Homes for Sale $300K to $500K in Longwood, FL
This page tracks every Longwood 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.
82 homes listed between $300,000 and $500,000 are for sale or pending in Longwood, FL today across 63 communities. The median asking price is $410,000, from $309,000 to $499,900. Listings in Longwood without that feature have a median of $597,450. Most listings right now: Wekiva Hunt Club 1 Fox Hunt Sec 1 (3), Casaluna Townhomes (3), Wekiva Hunt Club 2 Fox Hunt Sec 2 (3). Updated September 11, 2026 from the MLS.
Longwood homes $300K–$500K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most homes $300K–$500K listed are tabled; the rest follow.
| Community | Homes $300K–$500K | New build | Median list | From |
|---|---|---|---|---|
| 3 | 0 | $449,900 | $375,000 | |
| Casaluna Townhomes | 3 | 3 | $444,990 | $444,990 |
| 3 | 0 | $425,000 | $409,000 | |
| 3 | 0 | $415,000 | $350,000 | |
| Springs Glenwood Village Sec 1 Rev The | 3 | 0 | $389,999 | $360,000 |
| Sabal Point At Sabal Green | 2 | 0 | $462,000 | $429,000 |
| Windtree West Unit 2 | 2 | 0 | $459,450 | $449,000 |
| Hidden Oak Estates | 2 | 0 | $434,000 | $419,000 |
| Windtree West | 2 | 0 | $382,500 | $370,000 |
| Longwood North | 2 | 0 | $372,500 | $330,000 |
| Highcroft Pointe Twnhms | 2 | 0 | $359,450 | $339,900 |
| Shadowbay, Lake Vista At | 1 | 0 | $499,900 | $499,900 |
| Sleepy Hollow 1St Add | 1 | 0 | $499,000 | $499,000 |
| Forest Oaks Village | 1 | 0 | $498,000 | $498,000 |
| Sabal Point Amd | 1 | 0 | $494,900 | $494,900 |
| 1 | 0 | $475,000 | $475,000 | |
| 1 | 0 | $475,000 | $475,000 | |
| Palm Spgs Sub | 1 | 0 | $475,000 | $475,000 |
| Northridge | 1 | 0 | $474,900 | $474,900 |
| 1 | 0 | $469,900 | $469,900 | |
| Grove Estates | 1 | 0 | $460,000 | $460,000 |
| Columbus Harbor | 1 | 0 | $459,900 | $459,900 |
| 1 | 0 | $459,000 | $459,000 | |
| 1 | 0 | $455,000 | $455,000 | |
| 1 | 0 | $455,000 | $455,000 | |
| 1 | 0 | $450,000 | $450,000 | |
| 1 | 0 | $450,000 | $450,000 | |
| 1 | 0 | $439,900 | $439,900 | |
| Lake Wayman Heights | 1 | 0 | $435,000 | $435,000 |
| 1 | 0 | $430,000 | $430,000 | |
| Hunters Point | 1 | 0 | $425,000 | $425,000 |
| Nelson Court | 1 | 0 | $419,900 | $419,900 |
| Sanlando Spgs | 1 | 0 | $415,000 | $415,000 |
| 1 | 0 | $410,000 | $410,000 | |
| Tiberon Cove | 1 | 0 | $410,000 | $410,000 |
| Longwood Pine | 1 | 0 | $409,900 | $409,900 |
| 1 | 0 | $409,900 | $409,900 | |
| Winsor Manor 1St Add | 1 | 0 | $405,000 | $405,000 |
| 1 | 0 | $400,000 | $400,000 | |
| Harbour Isle Sub | 1 | 0 | $400,000 | $400,000 |
| Springs The Live Oak Village | 1 | 0 | $400,000 | $400,000 |
| 1 | 0 | $399,900 | $399,900 | |
| 1 | 0 | $395,000 | $395,000 | |
| Springs The Shadowood Village Sec 2 | 1 | 0 | $395,000 | $395,000 |
| Lake Wayman Heights Lake Add | 1 | 0 | $388,000 | $388,000 |
| Longdale | 1 | 0 | $385,000 | $385,000 |
| Lake Searcy Shores | 1 | 0 | $383,000 | $383,000 |
| 1 | 0 | $378,900 | $378,900 | |
| Lake Brantley Isles 2Nd Add | 1 | 0 | $369,900 | $369,900 |
| 1 | 0 | $366,000 | $366,000 | |
| Sky Lark Sub | 1 | 0 | $360,000 | $360,000 |
| Grandview At Lake Wildmere | 1 | 0 | $350,000 | $350,000 |
| 1 | 0 | $349,900 | $349,900 | |
| 1 | 0 | $349,900 | $349,900 | |
| Meadows West The | 1 | 0 | $349,700 | $349,700 |
| Forest Slopes-505 | 1 | 0 | $340,000 | $340,000 |
| 1 | 0 | $339,000 | $339,000 | |
| Wekiva Country Club Villas | 1 | 0 | $335,000 | $335,000 |
| Wekiva Landings | 1 | 0 | $329,900 | $329,900 |
| Wildmere | 1 | 0 | $322,000 | $322,000 |
Also with homes $300K–$500K for sale
- Pine View (1)
- Hanover Pointe Rep - Rep (1)
- (1)
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 Longwood?
What do homes $300K–$500K cost in Longwood?
Which Longwood community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Longwood
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- Longwood homes under $300K
- Homes $300K–$500K in every city
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 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.