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.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.24% Airbnb Rental Income: $null Traditional Rental Income: $2290 Airbnb ROI: N/A Traditional ROI: 6.24%
318 S Main Street Headland, AL Step into this beautifully restored Craftsman-style home in the heart of Headland, that ha...	3 beds \| 3 baths \| 2,384 sq.ft.	$349,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 3.13% Airbnb Rental Income: $1673 Traditional Rental Income: $1584 Airbnb ROI: 1.97% Traditional ROI: 3.13%
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%
202 Cabrio Way Headland, AL 4 bedrooms and 3 bathrooms. Primary and one guess bedroom with its own private bathroom. H...	4 beds \| 3 baths \| 2,087 sq.ft.	$324,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2276 Airbnb ROI: N/A Traditional ROI: 5.74%
113 Cabrio Way Headland, AL Immaculate like new home located in Trace Manor in Headland. Home is situated on cul-de-sa...	3 beds \| 2 baths \| 1,803 sq.ft.	$320,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.95% Airbnb Rental Income: $1673 Traditional Rental Income: $1706 Airbnb ROI: 2.29% Traditional ROI: 3.95%
213 Rock Creek Road Headland, AL Start your homeownership journey or downsize with purpose! This completely remodeled 3-bed...	3 beds \| 2 baths \| 1,056 sq.ft.	$159,999	Airbnb cash on cash: 5.86% Traditional cash on cash: 5.69% Airbnb Rental Income: $1673 Traditional Rental Income: $1179 Airbnb ROI: 5.86% Traditional ROI: 5.69%
603 Carr Circle Headland, AL Traditional style 3 bedroom, 1 bath home. Home features Electric fireplace, LVP flooring, ...	3 beds \| 1 baths \| 1,366 sq.ft.	$178,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 5.38% Airbnb Rental Income: $1673 Traditional Rental Income: $1244 Airbnb ROI: 5.15% Traditional ROI: 5.38%
195 Hazel Drive Headland, AL UPDATED!!! and OVER 2,000 sq. ft. of living space, plus an oversized 800+ sq. ft. OVERSIZE...	4 beds \| 2 baths \| 2,654 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.44% Airbnb Rental Income: $null Traditional Rental Income: $2061 Airbnb ROI: N/A Traditional ROI: 10.44%
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.	$388,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2326 Airbnb ROI: N/A Traditional ROI: 4.73%
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.	$839,900	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.5% Airbnb Rental Income: $1673 Traditional Rental Income: $2364 Airbnb ROI: 0.01% Traditional ROI: 1.5%
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.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $1786 Airbnb ROI: N/A Traditional ROI: 4.88%
209 Heritage Way Headland, AL Lot 21 Heritage Ridge Sub-Division on 2.36 Acres. Granite countertops, kitchen pantry, bed...	4 beds \| 3 baths \| 2,350 sq.ft.	$454,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 2.74%
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.	$247,500	Airbnb cash on cash: 3.34% Traditional cash on cash: 5.7% Airbnb Rental Income: $1673 Traditional Rental Income: $1756 Airbnb ROI: 3.34% Traditional ROI: 5.7%
3405 CR-22 Headland, AL MOTIVATED SELLER Stunning 5-Bedroom Home on 8 Acres - Headland, AL Paradise! Welcome to ...	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%
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.	$629,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 2.45% Airbnb Rental Income: $1673 Traditional Rental Income: $2358 Airbnb ROI: 0.49% Traditional ROI: 2.45%
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: -0.59% Traditional cash on cash: -0.71% Airbnb Rental Income: $1051 Traditional Rental Income: $598 Airbnb ROI: -0.59% Traditional ROI: -0.71%
238 County Road 263 Headland, AL Traditional style home, with a wood burning fireplace. 3 bedrooms and 2 full bathrooms on ...	4 beds \| 3 baths \| 2,656 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.28% Airbnb Rental Income: $null Traditional Rental Income: $3097 Airbnb ROI: N/A Traditional ROI: 8.28%
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.	$388,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $2491 Airbnb ROI: N/A Traditional ROI: 5.25%
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.	$432,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.41% Airbnb Rental Income: $null Traditional Rental Income: $2818 Airbnb ROI: N/A Traditional ROI: 5.41%
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 S 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.	$120,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 11% Airbnb Rental Income: $1673 Traditional Rental Income: $1570 Airbnb ROI: 7.85% Traditional ROI: 11%
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: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $2340 Airbnb ROI: N/A Traditional ROI: 4.66%
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%
409 Peachtree St Headland, AL Beautifully remodeled and move-in ready, this charming 3-bedroom, 2-bath home is located i...	3 beds \| 2 baths \| 1,559 sq.ft.	$209,900	Airbnb cash on cash: 4.34% Traditional cash on cash: 5.91% Airbnb Rental Income: $1673 Traditional Rental Income: $1519 Airbnb ROI: 4.34% Traditional ROI: 5.91%
608 E 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.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.71% Airbnb Rental Income: $null Traditional Rental Income: $2122 Airbnb ROI: N/A Traditional ROI: 5.71%
869 County Road 45 Headland, AL Enjoy peaceful country living with modern updates in this beautifully remodeled mobile hom...	2 beds \| 2 baths \| 1,315 sq.ft.	$89,999	Airbnb cash on cash: N/A Traditional cash on cash: 8.74% Airbnb Rental Income: $null Traditional Rental Income: $987 Airbnb ROI: N/A Traditional ROI: 8.74%
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: 3.71% Traditional cash on cash: 1.49% Airbnb Rental Income: $1051 Traditional Rental Income: $430 Airbnb ROI: 3.71% Traditional ROI: 1.49%
1960 E 134 Headland, AL Fabulous custom built 4 bedroom, 2.5 bathroom, oversized 2 car garage, Craftsman open conc...	4 beds \| 3 baths \| 2,318 sq.ft.	$389,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.08% Airbnb Rental Income: $null Traditional Rental Income: $2345 Airbnb ROI: N/A Traditional ROI: 5.08%
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%
891 County Road 20 Headland, AL HOME WILL BE COMPLETED IN LESS THAN 45 DAYS! Beautiful custom new construction home that i...	4 beds \| 2 baths \| 1,975 sq.ft.	$401,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $2038 Airbnb ROI: N/A Traditional ROI: 3.76%
4200 S County Road 83 Headland, AL Nice updated home on 3.46 acres located just outside of the Headland. This property includ...	4 beds \| 3 baths \| 2,860 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2796 Airbnb ROI: N/A Traditional ROI: 4.8%
132 Edgewood Trail Headland, AL Spacious and thoughtfully designed, this 1,827 sq. ft. home offers 3 bedrooms, 2 bathrooms...	3 beds \| 2 baths \| 1,827 sq.ft.	$273,900	Airbnb cash on cash: 2.89% Traditional cash on cash: 5.09% Airbnb Rental Income: $1673 Traditional Rental Income: $1772 Airbnb ROI: 2.89% Traditional ROI: 5.09%
200 Cable St Headland, AL Welcome to this beautifully remodeled 3 bedroom, 2 bath home in Headland! Conveniently loc...	3 beds \| 2 baths \| 1,452 sq.ft.	$180,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 6.57% Airbnb Rental Income: $1673 Traditional Rental Income: $1461 Airbnb ROI: 5.08% Traditional ROI: 6.57%
209 Cambridge Dr Headland, AL This spacious 2,563 SqFt home offers an exceptional blend of style, comfort, and functiona...	4 beds \| 3 baths \| 2,563 sq.ft.	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $2346 Airbnb ROI: N/A Traditional ROI: 5.17%
925 W King St Headland, AL Charming country home on 2+ acres - minutes from downtown Headland and Dothan! This 3-bed,...	3 beds \| 2 baths \| 1,570 sq.ft.	$299,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.77% Airbnb Rental Income: $1673 Traditional Rental Income: $1529 Airbnb ROI: 2.62% Traditional ROI: 3.77%
300 E County Rd 32 E Headland, AL Barndominium on 10 Acres w/ entrance gate. Bldg is 56'x56' w/ 18' eaves & 26' peak upgrade...	1 beds \| 2 baths \| 2,292 sq.ft.	$835,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.22% Airbnb Rental Income: $null Traditional Rental Income: $2136 Airbnb ROI: N/A Traditional ROI: 1.22%
133 Edgewood Trail Headland, AL This beautifully crafted 2,086 sq. ft. home offers 4 bedrooms, 2 bathrooms, and a two-car ...	4 beds \| 2 baths \| 2,086 sq.ft.	$291,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $2023 Airbnb ROI: N/A Traditional ROI: 5.62%
134 Edgewood Trail Headland, AL This inviting 1,839 sq. ft. home features 3 bedrooms, 2 bathrooms, and a two-car garage, o...	3 beds \| 2 baths \| 1,839 sq.ft.	$276,900	Airbnb cash on cash: 2.85% Traditional cash on cash: 5.03% Airbnb Rental Income: $1673 Traditional Rental Income: $1774 Airbnb ROI: 2.85% Traditional ROI: 5.03%

