Real Estate Investments for Sale in Chipley, FL With High ROI

Are you looking for a vacation rental in Chipley, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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
2391 Shenandoah Boulevard Chipley, FL NEW CONSTRUCTION! Completed in February 2024, this distinctively designed 3-bedroom, 2-bat...	3 beds \| 2 baths \| 1,619 sq.ft.	$369,900	Airbnb cash on cash: 2.49% Traditional cash on cash: 4.19% Airbnb Rental Income: $1801 Traditional Rental Income: $1903 Airbnb ROI: 2.49% Traditional ROI: 4.19%
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: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $2876 Airbnb ROI: N/A Traditional ROI: 3.34%
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.	$249,900	Airbnb cash on cash: 4.13% Traditional cash on cash: 6.65% Airbnb Rental Income: $1801 Traditional Rental Income: $1907 Airbnb ROI: 4.13% Traditional ROI: 6.65%
2209 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Sage floorplan from Homes by Delt...	3 beds \| 2 baths \| 1,556 sq.ft.	$302,322	Airbnb cash on cash: 3.25% Traditional cash on cash: 5.18% Airbnb Rental Income: $1801 Traditional Rental Income: $1862 Airbnb ROI: 3.25% Traditional ROI: 5.18%
2227 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$313,535	Airbnb cash on cash: 3.1% Traditional cash on cash: 5.21% Airbnb Rental Income: $1801 Traditional Rental Income: $1934 Airbnb ROI: 3.1% Traditional ROI: 5.21%
3984 Quail Court Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$320,891	Airbnb cash on cash: 3.01% Traditional cash on cash: 5.07% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 3.01% Traditional ROI: 5.07%
2030 Coachman Drive Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$315,869	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.31% Airbnb Rental Income: $1801 Traditional Rental Income: $1934 Airbnb ROI: 2.22% Traditional ROI: 4.31%
4208 Auburndale Drive Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Sage floorplan from Homes by Del...	3 beds \| 2 baths \| 1,556 sq.ft.	$320,666	Airbnb cash on cash: 3.01% Traditional cash on cash: 4.83% Airbnb Rental Income: $1801 Traditional Rental Income: $1861 Airbnb ROI: 3.01% Traditional ROI: 4.83%
4210 Auburndale Drive Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$319,494	Airbnb cash on cash: 3.03% Traditional cash on cash: 5.1% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 3.03% Traditional ROI: 5.1%
2208 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Sage floorplan from Homes by Del...	3 beds \| 2 baths \| 1,556 sq.ft.	$321,469	Airbnb cash on cash: 3% Traditional cash on cash: 4.82% Airbnb Rental Income: $1801 Traditional Rental Income: $1861 Airbnb ROI: 3% Traditional ROI: 4.82%
2213 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$310,710	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.42% Airbnb Rental Income: $1801 Traditional Rental Income: $1934 Airbnb ROI: 2.29% Traditional ROI: 4.42%
2216 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$310,094	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.43% Airbnb Rental Income: $1801 Traditional Rental Income: $1934 Airbnb ROI: 2.3% Traditional ROI: 4.43%
2789 Summers Drive Chipley, FL **Country-Luxury-Living on 3.6 lakefront acres with 950 sqft apartment/shop and High-Speed...	3 beds \| 3 baths \| 2,324 sq.ft.	$774,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.39% Airbnb Rental Income: $1801 Traditional Rental Income: $2853 Airbnb ROI: 0.26% Traditional ROI: 2.39%
1000 Oswald Road Chipley, FL This charming ranch-style retreat offers 3-bedroom, 3-bathroom home sits on 3 sprawling ac...	3 beds \| 3 baths \| 1,845 sq.ft.	$299,999	Airbnb cash on cash: 3.05% Traditional cash on cash: 7.43% Airbnb Rental Income: $1801 Traditional Rental Income: $2548 Airbnb ROI: 3.05% Traditional ROI: 7.43%
1971 Sunny Hills Boulevard Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Don't miss the exceptional chance to acquire the...	3 beds \| 2 baths \| 1,650 sq.ft.	$316,900	Airbnb cash on cash: 3.06% Traditional cash on cash: 5.15% Airbnb Rental Income: $1801 Traditional Rental Income: $1934 Airbnb ROI: 3.06% Traditional ROI: 5.15%
4025 Zinnia Drive Chipley, FL Brand new construction, almost completed in Sunny Hills! This home was created by a skille...	3 beds \| 2 baths \| 1,386 sq.ft.	$229,999	Airbnb cash on cash: 4.55% Traditional cash on cash: 7.51% Airbnb Rental Income: $1801 Traditional Rental Income: $1956 Airbnb ROI: 4.55% Traditional ROI: 7.51%
748 3rd Street Chipley, FL Feel in the country while in the middle of town!! Check out this amazing log cabin feelin...	3 beds \| 2 baths \| 1,795 sq.ft.	$249,900	Airbnb cash on cash: 2.98% Traditional cash on cash: 5.88% Airbnb Rental Income: $1801 Traditional Rental Income: $1996 Airbnb ROI: 2.98% Traditional ROI: 5.88%
1997 Shenandoah Boulevard Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$329,972	Airbnb cash on cash: 2.9% Traditional cash on cash: 4.9% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 2.9% Traditional ROI: 4.9%
2221 Chase Street Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Sage floorplan from Homes by Delt...	3 beds \| 2 baths \| 1,556 sq.ft.	$304,658	Airbnb cash on cash: 2.37% Traditional cash on cash: 4.29% Airbnb Rental Income: $1801 Traditional Rental Income: $1862 Airbnb ROI: 2.37% Traditional ROI: 4.29%
