Homes for Sale $300K to $500K in Winter Garden, FL
This page tracks every Winter Garden 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.
218 homes listed between $300,000 and $500,000 are for sale or pending in Winter Garden, FL today across 127 communities. The median asking price is $435,000, from $300,000 to $499,900. Listings in Winter Garden without that feature have a median of $699,000. Most listings right now: Waterleigh (11), Serenade At Ovation (8), Hamlin Meadows (7). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Winter Garden: the listings
156 active listings match today (24% of Winter Garden inventory), median asking $425,000, $254/sq ft, median 35 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Winter Garden
The most expensive $300k–$500k homes in Winter Garden
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 13953 Easdale Alley | $499,900 | 1,770 | Westhaven At Ovation |
| 15101 Purple Martin Street | $499,900 | 1,998 | Summerlake Pd |
| 6355 Argent Wood Drive | $499,690 | 1,652 | Silverleaf Oaks |
| 13861 Easdale Alley | $499,000 | 2,031 | Westhaven At Ovation |
| 9231 Grand Island Way | $495,000 | 2,060 | Watermark |
| 14543 Golden Harbor Lane | $495,000 | 2,039 | Watermark |
| 15159 Groveside Road | $492,990 | 1,881 | Parkview At Hamlin |
| 1112 Juniper Hammock Court | $490,000 | 2,545 | Fullers Crossing |
| 15075 Groveside Road | $489,990 | 1,881 | Parkview At Hamlin |
| 15207 Groveside Road | $489,140 | 1,881 | Parkview At Hamlin |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 156 | 100% |
Winter Garden 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 |
|---|---|---|---|---|
| Waterleigh | 11 | 11 | $464,500 | $424,990 |
| Serenade At Ovation | 8 | 8 | $435,048 | $425,370 |
| Hamlin Meadows | 7 | 7 | $465,198 | $456,213 |
| Parkview At Hamlin | 6 | 6 | $489,940 | $478,990 |
| Silverleaf Oaks | 5 | 5 | $469,690 | $434,490 |
| Westhaven At Ovation | 5 | 5 | $465,000 | $411,995 |
| Del Webb Oasis Ph 3 | 4 | 1 | $419,500 | $400,000 |
| Grove Resort | 4 | 0 | $370,725 | $325,890 |
| Stoneybrook West I | 4 | 0 | $364,949 | $359,900 |
| Grove Resort And Spa Hotel Condominium | 4 | 0 | $342,500 | $325,000 |
| Waterleigh Ph 4A | 3 | 0 | $485,000 | $395,000 |
| Summerlake Pd Ph 2C 2D 2E | 3 | 0 | $465,900 | $434,900 |
| Waterleigh Ph 3A | 3 | 0 | $455,000 | $379,990 |
| Storey Grove Ph 4 | 3 | 0 | $434,900 | $419,000 |
| Storey Grove | 3 | 1 | $420,000 | $418,400 |
| Grove Resort And Spa Hotel Condominium 1 | 3 | 0 | $410,990 | $325,000 |
| Watermark Ph 3 | 3 | 0 | $380,000 | $375,000 |
| Grove Residence & Spa Hotel Condo Ii | 3 | 0 | $319,000 | $314,900 |
| Tucker Oaks | 3 | 0 | $310,000 | $300,000 |
| Highland Rdg Ph 2 | 2 | 0 | $492,000 | $485,000 |
| Waterleigh Ph 3B 3C & 3D | 2 | 0 | $487,000 | $485,000 |
| Westhaven/Ovation | 2 | 0 | $483,950 | $468,000 |
| Crown Point Spgs | 2 | 0 | $477,450 | $475,000 |
| Highland Rdg | 2 | 0 | $474,500 | $450,000 |
| Mezzano | 2 | 0 | $472,000 | $469,000 |
| Highland Ridge | 2 | 0 | $467,000 | $449,000 |
| Northlake At Ovation | 2 | 2 | $465,352 | $459,922 |
| Signature Lakes Ph 02 A B H I J | 2 | 0 | $451,500 | $415,000 |
| Orange Cove | 2 | 0 | $449,000 | $409,000 |
| Stoneybrook West D | 2 | 0 | $443,950 | $438,000 |
| Overstreet Crate | 2 | 1 | $437,500 | $410,000 |
| Osprey Ranch Ph 1 | 2 | 0 | $415,500 | $391,000 |
| Waterleigh Ph 2E | 2 | 0 | $412,000 | $399,000 |
| Storey Grove Ph 1B-1 | 2 | 0 | $409,950 | $409,900 |
| Orchard Hills Ph 4 | 2 | 0 | $409,950 | $369,900 |
| Stoneybrook West | 2 | 0 | $405,000 | $350,000 |
| Villas/Tucker Oaks | 2 | 0 | $381,950 | $379,000 |
| Stone Crk | 2 | 0 | $379,450 | $359,900 |
| Signature Lakes Ph 3B-6 | 2 | 0 | $372,500 | $370,000 |
| Grove Residence & Spa Hotel Condo I | 2 | 0 | $368,950 | $350,000 |
| Orchard A1-A26 B1 B2 C D1-D4 | 2 | 0 | $360,000 | $355,000 |
