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
40 Country Manor Boulevard Madison, IN MOTIVATED SELLERS! Welcome to Country Manor where YOUR home awaits! NEW ROOF July 2026! Fe...	3 beds \| 3 baths \| 1,434 sq.ft.	$259,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 5.69% Airbnb Rental Income: $1443 Traditional Rental Income: $1925 Airbnb ROI: 1.98% 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: -0.12% Traditional cash on cash: 1.62% Airbnb Rental Income: $1443 Traditional Rental Income: $1939 Airbnb ROI: -0.12% 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: -0.38% Traditional cash on cash: 1.48% Airbnb Rental Income: $802 Traditional Rental Income: $1279 Airbnb ROI: -0.38% 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: 1.9% Traditional cash on cash: 3.94% Airbnb Rental Income: $1443 Traditional Rental Income: $1590 Airbnb ROI: 1.9% 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: 4.44% Traditional cash on cash: 5.43% Airbnb Rental Income: $2294 Traditional Rental Income: $1979 Airbnb ROI: 4.44% 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: 2.38% Traditional cash on cash: 7.4% Airbnb Rental Income: $2294 Traditional Rental Income: $3952 Airbnb ROI: 2.38% 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: 1.65% Traditional cash on cash: 3.91% Airbnb Rental Income: $1443 Traditional Rental Income: $1610 Airbnb ROI: 1.65% 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: 1.38% Traditional cash on cash: 5.26% Airbnb Rental Income: $2294 Traditional Rental Income: $3827 Airbnb ROI: 1.38% 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: 1.22% Traditional cash on cash: 4.34% Airbnb Rental Income: $1443 Traditional Rental Income: $1953 Airbnb ROI: 1.22% Traditional ROI: 4.34%
904 E Second Street Madison, IN Price adjustment! This charming home on a corner lot is perfectly positioned in the heart ...	2 beds \| 1 baths \| 1,296 sq.ft.	$160,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 6.41% Airbnb Rental Income: $1464 Traditional Rental Income: $1342 Airbnb ROI: 4.37% Traditional ROI: 6.41%
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: 0.44% Traditional cash on cash: 4.91% Airbnb Rental Income: $1443 Traditional Rental Income: $2642 Airbnb ROI: 0.44% 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.	$380,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.24% Airbnb Rental Income: $1443 Traditional Rental Income: $2189 Airbnb ROI: 0.94% Traditional ROI: 4.24%
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 \| 1,842 sq.ft.	$245,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.17% Airbnb Rental Income: $1443 Traditional Rental Income: $1911 Airbnb ROI: 1.3% Traditional ROI: 5.17%
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: 2.78% Traditional cash on cash: 6.5% Airbnb Rental Income: $1443 Traditional Rental Income: $1893 Airbnb ROI: 2.78% 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.	$159,900	Airbnb cash on cash: 8.68% Traditional cash on cash: 7.88% Airbnb Rental Income: $2294 Traditional Rental Income: $1600 Airbnb ROI: 8.68% Traditional ROI: 7.88%
609 Walnut Street Madison, IN Looking to own an Air B&B in a Tourist Town, Rare opportunity to own a Historic pre 1900 2...	3 beds \| 2 baths \| 1,728 sq.ft.	$242,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 6.08% Airbnb Rental Income: $1443 Traditional Rental Income: $1926 Airbnb ROI: 2.11% Traditional ROI: 6.08%
712 E Main Street Madison, IN Historic downtown Madison living! This 2 story home blends history with modern updates for...	2 beds \| 2 baths \| 1,990 sq.ft.	$339,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 5.53% Airbnb Rental Income: $1464 Traditional Rental Income: $2356 Airbnb ROI: 1.38% Traditional ROI: 5.53%
604 Mulberry Street Madison, IN Stunning full transformation of a mid-1800s brick home in Madison's Historic District. Nea...	2 beds \| 3 baths \| 2,004 sq.ft.	$465,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 4.28% Airbnb Rental Income: $1464 Traditional Rental Income: $2522 Airbnb ROI: 0.86% Traditional ROI: 4.28%
406 Mouser Street Madison, IN MOTIVATED SELLERS!! WOW - FIVE bedrooms on ONE level! Yes, please!! This spacious ranch-st...	5 beds \| 2 baths \| 1,686 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.89% Airbnb Rental Income: $null Traditional Rental Income: $2177 Airbnb ROI: N/A Traditional ROI: 6.89%
2246 Flint Road Madison, IN Move right into this beautifully updated 4-bedroom, 2-bath Bedford stone ranch! This well-...	4 beds \| 2 baths \| 1,416 sq.ft.	$259,900	Airbnb cash on cash: 5.16% Traditional cash on cash: 6.49% Airbnb Rental Income: $2294 Traditional Rental Income: $2048 Airbnb ROI: 5.16% Traditional ROI: 6.49%
952 W Main Street Madison, IN This charming, historic, Main Street Madison, shotgun home is on the west side of town clo...	3 beds \| 2 baths \| 1,385 sq.ft.	$285,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.25% Airbnb Rental Income: $1443 Traditional Rental Income: $1824 Airbnb ROI: 2.23% Traditional ROI: 5.25%
605 Walnut Street Madison, IN Positioned within walking distance to Downtown Amenities, this move-in-ready Federal-style...	2 beds \| 2 baths \| 1,512 sq.ft.	$244,998	Airbnb cash on cash: 2.75% Traditional cash on cash: 6.2% Airbnb Rental Income: $1464 Traditional Rental Income: $1831 Airbnb ROI: 2.75% Traditional ROI: 6.2%
2357 Sunset Court Madison, IN Welcome to your dream home in beautiful Madison, Indiana! Priced at $289,900, this stunnin...	3 beds \| 2 baths \| 1,867 sq.ft.	$289,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 6.82% Airbnb Rental Income: $1443 Traditional Rental Income: $2459 Airbnb ROI: 1.53% Traditional ROI: 6.82%
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: 2.99% Traditional cash on cash: 6.44% Airbnb Rental Income: $1443 Traditional Rental Income: $1717 Airbnb ROI: 2.99% Traditional ROI: 6.44%
2000 Fairway Drive Madison, IN Check out this wonderful maintained tri-level home in the Sunrise Falls Subdivision next t...	4 beds \| 3 baths \| 2,000 sq.ft.	$349,900	Airbnb cash on cash: 3.44% Traditional cash on cash: 5.43% Airbnb Rental Income: $2294 Traditional Rental Income: $2378 Airbnb ROI: 3.44% Traditional ROI: 5.43%

