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.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: 6.47%
117 Walden Pond Road Headland, AL Conveniently located just 7.5 miles from the Ross Clark Circle, this 3-bedroom, 2.5-bath h...	3 beds \| 3 baths \| 2,407 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $2334 Airbnb ROI: N/A Traditional ROI: 5.92%
204 Cabrio Way Headland, AL Welcome to this beautiful 4-bedroom, 2-bath home in the Trace Manor subdivision. Featuring...	4 beds \| 2 baths \| 1,929 sq.ft.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $1947 Airbnb ROI: N/A Traditional ROI: 4.95%
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: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $2025 Airbnb ROI: N/A Traditional ROI: 3.56%
622 Peachtree Street Headland, AL This Headland gem has it allâlocation, updates, and plenty of charm! Sitting on a genero...	3 beds \| 2 baths \| 1,622 sq.ft.	$227,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $1518 Airbnb ROI: N/A Traditional ROI: 5.22%
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.	$394,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 4.77%
116 Heritage Way Headland, AL This incredible home is on Lot 47 in Headland's Heritage Ridge Subdivision. Large 1.12 acr...	4 beds \| 3 baths \| 2,436 sq.ft.	$448,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 3.81%
2944 County Road 13 Headland, AL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering 1,272 sq ft of ...	3 beds \| 2 baths \| 1,272 sq.ft.	$214,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $1329 Airbnb ROI: N/A Traditional ROI: 4.68%
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.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $2025 Airbnb ROI: N/A Traditional ROI: 4.64%
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.	$302,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $1988 Airbnb ROI: N/A Traditional ROI: 5.24%
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.	$302,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.79%
200 Benfield Headland, AL 3 Bedrooms \| 2 Bathrooms \| 1416 sq ft. Open concept living , dining, and kitchen. Kitchen ...	3 beds \| 2 baths \| 1,416 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $1789 Airbnb ROI: N/A Traditional ROI: 6.14%
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: N/A Traditional cash on cash: 7.26% Airbnb Rental Income: $null Traditional Rental Income: $1218 Airbnb ROI: N/A 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.	$342,400	Airbnb cash on cash: N/A Traditional cash on cash: 6.05% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 6.05%
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.	$302,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 5.29%
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.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 5.11%
4770 County Road 49 Headland, AL Like new 4-bedroom, 3-bath brick home in the desirable Headland School District! Completed...	4 beds \| 3 baths \| 2,353 sq.ft.	$516,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $2319 Airbnb ROI: N/A Traditional ROI: 3.56%
771 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.	$449,804	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $2125 Airbnb ROI: N/A Traditional ROI: 3.8%
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.	$347,400	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $2430 Airbnb ROI: N/A Traditional ROI: 6.1%
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.	$308,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1761 Airbnb ROI: N/A Traditional ROI: 4.63%
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.	$356,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.59% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 5.59%
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.	$321,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $1917 Airbnb ROI: N/A Traditional ROI: 4.92%
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.	$308,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 4.64%
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.	$354,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $2323 Airbnb ROI: N/A Traditional ROI: 5.6%
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.	$229,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $1808 Airbnb ROI: N/A Traditional ROI: 6.47%
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.	$325,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2065 Airbnb ROI: N/A Traditional ROI: 5.36%
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.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.31%
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: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $1718 Airbnb ROI: N/A Traditional ROI: 5.21%
505 CLEVELAND STREET Headland, AL Charming home on a large lot conveniently located adjoining Headland High School. Approxim...	3 beds \| 2 baths \| 1,648 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 8% Airbnb Rental Income: $null Traditional Rental Income: $1662 Airbnb ROI: N/A Traditional ROI: 8%
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: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2211 Airbnb ROI: N/A 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.	$356,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $2334 Airbnb ROI: N/A Traditional ROI: 5.28%
111 Creekridge Street Headland, AL Welcome to 111 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$321,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.66%
110 Creekridge Street Headland, AL Welcome to 110 Creekridge Street Headland, AL 36345.The Rhett is one of our single-story f...	4 beds \| 2 baths \| 1,774 sq.ft.	$316,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $1780 Airbnb ROI: N/A Traditional ROI: 4.25%
108 Creekridge Street Headland, AL Welcome to 108 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$323,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.62%
218 Azalea Lane Headland, AL Location LOCATION! Minutes to Dothan and Headland Schools! This S/D is Convenient to ALL! ...	4 beds \| 2 baths \| 2,117 sq.ft.	$306,300	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $1918 Airbnb ROI: N/A Traditional ROI: 4.99%
102 Tyler Way Headland, AL Welcome to 102 Tyler Way in our Creekridge community. The Madison, a new home floor plan a...	4 beds \| 3 baths \| 1,942 sq.ft.	$336,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.7% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.7%

Real Estate investment in Headland, AL

There are 83 properties for sale in the city of Headland . The median list price in Headland is $325,000 and the average price per square foot is $151. In October 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 83 investment properties available for sale in Headland.

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

The ROI for Short-Term is higher than the Long-Term in Headland with average rental income of $1,503.

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.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: 6.47%

117 Walden Pond Road

Headland, AL

3 beds | 3 baths | 2,407 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2334

Airbnb ROI: N/A

Traditional ROI: 5.92%

204 Cabrio Way

Headland, AL

4 beds | 2 baths | 1,929 sq.ft.

$310,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.95%

Airbnb Rental Income: $null

Traditional Rental Income: $1947

Airbnb ROI: N/A

Traditional ROI: 4.95%

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: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2025

Airbnb ROI: N/A

Traditional ROI: 3.56%

622 Peachtree Street

Headland, AL

3 beds | 2 baths | 1,622 sq.ft.

$227,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.22%

Airbnb Rental Income: $null

Traditional Rental Income: $1518

Airbnb ROI: N/A

Traditional ROI: 5.22%

264 Weeping Willow Trail

Headland, AL

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

$394,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.77%

Airbnb Rental Income: $null

Traditional Rental Income: $2375

Airbnb ROI: N/A

Traditional ROI: 4.77%

116 Heritage Way

Headland, AL

4 beds | 3 baths | 2,436 sq.ft.

$448,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2281

Airbnb ROI: N/A