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
505 Church Street Headland, AL This beautifully updated Headland home offers the perfect blend of classic charm and moder...	3 beds \| 2 baths \| 1,583 sq.ft.	$214,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 5.66% Airbnb Rental Income: $873 Traditional Rental Income: $1533 Airbnb ROI: 0.78% Traditional ROI: 5.66%
203 Cleveland St Headland, AL Beautifully updated 1930s Queen-Anne style home. The moment you walk up to the refurbished...	2 beds \| 2 baths \| 1,800 sq.ft.	$239,999	Airbnb cash on cash: 2.64% Traditional cash on cash: 6.34% Airbnb Rental Income: $1463 Traditional Rental Income: $1887 Airbnb ROI: 2.64% Traditional ROI: 6.34%
117 Walden Pond Rd Headland, AL Conveniently located just 7.5 miles from the Ross Clark Circle, this 3-bedroom, 2.5-bath h...	3 beds \| 2 baths \| 2,407 sq.ft.	$319,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 6.06% Airbnb Rental Income: $873 Traditional Rental Income: $2334 Airbnb ROI: 0.08% Traditional ROI: 6.06%
106 Cabrio Way Headland, AL Welcome to 106 Cabrio Way in the highly sought-after Trace Manor subdivision of Headland. ...	3 beds \| 2 baths \| 1,662 sq.ft.	$269,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 5.44% Airbnb Rental Income: $873 Traditional Rental Income: $1809 Airbnb ROI: 0.62% Traditional ROI: 5.44%
3885 County Road 12 Headland, AL Spacious Brick Beauty in Headland School District â 3,146 SQ FT Step into this stunning...	4 beds \| 3 baths \| 3,146 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.36% Airbnb Rental Income: $null Traditional Rental Income: $2876 Airbnb ROI: N/A Traditional ROI: 6.36%
983 County Road 21 Headland, AL Set on 30 acres in the desirable Headland school district, this private estate offers luxu...	4 beds \| 3 baths \| 3,488 sq.ft.	$869,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.09% Airbnb Rental Income: $null Traditional Rental Income: $1162 Airbnb ROI: N/A Traditional ROI: -0.09%
208 Willow Oaks Dr Headland, AL Don't miss this peaceful home situated in Willow Oaks subdivision in Headland. This 4-bedr...	6 beds \| 3 baths \| 2,884 sq.ft.	$352,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.49% Airbnb Rental Income: $null Traditional Rental Income: $2652 Airbnb ROI: N/A Traditional ROI: 6.49%
2589 County Road 6 Headland, AL Tucked away on 1 acre you'll find this cozy country home only minutes from Downtown Headla...	3 beds \| 2 baths \| 1,560 sq.ft.	$199,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 6.61% Airbnb Rental Income: $873 Traditional Rental Income: $1566 Airbnb ROI: 1.19% Traditional ROI: 6.61%
516 County Road 521 Headland, AL Welcome to your dream country home- A beautifully updated farmhouse on 3 unrestricted sere...	3 beds \| 2 baths \| 2,530 sq.ft.	$405,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.68% Airbnb Rental Income: $873 Traditional Rental Income: $2025 Airbnb ROI: -0.23% Traditional ROI: 3.68%
264 Weeping Willow Trl 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.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 4.91%
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.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 4.02%
0 County Road 33 Headland, AL	N/A beds \| N/A baths \| N/A	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.83% Airbnb Rental Income: $null Traditional Rental Income: $1067 Airbnb ROI: N/A Traditional ROI: 0.83%
127 Lake Lane Headland, AL Situated in the Twin Lakes Subdivision and zoned for Headland Schools, the lovely home is ...	4 beds \| 4 baths \| 2,207 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $2568 Airbnb ROI: N/A Traditional ROI: 6.12%
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.	$312,900	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%
296 County Road 250 Headland, AL Charming three-bedroom, two-bathroom home, perfectly suited for anyone seeking comfort, sp...	3 beds \| 2 baths \| 1,100 sq.ft.	$140,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 6.96% Airbnb Rental Income: $873 Traditional Rental Income: $1218 Airbnb ROI: 1.9% Traditional ROI: 6.96%
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.	$312,900	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.	$329,900	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%
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%
101 Creekridge St 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.	$318,900	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 St Headland, AL Welcome to 100 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $1916 Airbnb ROI: N/A Traditional ROI: 4.96%
103 Creekridge St 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.	$374,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.42% Airbnb Rental Income: $null Traditional Rental Income: $2431 Airbnb ROI: N/A Traditional ROI: 5.42%
105 Creekridge St Headland, AL Welcome to 105 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$331,900	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 St 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.	$318,900	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%
305 Heritage Way Headland, AL Welcome to 305 Heritage Way, our Madison floor plan at our beautiful Heritage Ridge Commun...	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 MOTIVATED SELLER Stunning 5-Bedroom Home on 8 Acres â Headland, AL Paradise! Welcome t...	5 beds \| 2 baths \| 3,250 sq.ft.	$624,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.67%
505 Cleveland St Headland, AL Charming home on a large lot conveniently located adjoining Headland High School. Approxim...	3 beds \| 2 baths \| 1,648 sq.ft.	$172,500	Airbnb cash on cash: 1.3% Traditional cash on cash: 8.13% Airbnb Rental Income: $873 Traditional Rental Income: $1662 Airbnb ROI: 1.3% Traditional ROI: 8.13%
109 Creekridge St Headland, AL Welcome to 109 Creekridge Street Headland, AL 36345 in our Creekridge Community. Find all ...	5 beds \| 3 baths \| 2,599 sq.ft.	$366,900	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 St 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.	$326,900	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 St Headland, AL Welcome to 108 Creekridge Street Headland, AL 36345 in our Creekridge community. The Madis...	4 beds \| 3 baths \| 1,942 sq.ft.	$333,900	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 NEW PRICE & Home Warranty with Roof Coverage!! Location LOCATION! Minutes to Dothan and He...	4 beds \| 2 baths \| 2,117 sq.ft.	$304,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $1918 Airbnb ROI: N/A Traditional ROI: 5.02%
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.	$331,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.96%
654 County Rd 21 Headland, AL EQUESTRIAN DREAM - Escape to the tranquility of country living with this exceptional pro...	4 beds \| 3 baths \| 2,997 sq.ft.	$589,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 4.75%
220 Wellington Way Headland, AL Step into style and comfort with this spacious 4-bedroom, 2-bath home featuring an open, s...	4 beds \| 2 baths \| 2,181 sq.ft.	$298,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.07% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: 6.07%
4876 County Road 49 Headland, AL New Construction home in Willow Walk Subdivision! This 4 Bedroom, 3 Bath home with upstair...	4 beds \| 3 baths \| 2,429 sq.ft.	$449,365	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2353 Airbnb ROI: N/A Traditional ROI: 4.31%
203 Heritage Way Headland, AL New Construction in Headland. Lot 18 Heritage Ridge S/D is one of the larger premium lots....	4 beds \| 2 baths \| 1,830 sq.ft.	$324,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.55% Airbnb Rental Income: $null Traditional Rental Income: $1834 Airbnb ROI: N/A Traditional ROI: 4.55%
113 Aubrey Ave Headland, AL Welcome to 113 Aubrey Avenue, our Aria, single-story floorplan at our Sagebrush community ...	3 beds \| 2 baths \| 1,618 sq.ft.	$242,400	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.97% Airbnb Rental Income: $873 Traditional Rental Income: $1784 Airbnb ROI: 0.53% Traditional ROI: 5.97%
100 Willow Oaks Dr Headland, AL Welcome to this beautiful 5 bedroom, 3.5 bath home situated on a large corner lot in the d...	5 beds \| 3 baths \| 3,041 sq.ft.	$449,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.3% Airbnb Rental Income: $null Traditional Rental Income: $5398 Airbnb ROI: N/A Traditional ROI: 11.3%

