Real Estate Investment Properties for Sale in Headland, AL

Looking for investment property in Headland, AL with high ROI ?

Explore a variety of short-term homes & houses in Headland, AL. Invest wisely with VRBO & Headland, AL 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 Headland, AL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1782 COUNTY ROAD 3 Headland, AL Are you seeking a privately located colonial style brick exterior home that has four (4) l...	4 beds \| 4 baths \| 2,480 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: 6.08%
109 Buckhead Drive Headland, AL Tucked away on nearly 8 acres in Headland, this 4BD 4.5BA estate is a true Southern retrea...	4 beds \| 5 baths \| 4,978 sq.ft.	$739,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.21% Airbnb Rental Income: $null Traditional Rental Income: $6724 Airbnb ROI: N/A Traditional ROI: 8.21%
516 County Road 521 Headland, AL Welcome to the perfect mix of elegance and costum farmhouse combined. Tucked away on almos...	3 beds \| 2 baths \| 2,530 sq.ft.	$415,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.56% Airbnb Rental Income: $1461 Traditional Rental Income: $2025 Airbnb ROI: 1% Traditional ROI: 3.56%
202 Cabrio Way Headland, AL Stunning 4 bedroom, 3 bath home located in the heart of Headland with modern upgrades and ...	4 beds \| 3 baths \| 2,087 sq.ft.	$314,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.96% Airbnb Rental Income: $null Traditional Rental Income: $2276 Airbnb ROI: N/A Traditional ROI: 5.96%
264 Weeping Willow Trail Headland, AL Like-new brick home of 2,672 square feet, located in the beautiful Willow Walk Subdivision...	4 beds \| 3 baths \| 2,672 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 4.68%
126 Heritage Way Headland, AL Like New Lot 52 Heritage Ridge Sub-Division Headland, AL. Large Lot @ .76 Acre. Granite co...	4 beds \| 3 baths \| 2,350 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.94% Airbnb Rental Income: $null Traditional Rental Income: $2326 Airbnb ROI: N/A Traditional ROI: 4.94%
204 Scarlet Oak Drive Headland, AL Welcome to refined living in this beautifully designed 4-bedroom, 2-bath home, perfectly s...	4 beds \| 2 baths \| 2,245 sq.ft.	$346,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.52% Airbnb Rental Income: $null Traditional Rental Income: $2025 Airbnb ROI: N/A Traditional ROI: 4.52%
209 Heritage Way Headland, AL Lot 21 Heritage Ridge Sub-Division on 2.36 Acres. Granite countertops, kitchen pantry, bed...	4 beds \| 3 baths \| 2,350 sq.ft.	$459,650	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 2.7%
317 Heritage Way Headland, AL The Rhett is one of our single-story floorplans featured in our Heritage Ridge community i...	4 beds \| 2 baths \| 1,835 sq.ft.	$317,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $1988 Airbnb ROI: N/A Traditional ROI: 4.93%
328 Heritage Way Headland, AL The Rhett is one of our single-story floorplans featured in our Heritage Ridge community i...	4 beds \| 2 baths \| 1,835 sq.ft.	$317,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.49%
330 Heritage Way Headland, AL Introducing the Hawthorne floorplan at Heritage Ridge, where every square foot is put to u...	4 beds \| 3 baths \| 2,435 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $2473 Airbnb ROI: N/A Traditional ROI: 5.45%
200 Benfield Headland, AL New Construction home , approx. completion date of May 2025, with 1416 sq. ft. This char...	3 beds \| 3 baths \| 1,416 sq.ft.	$252,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 6.08% Airbnb Rental Income: $1461 Traditional Rental Income: $1789 Airbnb ROI: 2.88% Traditional ROI: 6.08%
296 County Road 250 Headland, AL Brick home and 3 lots. Convenient to Headland, Dothan, and Abbeville. Large closed in bac...	3 beds \| 2 baths \| 1,100 sq.ft.	$135,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 7.26% Airbnb Rental Income: $1461 Traditional Rental Income: $1218 Airbnb ROI: 5.8% Traditional ROI: 7.26%
310 Heritage Way Headland, AL Step into the Destin at Heritage Ridge, one of our popular floorplans available in Headlan...	4 beds \| 3 baths \| 2,273 sq.ft.	$357,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.76% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 5.76%
324 Heritage Way Headland, AL The Rhett is one of our single-story floorplans featured in our Heritage Ridge community i...	4 beds \| 2 baths \| 1,835 sq.ft.	$317,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.97% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 4.97%
314 Heritage Way Headland, AL The Jasmine is one of our single-story floorplans featured in our Heritage Ridge community...	4 beds \| 2 baths \| 2,025 sq.ft.	$334,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.82% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 4.82%
4770 County Rd 49 Headland, AL Gorgeous like-new home, built in 2024, offering 4 bedrooms, 3 bathrooms, and a thoughtfull...	4 beds \| 3 baths \| 2,353 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $2319 Airbnb ROI: N/A Traditional ROI: 3.75%
204 Cambridge Dr Headland, AL New construction home with 4 bedroom and 3 baths with 2556 sq ft. located in the Cove on M...	4 beds \| 3 baths \| 2,556 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $2359 Airbnb ROI: N/A Traditional ROI: 5.67%
1085 County Road 122 Headland, AL Private custom home on 10 acres in Headland, AL. with luxury & comfort in mind. 3270 Heat...	3 beds \| 5 baths \| 3,270 sq.ft.	$698,500	Airbnb cash on cash: 0.43% Traditional cash on cash: 6.23% Airbnb Rental Income: $1461 Traditional Rental Income: $4808 Airbnb ROI: 0.43% Traditional ROI: 6.23%
