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.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: 6.68%
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: 0.05% Traditional cash on cash: 5.92% Airbnb Rental Income: $873 Traditional Rental Income: $2334 Airbnb ROI: 0.05% Traditional ROI: 5.92%
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%
209 Weeping Willow Trl Headland, AL Welcome to the best of both worlds. The ease of subdivision living, mixed with the quietne...	3 beds \| 2 baths \| 2,097 sq.ft.	$287,500	Airbnb cash on cash: 0.43% Traditional cash on cash: 6.96% Airbnb Rental Income: $873 Traditional Rental Income: $2308 Airbnb ROI: 0.43% Traditional ROI: 6.96%
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.	$220,000	Airbnb cash on cash: 1% Traditional cash on cash: 4.44% Airbnb Rental Income: $873 Traditional Rental Income: $1255 Airbnb ROI: 1% Traditional ROI: 4.44%
516 County Road 521 Headland, AL Welcome to the perfect mix of elegance and costum farmhouse combined. Tucked away on 3 acr...	3 beds \| 2 baths \| 2,530 sq.ft.	$415,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 3.56% Airbnb Rental Income: $873 Traditional Rental Income: $2025 Airbnb ROI: -0.26% 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: 0.66% Traditional cash on cash: 5.22% Airbnb Rental Income: $873 Traditional Rental Income: $1518 Airbnb ROI: 0.66% 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.	$443,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 3.87%
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: 0.79% Traditional cash on cash: 4.68% Airbnb Rental Income: $873 Traditional Rental Income: $1329 Airbnb ROI: 0.79% Traditional ROI: 4.68%
1532 County Road 20 Headland, AL STUNNING 2022-BUILT CRAFTSMAN IN HEADLAND! This 4BR/2BA home on a full acre blends modern ...	4 beds \| 2 baths \| 1,978 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $2039 Airbnb ROI: N/A Traditional ROI: 4.59%
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%
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.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.93% Airbnb Rental Income: $null Traditional Rental Income: $2568 Airbnb ROI: N/A Traditional ROI: 5.93%
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%
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.	$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%
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%
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.	$371,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 5.33%
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%
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%
3405 CR-22 Headland, AL SELLER OFFERING $10K UPFRONT CONCESSION TO BE USED AT THE BUYER'S DISCRETION Stunning 5-...	5 beds \| 4 baths \| 3,250 sq.ft.	$649,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.44%
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.	$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 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%
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.	$336,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.39%
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.	$331,900	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $1780 Airbnb ROI: N/A Traditional ROI: 4%
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.	$338,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.36%
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.	$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%
514 Main Street Headland, AL Welcome to 514 S Main Street, an elegant Southern ranch-style residence located in the sou...	5 beds \| 4 baths \| 4,014 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.38% Airbnb Rental Income: $null Traditional Rental Income: $4058 Airbnb ROI: N/A Traditional ROI: 9.38%
206 Cambridge Dr Headland, AL Welcome to this beautifully designed 2,309 sq ft, 4-bedroom, 2.5-bath home with a smart sp...	4 beds \| 3 baths \| 2,309 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.89% Airbnb Rental Income: $null Traditional Rental Income: $2243 Airbnb ROI: N/A Traditional ROI: 5.89%
390 County Road 11 Headland, AL BEAUTIFUL CUSTOM HOME W/ ACREAGE WELCOMES YOU AS SOON AS YOU PULL INTO THE DRIVEWAY. GORGE...	4 beds \| 4 baths \| 3,089 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $3126 Airbnb ROI: N/A Traditional ROI: 4.18%
654 County Rd 21 Headland, AL EQUESTRIAN DREAM - Escape to the tranquility of country living with this exceptional pro...	4 beds \| 4 baths \| 3,000 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 3.95%
128 Edgewood Trail Headland, AL Welcome to this thoughtfully designed 1,531 sq. ft. home featuring 3 bedrooms, 2 bathrooms...	3 beds \| 2 baths \| 1,531 sq.ft.	$238,900	Airbnb cash on cash: 0.91% Traditional cash on cash: 5.66% Airbnb Rental Income: $873 Traditional Rental Income: $1612 Airbnb ROI: 0.91% Traditional ROI: 5.66%

Real Estate investment in Headland, AL

There are 78 properties for sale in the city of Headland . The median list price in Headland is $333,400 and the average price per square foot is $148. In December 2025, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $2,030.

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

There are 78 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 $2,030.

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.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: 6.68%

117 Walden Pond Road

Headland, AL

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

$325,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $873

Traditional Rental Income: $2334

Airbnb ROI: 0.05%

Traditional ROI: 5.92%

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%

209 Weeping Willow Trl

Headland, AL

3 beds | 2 baths | 2,097 sq.ft.

$287,500

Airbnb cash on cash: 0.43%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $873

Traditional Rental Income: $2308

Airbnb ROI: 0.43%

Traditional ROI: 6.96%

2589 County Road 6

Headland, AL

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

$220,000

Airbnb cash on cash: 1%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $873

Traditional Rental Income: $1255

Airbnb ROI: 1%

Traditional ROI: 4.44%

516 County Road 521

Headland, AL

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

$415,000

Airbnb cash on cash: -0.26%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $873

Traditional Rental Income: $2025

Airbnb ROI: -0.26%

Traditional ROI: 3.56%

622 Peachtree Street

Headland, AL

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

$227,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $873

Traditional Rental Income: $1518

Airbnb ROI: 0.66%

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