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
103 WEEPING WILLOW TRL Headland, AL This beautifully maintained 4-bedroom, 2-bath home offers an inviting open floor plan desi...	4 beds \| 2 baths \| 2,118 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 4.91%
983 COUNTY ROAD 21 Headland, AL Welcome to this 30 Acres Estate with CREEK ACCESS in Headland, Alabama home offering 3,488...	4 beds \| 4 baths \| 3,488 sq.ft.	$815,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.23% Airbnb Rental Income: $null Traditional Rental Income: $3616 Airbnb ROI: N/A Traditional ROI: 3.23%
213 Rock Creek Rd Headland, AL Welcome to 213 Rock Creek Rd in Headland! This 3-bedroom, 2-bathroom home offers 1,056 squ...	3 beds \| 2 baths \| 1,056 sq.ft.	$129,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 7.34% Airbnb Rental Income: $946 Traditional Rental Income: $1179 Airbnb ROI: 2.66% Traditional ROI: 7.34%
407 County Road 17 Headland, AL Stunning Barndominium on 10 Fully Fenced Acres in Headland! If you've been looking for spa...	3 beds \| 3 baths \| 2,891 sq.ft.	$525,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.32% Airbnb Rental Income: $946 Traditional Rental Income: $2411 Airbnb ROI: -0.38% Traditional ROI: 3.32%
116 Heritage Way Headland, AL This beautiful 4 bedroom, 3 bathroom custom-built home offers the perfect combination of m...	4 beds \| 3 baths \| 2,436 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 4.1%
772 Geiger Rd Headland, AL Like-new and move-in ready! Built in 2023, this beautiful home offers modern finishes, a f...	3 beds \| 2 baths \| 1,708 sq.ft.	$262,400	Airbnb cash on cash: 0.63% Traditional cash on cash: 3.26% Airbnb Rental Income: $946 Traditional Rental Income: $1251 Airbnb ROI: 0.63% Traditional ROI: 3.26%
106 Lakeview Lane Headland, AL Luxury lakefront living in the highly sought-after Headland School District! This newly bu...	3 beds \| 4 baths \| 3,497 sq.ft.	$799,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.64% Airbnb Rental Income: $946 Traditional Rental Income: $2364 Airbnb ROI: -0.73% Traditional ROI: 1.64%
2324 County Road 33 Headland, AL Updated Cutie on 1 acre! 4 bedrooms, 2 bathrooms home sits on large wooded lot. Open floor...	4 beds \| 2 baths \| 1,907 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 5% Airbnb Rental Income: $null Traditional Rental Income: $1786 Airbnb ROI: N/A Traditional ROI: 5%
124 Weeping Willow Trl Headland, AL This newly built Craftsman-style home offers a beautiful blend of comfort, style, and spac...	4 beds \| 3 baths \| 2,234 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2439 Airbnb ROI: N/A Traditional ROI: 4.42%
501 Early Walden Rd Headland, AL Beautifully crafted and thoughtfully designed, this stunning Craftsman home, built in 2022...	4 beds \| 4 baths \| 2,311 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $2709 Airbnb ROI: N/A Traditional ROI: 5.24%
108 Melissa Lane Headland, AL Welcome home to this charming three-bedroom, two-bath retreat in Headland, where comfort, ...	3 beds \| 2 baths \| 1,727 sq.ft.	$238,500	Airbnb cash on cash: 0.84% Traditional cash on cash: 5.97% Airbnb Rental Income: $946 Traditional Rental Income: $1756 Airbnb ROI: 0.84% Traditional ROI: 5.97%
208 Wellington Way Headland, AL Why wait on new construction when this one is already complete and move-in ready? Welcome ...	4 beds \| 2 baths \| 2,146 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $2019 Airbnb ROI: N/A Traditional ROI: 5.33%
618 Peachtree Street Headland, AL Affordable Headland living with room to spread out! Welcome to 618 Peachtree Street, a ver...	3 beds \| 2 baths \| 1,618 sq.ft.	$159,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 8.27% Airbnb Rental Income: $946 Traditional Rental Income: $1573 Airbnb ROI: 1.9% Traditional ROI: 8.27%
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.	$315,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.53%
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: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 4.84%
907 Early Walden Rd. Headland, AL Seclusion and Serenity await you in Headland, Alabama! Come tour this "One of a Kind Prope...	4 beds \| 3 baths \| 2,548 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.52% Airbnb Rental Income: $null Traditional Rental Income: $2630 Airbnb ROI: N/A Traditional ROI: 4.52%
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.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $1917 Airbnb ROI: N/A Traditional ROI: 4.87%
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.	$315,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 4.42%
405 Cleveland Headland, AL Charming Historic Home in the Heart of Headland. Enjoy the charm of historic Headland in t...	3 beds \| 2 baths \| 1,900 sq.ft.	$219,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 7.19% Airbnb Rental Income: $946 Traditional Rental Income: $1877 Airbnb ROI: 1.03% Traditional ROI: 7.19%
296 County Road 79 Headland, AL Escape to your own slice of country paradise in this spacious 3-bedroom, 2-bath home on 3 ...	3 beds \| 2 baths \| 1,756 sq.ft.	$277,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.8% Airbnb Rental Income: $946 Traditional Rental Income: $1716 Airbnb ROI: 0.53% Traditional ROI: 4.8%
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.	$315,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $1780 Airbnb ROI: N/A Traditional ROI: 4.17%
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.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.6% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.6%
