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 |
|---|---|---|---|
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%
|
3781 Pine Log RoadChipley, FLThis 4-bedroom, 2-bath log cabin-style home on a paved road is situated on 4.5 acres and f... |
2 beds | 2 baths | 2,416 sq.ft. |
$395,000 |
Airbnb cash on cash: 3.15%
|
1138 Pine Bluff DriveChipley, FLLocated in the sought-after Pine Bluff area, this beautifully maintained 4-bedroom, 3-bath... |
4 beds | 3 baths | 2,744 sq.ft. |
$549,900 |
Airbnb cash on cash: 5.82%
|
4053 Linwood DriveChipley, FLPrivately negotiated, arms-length sale of a non-listed property. Entered for comparative p... |
2 beds | 2 baths | 1,000 sq.ft. |
$325,000 |
Airbnb cash on cash: 5.08%
|
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%
|
3130 Magnolia DriveChipley, FLCustom, ICF CONSTRUCTION, WATERFRONT home with acreage located in Paradise Lakes, Washingt... |
2 beds | 2 baths | 1,848 sq.ft. |
$789,000 |
Airbnb cash on cash: 1.25%
|
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: 8.5%
|
2351 Dumajack RoadChipley, FLBuyer gets $7,000 toward closing costs or options! You won't find this quality at this pri... |
2 beds | 2 baths | 957 sq.ft. |
$189,900 |
Airbnb cash on cash: 8.84%
|
2474 Tiller Cemetery DriveChipley, FL35 acres, Heated pool, Ponds, abundant wildlife, and room to breathe. This isn't just a pr... |
4 beds | 3 baths | 1,941 sq.ft. |
$599,900 |
Airbnb cash on cash: 4.93%
|
3955 Hwy. 77Chipley, FLOW -- what an incredible property! Nearly 20 acres featuring a spacious home designed for ... |
4 beds | 3 baths | 3,564 sq.ft. |
$675,000 |
Airbnb cash on cash: 4.67%
|
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. |
$475,000 |
Airbnb cash on cash: 5.78%
|
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%
|
2121 Angora DriveChipley, FLWelcome to 2121 Angora Dr! This home sits on almost a half an acre with an inground pool. ... |
3 beds | 2 baths | 1,642 sq.ft. |
$299,000 |
Airbnb cash on cash: 9.86%
|
1186 Pine Forest RoadChipley, FLTucked away on a generous 17.5-acre parcel, this charming 2,899 SF, 4-bedroom, 2.5-bath ho... |
4 beds | 3 baths | 2,899 sq.ft. |
$575,000 |
Airbnb cash on cash: 5.22%
|
434 Tinker LaneChipley, FLTucked away on 3.66 peaceful acres with very few neighbors, this newer, upgraded home offe... |
2 beds | 2 baths | 1,500 sq.ft. |
$385,000 |
Airbnb cash on cash: 3.78%
|
3385 Orange Hill RoadChipley, FLNestled on 4.83 picturesque acres, this charming 3-bedroom, 2.5-bath home at 3385 Orange H... |
3 beds | 3 baths | 1,538 sq.ft. |
$324,900 |
Airbnb cash on cash: 9.23%
|
Real Estate investment in Chipley, FL
There are 22 properties for sale in the city of Chipley . The median list price in Chipley is $242,450 and the average price per square foot is $123. In May 2026, the average monthly cash on cash return in Chipley is 7.00%. The average monthly rental income in Chipley is $2,105.