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
102 Weeping Willow Trail Headland, AL Beautifully maintained 4-bedroom home near Headland Country Club! Enjoy the perks of livin...	4 beds \| 2 baths \| 2,271 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.78% Airbnb Rental Income: $null Traditional Rental Income: $2290 Airbnb ROI: N/A Traditional ROI: 5.78%
110 Willow Way Headland, AL Welcome home to this adorable gem in Headland! Nestled near the end of a quiet cul-de-sac ...	3 beds \| 2 baths \| 1,378 sq.ft.	$225,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.66% Airbnb Rental Income: $1342 Traditional Rental Income: $1428 Airbnb ROI: 2.32% Traditional ROI: 4.66%
115 Willow Way Headland, AL Welcome to a meticulously maintained home offering the perfect blend of modern convenience...	3 beds \| 2 baths \| 1,484 sq.ft.	$227,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 5.97% Airbnb Rental Income: $1342 Traditional Rental Income: $1685 Airbnb ROI: 2.47% Traditional ROI: 5.97%
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: 2.22% Traditional cash on cash: 5.67% Airbnb Rental Income: $1342 Traditional Rental Income: $1809 Airbnb ROI: 2.22% Traditional ROI: 5.67%
3885 County Road 12 Headland, AL NOW REDUCED TO $384,900! Discover unmatched value in this sprawling 3,146 sq. ft. all-bric...	4 beds \| 3 baths \| 3,146 sq.ft.	$384,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $2876 Airbnb ROI: N/A Traditional ROI: 6.55%
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.	$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%
616 Cleveland Street Headland, AL Traditional style home located in Headland AL. 3 bedrooms, and 2 bathrooms. Custom showe...	3 beds \| 2 baths \| 1,582 sq.ft.	$235,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.75% Airbnb Rental Income: $1342 Traditional Rental Income: $1165 Airbnb ROI: 2.69% Traditional ROI: 3.75%
104 Creekridge St Headland, AL Welcome to this beautifully maintained 2023 built home in the highly sought-after Headland...	4 beds \| 3 baths \| 2,682 sq.ft.	$413,800	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2326 Airbnb ROI: N/A Traditional ROI: 4.35%
200 forrest street Headland, AL Charming three-bedroom, two-bath home with a versatile bonus room that could serve as a fo...	3 beds \| 2 baths \| 1,814 sq.ft.	$193,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 8.87% Airbnb Rental Income: $1342 Traditional Rental Income: $1939 Airbnb ROI: 3.37% Traditional ROI: 8.87%
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.	$252,500	Airbnb cash on cash: 2.1% Traditional cash on cash: 5.56% Airbnb Rental Income: $1342 Traditional Rental Income: $1756 Airbnb ROI: 2.1% Traditional ROI: 5.56%
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.	$319,400	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.47%
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: 4.81% Traditional cash on cash: 6.96% Airbnb Rental Income: $1342 Traditional Rental Income: $1218 Airbnb ROI: 4.81% Traditional ROI: 6.96%
2087 County Rd 15 Headland, AL Located in Headland, this home is newly renovated and in a great location. Home comes with...	4 beds \| 3 baths \| 2,375 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $2410 Airbnb ROI: N/A Traditional ROI: 4.23%
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.	$319,400	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 4.95%
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: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 4.91%
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.	$331,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $1761 Airbnb ROI: N/A Traditional ROI: 4.25%
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.	$369,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.34% Airbnb Rental Income: $null Traditional Rental Income: $2431 Airbnb ROI: N/A Traditional ROI: 5.34%
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.	$326,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $1917 Airbnb ROI: N/A Traditional ROI: 4.84%
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.	$321,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 4.41%
3405 CR-22 Headland, AL MOTIVATED SELLER Stunning 5-Bedroom Home on 8 Acres â Headland, AL Paradise! Welcome t...	5 beds \| 4 baths \| 3,250 sq.ft.	$614,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.77%
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.	$168,500	Airbnb cash on cash: 3.79% Traditional cash on cash: 8.35% Airbnb Rental Income: $1342 Traditional Rental Income: $1662 Airbnb ROI: 3.79% Traditional ROI: 8.35%
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.	$361,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2334 Airbnb ROI: N/A Traditional ROI: 5.19%
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.	$321,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $1780 Airbnb ROI: N/A Traditional ROI: 4.16%
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.	$328,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 4.53%
654 County Rd 21 Headland, AL EQUESTRIAN DREAM - Escape to the tranquility of country living with this exceptional pro...	4 beds \| 4 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%
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: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1834 Airbnb ROI: N/A Traditional ROI: 4.63%
123 Edgewood Trail Headland, AL Welcome to this 2,136 square foot new construction home featuring 4 bedrooms, 2 bathrooms,...	4 beds \| 2 baths \| 2,136 sq.ft.	$291,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $2067 Airbnb ROI: N/A Traditional ROI: 6.14%
900 County Road 165 Headland, AL Quiet country setting on 5 acres with chlorine pool w/ NEW LINER , party barn 30x24 fully ...	3 beds \| 3 baths \| 3,637 sq.ft.	$649,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 2.33% Airbnb Rental Income: $1342 Traditional Rental Income: $2358 Airbnb ROI: -0.03% Traditional ROI: 2.33%
TBD Us Hwy 431 Ave Headland, AL TBD Us Hwy 431 Ave, Dothan, AL 36345 \| Other	N/A beds \| N/A baths \| N/A	$775,000	Airbnb cash on cash: -0.48% Traditional cash on cash: -0.71% Airbnb Rental Income: $1143 Traditional Rental Income: $598 Airbnb ROI: -0.48% Traditional ROI: -0.71%
238 County Road 263 Headland, AL SELLER MOTIVATED TO SELL Escape to the peace and privacy of country living with this 2,6...	4 beds \| 3 baths \| 2,656 sq.ft.	$376,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.26% Airbnb Rental Income: $null Traditional Rental Income: $3097 Airbnb ROI: N/A Traditional ROI: 7.26%
12 Solomon Road Headland, AL Perfectly located just south of the charming Headland Square in the sought-after Headland ...	4 beds \| 3 baths \| 2,280 sq.ft.	$399,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $2491 Airbnb ROI: N/A Traditional ROI: 5.07%
443 Ridge Drive Headland, AL HEADLAND!! Custom built brick home in a fantastic neighborhood in Headland, AL. 2588 sq ft...	4 beds \| 3 baths \| 2,588 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $2247 Airbnb ROI: N/A Traditional ROI: 3.5%
103 Stonegate Dr Headland, AL Immaculate all-brick home located in Stonegate Subdivision in Headland. This 1-owner home ...	4 beds \| 3 baths \| 2,717 sq.ft.	$436,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.35% Airbnb Rental Income: $null Traditional Rental Income: $2818 Airbnb ROI: N/A Traditional ROI: 5.35%
201 Heritage Way Headland, AL New Construction in Headland. Lot 17 Heritage Ridge. 2.77 Acres Lot. Pantry in Kitchen. Ma...	4 beds \| 3 baths \| 2,350 sq.ft.	$444,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2323 Airbnb ROI: N/A Traditional ROI: 4.31%
260 Weeping Willow Trail Headland, AL Charming New Cottage-Style Home in Willow Walk! Welcome to this beautiful brand-new 4-bed...	4 beds \| 2 baths \| 2,002 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.95% Airbnb Rental Income: $null Traditional Rental Income: $2136 Airbnb ROI: N/A Traditional ROI: 5.95%
418 Main Headland, AL Take a look at this recently updated home! This home is zoned for Headland Schools and has...	3 beds \| 2 baths \| 1,528 sq.ft.	$125,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 10.54% Airbnb Rental Income: $1342 Traditional Rental Income: $1570 Airbnb ROI: 5.21% Traditional ROI: 10.54%
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.	$414,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2340 Airbnb ROI: N/A Traditional ROI: 4.73%
319 County Rd 79 Headland, AL Nestled in a serene, 10-acre countryside setting, this unique property offers endless poss...	5 beds \| 2 baths \| 8,000 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $2031 Airbnb ROI: N/A Traditional ROI: 1.57%
125 Tanglewood Drive Headland, AL Welcome home to this beautifully maintained property thoughtfully designed with elegance &...	4 beds \| 3 baths \| 2,725 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2423 Airbnb ROI: N/A Traditional ROI: 4.61%