900 County Road 165 Headland, AL Discover the perfect blend of country charm and modern comfort on this exceptional 5- acre...	3 beds \| 3 baths \| 3,637 sq.ft.	$629,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.45% Airbnb Rental Income: $946 Traditional Rental Income: $2358 Airbnb ROI: -0.55% Traditional ROI: 2.45%
126 Edgewood Trail Headland, AL This beautiful home in the new construction subdivision of The Cove on Main has the extras...	3 beds \| 2 baths \| 1,820 sq.ft.	$279,500	Airbnb cash on cash: 0.76% Traditional cash on cash: 5.28% Airbnb Rental Income: $946 Traditional Rental Income: $1790 Airbnb ROI: 0.76% Traditional ROI: 5.28%
510 Woodham Headland, AL This home was completely updated and remodeled in 2024/25 with new architectural shingle r...	3 beds \| 2 baths \| 1,643 sq.ft.	$289,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.93% Airbnb Rental Income: $946 Traditional Rental Income: $1550 Airbnb ROI: 0.44% Traditional ROI: 3.93%
205 Heritage Way Headland, AL New Construction in Headland on Lot 19 Heritage Ridge Subdivision. 1.32 acres lot. Pantry ...	4 beds \| 3 baths \| 2,350 sq.ft.	$419,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2340 Airbnb ROI: N/A Traditional ROI: 4.61%
865 COUNTY ROAD 20 Headland, AL hOME WILL BE COMPLETED IN LESS THAN 30 DAYS! Beautiful custom new construction home that i...	4 beds \| 2 baths \| 1,950 sq.ft.	$401,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $1995 Airbnb ROI: N/A Traditional ROI: 3.64%
415 Bradford Headland, AL Move-in ready and beautifully updated with fresh neutral paint and brand-new flooring thro...	5 beds \| 2 baths \| 1,744 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.77% Airbnb Rental Income: $null Traditional Rental Income: $1840 Airbnb ROI: N/A Traditional ROI: 10.77%
3546 County Road 13 Headland, AL Beautiful almost-new home situated on 10 acres in the highly desirable Headland school dis...	5 beds \| 5 baths \| 3,448 sq.ft.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.43% Airbnb Rental Income: $null Traditional Rental Income: $5068 Airbnb ROI: N/A Traditional ROI: 5.43%
108 Buckhead Drive Headland, AL Welcome to timeless Southern charm on nearly 4 acres in Headland. This beautifully updated...	4 beds \| 3 baths \| 3,300 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2900 Airbnb ROI: N/A Traditional ROI: 3.73%
105 Heritage Way Headland, AL Welcome to 105 Heritage Way, our beautiful one-story Madison floorplan featured in the Her...	4 beds \| 3 baths \| 1,942 sq.ft.	$324,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2050 Airbnb ROI: N/A Traditional ROI: 5.26%
112 Aubrey Avenue Headland, AL Welcome to 112 Aubrey Avenue, our beautiful one-story Delilah floorplan featured in our Sa...	3 beds \| 2 baths \| 1,281 sq.ft.	$209,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 5.38% Airbnb Rental Income: $946 Traditional Rental Income: $1487 Airbnb ROI: 0.92% Traditional ROI: 5.38%
904 W KING STREET Headland, AL Well maintained 3 Bedroom, 2 Bath featuring an 2-car attached garage plus a detached garag...	3 beds \| 2 baths \| 1,562 sq.ft.	$248,500	Airbnb cash on cash: 0.58% Traditional cash on cash: 4.31% Airbnb Rental Income: $946 Traditional Rental Income: $1474 Airbnb ROI: 0.58% Traditional ROI: 4.31%
129 Sagebrush Drive Headland, AL Welcome to 129 Sagebrush Drive, the Aria floorplan featured in our Sagebrush Community in ...	3 beds \| 2 baths \| 1,618 sq.ft.	$244,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.83% Airbnb Rental Income: $946 Traditional Rental Income: $1578 Airbnb ROI: 0.6% Traditional ROI: 4.83%
761 County rd 45 Headland, AL Welcome to 761 County Road 45, where peaceful country living meets everyday comfort. Sitti...	3 beds \| 2 baths \| 1,611 sq.ft.	$175,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 6.01% Airbnb Rental Income: $946 Traditional Rental Income: $1331 Airbnb ROI: 1.62% Traditional ROI: 6.01%
501 Cable Rd. Headland, AL Welcome home to this charming brick residence situated on a spacious corner lot of approxi...	3 beds \| 3 baths \| 2,325 sq.ft.	$250,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 7.29% Airbnb Rental Income: $946 Traditional Rental Income: $2128 Airbnb ROI: 0.82% Traditional ROI: 7.29%
207 Cabrio Way Headland, AL Welcome to 207 Cabrio Way in the desirable Trace Manor Subdivision of Headland, Alabama. B...	3 beds \| 2 baths \| 2,085 sq.ft.	$329,500	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.8% Airbnb Rental Income: $946 Traditional Rental Income: $1924 Airbnb ROI: 0.53% Traditional ROI: 4.8%
129 Wellington Way Headland, AL Enjoy comfortable, low-maintenance living in this thoughtfully designed 1,534-square-foot ...	3 beds \| 2 baths \| 1,534 sq.ft.	$246,900	Airbnb cash on cash: 0.99% Traditional cash on cash: 5.05% Airbnb Rental Income: $946 Traditional Rental Income: $1547 Airbnb ROI: 0.99% Traditional ROI: 5.05%
267 Ridge Drive Headland, AL Welcome to this beautiful home offering the perfect blend of space, comfort, and scenic su...	4 beds \| 4 baths \| 3,292 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $3146 Airbnb ROI: N/A Traditional ROI: 4.44%
109 VICTORIA DR Headland, AL Welcome home to this beautifully updated 4-bedroom, 2-bath home offering 1,371 square feet...	4 beds \| 2 baths \| 1,371 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.12% Airbnb Rental Income: $null Traditional Rental Income: $1492 Airbnb ROI: N/A Traditional ROI: 7.12%

