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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3090 Turkey Run Road Chipley, FL This stunning 2-story country home is located in the gated Leisure Lakes community which o...	3 beds \| 2 baths \| 1,519 sq.ft.	$349,999	Airbnb cash on cash: 2.4% Traditional cash on cash: 4.41% Airbnb Rental Income: $1801 Traditional Rental Income: $1973 Airbnb ROI: 2.4% Traditional ROI: 4.41%
3835 Highway 77 Chipley, FL Welcome to this custom-built brick home, occupied by the original owner and builder, nestl...	5 beds \| 2 baths \| 2,410 sq.ft.	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 3.49%
4075 Parkview Drive Chipley, FL Discover the epitome of Florida living in this beautiful brick home located in Sunny Hills...	3 beds \| 2 baths \| 1,830 sq.ft.	$234,900	Airbnb cash on cash: 4.45% Traditional cash on cash: 8.4% Airbnb Rental Income: $1801 Traditional Rental Income: $2189 Airbnb ROI: 4.45% Traditional ROI: 8.4%
2641 Highway 77 Chipley, FL Discover the rare opportunity to own an authentic log cabin on nearly 6 acres of beautiful...	2 beds \| 2 baths \| 1,900 sq.ft.	$365,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 4.65% Airbnb Rental Income: $2660 Traditional Rental Income: $2247 Airbnb ROI: 4.01% Traditional ROI: 4.65%
1364 Watts Avenue Chipley, FL New Home Construction very close to completion with 6 acres in town. Enjoy living in this ...	3 beds \| 2 baths \| 1,200 sq.ft.	$299,500	Airbnb cash on cash: 3.04% Traditional cash on cash: 5.4% Airbnb Rental Income: $1801 Traditional Rental Income: $1976 Airbnb ROI: 3.04% Traditional ROI: 5.4%
3510 Crystal Lake Drive Chipley, FL Well maintained custom built home on a full acre - ideal for homestead, vacation home or i...	3 beds \| 2 baths \| 2,304 sq.ft.	$489,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.47% Airbnb Rental Income: $1801 Traditional Rental Income: $2225 Airbnb ROI: 1.47% Traditional ROI: 3.47%
1390 Forrest Avenue Chipley, FL Welcome to this beautifully renovated 3-bedroom, 2-bathroom home on over 0.9 acres in the ...	3 beds \| 2 baths \| 2,182 sq.ft.	$329,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 6% Airbnb Rental Income: $1801 Traditional Rental Income: $2346 Airbnb ROI: 2.67% Traditional ROI: 6%
1509 Southern Way Chipley, FL Welcome to your secluded retreat! Nestled on 10 acres of serene wooded privacy, this beaut...	3 beds \| 3 baths \| 1,440 sq.ft.	$289,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 5.57% Airbnb Rental Income: $1801 Traditional Rental Income: $1942 Airbnb ROI: 3.27% Traditional ROI: 5.57%
1701 Nearing Hills Circle Chipley, FL Situated on a large lot this beautiful cedar home has a feel about it that feels like you ...	3 beds \| 2 baths \| 2,911 sq.ft.	$399,500	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.94% Airbnb Rental Income: $1801 Traditional Rental Income: $2445 Airbnb ROI: 1.92% Traditional ROI: 4.94%
1842 Welton Place Chipley, FL Welcome to 1842 Welton Place, a stunning new construction home that combines modern elegan...	3 beds \| 2 baths \| 1,729 sq.ft.	$345,900	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.82% Airbnb Rental Income: $1801 Traditional Rental Income: $2272 Airbnb ROI: 1.87% Traditional ROI: 4.82%
4978 Derby Drive Chipley, FL Come visit this gorgeous lakefront community that is perfect for the sports minded enthusi...	3 beds \| 2 baths \| 1,296 sq.ft.	$195,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 7.31% Airbnb Rental Income: $1801 Traditional Rental Income: $1713 Airbnb ROI: 5.14% Traditional ROI: 7.31%
3229 Fox Court Chipley, FL Welcome to your new favorite cozy, secluded 3 Bed/2 bath home nestled on just shy of 2 Acr...	3 beds \| 2 baths \| 1,666 sq.ft.	$320,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 5.62% Airbnb Rental Income: $1801 Traditional Rental Income: $2214 Airbnb ROI: 2.62% Traditional ROI: 5.62%
1597 Clayton Road Chipley, FL UPDATE! Sellers offering a $3000 concession to buyer with acceptable offer. Welcome to you...	3 beds \| 2 baths \| 1,695 sq.ft.	$409,999	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.86% Airbnb Rental Income: $1801 Traditional Rental Income: $2227 Airbnb ROI: 1.48% Traditional ROI: 3.86%
