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.
90 homes listed under $300,000 are for sale or pending in Winter Park, FL today across 47 communities. The median asking price is $183,650, from $1,620 to $299,999. Listings in Winter Park without that feature have a median of $925,000. Most listings right now: Lakeside Manor Apts Condo (5), Colonies (5), Golfside Villas Condo (5). Updated October 2, 2026 from the MLS.
First-time buyers: what Winter Park costs at the entry level
69 active single-family homes, townhomes and condos at or below $300,000 — median $182,900, about $1,150/mo principal & interest at 6.95% 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 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 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 |
|---|---|---|---|---|
| Lakeside Manor Apts Condo | 5 | 0 | $184,400 | $130,000 |
| Colonies | 5 | 0 | $150,000 | $89,900 |
| Golfside Villas Condo | 5 | 0 | $138,000 | $105,000 |
| Lazy Oaks Condo | 4 | 0 | $275,000 | $269,000 |
| Stratford A Winter Park Condo | 4 | 0 | $186,400 | $147,000 |
| Waterfall Cove | 4 | 0 | $137,500 | $89,000 |
| Lake Killarney Condo | 3 | 0 | $285,000 | $269,000 |
| Cedarwood Village | 3 | 0 | $254,000 | $234,900 |
| Chateaux Du Lac | 3 | 0 | $235,000 | $164,500 |
| Whisperwood Condo | 3 | 0 | $199,000 | $184,900 |
| Hidden Oaks Condo Ph 09 | 3 | 0 | $179,900 | $171,900 |
| Parkview Village | 3 | 0 | $143,500 | $135,000 |
| Windward Square Sec 3 | 2 | 0 | $297,495 | $295,000 |
| Phillips Circle Rep | 2 | 0 | $277,000 | $275,000 |
| Windward Square Sec 2 | 2 | 0 | $270,000 | $255,000 |
| Coronation Add | 2 | 0 | $269,425 | $268,950 |
| Mead Garden | 2 | 0 | $255,000 | $245,000 |
| Winter Park Villas Condo | 2 | 0 | $210,950 | $194,900 |
| Hidden Oaks Condo Ph 10 | 2 | 0 | $199,500 | $170,000 |
| Lancelot/Winter Park | 2 | 0 | $162,450 | $159,900 |
| Winter Park Woods Condo | 2 | 0 | $104,700 | $100,000 |
| Lawndale Annex | 2 | 1 | $63,000 | $42,000 |
| Eastbrook Sub | 1 | 0 | $299,900 | $299,900 |
| Temple Terrace Annex | 1 | 0 | $299,900 | $299,900 |
| Ridge High Sub | 1 | 0 | $299,000 | $299,000 |
| Sandlewood Creek Condo | 1 | 0 | $290,000 | $290,000 |
| Sandlewood Creek Phase 2 | 1 | 0 | $285,000 | $285,000 |
| Windward Square Sec 1 | 1 | 0 | $270,000 | $270,000 |
| Mead Garden Condominium | 1 | 0 | $245,000 | $245,000 |
| Hidden Oaks Condo Ph 01 | 1 | 0 | $214,900 | $214,900 |
| Waterfall Cove At Winter Park | 1 | 0 | $205,000 | $205,000 |
| Hidden Oaks Condo Ph 03 | 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 |
| Waterfall Cove At Winter Park Condominium D107 | 1 | 0 | $180,000 | $180,000 |
| Hidden Oaks Condo Ph 12 | 1 | 0 | $175,000 | $175,000 |
| Wrenwood Condo | 1 | 0 | $175,000 | $175,000 |
| Hidden Oaks Condo Ph 7 | 1 | 0 | $172,000 | $172,000 |
| Hidden Oaks Condo Ph 02 | 1 | 0 | $170,000 | $170,000 |
| Four Seasons Condo | 1 | 0 | $159,000 | $159,000 |
| Parkview Village Condo | 1 | 0 | $150,000 | $150,000 |
| Whisperwood | 1 | 0 | $134,900 | $134,900 |
| Waterfall Cove/Winter Park | 1 | 0 | $102,500 | $102,500 |
| Winter Park Comm | 1 | 0 | $93,080 | $93,080 |
| North Goldenrod Commerce Park | 1 | 0 | $42,000 | $42,000 |
| Henkels Add/Winter Park | 1 | 0 | $3,060 | $3,060 |
| Lakemont Estates | 1 | 0 | $1,620 | $1,620 |
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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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 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.