Real Estate investment in Headland, AL

There are 83 properties for sale in the city of Headland . The median list price in Headland is $282,865 and the average price per square foot is $136. In November 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,868.

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

There are 83 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 $1,868.

Your search for investment property begins and ends here

Investment Property for Sale in Headland, AL

103 WEEPING WILLOW TRL

Headland, AL

4 beds | 2 baths | 2,118 sq.ft.

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.91%

Airbnb Rental Income: $null

Traditional Rental Income: $1995

Airbnb ROI: N/A

Traditional ROI: 4.91%

983 COUNTY ROAD 21

Headland, AL

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

$815,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.23%

Airbnb Rental Income: $null

Traditional Rental Income: $3616

Airbnb ROI: N/A

Traditional ROI: 3.23%

213 Rock Creek Rd

Headland, AL

3 beds | 2 baths | 1,056 sq.ft.

$129,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 7.34%

Airbnb Rental Income: $946

Traditional Rental Income: $1179

Airbnb ROI: 2.66%

Traditional ROI: 7.34%

407 County Road 17

Headland, AL

3 beds | 3 baths | 2,891 sq.ft.

$525,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $946

Traditional Rental Income: $2411

Airbnb ROI: -0.38%

Traditional ROI: 3.32%

116 Heritage Way

Headland, AL

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

$419,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2281

Airbnb ROI: N/A

Traditional ROI: 4.1%

772 Geiger Rd

Headland, AL

3 beds | 2 baths | 1,708 sq.ft.

$262,400

Airbnb cash on cash: 0.63%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $946

Traditional Rental Income: $1251

Airbnb ROI: 0.63%

Traditional ROI: 3.26%

106 Lakeview Lane

Headland, AL

3 beds | 4 baths | 3,497 sq.ft.

$799,900

Airbnb cash on cash: -0.73%

Traditional cash on cash: 1.64%

Airbnb Rental Income: $946

Traditional Rental Income: $2364

Airbnb ROI: -0.73%

Traditional ROI: 1.64%

2324 County Road 33

Headland, AL

4 beds | 2 baths | 1,907 sq.ft.

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5%

Airbnb Rental Income: $null

Traditional Rental Income: $1786

Airbnb ROI: N/A