1000 Oswald Road Chipley, FL Welcome to this ranch-style retreat, a 3-bedroom, 3-bathroom home nestled on 3 acres of be...	3 beds \| 3 baths \| 1,845 sq.ft.	$279,999	Airbnb cash on cash: 3.33% Traditional cash on cash: 8.51% Airbnb Rental Income: $1801 Traditional Rental Income: $2677 Airbnb ROI: 3.33% Traditional ROI: 8.51%
401 Red Deer Road Chipley, FL Dreaming of a serene country lifestyle with the freedom to explore outdoor hobbies and emb...	3 beds \| 2 baths \| 1,456 sq.ft.	$260,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 5.76% Airbnb Rental Income: $1801 Traditional Rental Income: $1873 Airbnb ROI: 3.47% Traditional ROI: 5.76%
877 Clayton Road Chipley, FL This charming fixer-upper is nestled in a highly desirable area, offering spacious rooms a...	3 beds \| 2 baths \| 2,004 sq.ft.	$239,900	Airbnb cash on cash: 4.22% Traditional cash on cash: 8.47% Airbnb Rental Income: $1801 Traditional Rental Income: $2276 Airbnb ROI: 4.22% Traditional ROI: 8.47%
1856 Gap Boulevard Chipley, FL Perched high above Gap lake on nearly 5 acres, this hand-built, one-owner cedar-sided lake...	2 beds \| 2 baths \| 1,658 sq.ft.	$359,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 5.55% Airbnb Rental Income: $2660 Traditional Rental Income: $2386 Airbnb ROI: 4.49% Traditional ROI: 5.55%
4064 Ramus Drive Chipley, FL Welcome to your future home in the up-and-coming Sunny Hills area, a community with endles...	3 beds \| 2 baths \| 1,260 sq.ft.	$219,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 6.42% Airbnb Rental Income: $1801 Traditional Rental Income: $1715 Airbnb ROI: 4.48% Traditional ROI: 6.42%
4092 Fairbanks Drive Chipley, FL 3.125% VA ASSUMABLE LOAN for qualified veterans only. This is a MUST SEE...1,360 sqft 2 be...	2 beds \| 2 baths \| 1,360 sq.ft.	$199,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 7.08% Airbnb Rental Income: $2660 Traditional Rental Income: $1792 Airbnb ROI: 8.32% Traditional ROI: 7.08%
4399 Leisure Lakes Drive Chipley, FL Welcome to Leisure Lakes. Enjoy peaceful living on a huge, clear lake in a security gated ...	2 beds \| 2 baths \| 1,250 sq.ft.	$299,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 5.11% Airbnb Rental Income: $2660 Traditional Rental Income: $2064 Airbnb ROI: 4.98% Traditional ROI: 5.11%
1788 Quintara Court Chipley, FL As one of the original sturdy concrete block homes that was built in Sunny Hills, this wel...	3 beds \| 2 baths \| 1,461 sq.ft.	$184,999	Airbnb cash on cash: 5.81% Traditional cash on cash: 8.87% Airbnb Rental Income: $1801 Traditional Rental Income: $1849 Airbnb ROI: 5.81% Traditional ROI: 8.87%
2179 Sunny Hills Boulevard Chipley, FL Brand New Affordable Home in Sunny Hills, not far from the Florida Panhandle's best offeri...	3 beds \| 2 baths \| 1,408 sq.ft.	$237,999	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.94% Airbnb Rental Income: $1801 Traditional Rental Income: $1893 Airbnb ROI: 4.36% Traditional ROI: 6.94%
2215 Shenandoah Boulevard Chipley, FL Single-Story Home in the Sunny Hills Classic Community! This is the desirable ''Beaumont''...	3 beds \| 2 baths \| 1,416 sq.ft.	$272,500	Airbnb cash on cash: 3.71% Traditional cash on cash: 6.51% Airbnb Rental Income: $1801 Traditional Rental Income: $2032 Airbnb ROI: 3.71% Traditional ROI: 6.51%
1751 Old Mill Road Chipley, FL This property features a spacious 2-bedroom, 2-bathroom home complete with a bonus room, s...	2 beds \| 2 baths \| 1,312 sq.ft.	$225,000	Airbnb cash on cash: 7.95% Traditional cash on cash: 6.17% Airbnb Rental Income: $2660 Traditional Rental Income: $1647 Airbnb ROI: 7.95% Traditional ROI: 6.17%
2763 Village Drive Chipley, FL Are you looking for a BRICK HOME, with ACREAGE close to the city? Check out this beautiful...	4 beds \| 2 baths \| 2,261 sq.ft.	$375,000	Airbnb cash on cash: 9.3% Traditional cash on cash: 4.66% Airbnb Rental Income: $4916 Traditional Rental Income: $2275 Airbnb ROI: 9.3% Traditional ROI: 4.66%
4002 Janet Circle Chipley, FL Don't miss this Sunny Hills 2023 custom built home on .4 of an acre that backs up to 62 ac...	3 beds \| 2 baths \| 1,155 sq.ft.	$218,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 8.62% Airbnb Rental Income: $1801 Traditional Rental Income: $2215 Airbnb ROI: 4.25% Traditional ROI: 8.62%
