Real Estate Investment Properties for Sale in Chipley, FL
Looking for investment property in Chipley, FL with high ROI ?
Explore a variety of short-term homes & houses in Chipley, FL. Invest wisely with VRBO & Chipley, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Chipley, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
3781 Pine LogChipley, FLLog cabin-style home situated on 4.5 private acres with frontage on Pine Log Lake, fed by ... |
4 beds | 2 baths | 2,416 sq.ft. |
$420,000 |
Airbnb cash on cash: 7.68%
|
561 Lakepointe DriveChipley, FLEscape to Your Private Lakepointe Sanctuary Nestled on a full acre in the coveted Lakepoin... |
3 beds | 2 baths | 1,642 sq.ft. |
$369,900 |
Airbnb cash on cash: 7.54%
|
2618 Hard Labor RoadChipley, FLDiscover this expansive land opportunity at 2618 Hard Labor Rd in Chipley, FL. Spanning ov... |
2 beds | 1 baths | 1,692 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.25%
|
4367 Carey BoulevardChipley, FLCURRENTLY UNDER CONTRACT, SELLER WILL CONSIDER BACKUP OFFERS - Brand New Home in Sunny Hil... |
3 beds | 3 baths | 1,680 sq.ft. |
$299,999 |
Airbnb cash on cash: 9.44%
|
2789 Summer DriveChipley, FLUNDER CONTRACT. SELLER ACCEPTING BACKUP OFFERS. Luxury Lakefront Retreat on 3.6 Acres | 27... |
3 beds | 3 baths | 2,324 sq.ft. |
$700,000 |
Airbnb cash on cash: 3.43%
|
657 Main StreetChipley, FLWelcome to a beautifully fully renovated home in the heart of Chipley that blends vintage ... |
3 beds | 2 baths | 1,804 sq.ft. |
$299,999 |
Airbnb cash on cash: 9.73%
|
3034 Paradise Lakes RoadChipley, FLGet your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront ... |
3 beds | 2 baths | 1,392 sq.ft. |
$450,000 |
Airbnb cash on cash: 6.03%
|
1371 Deadening RoadChipley, FLWaterfront Retreat at Econfina Springs Wildlife Management - Nature Lover's / Sportsman's ... |
3 beds | 2 baths | 1,484 sq.ft. |
$315,000 |
Airbnb cash on cash: 9.63%
|
490 Quail Hollow BoulevardChipley, FLOasis in the 'Hills! This property has everything you could ever need and is priced below ... |
4 beds | 2 baths | 2,304 sq.ft. |
$440,000 |
Airbnb cash on cash: 8.08%
|
1730 Firetower RoadChipley, FLGetaway in the country! This 3br/2ba block home has so much to offer: Metal roof, HVAC 202... |
3 beds | 2 baths | 2,030 sq.ft. |
$335,000 |
Airbnb cash on cash: 8.75%
|
2649 Bonnett Pond RoadChipley, FLLooking for a hunting or fishing lodge? Investment rental property? You have found it!! No... |
3 beds | 2 baths | 1,522 sq.ft. |
$330,000 |
Airbnb cash on cash: 8.89%
|
2437 Gilberts Mill RoadChipley, FLLooking for peaceful country living with room to roam? This inviting property offers the p... |
2 beds | 2 baths | 1,080 sq.ft. |
$209,900 |
Airbnb cash on cash: 8.49%
|
XXX Open Creek Rd #South LotChipley, FLXXX Open Creek Rd #South Lot, Chipley, FL 32428 | Other |
N/A beds | N/A baths | N/A |
$124,999 |
Airbnb cash on cash: 9.81%
|
652 N 2nd StreetChipley, FLExperience the perfect blend of small-town charm and expansive outdoor space with this stu... |
3 beds | 2 baths | 2,284 sq.ft. |
$299,900 |
Airbnb cash on cash: 9.18%
|
3955 Hwy. 77Chipley, FLWOW, what an amazing property! Nearly 20 acres, a big beautiful home with a super spacious... |
4 beds | 3 baths | 3,564 sq.ft. |
$675,000 |
Airbnb cash on cash: 4.67%
|
3399 Quail Ridge DriveChipley, FLWelcome to your slice of country paradise! Situated on 3.57 acres inside a gated community... |
4 beds | 3 baths | 2,294 sq.ft. |
$475,000 |
Airbnb cash on cash: 6.94%
|
3516 Enterprise CircleChipley, FLStep into this like-new, spacious home offering a comfortable split-bedroom layout and an ... |
3 beds | 2 baths | 1,680 sq.ft. |
$299,800 |
Airbnb cash on cash: 9.99%
|
901 PRISSY LANE #17Chipley, FLOne or more photo(s) has been virtually staged. Really nice park with 17 park owned units ... |
N/A beds | N/A baths | 19,200 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -0.2%
|
3980 Quail CourtChipley, FLCompletely renovated home with In-law/Guest house! This beautifully styled home has been c... |
3 beds | 3 baths | 1,810 sq.ft. |
$495,000 |
Airbnb cash on cash: 5.51%
|
2199 Sunny Hills BoulevardChipley, FLWelcome to this spacious, well-maintained home in the peaceful community of Sunny Hills. F... |
3 beds | 2 baths | 1,939 sq.ft. |
$299,000 |
Airbnb cash on cash: 9.81%
|
Real Estate investment in Chipley, FL
There are 20 properties for sale in the city of Chipley . The median list price in Chipley is $239,900 and the average price per square foot is $126. In April 2026, the average monthly cash on cash return in Chipley is 7.00%. The average monthly rental income in Chipley is $2,069.