0 County Road 9 Headland, AL Come step into the Collins Craftsman style Farm house. Sitting on a beautiful 3 acre lot, ...	4 beds \| 2 baths \| 2,134 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $2125 Airbnb ROI: N/A Traditional ROI: 4.39%
677 County Road 9 Headland, AL NEW CONSTRUCTION CUSTOM HOME ON COUNTY ROAD 9 IN HEADLAND AL. THE HOME IS IN HENRY COUNTY ...	4 beds \| 2 baths \| 2,000 sq.ft.	$421,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $2028 Airbnb ROI: N/A Traditional ROI: 3.49%
306 Heritage Way Headland, AL Welcome to 306 Heritage Way, Headland, AL 36345 in our Heritage Ridge Community. Step into...	4 beds \| 3 baths \| 2,273 sq.ft.	$362,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $2430 Airbnb ROI: N/A Traditional ROI: 5.81%
101 Creekridge Street Headland, AL Welcome to 101 Creekridge Street Headland, AL 36345.The Rhett is one of our single-story f...	4 beds \| 2 baths \| 1,774 sq.ft.	$323,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $1761 Airbnb ROI: N/A Traditional ROI: 4.38%
100 Creekridge Street Headland, AL Welcome to 100 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$334,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $1916 Airbnb ROI: N/A Traditional ROI: 4.69%
103 Creekridge Street Headland, AL Welcome to 103 Creekridge Street Headland, AL 36345 in our Creekridge Community. Find all ...	5 beds \| 3 baths \| 2,599 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 5.36%
105 Aubrey Ave Headland, AL Step into the Lakeside at our Sagebrush community in Headland, Alabama. This well thought ...	5 beds \| 3 baths \| 2,016 sq.ft.	$290,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.47% Airbnb Rental Income: $null Traditional Rental Income: $2526 Airbnb ROI: N/A Traditional ROI: 7.47%
308 Heritage Way Headland, AL Introducing the Hawthorne floorplan at Heritage Ridge, where every square foot is put to u...	4 beds \| 3 baths \| 2,435 sq.ft.	$379,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.16% Airbnb Rental Income: $null Traditional Rental Income: $2431 Airbnb ROI: N/A Traditional ROI: 5.16%
105 Creekridge Street Headland, AL Welcome to 105 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$336,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $1917 Airbnb ROI: N/A Traditional ROI: 4.66%
107 Creekridge Street Headland, AL Welcome to 107 Creekridge Street Headland, AL 36345.The Rhett is one of our single-story f...	4 beds \| 2 baths \| 1,774 sq.ft.	$323,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 4.38%
106 Creekridge Street Headland, AL Welcome to 106 Creekridge Street Headland, AL 36345 in our Creekridge Community. Find all ...	5 beds \| 3 baths \| 2,599 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.34% Airbnb Rental Income: $null Traditional Rental Income: $2323 Airbnb ROI: N/A Traditional ROI: 5.34%
100 Asher Circle Headland, AL Welcome to 100 Asher Drive Headland, AL 36345 in our Sagebrush Community. Step into the Fr...	4 beds \| 2 baths \| 1,497 sq.ft.	$244,900	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $1808 Airbnb ROI: N/A Traditional ROI: 6%
305 Heritage Way Headland, AL Welcome to the Madison, a new home floor plan at our Creek Ridge Community in Headland Ala...	4 beds \| 3 baths \| 1,942 sq.ft.	$340,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $2065 Airbnb ROI: N/A Traditional ROI: 5.09%
101 Riveredge Court Headland, AL Simply amazing home...you have to see it to believe it. Corner lot in gated community wit...	3 beds \| 2 baths \| 2,384 sq.ft.	$400,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.48% Airbnb Rental Income: $1461 Traditional Rental Income: $1927 Airbnb ROI: 1.08% Traditional ROI: 3.48%
218 Wellington Way Headland, AL This four bedroom, two bath, new construction home is located in the new Cove on Main S/D ...	4 beds \| 2 baths \| 2,086 sq.ft.	$287,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $1985 Airbnb ROI: N/A Traditional ROI: 5.57%
3405 CR-22 Headland, AL Stunning 5-Bedroom Home on 8 Acres â Headland, AL Paradise! Welcome to your dream retrea...	5 beds \| 4 baths \| 3,250 sq.ft.	$674,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.22%
215 Wellington Way Headland, AL This three bedroom, two bath, new construction home is located in the new Cove on Main S/D...	3 beds \| 2 baths \| 1,718 sq.ft.	$259,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 5.21% Airbnb Rental Income: $1461 Traditional Rental Income: $1718 Airbnb ROI: 2.4% Traditional ROI: 5.21%
219 Wellington Way Headland, AL This three bedroom, two bath, new construction home is located in the new Cove on Main S/D...	3 beds \| 2 baths \| 1,929 sq.ft.	$279,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 5.32% Airbnb Rental Income: $1461 Traditional Rental Income: $1870 Airbnb ROI: 2.13% Traditional ROI: 5.32%
106 Asher Circle Headland, AL Step into the Freeport, one of our floorplans we feature at our Sagebrush community in Hea...	4 beds \| 2 baths \| 1,497 sq.ft.	$243,400	Airbnb cash on cash: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $1815 Airbnb ROI: N/A Traditional ROI: 6.08%
119 Willow Oaks Drive Headland, AL Set on nearly 1.9 peaceful acres in the Willow Oaks Subdivision, this property offers the ...	3 beds \| 2 baths \| 2,205 sq.ft.	$392,500	Airbnb cash on cash: 1.13% Traditional cash on cash: 4.35% Airbnb Rental Income: $1461 Traditional Rental Income: $2211 Airbnb ROI: 1.13% Traditional ROI: 4.35%
109 Creekridge Street Headland, AL Welcome to 109 Creekridge Street Headland, AL 36345 in our Creekridge Community. Find all ...	5 beds \| 3 baths \| 2,599 sq.ft.	$371,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2334 Airbnb ROI: N/A Traditional ROI: 5.01%

