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.
64 homes listed between $300,000 and $500,000 are for sale or pending in Winter Springs, FL today across 46 communities. The median asking price is $396,950, from $301,000 to $499,999. Listings in Winter Springs without that feature have a median of $295,900. Most listings right now: Hickory Grove (5), Jesups Landing (4), Jesups Reserve Twnhms Rep (3). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Winter Springs: the listings
41 active listings match today (41% of Winter Springs inventory), median asking $399,000, $248/sq ft, median 26 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Winter Springs
The most expensive $300k–$500k homes in Winter Springs
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1010 W Pebble Beach Circle | $499,999 | 1,732 | — |
| 1389 Ponce De Leon Boulevard | $499,000 | 2,056 | sunrise winter springs |
| 909 Devon Creek Road | $497,500 | 2,256 | parkstone |
| 1541 Corkery Court #1541 | $489,900 | 1,926 | Greens At Tuscawilla |
| 1610 Fox Glen Court | $486,900 | 1,992 | Fox Glen At Chelsea Parc Tuscawilla |
| 1304 Ortega Street | $474,900 | 2,152 | — |
| 45 Hayes Road | $465,000 | 1,732 | — |
| 619 Coral Way | $464,000 | 1,919 | — |
| 288 Ringwood Drive | $460,000 | 1,700 | deer run casselberry |
| 1128 Spotted Sandpiper Loop | $455,000 | 2,344 | Seminole Crossing Townhomes |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 41 | 100% |
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 Landing | 4 | 0 | $374,500 | $360,000 |
| Jesups Reserve Twnhms Rep | 3 | 0 | $369,500 | $323,000 |
| Wedgewood Tennis Villas | 3 | 0 | $365,000 | $360,000 |
| Greenspointe | 3 | 0 | $365,000 | $340,000 |
| North Orlando Ranches Sec 02 | 2 | 0 | $419,450 | $374,900 |
| Country Club Village Unit 1 | 2 | 0 | $404,888 | $309,777 |
| Georgetowne Unit 1 | 2 | 0 | $397,000 | $385,000 |
| Highland Village 1 | 2 | 0 | $337,450 | $324,900 |
| Harbor Winds | 2 | 0 | $332,000 | $329,000 |
| Deer Run Unit 20 | 1 | 0 | $499,000 | $499,000 |
| Sunrise Unit 2-A | 1 | 0 | $499,000 | $499,000 |
| Parkstone | 1 | 0 | $497,500 | $497,500 |
| Greens At Tuscawilla | 1 | 0 | $489,900 | $489,900 |
| The Oaks Sub | 1 | 0 | $489,000 | $489,000 |
| Fox Glen At Chelsea Parc Tuscawilla | 1 | 0 | $486,900 | $486,900 |
| Parkstone Unit 2 | 1 | 0 | $484,900 | $484,900 |
| Amherst | 1 | 0 | $480,000 | $480,000 |
| Eagles Watch Ph 1 | 1 | 0 | $479,000 | $479,000 |
| The Highlands Sections Seven & Eight | 1 | 0 | $475,000 | $475,000 |
| Sunrise Estates Unit 1 | 1 | 0 | $474,900 | $474,900 |
| North Orlando Ranches Sec 02A | 1 | 0 | $465,000 | $465,000 |
| Deer Run Unit 23A | 1 | 0 | $460,000 | $460,000 |
| Seminole Crossing Twnhms | 1 | 0 | $455,000 | $455,000 |
| Talmo Sub | 1 | 0 | $449,900 | $449,900 |
| Stone Gable | 1 | 0 | $449,000 | $449,000 |
| Eagles Watch Ph 2 | 1 | 0 | $442,000 | $442,000 |
| North Orlando Ranches Sec 08 | 1 | 0 | $439,900 | $439,900 |
| Sunrise Unit 2-B | 1 | 0 | $434,900 | $434,900 |
| Fox Glen At Chelsea Parc Tuscawilla Ph 2 | 1 | 0 | $429,000 | $429,000 |
| Country Club Village Unit 2 | 1 | 0 | $425,000 | $425,000 |
| Wedgewood Unit 3 | 1 | 0 | $419,900 | $419,900 |
| Tusca Oaks | 1 | 0 | $409,900 | $409,900 |
| Hickory Grove Twnhms | 1 | 0 | $399,000 | $399,000 |
| Sunrise Estates Unit 2 | 1 | 0 | $394,900 | $394,900 |
| Sunrise Estates | 1 | 0 | $394,900 | $394,900 |
| North Orlando Ranches Sec 10 | 1 | 0 | $387,500 | $387,500 |
| North Orlando Terrace Unit 1 Sec 3 | 1 | 0 | $369,900 | $369,900 |
| North Orlando 2Nd Add | 1 | 0 | $365,500 | $365,500 |
| Sunrise Village Unit 4 | 1 | 0 | $359,900 | $359,900 |
| North Orlando Terrace Unit 1 Sec 6 | 1 | 0 | $355,000 | $355,000 |
| Tuscawilla Braewick At Ph 1 | 1 | 0 | $344,900 | $344,900 |
| North Orlando Terrace Unit 2 Sec 8 | 1 | 0 | $339,000 | $339,000 |
| Wildwood | 1 | 0 | $325,000 | $325,000 |
| Seasons The | 1 | 0 | $309,000 | $309,000 |
| 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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Homes $300K–$500K in nearby Seminole County cities
- Sanford homes $300K–$500K (246 for sale)
- Oviedo homes $300K–$500K (117 for sale)
- Altamonte Springs homes $300K–$500K (90 for sale)
- Longwood homes $300K–$500K (86 for sale)
- Lake Mary homes $300K–$500K (72 for sale)
- Casselberry homes $300K–$500K (55 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 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.