2003 Shenandoah Boulevard Chipley, FL * CONCRETE BLOCK CONSTRUCTION HOME * Introducing the Hyacinth floorplan from Homes by...	3 beds \| 2 baths \| 1,650 sq.ft.	$331,914	Airbnb cash on cash: 2.88% Traditional cash on cash: 4.87% Airbnb Rental Income: $1801 Traditional Rental Income: $1933 Airbnb ROI: 2.88% Traditional ROI: 4.87%
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.	$375,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.9% Airbnb Rental Income: $2660 Traditional Rental Income: $2037 Airbnb ROI: 3.88% Traditional ROI: 3.9%
672 Main Street Chipley, FL Charming 2-Bedroom Home with Florida Room in Chipley, FLWelcome to 672 Chipley, FL! Th...	2 beds \| 2 baths \| 1,740 sq.ft.	$258,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 5.82% Airbnb Rental Income: $2660 Traditional Rental Income: $1818 Airbnb ROI: 6.68% Traditional ROI: 5.82%
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: 5.16% Airbnb Rental Income: $1801 Traditional Rental Income: $1909 Airbnb ROI: 3.04% Traditional ROI: 5.16%
3892 Belmar Place Chipley, FL MOTIVATED SELLER & 3% Assumable Mortgage for approved buyer! Welcome to this beautiful 3-...	3 beds \| 2 baths \| 1,644 sq.ft.	$200,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 7.07% Airbnb Rental Income: $1801 Traditional Rental Income: $1780 Airbnb ROI: 4.6% Traditional ROI: 7.07%
4878 Springer Drive Chipley, FL Charming Country-Style Home in Leisure Lakes. Looking for an equestrian friendly community...	3 beds \| 2 baths \| 1,494 sq.ft.	$329,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.45% Airbnb Rental Income: $1801 Traditional Rental Income: $1862 Airbnb ROI: 2.67% Traditional ROI: 4.45%
1518 Duncan Community Road Chipley, FL Welcome to your serene country retreat! Located in the highly sought-after Duncan Communit...	3 beds \| 2 baths \| 1,190 sq.ft.	$219,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 5.31% Airbnb Rental Income: $1801 Traditional Rental Income: $1446 Airbnb ROI: 4.67% Traditional ROI: 5.31%
3510 Crystal Lake Drive Chipley, FL Well maintained custom built home on a full acre is ideal for homestead, vacation home or ...	3 beds \| 2 baths \| 2,304 sq.ft.	$499,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.94% Airbnb Rental Income: $1801 Traditional Rental Income: $2018 Airbnb ROI: 1.42% Traditional ROI: 2.94%
425 Coralvine Drive Chipley, FL VERY MOTIVATED SELLER Great location just off the highly desirable Orange Hill Rd. Beauti...	3 beds \| 2 baths \| 1,616 sq.ft.	$200,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 8.09% Airbnb Rental Income: $1801 Traditional Rental Income: $1884 Airbnb ROI: 5.08% Traditional ROI: 8.09%
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: 5% Airbnb Rental Income: $1801 Traditional Rental Income: $2035 Airbnb ROI: 2.67% Traditional ROI: 5%
2340 Deadening Road Chipley, FL Your next chapter begins here, in this expansive 2,151 square foot residence offering 4 be...	4 beds \| 3 baths \| 2,151 sq.ft.	$349,999	Airbnb cash on cash: 9.76% Traditional cash on cash: 6.02% Airbnb Rental Income: $4916 Traditional Rental Income: $2677 Airbnb ROI: 9.76% Traditional ROI: 6.02%
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.	$295,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 4.82% Airbnb Rental Income: $1801 Traditional Rental Income: $1763 Airbnb ROI: 3.19% Traditional ROI: 4.82%
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: 4.14% Airbnb Rental Income: $1801 Traditional Rental Income: $2143 Airbnb ROI: 1.92% Traditional ROI: 4.14%
2964 Monique Lane Chipley, FL This brand-new 2024 Clayton (16x76) mobile home has just been set up and is ready for it's...	3 beds \| 2 baths \| 1,216 sq.ft.	$169,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 11.93% Airbnb Rental Income: $1801 Traditional Rental Income: $2193 Airbnb ROI: 6.47% Traditional ROI: 11.93%
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.	$349,900	Airbnb cash on cash: 1.82% Traditional cash on cash: 5.43% Airbnb Rental Income: $1801 Traditional Rental Income: $2496 Airbnb ROI: 1.82% Traditional ROI: 5.43%
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: 9.31% Airbnb Rental Income: $1801 Traditional Rental Income: $2084 Airbnb ROI: 5.14% Traditional ROI: 9.31%
401 Red Deer Road Chipley, FL Professional Photos will be uploaded soon...Dreaming of a serene country lifestyle with th...	3 beds \| 2 baths \| 1,456 sq.ft.	$260,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 7.39% Airbnb Rental Income: $1801 Traditional Rental Income: $2273 Airbnb ROI: 3.47% Traditional ROI: 7.39%
3279 Wheeler Lane Chipley, FL Escape to the country and experience a simple way of living on the acreage you've been loo...	2 beds \| 1 baths \| 928 sq.ft.	$189,900	Airbnb cash on cash: 8.97% Traditional cash on cash: 7.98% Airbnb Rental Income: $2660 Traditional Rental Income: $1848 Airbnb ROI: 8.97% Traditional ROI: 7.98%
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.	$365,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 4.61% Airbnb Rental Income: $1801 Traditional Rental Income: $2118 Airbnb ROI: 2.26% Traditional ROI: 4.61%
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: 0.36% Airbnb Rental Income: $null Traditional Rental Income: $1753 Airbnb ROI: N/A Traditional ROI: 0.36%
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: 8.6% Airbnb Rental Income: $1801 Traditional Rental Income: $1604 Airbnb ROI: 6.68% Traditional ROI: 8.6%

