Homes for Sale Under $300K in Longwood, FL
This page tracks every Longwood 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.
57 homes listed under $300,000 are for sale or pending in Longwood, FL today across 28 communities. The median asking price is $215,000, from $1,325 to $299,900. Listings in Longwood without that feature have a median of $550,000. Most listings right now: Clubside At Sabal Point A Condo (12), Residences At Sabal Point A Condo (5), Windsor At Sabal Walk A Condo (5). Updated September 11, 2026 from the MLS.
Longwood 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 |
|---|---|---|---|---|
| 12 | 0 | $217,450 | $190,000 | |
| 5 | 0 | $211,900 | $164,990 | |
| 5 | 0 | $159,000 | $139,900 | |
| Springwood Village | 4 | 0 | $124,500 | $99,000 |
| San Marco Villas A Condo | 3 | 0 | $265,000 | $225,000 |
| Lake Wayman Heights | 2 | 0 | $290,000 | $285,000 |
| Wekiva Villas On The Green 2 | 2 | 0 | $264,500 | $250,000 |
| 2 | 0 | $249,450 | $199,000 | |
| Fairway Villas | 2 | 0 | $156,250 | $155,000 |
| Crown Oaks | 2 | 0 | $109,999 | $89,999 |
| Longwood North | 1 | 0 | $299,900 | $299,900 |
| Lake Wayman Heights Lake Add | 1 | 0 | $299,000 | $299,000 |
| Hanover Pointe Rep - Rep | 1 | 0 | $299,000 | $299,000 |
| East Lake Village | 1 | 0 | $299,000 | $299,000 |
| 1 | 0 | $275,000 | $275,000 | |
| Crown Point By The Spgs | 1 | 0 | $274,900 | $274,900 |
| 1 | 0 | $273,000 | $273,000 | |
| Palm Spgs Condo At The Spgs | 1 | 0 | $260,000 | $260,000 |
| Wildmere | 1 | 0 | $240,000 | $240,000 |
| Crown Oaks 1St Add | 1 | 0 | $229,900 | $229,900 |
| Residences At Sabal Point A Condominium | 1 | 0 | $229,000 | $229,000 |
| 1 | 0 | $220,900 | $220,900 | |
| 1 | 0 | $199,900 | $199,900 | |
| Rands Add To Longwood | 1 | 0 | $95,400 | $95,400 |
| Ciara Creek Executive Centre | 1 | 0 | $38,400 | $38,400 |
| Beason Sub | 1 | 0 | $30,000 | $30,000 |
| Monterey North | 1 | 0 | $2,500 | $2,500 |
| Oak Arbor | 1 | 0 | $1,325 | $1,325 |
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 Longwood?
What do homes under $300K cost in Longwood?
Which Longwood community has the most homes under $300K for sale?
What is the monthly payment on a home under $300,000?
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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 Longwood, 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.