Real Estate investment in Headland, AL

There are 74 properties for sale in the city of Headland . The median list price in Headland is $336,900 and the average price per square foot is $154. In September 2025, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $2,025.

Headland, AL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 74 investment properties available for sale in Headland.

In 2025, the best neighborhood to buy investment property is Headland.

The ROI for Long-Term is higher than the Short-Term in Headland with average rental income of $2,025.

Your search for investment property begins and ends here

Investment Property for Sale in Headland, AL

1782 COUNTY ROAD 3

Headland, AL

4 beds | 4 baths | 2,480 sq.ft.

$379,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.08%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: 6.08%

109 Buckhead Drive

Headland, AL

4 beds | 5 baths | 4,978 sq.ft.

$739,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.21%

Airbnb Rental Income: $null

Traditional Rental Income: $6724

Airbnb ROI: N/A

Traditional ROI: 8.21%

516 County Road 521

Headland, AL

3 beds | 2 baths | 2,530 sq.ft.

$415,000

Airbnb cash on cash: 1%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1461

Traditional Rental Income: $2025

Airbnb ROI: 1%

Traditional ROI: 3.56%

202 Cabrio Way

Headland, AL

4 beds | 3 baths | 2,087 sq.ft.

$314,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2276

Airbnb ROI: N/A

Traditional ROI: 5.96%

264 Weeping Willow Trail

Headland, AL

4 beds | 3 baths | 2,672 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2375

Airbnb ROI: N/A

Traditional ROI: 4.68%

126 Heritage Way

Headland, AL

4 beds | 3 baths | 2,350 sq.ft.

$374,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.94%

Airbnb Rental Income: $null

Traditional Rental Income: $2326

Airbnb ROI: N/A

Traditional ROI: 4.94%

204 Scarlet Oak Drive

Headland, AL

4 beds | 2 baths | 2,245 sq.ft.

$346,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2025

Airbnb ROI: N/A

Traditional ROI: 4.52%

209 Heritage Way

Headland, AL

4 beds | 3 baths | 2,350 sq.ft.

$459,650

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $1859

Airbnb ROI: N/A