748 3rd Street Chipley, FL Check out this cedar sided country home in the middle of town! It's got character and char...	3 beds \| 2 baths \| 1,795 sq.ft.	$253,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 6.58% Airbnb Rental Income: $1801 Traditional Rental Income: $2188 Airbnb ROI: 2.92% Traditional ROI: 6.58%
781 BRICKYARD ROAD Chipley, FL Nice three bedrooms two baths mobile home on 1.5 acres in rural setting and one mile to ma...	3 beds \| 2 baths \| 1,216 sq.ft.	$159,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 9.25% Airbnb Rental Income: $1801 Traditional Rental Income: $1702 Airbnb ROI: 6.68% Traditional ROI: 9.25%
1569 Valiant Drive Chipley, FL Experience the beauty of this stunning new home in a unique and private country setting! S...	3 beds \| 2 baths \| 1,100 sq.ft.	$224,900	Airbnb cash on cash: 4.68% Traditional cash on cash: 6.69% Airbnb Rental Income: $1801 Traditional Rental Income: $1740 Airbnb ROI: 4.68% Traditional ROI: 6.69%
1821 Trellis Drive Chipley, FL Welcome to 1821 Trellis Drive, Chipley - a stunning brand-new construction ready for its f...	3 beds \| 2 baths \| 1,725 sq.ft.	$349,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 5.41% Airbnb Rental Income: $1801 Traditional Rental Income: $2206 Airbnb ROI: 2.69% Traditional ROI: 5.41%
901 PRISSY LANE Chipley, FL Nice mobile home park on 32 acres. There are 17 park owned homes. Expenses are limited to...	46 beds \| N/A baths \| 16,000 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.68% Airbnb Rental Income: $null Traditional Rental Income: $2092 Airbnb ROI: N/A Traditional ROI: 0.68%
3984 Quail Court Chipley, FL Discover the Hyacinth floorplan by Homes by Deltona, an exceptional residence nestled in t...	3 beds \| 2 baths \| 1,650 sq.ft.	$308,134	Airbnb cash on cash: 3.17% Traditional cash on cash: 5.31% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 3.17% Traditional ROI: 5.31%
4208 Auburndale Drive Chipley, FL Discover the Sage floorplan by Homes by Deltona, an exceptional residence nestled in the t...	3 beds \| 2 baths \| 1,556 sq.ft.	$316,376	Airbnb cash on cash: 3.06% Traditional cash on cash: 4.91% Airbnb Rental Income: $1801 Traditional Rental Income: $1861 Airbnb ROI: 3.06% Traditional ROI: 4.91%
4210 Auburndale Drive Chipley, FL Discover the Hyacinth floorplan by Homes by Deltona, an exceptional residence nestled in t...	3 beds \| 2 baths \| 1,650 sq.ft.	$316,734	Airbnb cash on cash: 3.06% Traditional cash on cash: 5.14% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 3.06% Traditional ROI: 5.14%
2080 Babcock Street Chipley, FL Sage floor plan presented by... Homes by Deltona. Discover an exceptional residence nestle...	3 beds \| 2 baths \| 1,556 sq.ft.	$296,676	Airbnb cash on cash: 3.33% Traditional cash on cash: 5.7% Airbnb Rental Income: $1801 Traditional Rental Income: $1973 Airbnb ROI: 3.33% Traditional ROI: 5.7%
4025 Zinnia Drive Chipley, FL CURRENTLY UNDER CONTRACT, SELLER WILL CONSIDER BACKUP OFFERS. Brand new construction, almo...	3 beds \| 2 baths \| 1,386 sq.ft.	$230,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 7.72% Airbnb Rental Income: $1801 Traditional Rental Income: $2001 Airbnb ROI: 4.55% Traditional ROI: 7.72%
3915 Country Club Boulevard Chipley, FL Welcome to 3915 Country Club Boulevard in Chipley, a stunning waterfront property nestled ...	4 beds \| 2 baths \| 2,970 sq.ft.	$419,900	Airbnb cash on cash: 8.3% Traditional cash on cash: 5.48% Airbnb Rental Income: $4916 Traditional Rental Income: $2797 Airbnb ROI: 8.3% Traditional ROI: 5.48%
1906 Mud Hill Rd Road Chipley, FL Beautifully remodeled home on over 2 1/2 acres. Featuring all new appliances, paint inside...	3 beds \| 1 baths \| 990 sq.ft.	$179,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.63% Airbnb Rental Income: $1801 Traditional Rental Income: $1373 Airbnb ROI: 5.27% Traditional ROI: 5.63%
3923 Country Club Boulevard Chipley, FL Discover lakeside living at its best in this spacious 2,940 sq. ft. home on the tranquil s...	4 beds \| 3 baths \| 3,185 sq.ft.	$405,000	Airbnb cash on cash: 8.56% Traditional cash on cash: 7.03% Airbnb Rental Income: $4916 Traditional Rental Income: $3329 Airbnb ROI: 8.56% Traditional ROI: 7.03%