Real Estate investment in Madison, IN

There are 27 properties for sale in the city of Madison . The median list price in Madison is $269,839 and the average price per square foot is $139. In August 2026, the average monthly cash on cash return in Madison is 5.00%. The average monthly rental income in Madison is $1,926.

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

There are 27 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 $1,926.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, IN

40 Country Manor Boulevard

Madison, IN

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

$259,900

Airbnb cash on cash: 1.98%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1443

Traditional Rental Income: $1925

Airbnb ROI: 1.98%

Traditional ROI: 5.69%

380 N Lakeside Drive

Madison, IN

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

$569,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1443

Traditional Rental Income: $1939

Airbnb ROI: -0.12%

Traditional ROI: 1.62%

2945 N Greenbrier Road

Madison, IN

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

$459,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $802

Traditional Rental Income: $1279

Airbnb ROI: -0.38%

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: 1.9%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1443

Traditional Rental Income: $1590

Airbnb ROI: 1.9%

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: 4.44%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $2294

Traditional Rental Income: $1979

Airbnb ROI: 4.44%

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: 2.38%

Traditional cash on cash: 7.4%

Airbnb Rental Income: $2294

Traditional Rental Income: $3952

Airbnb ROI: 2.38%

Traditional ROI: 7.4%

4510 vineyard Road

Madison, IN

3 beds | 2 baths | 1,248 sq.ft.

$279,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1443

Traditional Rental Income: $1610

Airbnb ROI: 1.65%