Homes for Sale Under $300K in Winter Park, FL
This page tracks every Winter Park 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.
84 homes listed under $300,000 are for sale or pending in Winter Park, FL today across 47 communities. The median asking price is $212,450, from $89,900 to $299,999. Listings in Winter Park without that feature have a median of $785,000. Most listings right now: Cedarwood Village 1 (5), Stratford A Winter Park Condo (5), Golfside Villas Condo (5). Updated November 11, 2026 from the MLS.
First-time buyers: what Winter Park costs at the entry level
72 active single-family homes, townhomes and condos at or below $300,000 — median $207,500, about $1,335/mo principal & interest at 7.18% with 5% down. Live from the MLS, refreshed nightly.
Newest homes under $300K in Winter Park
What the payment looks like
| Purchase price | P&I at 7.18%, 5% down | P&I, 20% down | Cash to close at 5% down (est.) |
|---|---|---|---|
| $150,000 | $965 | $813 | $12,000 |
| $200,000 | $1,287 | $1,084 | $16,000 |
| $250,000 | $1,609 | $1,355 | $20,000 |
| $300,000 | $1,931 | $1,626 | $24,000 |
Estimates only; taxes, insurance, HOA and mortgage insurance are on top. Closing costs assumed at 3%.
Down-payment assistance in Orange County · First-time buyer guide
Winter Park 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 |
|---|---|---|---|---|
| Cedarwood Village 1 | 5 | 0 | $268,000 | $249,000 |
| Stratford A Winter Park Condo | 5 | 0 | $182,900 | $140,000 |
| Golfside Villas Condo | 5 | 0 | $138,000 | $97,000 |
| Wrenwood Condo | 4 | 0 | $204,400 | $185,000 |
| Colonies | 4 | 0 | $145,000 | $89,900 |
| Lake Killarney Condo | 3 | 0 | $285,000 | $269,000 |
| Lazy Oaks Condo | 3 | 0 | $268,000 | $255,000 |
| Cedarwood Village | 3 | 0 | $247,000 | $234,900 |
| Chateaux Du Lac | 3 | 0 | $235,000 | $159,900 |
| Lakeside Manor Apts Condo | 3 | 0 | $184,400 | $159,900 |
| Four Seasons Condo | 3 | 0 | $170,000 | $159,000 |
| Phillips Circle Rep | 2 | 0 | $289,000 | $279,000 |
| Windward Square Sec 3 | 2 | 0 | $277,499 | $275,000 |
| Mead Garden | 2 | 0 | $255,000 | $245,000 |
| Whisperwood Condo | 2 | 0 | $240,000 | $210,000 |
| Hidden Oaks Condo Ph 10 | 2 | 0 | $199,500 | $170,000 |
| Parkview Village | 2 | 0 | $137,499 | $135,000 |
| Winter Park Woods Condo | 2 | 0 | $104,500 | $100,000 |
| Suburban Homes | 1 | 0 | $299,900 | $299,900 |
| Temple Terrace Annex | 1 | 0 | $299,900 | $299,900 |
| Fernbrook Trails | 1 | 0 | $299,000 | $299,000 |
| Winter Park Pointe 01 | 1 | 0 | $299,000 | $299,000 |
| Winter Park Gardens Condo | 1 | 0 | $295,000 | $295,000 |
| Sandlewood Creek Condo | 1 | 0 | $290,000 | $290,000 |
| Windward Square Sec 2 | 1 | 0 | $285,000 | $285,000 |
| Sandlewood Creek Phase 2 | 1 | 0 | $279,000 | $279,000 |
| Winterpark | 1 | 0 | $259,900 | $259,900 |
| Oakcrest-516 | 1 | 0 | $255,000 | $255,000 |
| Mead Garden Condominium | 1 | 0 | $242,500 | $242,500 |
| Stratford A Winter Park Condominium | 1 | 0 | $230,000 | $230,000 |
| Slovak Village | 1 | 0 | $230,000 | $230,000 |
| Eastbrook Sub | 1 | 0 | $225,000 | $225,000 |
| Hidden Oaks Condo Ph 01 | 1 | 0 | $214,900 | $214,900 |
| Waterfall Cove At Winter Park | 1 | 0 | $205,000 | $205,000 |
| Lake Killarney Condominium Assn Inc. | 1 | 0 | $199,900 | $199,900 |
| Winter Park Villas Condo | 1 | 0 | $199,900 | $199,900 |
| Winter Park Villas Condo | 1 | 0 | $194,900 | $194,900 |
| Parkview Village Condo Blvd 2918 | 1 | 0 | $189,000 | $189,000 |
| Waterfall Cove At Winter Park Condominium D107 | 1 | 0 | $180,000 | $180,000 |
| Hidden Oaks Condo Ph 09 | 1 | 0 | $179,990 | $179,990 |
| Hidden Oaks Condo Ph 12 | 1 | 0 | $175,000 | $175,000 |
| Hidden Oaks Condo Ph 02 | 1 | 0 | $170,000 | $170,000 |
| Hidden Oaks Condo Ph 06 | 1 | 0 | $169,000 | $169,000 |
| Lancelot/Winter Park | 1 | 0 | $165,000 | $165,000 |
| Waterfall Cove | 1 | 0 | $140,000 | $140,000 |
| Parkview Village Condominium | 1 | 0 | $129,000 | $129,000 |
| Waterfall Cove/Winter Park | 1 | 0 | $99,900 | $99,900 |
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 Park?
What do homes under $300K cost in Winter Park?
Which Winter Park community has the most homes under $300K for sale?
What is the monthly payment on a home under $300,000?
Keep exploring Winter Park
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Homes Under $300K in nearby Orange County cities
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Live data: Florida Gulf Coast MLS, Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Winter Park, 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.