Homes for Sale $300K to $500K in Winter Springs, FL
This page tracks every Winter Springs 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.
67 homes listed between $300,000 and $500,000 are for sale or pending in Winter Springs, FL today across 50 communities. The median asking price is $399,000, from $300,000 to $499,900. Listings in Winter Springs without that feature have a median of $513,495. Most listings right now: Hickory Grove (5), Jesups Reserve Twnhms Rep (3), Jesups Landing (3). Updated September 11, 2026 from the MLS.
Winter Springs homes $300K–$500K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Homes $300K–$500K | New build | Median list | From |
|---|---|---|---|---|
| Hickory Grove | 5 | 5 | $401,990 | $386,990 |
| Jesups Reserve Twnhms Rep | 3 | 0 | $369,500 | $323,000 |
| Jesups Landing | 3 | 0 | $365,000 | $360,000 |
| Stone Gable | 2 | 0 | $464,000 | $449,000 |
| 2 | 0 | $424,450 | $384,900 | |
| Sunrise Unit 2-B | 2 | 0 | $417,450 | $400,000 |
| 2 | 0 | $405,000 | $385,000 | |
| Greenspointe | 2 | 0 | $369,950 | $365,000 |
| 2 | 0 | $369,000 | $339,000 | |
| Highland Village 1 | 2 | 0 | $339,950 | $329,900 |
| Harbor Winds | 2 | 0 | $332,000 | $329,000 |
| Seasons The | 2 | 0 | $320,000 | $300,000 |
| Parkstone | 1 | 0 | $499,900 | $499,900 |
| Deer Run Unit 20 | 1 | 0 | $499,000 | $499,000 |
| Sunrise Unit 2-A | 1 | 0 | $499,000 | $499,000 |
| Fox Glen At Chelsea Parc Tuscawilla | 1 | 0 | $497,000 | $497,000 |
| 1 | 0 | $490,000 | $490,000 | |
| Greens At Tuscawilla | 1 | 0 | $489,900 | $489,900 |
| The Oaks Sub | 1 | 0 | $489,000 | $489,000 |
| Parkstone Unit 2 | 1 | 0 | $484,900 | $484,900 |
| Amherst | 1 | 0 | $480,000 | $480,000 |
| 1 | 0 | $479,000 | $479,000 | |
| The Highlands Sections Seven & Eight | 1 | 0 | $475,000 | $475,000 |
| 1 | 0 | $474,900 | $474,900 | |
| Seminole Crossing Twnhms | 1 | 0 | $455,000 | $455,000 |
| Talmo Sub | 1 | 0 | $449,900 | $449,900 |
| Fox Glen At Chelsea Parc Tuscawilla Ph 2 | 1 | 0 | $449,000 | $449,000 |
| 1 | 0 | $442,000 | $442,000 | |
| 1 | 0 | $439,900 | $439,900 | |
| 1 | 0 | $425,000 | $425,000 | |
| Seminole Crossing Townhomes | 1 | 0 | $424,990 | $424,990 |
| Wedgewood Tennis Villas | 1 | 0 | $419,900 | $419,900 |
| Tusca Oaks | 1 | 0 | $409,900 | $409,900 |
| 1 | 0 | $409,900 | $409,900 | |
| 1 | 0 | $399,900 | $399,900 | |
| Hickory Grove Twnhms | 1 | 0 | $399,000 | $399,000 |
| 1 | 0 | $394,000 | $394,000 | |
| 1 | 0 | $392,500 | $392,500 | |
| 1 | 0 | $375,000 | $375,000 | |
| 1 | 0 | $359,900 | $359,900 | |
| 1 | 0 | $359,900 | $359,900 | |
| Sunrise Village Unit 4 | 1 | 0 | $359,900 | $359,900 |
| 1 | 0 | $359,000 | $359,000 | |
| 1 | 0 | $351,900 | $351,900 | |
| The Seasons | 1 | 0 | $349,900 | $349,900 |
| 1 | 0 | $344,900 | $344,900 | |
| Deersong 2 | 1 | 0 | $310,000 | $310,000 |
| 1 | 0 | $309,777 | $309,777 | |
| Sunrise Village Unit 3 | 1 | 0 | $304,987 | $304,987 |
| Highland Patio Homes Amended Plat | 1 | 0 | $301,000 | $301,000 |
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 Springs?
What do homes $300K–$500K cost in Winter Springs?
Which Winter Springs community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Winter Springs
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- Winter Springs 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 Springs, 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.