Real Estate investment in Headland, AL

There are 99 properties for sale in the city of Headland . The median list price in Headland is $239,900 and the average price per square foot is $110. In March 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,162.

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

There are 99 investment properties available for sale in Headland.

In 2026, 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 $1,162.

Your search for investment property begins and ends here

Investment Property for Sale in Headland, AL

505 Church Street

Headland, AL

3 beds | 2 baths | 1,583 sq.ft.

$214,900

Airbnb cash on cash: 0.78%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $873

Traditional Rental Income: $1533

Airbnb ROI: 0.78%

Traditional ROI: 5.66%

203 Cleveland St

Headland, AL

2 beds | 2 baths | 1,800 sq.ft.

$239,999

Airbnb cash on cash: 2.64%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $1463

Traditional Rental Income: $1887

Airbnb ROI: 2.64%

Traditional ROI: 6.34%

117 Walden Pond Rd

Headland, AL

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

$319,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $873

Traditional Rental Income: $2334

Airbnb ROI: 0.08%

Traditional ROI: 6.06%

106 Cabrio Way

Headland, AL

3 beds | 2 baths | 1,662 sq.ft.

$269,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 5.44%

Airbnb Rental Income: $873

Traditional Rental Income: $1809

Airbnb ROI: 0.62%

Traditional ROI: 5.44%

3885 County Road 12

Headland, AL

4 beds | 3 baths | 3,146 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.36%

Airbnb Rental Income: $null

Traditional Rental Income: $2876

Airbnb ROI: N/A

Traditional ROI: 6.36%

983 County Road 21

Headland, AL

4 beds | 3 baths | 3,488 sq.ft.

$869,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.09%

Airbnb Rental Income: $null

Traditional Rental Income: $1162

Airbnb ROI: N/A

Traditional ROI: -0.09%

208 Willow Oaks Dr

Headland, AL

6 beds | 3 baths | 2,884 sq.ft.

$352,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.49%

Airbnb Rental Income: $null

Traditional Rental Income: $2652

Airbnb ROI: N/A

Traditional ROI: 6.49%

2589 County Road 6

Headland, AL

3 beds | 2 baths | 1,560 sq.ft.

$199,900

Airbnb cash on cash: 1.19%

Traditional cash on cash: 6.61%

Airbnb Rental Income: $873

Traditional Rental Income: $1566

Airbnb ROI: 1.19%