Spa Hotel Condo Ii | 13 | 1 | $249,000 | $185,000 |
| Grove Residence & Spa Hotel Condo 3 | 9 | 0 | $250,000 | $179,000 |
| 8 | 0 | $202,000 | $169,900 | |
| Townhomes Winter Garden | 6 | 0 | $212,000 | $162,900 |
| Palisades | 4 | 0 | $234,500 | $215,000 |
| 3 | 0 | $249,000 | $210,000 | |
| 3 | 0 | $235,000 | $209,000 | |
| 3 | 0 | $190,000 | $185,000 | |
| Tribute/Ovation | 3 | 0 | $2,900 | $2,895 |
| Grove Resort And Spa | 2 | 0 | $255,250 | $239,500 |
| The Grove Resort | 2 | 0 | $217,500 | $210,000 |
| 2 | 0 | $201,950 | $184,900 | |
| 2 | 0 | $194,999 | $174,999 | |
| 2 | 0 | $174,975 | $169,950 | |
| J S Loveless Add | 2 | 1 | $38,097 | $32,400 |
| 1 | 0 | $299,900 | $299,900 | |
| 1 | 0 | $299,000 | $299,000 | |
| 1 | 0 | $290,000 | $290,000 | |
| Southern Pines | 1 | 0 | $290,000 | $290,000 |
| Joe Louis Park First Add | 1 | 0 | $289,000 | $289,000 |
| 1 | 0 | $288,000 | $288,000 | |
| Westchester Place | 1 | 0 | $285,000 | $285,000 |
| Joe Louis Park | 1 | 0 | $275,000 | $275,000 |
| 1 | 0 | $275,000 | $275,000 | |
| 1 | 0 | $274,900 | $274,900 | |
| Troynelle By Lake Apopka | 1 | 0 | $252,000 | $252,000 |
| 1 | 0 | $250,000 | $250,000 | |
| 1 | 0 | $244,990 | $244,990 | |
| 1 | 0 | $239,000 | $239,000 | |
| 1 | 0 | $235,100 | $235,100 | |
| 1 | 0 | $230,000 | $230,000 | |
| 1 | 0 | $229,900 | $229,900 | |
| 1 | 0 | $225,000 | $225,000 | |
| 1 | 0 | $218,000 | $218,000 | |
| 1 | 0 | $215,000 | $215,000 | |
| 1 | 0 | $214,000 | $214,000 | |
| 1 | 0 | $205,000 | $205,000 | |
| 1 | 0 | $204,900 | $204,900 | |
| 1 | 0 | $199,999 | $199,999 | |
| Loveless J S Add 01 | 1 | 0 | $199,999 | $199,999 |
| 1 | 0 | $194,900 | $194,900 | |
| 1 | 0 | $179,000 | $179,000 | |
| Grove Resort And Spa Hotel Condo Ii | 1 | 0 | $165,000 | $165,000 |
| Story Road Bus Park | 1 | 0 | $155,100 | $155,100 |
| 1 | 1 | $150,000 | $150,000 | |
| Siplin Heights | 1 | 0 | $129,900 | $129,900 |
| Mary Jean Sub | 1 | 0 | $119,000 | $119,000 |
| Osprey | 1 | 1 | $3,200 | $3,200 |
| Hamlin Reserve 1St Amd | 1 | 0 | $3,100 | $3,100 |
| Manns First Add | 1 | 0 | $1,695 | $1,695 |
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 Garden?
What do homes under $300K cost in Winter Garden?
Which Winter Garden community has the most homes under $300K for sale?
What is the monthly payment on a home under $300,000?
Keep exploring Winter Garden
- All homes for sale in Winter Garden
- Winter Garden ZIP codes with prices
- Winter Garden pool homes
- Winter Garden waterfront homes
- Winter Garden golf course homes
- Winter Garden gated community homes
- Winter Garden 4-bedroom homes
- Winter Garden homes $300K–$500K
- Homes Under $300K in every city
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 Garden, 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.