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.
213 homes listed between $300,000 and $500,000 are for sale or pending in Winter Garden, FL today across 128 communities. The median asking price is $433,000, from $304,000 to $499,900. Listings in Winter Garden without that feature have a median of $699,000. Most listings right now: Waterleigh (10), Parkview At Hamlin (5), Westhaven At Ovation (5). Updated September 11, 2026 from the MLS.
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 | 10 | 10 | $436,245 | $414,990 |
| Parkview At Hamlin | 5 | 5 | $491,080 | $480,085 |
| Westhaven At Ovation | 5 | 5 | $465,000 | $411,995 |
| Hamlin Meadows | 5 | 5 | $462,125 | $456,213 |
| Silverleaf Oaks | 4 | 4 | $465,690 | $434,490 |
| Waterleigh Ph 4A | 4 | 0 | $457,500 | $395,000 |
| 4 | 0 | $394,995 | $325,000 | |
| 4 | 0 | $370,725 | $325,890 | |
| 4 | 0 | $347,500 | $330,000 | |
| Westhaven/Ovation | 3 | 0 | $490,000 | $468,000 |
| 3 | 0 | $485,000 | $409,990 | |
| Highland Rdg Ph 2 | 3 | 0 | $485,000 | $485,000 |
| Crown Point Spgs | 3 | 0 | $475,000 | $424,900 |
| Waterleigh Ph 3A | 3 | 0 | $455,000 | $379,990 |
| Winding Bay Preserve | 3 | 0 | $439,000 | $410,000 |
| Waterleigh Ph 2E | 3 | 0 | $425,000 | $399,000 |
| Del Webb Oasis Ph 3 | 3 | 1 | $419,000 | $400,000 |
| Osprey Ranch Ph 1 | 3 | 0 | $398,000 | $398,000 |
| Stone Crk | 3 | 0 | $393,000 | $375,000 |
| Stoneybrook West I | 3 | 0 | $369,900 | $369,900 |
| Orchard A1-A26 B1 B2 C D1-D4 | 3 | 0 | $355,000 | $309,000 |
| Tucker Oaks | 3 | 0 | $319,500 | $310,000 |
| Grove Residence & Spa Hotel Condo Ii | 3 | 0 | $319,000 | $314,900 |
| Mezzano | 2 | 0 | $472,000 | $469,000 |
| Highland Ridge | 2 | 0 | $467,000 | $449,000 |
| Northlake At Ovation | 2 | 2 | $465,352 | $459,922 |
| Orange Cove | 2 | 0 | $464,500 | $440,000 |
| 2 | 0 | $464,250 | $435,000 | |
| 2 | 0 | $456,950 | $434,900 | |
| Storey Grove Ph 2 | 2 | 0 | $448,000 | $399,000 |
| Serenade At Ovation | 2 | 2 | $440,933 | $425,370 |
| Overstreet Crate | 2 | 1 | $437,500 | $410,000 |
| Storey Grove Ph 4 | 2 | 0 | $426,950 | $419,000 |
| Storey Grove | 2 | 0 | $419,250 | $418,500 |
| Hamilton Gardens | 2 | 0 | $412,500 | $390,000 |
| 2 | 0 | $409,950 | $369,900 | |
| 2 | 0 | $385,000 | $310,000 | |
| Watermark Ph 3 | 2 | 0 | $377,500 | $375,000 |
| Signature Lakes Ph 3B-6 | 2 | 0 | $372,500 | $370,000 |
| 2 | 0 | $368,950 | $350,000 | |
| 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 |
| Longleaf At Oakland | 1 | 0 | $499,900 | $499,900 |
| 1 | 0 | $499,900 | $499,900 | |
| Black Lake Park Ph 02 | 1 | 0 | $499,000 | $499,000 |
| Highland Rdg | 1 | 0 | $499,000 | $499,000 |
| Watermark | 1 | 0 | $495,000 | $495,000 |
| Watermark Phase 2C | 1 | 0 | $495,000 | $495,000 |
| Rep Pt Pleasant Park Sub | 1 | 0 | $495,000 | $495,000 |
| Deerfield Place A-G | 1 | 0 | $494,995 | $494,995 |
| Black Lake Park Ph 01 | 1 | 0 | $489,000 | $489,000 |
| Alexander Rdg | 1 | 0 | $489,000 | $489,000 |
| Signature Lakes Ph 02 A B H I J | 1 | 0 | $488,000 | $488,000 |
| 1 | 0 | $485,000 | $485,000 | |
| 1 | 0 | $485,000 | $485,000 | |
| 1 | 0 | $480,000 | $480,000 | |
| 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)
- (1)
- (1)
- Fullers Crossing Ph 02 49 31 (1)
- Winter Garden Shores Rep (1)
- Summerlake Pd Ph 01B (1)
- Hickory Hammock Ph 1C (1)
- Emerald Ridge (1)
- Hawksmoor Ph 3 (1)
- Covington Chase Ph 2A (1)
- Encore At Ovation (1)
- (1)
- Hamlin Rdg (1)
- Waterleigh Ph 2C-1 (1)
- Watermark Ph 1B (1)
- Harvest/Ovation (1)
- K Hovnanian Winding Bay Preserve (1)
- (1)
- (1)
- (1)
- Stoneybrook West 47/78 (1)
- Stoneybrook West D (1)
- (1)
- Storey Grove Ph 1B-2 (1)
- (1)
- (1)
- (1)
- Edgewater Beach (1)
- Watermark Ph 2B (1)
- Osprey Ranch-Ph 1 (1)
- Lakeview Pointe At Horizon West (1)
- (1)
- (1)
- Hawksmoor (1)
- Hawksmoor-Ph 3 (1)
- Storey Grove Ph 1B-3 (1)
- Storey Grove Ph 1B-1 (1)
- Crown Point Springs Ut 2 (1)
- Stone Crk A-1 & A-2 (1)
- Ravenna Ph 1 (1)
- Del Webb Oasis Ph 2 (1)
- Summerlake (1)
- Osprey Ranch Ph I (1)
- Hickory Hammock Phase 2B (1)
- (1)
- Summerlake Grvs Ph 2 (1)
- Northlake At Ovation Phase 1 (1)
- (1)
- Waterleigh Ph 2D (1)
- Villas/Tucker Oaks (1)
- Loveless J S Add 01 (1)
- Stoneybrook West Unit 8 (1)
- (1)
- Grove Residence & Spa Hotel (1)
- Grove Residence & Spa Hotel Condo 3 (1)
- Stoneybrook West (1)
- (1)
- Edgewater Beach Sub (1)
- Tucker Oaks Bldg 5 (1)
- Westchester Place (1)
- (1)
- East Garden Manor Add 03 (1)
- Tucker Oaks Ph 8 (1)
- Grove Resort And Spa Hotel (1)
- (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
- 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 under $300K
- Homes $300K–$500K 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 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.