Real Estate Investment Properties for Sale in Madison, IN

Looking for investment property in Madison, IN with high ROI ?

Explore a variety of short-term homes & houses in Madison, IN. Invest wisely with VRBO & Madison, IN 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 Madison, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
379 Brentwood Drive Madison, IN EXECUTIVE CONTEMPORARY/MID CENTURY HOME Over 3500 SQ.FT. lives like a ranch with an abunda...	4 beds \| 4 baths \| 3,506 sq.ft.	$459,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.64% Airbnb Rental Income: $2181 Traditional Rental Income: $2883 Airbnb ROI: 1.72% Traditional ROI: 4.64%
40 Country Manor Boulevard Madison, IN MOTIVATED SELLERS! Welcome to Country Manor where YOUR home awaits! Featuring 3 bedrooms, ...	3 beds \| 3 baths \| 1,434 sq.ft.	$259,900	Airbnb cash on cash: 2.46% Traditional cash on cash: 5.69% Airbnb Rental Income: $1584 Traditional Rental Income: $1925 Airbnb ROI: 2.46% Traditional ROI: 5.69%
380 N Lakeside Drive Madison, IN Your private resort awaits! This beautiful 3 bedroom, 2 bath, single story brick home offe...	3 beds \| 2 baths \| 1,750 sq.ft.	$569,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.62% Airbnb Rental Income: $1584 Traditional Rental Income: $1939 Airbnb ROI: 0.11% Traditional ROI: 1.62%
2945 N Greenbrier Road Madison, IN If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a uniqu...	1 beds \| 1 baths \| 1,233 sq.ft.	$459,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 1.48% Airbnb Rental Income: $929 Traditional Rental Income: $1279 Airbnb ROI: -0.13% Traditional ROI: 1.48%
1122 W Second Street Madison, IN Check out this charming and fully renovated home with a new addition, covered patio and ga...	2 beds \| 2 baths \| 1,021 sq.ft.	$275,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 3.88% Airbnb Rental Income: $1464 Traditional Rental Income: $1457 Airbnb ROI: 2.24% Traditional ROI: 3.88%
6734 N SR 7 Madison, IN Country Living with Convenience! Enjoy the best of both worlds with this brick 3 bedroom, ...	3 beds \| 1 baths \| 1,575 sq.ft.	$299,900	Airbnb cash on cash: 2.32% Traditional cash on cash: 3.94% Airbnb Rental Income: $1584 Traditional Rental Income: $1590 Airbnb ROI: 2.32% Traditional ROI: 3.94%
8273 E State Road 56 Madison, IN 8273 E State Road 56, Madison, IN 47250 \| Single Family Residential	4 beds \| 2 baths \| 2,708 sq.ft.	$275,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 5.43% Airbnb Rental Income: $2181 Traditional Rental Income: $1979 Airbnb ROI: 4.08% Traditional ROI: 5.43%
7877 Upper Dry Fork Road Madison, IN Beautiful Cape Cod-style home situated on nearly 6 acres, offering the perfect blend of sp...	4 beds \| 5 baths \| 2,885 sq.ft.	$474,900	Airbnb cash on cash: 2.17% Traditional cash on cash: 7.4% Airbnb Rental Income: $2181 Traditional Rental Income: $3952 Airbnb ROI: 2.17% Traditional ROI: 7.4%
4510 vineyard Road Madison, IN Country living with room to grow! This charming 3-bedroom, 1-bath home sits on a peaceful ...	3 beds \| 2 baths \| 1,248 sq.ft.	$279,900	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.91% Airbnb Rental Income: $1584 Traditional Rental Income: $1610 Airbnb ROI: 2.09% Traditional ROI: 3.91%
1006 Fairmount Farms Ln Madison, IN Discover the perfect blend of traditional elegance and modern luxury in this spacious 4-be...	4 beds \| 4 baths \| 3,632 sq.ft.	$580,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 5.26% Airbnb Rental Income: $2181 Traditional Rental Income: $3827 Airbnb ROI: 1.2% Traditional ROI: 5.26%
2197 N 950 E Madison, IN Nestled on 5.59+/- scenic acres with a park-like setting, this 3-bedroom, 2-bath home offe...	3 beds \| 2 baths \| 1,568 sq.ft.	$319,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 4.34% Airbnb Rental Income: $1584 Traditional Rental Income: $1953 Airbnb ROI: 1.61% Traditional ROI: 4.34%
904 E Second Street Madison, IN Open House 6/27 12-2. This charming home on a corner lot is perfectly positioned in the he...	2 beds \| 1 baths \| 1,296 sq.ft.	$190,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 5.27% Airbnb Rental Income: $1464 Traditional Rental Income: $1342 Airbnb ROI: 3.55% Traditional ROI: 5.27%
322 E 2nd Madison, IN Historic 1904 Queen Anne, once the home of Dr NA Kremer situate in the heart of downtown H...	3 beds \| 3 baths \| 2,462 sq.ft.	$387,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 4.91% Airbnb Rental Income: $1584 Traditional Rental Income: $2642 Airbnb ROI: 0.76% Traditional ROI: 4.91%
195 Autumnwood Court Madison, IN Welcome to Autumnwood Estates! Enjoy this beautifully maintained home that offers the perf...	3 beds \| 2 baths \| 2,156 sq.ft.	$390,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.1% Airbnb Rental Income: $1584 Traditional Rental Income: $2189 Airbnb ROI: 1.21% Traditional ROI: 4.1%
2836 Springwood Drive Madison, IN Here's your chance! Back on the market at no fault of the seller; buyer financing fell thr...	3 beds \| 2 baths \| 1,296 sq.ft.	$215,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 6.44% Airbnb Rental Income: $1584 Traditional Rental Income: $1717 Airbnb ROI: 3.57% Traditional ROI: 6.44%
234 Hargan Drive Madison, IN Don't miss this Bedford stone beauty located on a corner lot in the established Highland H...	3 beds \| 2 baths \| 1,564 sq.ft.	$249,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 5.07% Airbnb Rental Income: $1584 Traditional Rental Income: $1911 Airbnb ROI: 1.76% Traditional ROI: 5.07%
9727 E Vernon Ridge Road Madison, IN Check out this peaceful small homestead waiting for you! A well maintained 3 bedroom, 2 ba...	3 beds \| 2 baths \| 1,782 sq.ft.	$250,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 6.5% Airbnb Rental Income: $1584 Traditional Rental Income: $1893 Airbnb ROI: 3.27% Traditional ROI: 6.5%
7583 E Riverside Drive Madison, IN Peaceful river retreat with plenty of space to relax and enjoy the outdoors. This open-flo...	2 beds \| 1 baths \| 896 sq.ft.	$149,900	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.85% Airbnb Rental Income: $1464 Traditional Rental Income: $1102 Airbnb ROI: 5.35% Traditional ROI: 5.85%
1037 W Main Street Madison, IN Wow! This home is so cool with river views and tons of exposed brick! Walk to downtown Mad...	4 beds \| 1 baths \| 2,400 sq.ft.	$169,900	Airbnb cash on cash: 7.55% Traditional cash on cash: 7.37% Airbnb Rental Income: $2181 Traditional Rental Income: $1600 Airbnb ROI: 7.55% Traditional ROI: 7.37%
2099 E Gardner Lane Madison, IN Located in the Rykers Ridge area of Madison, 2099 E Gardner Ln offers 4 bedrooms, 2 full b...	4 beds \| 2 baths \| 1,560 sq.ft.	$175,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 9.05% Airbnb Rental Income: $2181 Traditional Rental Income: $1922 Airbnb ROI: 7.29% Traditional ROI: 9.05%
330 State Street Madison, IN This wonderful home was in one family for the last 60 + years! It has been fully renovated...	4 beds \| 2 baths \| 2,058 sq.ft.	$299,800	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.59% Airbnb Rental Income: $2181 Traditional Rental Income: $2257 Airbnb ROI: 4.36% Traditional ROI: 6.59%

