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: 2.29% Traditional cash on cash: 4.66% Airbnb Rental Income: $1335 Traditional Rental Income: $1428 Airbnb ROI: 2.29% Traditional ROI: 4.66%
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: 2.19% Traditional cash on cash: 5.67% Airbnb Rental Income: $1335 Traditional Rental Income: $1809 Airbnb ROI: 2.19% Traditional ROI: 5.67%
3885 County Road 12 Headland, AL Discover unmatched value and versatility in this sprawling 3,146 sq. ft. all-brick residen...	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%
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: 2.67% Traditional cash on cash: 3.75% Airbnb Rental Income: $1335 Traditional Rental Income: $1165 Airbnb ROI: 2.67% 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%
501 Early Walden Rd Headland, AL This beautiful two story home is located in the desirable Headland community. Offering a g...	4 beds \| 4 baths \| 2,921 sq.ft.	$429,300	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $2709 Airbnb ROI: N/A Traditional ROI: 5.1%
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: 2.07% Traditional cash on cash: 5.56% Airbnb Rental Income: $1335 Traditional Rental Income: $1756 Airbnb ROI: 2.07% 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: 4.77% Traditional cash on cash: 6.96% Airbnb Rental Income: $1335 Traditional Rental Income: $1218 Airbnb ROI: 4.77% 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 Welcome to 308 Heritage Way, our beautiful single-story Hawthorne floorplan in our Heritag...	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.	$599,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $3639 Airbnb ROI: N/A Traditional ROI: 4.92%
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%
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: -0.04% Traditional cash on cash: 2.33% Airbnb Rental Income: $1335 Traditional Rental Income: $2358 Airbnb ROI: -0.04% 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: -0.51% Traditional cash on cash: -0.71% Airbnb Rental Income: $1116 Traditional Rental Income: $598 Airbnb ROI: -0.51% Traditional ROI: -0.71%
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.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $2247 Airbnb ROI: N/A Traditional ROI: 3.59%
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%
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: 5.17% Traditional cash on cash: 10.54% Airbnb Rental Income: $1335 Traditional Rental Income: $1570 Airbnb ROI: 5.17% 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%
608 Church Headland, AL New Construction in the beautiful city of Headland. Come view this 4 bed 2 1/2 bath homes ...	4 beds \| 3 baths \| 2,009 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.51% Airbnb Rental Income: $null Traditional Rental Income: $2122 Airbnb ROI: N/A Traditional ROI: 5.51%
466 COUNTY ROAD 18 Headland, AL UPDATED PHOTOS ADDED TO REFLECT CURRENT CONSTRUCTION PROGRESS New Construction â Nea...	5 beds \| 3 baths \| 3,014 sq.ft.	$452,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.85% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 4.85%
10 +-ac,Lot 1PL Cty Rd 140/ Cty Rd 141 Headland, AL 10 +-ac,Lot 1PL Cty Rd 140/ Cty Rd 141, Headland, AL 36345 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 1.49% Airbnb Rental Income: $1116 Traditional Rental Income: $430 Airbnb ROI: 4.18% Traditional ROI: 1.49%
Lot 7 Gilley Mill Rd Headland, AL Lot 7 Gilley Mill Rd, Headland, AL 36345 \| Other	N/A beds \| N/A baths \| N/A	$59,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 4.26% Airbnb Rental Income: $1116 Traditional Rental Income: $430 Airbnb ROI: 9.51% Traditional ROI: 4.26%
714 Main St. Headland, AL Full Brick home sitting on a sprawling 1.64 Acres for you to enjoy the serene views. Pull ...	3 beds \| 3 baths \| 2,217 sq.ft.	$258,000	Airbnb cash on cash: 2% Traditional cash on cash: 8.94% Airbnb Rental Income: $1335 Traditional Rental Income: $2613 Airbnb ROI: 2% Traditional ROI: 8.94%
1960 134 Headland, AL Fabulous custom built 4 bedroom, 2.5 bathroom, oversized 2 car garage, Craftsman open con...	4 beds \| 3 baths \| 2,318 sq.ft.	$399,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $2345 Airbnb ROI: N/A Traditional ROI: 4.93%

Real Estate investment in Headland, AL

There are 75 properties for sale in the city of Headland . The median list price in Headland is $299,000 and the average price per square foot is $137. In May 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,834.

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

There are 75 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 $1,834.

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: 2.29%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $1335

Traditional Rental Income: $1428

Airbnb ROI: 2.29%

Traditional ROI: 4.66%

106 Cabrio Way

Headland, AL

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

$269,900

Airbnb cash on cash: 2.19%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1335

Traditional Rental Income: $1809

Airbnb ROI: 2.19%

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%

616 Cleveland Street

Headland, AL

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

$235,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1335

Traditional Rental Income: $1165

Airbnb ROI: 2.67%

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

Traditional ROI: 4.35%

501 Early Walden Rd

Headland, AL

4 beds | 4 baths | 2,921 sq.ft.

$429,300

Airbnb cash on cash: N/A

Traditional cash on cash: 5.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2709

Airbnb ROI: N/A

Traditional ROI: 5.1%

108 Melissa Lane

Headland, AL

3 beds | 2 baths | 1,727 sq.ft.

$252,500

Airbnb cash on cash: 2.07%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $1335

Traditional Rental Income: $1756

Airbnb ROI: 2.07%