Real Estate investment in Headland, AL

There are 77 properties for sale in the city of Headland . The median list price in Headland is $309,900 and the average price per square foot is $143. In April 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,917.

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

There are 77 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 $1,917.

Your search for investment property begins and ends here

Investment Property for Sale in Headland, AL

102 Weeping Willow Trail

Headland, AL

4 beds | 2 baths | 2,271 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2290

Airbnb ROI: N/A

Traditional ROI: 5.78%

110 Willow Way

Headland, AL

3 beds | 2 baths | 1,378 sq.ft.

$225,000

Airbnb cash on cash: 2.32%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $1342

Traditional Rental Income: $1428

Airbnb ROI: 2.32%

Traditional ROI: 4.66%

115 Willow Way

Headland, AL

3 beds | 2 baths | 1,484 sq.ft.

$227,900

Airbnb cash on cash: 2.47%

Traditional cash on cash: 5.97%

Airbnb Rental Income: $1342

Traditional Rental Income: $1685

Airbnb ROI: 2.47%

Traditional ROI: 5.97%

106 Cabrio Way

Headland, AL

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

$269,900

Airbnb cash on cash: 2.22%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1342

Traditional Rental Income: $1809

Airbnb ROI: 2.22%

Traditional ROI: 5.67%

3885 County Road 12

Headland, AL

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

$384,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2876

Airbnb ROI: N/A

Traditional ROI: 6.55%

264 Weeping Willow Trail

Headland, AL

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%

616 Cleveland Street

Headland, AL

3 beds | 2 baths | 1,582 sq.ft.

$235,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1342

Traditional Rental Income: $1165

Airbnb ROI: 2.69%

Traditional ROI: 3.75%

104 Creekridge St

Headland, AL

4 beds | 3 baths | 2,682 sq.ft.

$413,800

Airbnb cash on cash: N/A

Traditional cash on cash: 4.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2326

Airbnb ROI: N/A