Real Estate investment in Madison, IN

There are 21 properties for sale in the city of Madison . The median list price in Madison is $249,871 and the average price per square foot is $128. In June 2026, the average monthly cash on cash return in Madison is 5.00%. The average monthly rental income in Madison is $1,917.

Madison, IN Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 21 investment properties available for sale in Madison.

In 2026, the best neighborhood to buy investment property is Madison.

The ROI for Long-Term is higher than the Short-Term in Madison with average rental income of $1,917.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, IN

379 Brentwood Drive

Madison, IN

4 beds | 4 baths | 3,506 sq.ft.

$459,900

Airbnb cash on cash: 1.72%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2181

Traditional Rental Income: $2883

Airbnb ROI: 1.72%

Traditional ROI: 4.64%

40 Country Manor Boulevard

Madison, IN

3 beds | 3 baths | 1,434 sq.ft.

$259,900

Airbnb cash on cash: 2.46%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1584

Traditional Rental Income: $1925

Airbnb ROI: 2.46%

Traditional ROI: 5.69%

380 N Lakeside Drive

Madison, IN

3 beds | 2 baths | 1,750 sq.ft.

$569,900

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1584

Traditional Rental Income: $1939

Airbnb ROI: 0.11%

Traditional ROI: 1.62%

2945 N Greenbrier Road

Madison, IN

1 beds | 1 baths | 1,233 sq.ft.

$459,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $929

Traditional Rental Income: $1279

Airbnb ROI: -0.13%

Traditional ROI: 1.48%

1122 W Second Street

Madison, IN

2 beds | 2 baths | 1,021 sq.ft.

$275,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1464

Traditional Rental Income: $1457

Airbnb ROI: 2.24%

Traditional ROI: 3.88%

6734 N SR 7

Madison, IN

3 beds | 1 baths | 1,575 sq.ft.

$299,900

Airbnb cash on cash: 2.32%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1584

Traditional Rental Income: $1590

Airbnb ROI: 2.32%

Traditional ROI: 3.94%

8273 E State Road 56

Madison, IN

4 beds | 2 baths | 2,708 sq.ft.

$275,000

Airbnb cash on cash: 4.08%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $2181

Traditional Rental Income: $1979

Airbnb ROI: 4.08%

Traditional ROI: 5.43%

7877 Upper Dry Fork Road

Madison, IN

4 beds | 5 baths | 2,885 sq.ft.

$474,900

Airbnb cash on cash: 2.17%

Traditional cash on cash: 7.4%

Airbnb Rental Income: $2181

Traditional Rental Income: $3952

Airbnb ROI: 2.17%