Real Estate investment in Chipley, FL

There are 46 properties for sale in the city of Chipley . The median list price in Chipley is $316,385 and the average price per square foot is $166. In September 2024, the average monthly cash on cash return in Chipley is 5.00%. The average monthly rental income in Chipley is $1,956.

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

There are 46 investment properties available for sale in Chipley.

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

The ROI for Short-Term is higher than the Long-Term in Chipley with average rental income of $1,801.

Your search for investment property begins and ends here

Investment Property for Sale in Chipley, FL

2391 Shenandoah Boulevard

Chipley, FL

3 beds | 2 baths | 1,619 sq.ft.

$369,900

Airbnb cash on cash: 2.49%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $1801

Traditional Rental Income: $1903

Airbnb ROI: 2.49%

Traditional ROI: 4.19%

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: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2876

Airbnb ROI: N/A

Traditional ROI: 3.34%

4075 Parkview Drive

Chipley, FL

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

$249,900

Airbnb cash on cash: 4.13%

Traditional cash on cash: 6.65%

Airbnb Rental Income: $1801

Traditional Rental Income: $1907

Airbnb ROI: 4.13%

Traditional ROI: 6.65%

2209 Chase Street

Chipley, FL

3 beds | 2 baths | 1,556 sq.ft.

$302,322

Airbnb cash on cash: 3.25%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $1801

Traditional Rental Income: $1862

Airbnb ROI: 3.25%

Traditional ROI: 5.18%

2227 Chase Street

Chipley, FL

3 beds | 2 baths | 1,650 sq.ft.

$313,535

Airbnb cash on cash: 3.1%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1801

Traditional Rental Income: $1934

Airbnb ROI: 3.1%

Traditional ROI: 5.21%

3984 Quail Court

Chipley, FL

3 beds | 2 baths | 1,650 sq.ft.

$320,891

Airbnb cash on cash: 3.01%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1801

Traditional Rental Income: $1933

Airbnb ROI: 3.01%

Traditional ROI: 5.07%

2030 Coachman Drive

Chipley, FL

3 beds | 2 baths | 1,650 sq.ft.

$315,869

Airbnb cash on cash: 2.22%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1801

Traditional Rental Income: $1934

Airbnb ROI: 2.22%

Traditional ROI: 4.31%

4208 Auburndale Drive

Chipley, FL

3 beds | 2 baths | 1,556 sq.ft.

$320,666

Airbnb cash on cash: 3.01%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1801

Traditional Rental Income: $1861

Airbnb ROI: 3.01%