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.
86 homes listed between $300,000 and $500,000 are for sale or pending in Longwood, FL today across 60 communities. The median asking price is $402,500, from $304,999 to $499,000. Listings in Longwood without that feature have a median of $599,900. Most listings right now: Windtree West Unit 2 (5), Casaluna Townhomes (3), Wekiva Hunt Club 3 Fox Hunt Sec 3 (3). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Longwood: the listings
62 active listings match today (33% of Longwood inventory), median asking $409,450, $239/sq ft, median 37 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Longwood
The most expensive $300k–$500k homes in Longwood
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 322 N Shadowbay Boulevard | $499,000 | 1,599 | Shadowbay, Lake Vista |
| 2538 Long Iron Court | $495,000 | 1,948 | Sabal Point At Sabal Green |
| 211 Hickory Drive | $485,000 | 2,033 | Sweetwater Oaks |
| 1310 Stanley Street | $485,000 | 1,658 | Sanlando Springs Longwood |
| 228 S Fox Chase Point | $475,000 | 1,928 | — |
| 580 Devonshire Boulevard | $470,000 | 1,680 | — |
| 1040 Waverly Drive | $469,900 | 2,140 | Windtree West |
| 211 Stevenage Drive | $464,900 | 1,974 | — |
| 207 Harrogate Place | $460,000 | 1,905 | — |
| 572 Lake Wildmere Cove | $455,000 | 2,294 | — |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 62 | 100% |
Longwood homes $300K–$500K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Homes $300K–$500K | New build | Median list | From |
|---|---|---|---|---|
| Windtree West Unit 2 | 5 | 0 | $395,000 | $369,900 |
| Casaluna Townhomes | 3 | 3 | $444,990 | $444,990 |
| Wekiva Hunt Club 3 Fox Hunt Sec 3 | 3 | 0 | $439,000 | $415,000 |
| Wekiva Hunt Club 1 Fox Hunt Sec 1 | 3 | 0 | $429,000 | $375,000 |
| Wekiva Hunt Club 2 Fox Hunt Sec 2 | 3 | 0 | $419,500 | $409,000 |
| Springs Glenwood Village Sec 1 Rev The | 3 | 0 | $379,999 | $360,000 |
| Highcroft Pointe Twnhms | 3 | 0 | $337,500 | $334,900 |
| Sabal Point At Sabal Green | 2 | 0 | $462,000 | $429,000 |
| Columbus Harbor | 2 | 0 | $454,900 | $449,900 |
| Sanlando Spgs | 2 | 0 | $450,000 | $415,000 |
| Wekiva Hills Sec 01 | 2 | 0 | $442,500 | $425,000 |
| Longwood North | 2 | 0 | $364,500 | $330,000 |
| Wekiva Country Club Villas | 2 | 0 | $349,950 | $335,000 |
| Hanover Pointe Rep - Rep | 2 | 0 | $306,849 | $304,999 |
| Sweetwater Oaks Sec 11 | 1 | 0 | $499,000 | $499,000 |
| Shadowbay, Lake Vista At | 1 | 0 | $499,000 | $499,000 |
| Sleepy Hollow 1St Add | 1 | 0 | $499,000 | $499,000 |
| Sweetwater Oaks Sec 06 | 1 | 0 | $485,000 | $485,000 |
| Hunters Glen | 1 | 0 | $475,000 | $475,000 |
| Devonshire | 1 | 0 | $470,000 | $470,000 |
| Wekiva Hills Sec 09 | 1 | 0 | $464,900 | $464,900 |
| Tiberon Hills Ph 3 | 1 | 0 | $459,000 | $459,000 |
| Reserve At Lake Wildmere - Ph 1 | 1 | 0 | $455,000 | $455,000 |
| Meadows Unit 1 | 1 | 0 | $450,000 | $450,000 |
| Palm Spgs Sub | 1 | 0 | $450,000 | $450,000 |
| Woodlands Sec 3 | 1 | 0 | $449,900 | $449,900 |
| The Springs Glenwood Village Sec 2 | 1 | 0 | $439,900 | $439,900 |
| Golden Grove | 1 | 0 | $439,000 | $439,000 |
| Lake Wayman Heights | 1 | 0 | $435,000 | $435,000 |
| Wekiva Club Estates Sec 04 | 1 | 0 | $429,900 | $429,900 |
| Nelson Court | 1 | 0 | $416,900 | $416,900 |
| Tiberon Cove | 1 | 0 | $410,000 | $410,000 |
| West Brantley Lake Road Heights | 1 | 0 | $409,900 | $409,900 |
| Winsor Manor 1St Add | 1 | 0 | $405,000 | $405,000 |
| The Spgs Glenwood Village Sec 2 | 1 | 0 | $400,000 | $400,000 |
| Springs The Live Oak Village | 1 | 0 | $400,000 | $400,000 |
| Hunters Point | 1 | 0 | $400,000 | $400,000 |
| Longwood Pine | 1 | 0 | $399,900 | $399,900 |
| Windtree West | 1 | 0 | $395,000 | $395,000 |
| Springs The Shadowood Village Sec 2 | 1 | 0 | $395,000 | $395,000 |
| Hidden Oak Estates | 1 | 0 | $389,500 | $389,500 |
| Harbour Isle Sub | 1 | 0 | $389,000 | $389,000 |
| Lake Searcy Shores | 1 | 0 | $383,000 | $383,000 |
| Meredith Manor Golf View Estates Sec | 1 | 0 | $378,900 | $378,900 |
| Lake Wayman Heights Lake Add | 1 | 0 | $376,000 | $376,000 |
| Meusers Sub | 1 | 0 | $375,000 | $375,000 |
| Longdale | 1 | 0 | $369,000 | $369,000 |
| Monterey South | 1 | 0 | $366,000 | $366,000 |
| Governors Point Ph 1 | 1 | 0 | $356,000 | $356,000 |
| Monterey North | 1 | 0 | $349,900 | $349,900 |
| Sky Lark Unit 2 Rep | 1 | 0 | $349,900 | $349,900 |
| Monterey North | 1 | 0 | $349,900 | $349,900 |
| Meadows West The | 1 | 0 | $349,700 | $349,700 |
| Shadowbay | 1 | 0 | $345,000 | $345,000 |
| Governors Point Ph 3 Sec 1 | 1 | 0 | $344,900 | $344,900 |
| Grandview At Lake Wildmere | 1 | 0 | $340,000 | $340,000 |
| Wildmere Amd | 1 | 0 | $330,000 | $330,000 |
| Wildmere | 1 | 0 | $322,000 | $322,000 |
| Pine View | 1 | 0 | $312,500 | $312,500 |
| Longwood | 1 | 0 | $309,000 | $309,000 |
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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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.