4 Bedroom Homes for Sale in Chipley, FL

Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Chipley listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.

37 homes with four or more bedrooms are for sale or pending in Chipley, FL today across 10 communities. The median asking price is $278,848, from $189,000 to $650,000. Listings in Chipley without that feature have a median of $227,490. Most listings right now: Sunny Hills (22), Sunny Hills Unit 6 (3), Chipley (2). Updated October 2, 2026 from the MLS.

Live 4-bedroom homes in Chipley: the listings

30 active listings match today (35% of Chipley inventory), median asking $278,958, median 43 days on market. Photo cards link to the listing; refreshed nightly.

Newest 4-bedroom homes in Chipley

$371,400 New
5 bd · 3 ba · built 2026
4059 Falcon Drive, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$369,900 New
4 bd · 3 ba · built 1995
4152 Leisure Lakes Drive, Chipley, Fl 32428, 32428
Leisure Lakes
Listing courtesy of Beachy Beach Real Estate
$361,400 New
5 bd · 3 ba · built 2026
2014 Ambassador Court, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$299,900 New
4 bd · 2 ba · built 2026
3278 Elkcam Boulevard, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Beycome of Florida LLC
$289,900 New
5 bd · 3 ba · built 2026
3984 Horizon Avenue, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$283,956 New
4 bd · 2 ba · built 2023
2225 Chase Street, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Deltona Marketing at Sunny Hills Inc
$252,990 New
4 bd · 2 ba · built 2026
1579 Aldoro Circle, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$399,900 New
4 bd · 3 ba · built 1985
2924 Paradise Lakes Road, Chipley, Fl 32428, 32428
Paradise Lakes
Listing courtesy of CENTURY 21 Commander Realty
$299,995 New
4 bd · 2 ba · built 1985
1192 Florence Court, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Coldwell Banker Realty
$249,990 New
4 bd · 2 ba · built 2026
4104 Olive Place, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$254,900
4 bd · 2 ba · built 2026
4114 Irene Lane, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$257,990
4 bd · 2 ba · built 2026
3716 Country Club Boulevard, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$229,999
4 bd · 3 ba · built 1999
940 Jamie Drive, Chipley, Fl 32428, 32428
Ridgeway Country Estates
Listing courtesy of SOUTHERN WAY REALTY, INC.
$265,990
4 bd · 2 ba · built 2026
1710 Vicki Court, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$264,990
4 bd · 2 ba · built 2026
4301 Country Club Boulevard, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$262,990
4 bd · 2 ba · built 2026
1714 Dora Lane, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$259,990
4 bd · 2 ba · built 2026
2294 Geraldine Circle, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$254,900
4 bd · 2 ba · built 2026
3993 Oxford Avenue, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$249,990
4 bd · 2 ba · built 2026
1583 Fountain Court, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$289,900
5 bd · 3 ba · built 2026
4010 Linwood Drive, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$293,344
4 bd · 2 ba · built 2023
2205 Chase Street, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Deltona Marketing at Sunny Hills Inc
$278,848
4 bd · 2 ba · built 2023
2212 Chase Street, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Deltona Marketing at Sunny Hills Inc
$252,900
4 bd · 2 ba · built 2026
4069 Ramus Drive, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$249,990
4 bd · 2 ba · built 2026
4135 Aquarius Drive, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of WJH Brokerage FL LLC
$329,999
4 bd · 2 ba · built 2007
3995 Quail Avenue, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Corcoran Reverie
$279,068
4 bd · 2 ba · built 2023
3989 Horizon Avenue, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of Deltona Marketing at Sunny Hills Inc
$279,355
5 bd · 3 ba · built 2026
1994 Ambassador Court, Chipley, Fl 32428, 32428
Sunny Hills
Listing courtesy of DR Horton Realty of Emerald Coast, LLC
$189,000
4 bd · 2 ba · built 1948
768 Main Street, Chipley, Fl 32428, 32428
Chipley
Listing courtesy of AMERICAN REALTY of Bay Co, Inc
$349,900
4 bd · 2 ba · built 2000
3243 Quail Ridge Drive, Chipley, Fl 32428, 32428
Leisure Lakes
Listing courtesy of Hennessy Real Estate Group LLC
$650,000
5 bd · 3 ba · built 1936
896 Main Street, Chipley, Fl 32428, 32428
Chipley
Listing courtesy of SOUTHERN WAY REALTY, INC.

The most expensive 4-bedroom homes in Chipley

ListingAskingSq ftCommunity
896 Main Street, Chipley, Fl 32428$650,000—Chipley
2924 Paradise Lakes Road, Chipley, Fl 32428$399,900—Paradise Lakes
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
3995 Quail Avenue, Chipley, Fl 32428$329,999—Sunny Hills
1192 Florence Court, Chipley, Fl 32428$299,995—Sunny Hills
3278 Elkcam Boulevard, Chipley, Fl 32428$299,900—Sunny Hills
2205 Chase Street, Chipley, Fl 32428$293,344—Sunny Hills

4-Bedroom Homes by price

BandFor saleShare
Under $300K2377%
$300K–$500K620%
$500K–$750K13%

Chipley 4-bedroom homes by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

Community4-Bedroom HomesNew buildMedian listFrom
Sunny Hills2220$261,031$249,990
Sunny Hills Unit 633$361,400$361,400
Chipley20$419,500$189,000
Leisure Lakes20$412,400$369,900
Sunny Hills Unit 1922$286,096$278,848
Sunny Hills Unit 122$264,529$249,990
Sunset Pines10$444,900$444,900
Paradise Lakes10$399,900$399,900
Leisure Lakes 1st Add10$349,900$349,900
Ridgeway Country Estates10$229,999$229,999

What the fourth bedroom costs

The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.

Questions to ask about any four-bedroom listing

Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.

Common questions

How many homes with four or more bedrooms are for sale in Chipley?
As of October 2, 2026, 37 Chipley, FL listings whose MLS record reports four or more bedrooms are active or pending, across 10 communities. The count updates with every MLS refresh.
What do 4-bedroom homes cost in Chipley?
The median asking price today is $278,848, with listings from $189,000 to $650,000. Chipley listings without that feature have a median of $227,490.
Which Chipley community has the most 4-bedroom homes for sale?
Sunny Hills has the most right now (22), followed by Sunny Hills Unit 6 (3), Chipley (2), Leisure Lakes (2).
How much more does a 4-bedroom home cost?
It depends on the city and the age of the housing stock. The answer block on this page states today’s median asking price for four-plus-bedroom homes next to the median for other listings in the same city, and each listing page shows square footage so you can compare on a per-square-foot basis.

Keep exploring Chipley

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 four or more bedrooms. 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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