Real Estate investment in Headland, AL

There are 65 properties for sale in the city of Headland . The median list price in Headland is $285,517 and the average price per square foot is $126. In June 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,780.

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

There are 65 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 $1,780.

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.

$305,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2290

Airbnb ROI: N/A

Traditional ROI: 6.24%

318 S Main Street

Headland, AL

3 beds | 3 baths | 2,384 sq.ft.

$349,900

Airbnb cash on cash: 1.97%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $1673

Traditional Rental Income: $1584

Airbnb ROI: 1.97%

Traditional ROI: 3.13%

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%

202 Cabrio Way

Headland, AL

4 beds | 3 baths | 2,087 sq.ft.

$324,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2276

Airbnb ROI: N/A

Traditional ROI: 5.74%

113 Cabrio Way

Headland, AL

3 beds | 2 baths | 1,803 sq.ft.

$320,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1673

Traditional Rental Income: $1706

Airbnb ROI: 2.29%

Traditional ROI: 3.95%

213 Rock Creek Road

Headland, AL

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

$159,999

Airbnb cash on cash: 5.86%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1673

Traditional Rental Income: $1179

Airbnb ROI: 5.86%

Traditional ROI: 5.69%

603 Carr Circle

Headland, AL

3 beds | 1 baths | 1,366 sq.ft.

$178,000

Airbnb cash on cash: 5.15%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $1673

Traditional Rental Income: $1244

Airbnb ROI: 5.15%

Traditional ROI: 5.38%

195 Hazel Drive

Headland, AL

4 beds | 2 baths | 2,654 sq.ft.

$179,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2061

Airbnb ROI: N/A