Homes for Sale $300K to $500K in Chipley, FL
This page tracks every Chipley 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.
21 homes listed between $300,000 and $500,000 are for sale or pending in Chipley, FL today across 10 communities. The median asking price is $361,400, from $300,000 to $454,900. Listings in Chipley without that feature have a median of $245,900. Most listings right now: Paradise Lakes (4), Sunny Hills Unit 6 (3), Leisure Lakes 1st Add (3). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Chipley: the listings
16 active listings match today (19% of Chipley inventory), median asking $355,650, median 69 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Chipley
The most expensive $300k–$500k homes in Chipley
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 3421 Quail Ridge Drive, Chipley, Fl 32428 | $449,900 | — | Leisure Lakes |
| 3034 Paradise Lakes Road, Chipley, Fl 32428 | $400,000 | — | Paradise Lakes |
| 2924 Paradise Lakes Road, Chipley, Fl 32428 | $399,900 | — | Paradise Lakes |
| 2942 Paradise Lakes Road, Chipley, Fl 32428 | $385,000 | — | Paradise Lakes |
| 434 Tinker Lane, Chipley, Fl 32428 | $375,000 | — | Buckhorn Creek |
| 4059 Falcon Drive, Chipley, Fl 32428 | $371,400 | — | Sunny Hills |
| 4152 Leisure Lakes Drive, Chipley, Fl 32428 | $369,900 | — | Leisure Lakes |
| 2014 Ambassador Court, Chipley, Fl 32428 | $361,400 | — | Sunny Hills |
| 3243 Quail Ridge Drive, Chipley, Fl 32428 | $349,900 | — | Leisure Lakes |
| 3445 Cardinal Place, Chipley, Fl 32428 | $349,900 | — | Leisure Lakes |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 16 | 100% |
Chipley 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 |
|---|---|---|---|---|
| Paradise Lakes | 4 | 0 | $392,450 | $330,000 |
| Sunny Hills Unit 6 | 3 | 3 | $361,400 | $361,400 |
| Leisure Lakes 1st Add | 3 | 0 | $349,900 | $349,900 |
| Sunny Hills | 3 | 0 | $329,999 | $325,000 |
| Leisure Lakes | 2 | 0 | $412,400 | $369,900 |
| Sunset Pines | 2 | 0 | $372,450 | $300,000 |
| Buckhorn Creek | 1 | 0 | $375,000 | $375,000 |
| River Lake | 1 | 0 | $330,000 | $330,000 |
| Dekle | 1 | 0 | $324,900 | $324,900 |
| Sunny Hills Unit 1 | 1 | 1 | $309,459 | $309,459 |
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 Chipley?
What do homes $300K–$500K cost in Chipley?
Which Chipley community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Chipley
- All homes for sale in Chipley
- Chipley 4-bedroom homes
- Chipley homes under $300K
- Homes $300K–$500K in every city
Live data: Central Panhandle AOR, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Chipley, 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.