By Jon Brooks, Co-Founder, Momentum Realty · Updated October 2, 2026
This page tracks every Chipley 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.
87 homes listed under $300,000 are for sale or pending in Chipley, FL today across 13 communities. The median asking price is $244,900, from $79,900 to $299,995. Listings in Chipley without that feature have a median of $361,400. Most listings right now: Sunny Hills (58), Sunny Hills Unit 1 (7), Sunny Hills Unit 19 (6). Updated October 2, 2026 from the MLS.
First-time buyers: what Chipley costs at the entry level
61 active single-family homes, townhomes and condos at or below $300,000 — median $254,900, about $1,603/mo principal & interest at 6.95% with 5% down. Live from the MLS, refreshed nightly.
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 Chipley?
As of October 2, 2026, 87 Chipley, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 13 communities. The count updates with every MLS refresh.
What do homes under $300K cost in Chipley?
The median asking price today is $244,900, with listings from $79,900 to $299,995. Chipley listings without that feature have a median of $361,400.
Which Chipley community has the most homes under $300K for sale?
Sunny Hills has the most right now (58), followed by Sunny Hills Unit 1 (7), Sunny Hills Unit 19 (6), Chipley (5).
What is the monthly payment on a home under $300,000?
At today’s rates with 20% down, principal and interest on a $300,000 purchase runs in the $1,500–$1,700 a month range before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator linked above turns them into one monthly number.
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 under $300,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.
Listing information provided by the Central Panhandle Association of REALTORS®. Information is deemed reliable but not guaranteed by the MLS to be accurate.
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