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: 0.04% Traditional cash on cash: 3.13% Airbnb Rental Income: $911 Traditional Rental Income: $1584 Airbnb ROI: 0.04% 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%
720 S Main Street Headland, AL Here's your opportunity to own this beautiful 1907 built home, full of the charm and chara...	3 beds \| 3 baths \| 2,722 sq.ft.	$415,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 6.41% Airbnb Rental Income: $911 Traditional Rental Income: $3058 Airbnb ROI: 0.01% Traditional ROI: 6.41%
202 Cabrio Way Headland, AL 4 Bedroom, 3 Bathroom Craftsman Home \| Trace Manor \| Headland Schools \| 100% USDA, VA, FHA...	4 beds \| 3 baths \| 2,087 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $2276 Airbnb ROI: N/A Traditional ROI: 5.85%
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.	$150,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.15% Airbnb Rental Income: $911 Traditional Rental Income: $1179 Airbnb ROI: 1.91% Traditional ROI: 6.15%
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: 1.4% Traditional cash on cash: 5.38% Airbnb Rental Income: $911 Traditional Rental Income: $1244 Airbnb ROI: 1.4% Traditional ROI: 5.38%
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.	$434,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 3.96%
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%
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.	$284,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.9% Airbnb Rental Income: $911 Traditional Rental Income: $1251 Airbnb ROI: 0.37% Traditional ROI: 2.9%
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: -0.8% Traditional cash on cash: 1.5% Airbnb Rental Income: $911 Traditional Rental Income: $2364 Airbnb ROI: -0.8% 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%
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.	$419,800	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.	$247,500	Airbnb cash on cash: 0.63% Traditional cash on cash: 5.7% Airbnb Rental Income: $911 Traditional Rental Income: $1756 Airbnb ROI: 0.63% Traditional ROI: 5.7%
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.	$329,400	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.29%
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.	$329,400	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 4.75%
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.	$344,400	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 4.65%
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.	$331,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 4.25%
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%
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%
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%
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.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.38% Airbnb Rental Income: $null Traditional Rental Income: $3097 Airbnb ROI: N/A Traditional ROI: 9.38%
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: 1.15% Traditional cash on cash: 5.91% Airbnb Rental Income: $911 Traditional Rental Income: $1519 Airbnb ROI: 1.15% Traditional ROI: 5.91%
608 E Church Headland, AL Complete and move in ready! New Construction in the beautiful city of Headland. Come view ...	4 beds \| 3 baths \| 2,009 sq.ft.	$299,998	Airbnb cash on cash: N/A Traditional cash on cash: 6.15% Airbnb Rental Income: $null Traditional Rental Income: $2122 Airbnb ROI: N/A Traditional ROI: 6.15%
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: 4.09% Traditional cash on cash: 1.49% Airbnb Rental Income: $1103 Traditional Rental Income: $430 Airbnb ROI: 4.09% 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%
131 Sagebrush Drive Headland, AL Welcome to 131 Sagebrush Drive, the Delilah is a single-story floorplan at our Sagebrush c...	3 beds \| 2 baths \| 1,281 sq.ft.	$221,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 5.15% Airbnb Rental Income: $911 Traditional Rental Income: $1473 Airbnb ROI: 0.86% Traditional ROI: 5.15%
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%
125 Sagebrush Drive Headland, AL Welcome to 125 Sagebrush Drive, our beautiful one-story Lakeside floorplan featured in our...	5 beds \| 3 baths \| 2,016 sq.ft.	$289,400	Airbnb cash on cash: N/A Traditional cash on cash: 6.23% Airbnb Rental Income: $null Traditional Rental Income: $2177 Airbnb ROI: N/A Traditional ROI: 6.23%
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%
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: 1.37% Traditional cash on cash: 6.57% Airbnb Rental Income: $911 Traditional Rental Income: $1461 Airbnb ROI: 1.37% 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.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2346 Airbnb ROI: N/A Traditional ROI: 5.26%

Real Estate investment in Headland, AL

There are 79 properties for sale in the city of Headland . The median list price in Headland is $266,840 and the average price per square foot is $126. In July 2026, the average monthly cash on cash return in Headland is 5.00%. The average monthly rental income in Headland is $1,783.

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

There are 79 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 $1,783.

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: 0.04%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $911

Traditional Rental Income: $1584

Airbnb ROI: 0.04%

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%

720 S Main Street

Headland, AL

3 beds | 3 baths | 2,722 sq.ft.

$415,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 6.41%

Airbnb Rental Income: $911

Traditional Rental Income: $3058

Airbnb ROI: 0.01%

Traditional ROI: 6.41%

202 Cabrio Way

Headland, AL

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

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2276

Airbnb ROI: N/A

Traditional ROI: 5.85%

213 Rock Creek Road

Headland, AL

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

$150,000

Airbnb cash on cash: 1.91%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $911

Traditional Rental Income: $1179

Airbnb ROI: 1.91%

Traditional ROI: 6.15%

603 Carr Circle

Headland, AL

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

$178,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $911

Traditional Rental Income: $1244

Airbnb ROI: 1.4%

Traditional ROI: 5.38%

116 Heritage Way

Headland, AL

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

$434,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2281

Airbnb ROI: N/A