| Grove Resort And Spa Hotel Condominium 3 | 2 | 0 | $352,495 | $335,000 |
| Park Ave Estates | 2 | 0 | $322,450 | $319,900 |
| Daniels Lndg A-J | 2 | 0 | $317,000 | $309,000 |
| Summerlake Pd Ph 3B | 1 | 0 | $499,900 | $499,900 |
| Summerlake Pd Ph 3B | 1 | 0 | $499,900 | $499,900 |
| Longleaf At Oakland | 1 | 0 | $499,900 | $499,900 |
| Harbor | 1 | 0 | $499,900 | $499,900 |
| Storey Grove Ph 2 | 1 | 0 | $497,000 | $497,000 |
| Watermark Phase 2C | 1 | 0 | $495,000 | $495,000 |
| Watermark | 1 | 0 | $495,000 | $495,000 |
| Fullers Crossing Ph 02 49 31 | 1 | 0 | $490,000 | $490,000 |
| Alexander Rdg | 1 | 0 | $489,000 | $489,000 |
| Waterside/Johns Lake Ph 2A | 1 | 0 | $485,000 | $485,000 |
| Encore/Ovation Ph 3 | 1 | 0 | $485,000 | $485,000 |
| Walkers Grove Twnhms | 1 | 0 | $485,000 | $485,000 |
| Encore/Ovation Ph 4B | 1 | 0 | $483,500 | $483,500 |
| Grova Residence & Spa Hotel Condo 3 | 1 | 0 | $480,000 | $480,000 |
| M C Britt Sub 1 | 1 | 1 | $479,900 | $479,900 |
| Lakeview Pointe/Horizon West P | 1 | 0 | $479,000 | $479,000 |
Also with homes $300K–$500K for sale
- Latham Park North (1)
- Crown Point Springs (1)
- Hamilton Gardens Ph 2A 2B (1)
- Hickory Hammock (1)
- Winter Garden Shores Rep (1)
- Rep Pt Pleasant Park Sub (1)
- Summerlake Pd Ph 01B (1)
- Summerlake Pd Ph 01B (1)
- Hawksmoor Ph 3 (1)
- Grove Resort And Spa Hotel Condo 1 (1)
- Del Webb Oasis (1)
- Covington Chase Ph 2A (1)
- Oak Park At Winter Garden (1)
- Hamlin Rdg (1)
- Signature Lakes, Independence (1)
- Waterleigh Ph 2C-1 (1)
- Stone Creek (1)
- K Hovnanian Winding Bay Preserve (1)
- Storey Grv Ph 4 (1)
- Borders & Woosley Sub (1)
- Stoneybrook West 47/78 (1)
- Winding Bay Preserve (1)
- Watermark Ph 1B (1)
- Storey Grove Ph 1B-2 (1)
- Twin City Dev Co Sub (1)
- Mezzano Townhomes (1)
- Corsino Place (1)
- Overlook 2/Hamlin Ph 1 & 6 (1)
- Stone Crk Un #4 (1)
- Hickory Hammock Ph 1C (1)
- Glenview Estates 1St Add (1)
- Edgewater Beach (1)
- Osprey Ranch-Ph 1 (1)
- Deerfield Place (1)
- Storey Grove Ph 1B-3 (1)
- Crown Point Springs Ut 2 (1)
- Northlake/Ovation Ph 1 (1)
- Highlands/Summerlake Grvs Ph I (1)
- Del Webb Oasis Ph 2 (1)
- Stone Creek 48 140 (1)
- Osprey Ranch Ph I (1)
- Hamilton Gardens Ph 2A & 2B (1)
- Stone Crk A-1 & A-2 (1)
- Ravenna Ph 1 (1)
- Joe Louis Park Q162 (1)
- Hamlin Reserve (1)
- Hawksmoor (1)
- Northlake At Ovation Phase 1 (1)
- Hamilton Gardens (1)
- Regal Pointe Ph 02 47/133 (1)
- Summerlake Grvs Ph 2 (1)
- Signature Lks-Pcl 01D Ph 01 (1)
- Loveless J S Add 01 (1)
- Stoneybrook West Unit 8 (1)
- Orchard (1)
- Grove Residence & Spa Hotel (1)
- Grove Residence & Spa Hotel Condo 3 (1)
- Grove Resort And Spa Hote Condominium 3 (1)
- Tucker Oaks Bldg 5 (1)
- Westchester Place (1)
- Signature Lakes Parcel 1B (1)
- Tucker Oaks Ph 8 (1)
- East Garden Manor Add 03 (1)
- Grove Resort And Spa Hotel (1)
- Grove Resort And Spa Hotel Condominium Ii (1)
- Daniels Landing (1)
- Grove Resort And Water Park (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 Garden?
What do homes $300K–$500K cost in Winter Garden?
Which Winter Garden community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Winter Garden
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- Winter Garden ZIP codes with prices
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- Winter Garden waterfront homes
- Winter Garden golf course homes
- Winter Garden gated community homes
- Winter Garden 4-bedroom homes
- Winter Garden homes under $300K
- Homes $300K–$500K in every city
Homes $300K–$500K in nearby Orange County cities
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- Ocoee homes $300K–$500K (115 for sale)
- Winter Park homes $300K–$500K (64 for sale)
- Windermere homes $300K–$500K (53 for sale)
- Maitland homes $300K–$500K (25 for sale)
- Zellwood homes $300K–$500K (13 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 Garden, 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.