Real Estate investment in Chipley, FL

There are 39 properties for sale in the city of Chipley . The median list price in Chipley is $289,900 and the average price per square foot is $148. In December 2024, the average monthly cash on cash return in Chipley is 6.00%. The average monthly rental income in Chipley is $1,973.

Chipley, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 39 investment properties available for sale in Chipley.

In 2024, the best neighborhood to buy investment property is Chipley.

The ROI for Long-Term is higher than the Short-Term in Chipley with average rental income of $1,973.

Your search for investment property begins and ends here

Investment Property for Sale in Chipley, FL

3090 Turkey Run Road

Chipley, FL

3 beds | 2 baths | 1,519 sq.ft.

$349,999

Airbnb cash on cash: 2.4%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1801

Traditional Rental Income: $1973

Airbnb ROI: 2.4%

Traditional ROI: 4.41%

3835 Highway 77

Chipley, FL

5 beds | 2 baths | 2,410 sq.ft.

$660,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.49%

Airbnb Rental Income: $null

Traditional Rental Income: $2971

Airbnb ROI: N/A

Traditional ROI: 3.49%

4075 Parkview Drive

Chipley, FL

3 beds | 2 baths | 1,830 sq.ft.

$234,900

Airbnb cash on cash: 4.45%

Traditional cash on cash: 8.4%

Airbnb Rental Income: $1801

Traditional Rental Income: $2189

Airbnb ROI: 4.45%

Traditional ROI: 8.4%

2641 Highway 77

Chipley, FL

2 beds | 2 baths | 1,900 sq.ft.

$365,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $2660

Traditional Rental Income: $2247

Airbnb ROI: 4.01%

Traditional ROI: 4.65%

1364 Watts Avenue

Chipley, FL

3 beds | 2 baths | 1,200 sq.ft.

$299,500

Airbnb cash on cash: 3.04%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $1801

Traditional Rental Income: $1976

Airbnb ROI: 3.04%

Traditional ROI: 5.4%

3510 Crystal Lake Drive

Chipley, FL

3 beds | 2 baths | 2,304 sq.ft.

$489,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1801

Traditional Rental Income: $2225

Airbnb ROI: 1.47%

Traditional ROI: 3.47%

1390 Forrest Avenue

Chipley, FL

3 beds | 2 baths | 2,182 sq.ft.

$329,900

Airbnb cash on cash: 2.67%

Traditional cash on cash: 6%

Airbnb Rental Income: $1801

Traditional Rental Income: $2346

Airbnb ROI: 2.67%

Traditional ROI: 6%

1509 Southern Way

Chipley, FL

3 beds | 3 baths | 1,440 sq.ft.

$289,900

Airbnb cash on cash: 3.27%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1801

Traditional Rental Income: $1942

Airbnb ROI: 3.27%