Homes for Sale Under $300K in Winter Springs, FL
This page tracks every Winter Springs 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.
42 homes listed under $300,000 are for sale or pending in Winter Springs, FL today across 22 communities. The median asking price is $240,950, from $11,400 to $297,000. Listings in Winter Springs without that feature have a median of $465,000. Most listings right now: Seasons The (4), Wildwood (4), Baytree Village (4). Updated October 2, 2026 from the MLS.
First-time buyers: what Winter Springs costs at the entry level
28 active single-family homes, townhomes and condos at or below $300,000 — median $240,950, about $1,515/mo principal & interest at 6.95% with 5% down. Live from the MLS, refreshed nightly.
Newest homes under $300K in Winter Springs
What the payment looks like
| Purchase price | P&I at 6.95%, 5% down | P&I, 20% down | Cash to close at 5% down (est.) |
|---|---|---|---|
| $150,000 | $943 | $794 | $12,000 |
| $200,000 | $1,258 | $1,059 | $16,000 |
| $250,000 | $1,572 | $1,324 | $20,000 |
| $300,000 | $1,887 | $1,589 | $24,000 |
Estimates only; taxes, insurance, HOA and mortgage insurance are on top. Closing costs assumed at 3%.
Down-payment assistance in Seminole County · First-time buyer guide
Winter Springs 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 |
|---|---|---|---|---|
| Seasons The | 4 | 0 | $284,500 | $279,900 |
| Wildwood | 4 | 0 | $279,950 | $275,000 |
| Baytree Village | 4 | 0 | $155,000 | $130,000 |
| Heritage Commons | 3 | 0 | $276,200 | $263,000 |
| Mount Greenwood Unit 4 Of | 3 | 0 | $244,000 | $175,000 |
| Heritage Park Twnhms | 2 | 0 | $284,950 | $280,000 |
| Deersong 2 | 2 | 0 | $258,500 | $242,000 |
| Casa Park Villas Ph 1 | 2 | 0 | $237,400 | $234,900 |
| Casa Park Villas Ph 2 | 2 | 0 | $234,999 | $225,000 |
| Cypress Club | 2 | 0 | $233,250 | $199,000 |
| Moss Cove | 2 | 0 | $208,499 | $206,999 |
| Indian Ridge | 2 | 0 | $161,950 | $145,000 |
| North Orlando Terrace | 1 | 0 | $297,000 | $297,000 |
| Williamson Heights | 1 | 0 | $285,000 | $285,000 |
| Mount Greenwood Unit 2 Of | 1 | 0 | $235,000 | $235,000 |
| Moss Place | 1 | 0 | $220,000 | $220,000 |
| North Orlando | 1 | 0 | $214,000 | $214,000 |
| Bay Tree Sec 09 | 1 | 0 | $179,900 | $179,900 |
| Sheoah Sec 1 | 1 | 0 | $167,777 | $167,777 |
| Sheoah Sec 3 | 1 | 0 | $166,000 | $166,000 |
| Foxmoor East | 1 | 0 | $110,000 | $110,000 |
| Tuskawilla Office Park | 1 | 0 | $11,400 | $11,400 |
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 Springs?
What do homes under $300K cost in Winter Springs?
Which Winter Springs community has the most homes under $300K for sale?
What is the monthly payment on a home under $300,000?
Keep exploring Winter Springs
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Homes Under $300K in nearby Seminole County cities
- Altamonte Springs homes under $300K (256 for sale)
- Sanford homes under $300K (143 for sale)
- Lake Mary homes under $300K (89 for sale)
- Casselberry homes under $300K (70 for sale)
- Longwood homes under $300K (56 for sale)
- Oviedo homes under $300K (24 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 under $300,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.