Real Estate Investment Properties for Sale in Madison, CT

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

Explore a variety of short-term homes & houses in Madison, CT. Invest wisely with VRBO & Madison, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Madison, CT

Search for Single Family Residential for Sale in Madison, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 2 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 Indigo Trl Madison, CT Luxury Property Auction: 11-25 June. Current High Bid: $1,300,000. Estimated Sale Price: $...	4 beds \| 5 baths \| 6,194 sq.ft.	$2,650,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 1.52% Airbnb Rental Income: $2266 Traditional Rental Income: $8549 Airbnb ROI: -1.27% Traditional ROI: 1.52%
50 East Street Madison, CT LOCATION ~ LOCATION ~ It matters !! Situated in the Coastal Charm of Madison, this Seasona...	2 beds \| 1 baths \| 480 sq.ft.	$200,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 9.25% Airbnb Rental Income: $2117 Traditional Rental Income: $2236 Airbnb ROI: 5.77% Traditional ROI: 9.25%
Other Investment Properties for Sale in Madison
6 Ladshaw Drive #6 Madison , CT Privacy & convenience are both found within this updated detached stand-alone Ranch home i...	2 beds \| 2 baths \| 1,360 sq.ft.	$499,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.4% Airbnb Rental Income: $2117 Traditional Rental Income: $3114 Airbnb ROI: 0.1% Traditional ROI: 3.4%
34 Canborne Way #34 Madison , CT Nestled quietly at the rear of the Windemere Complex, this freestanding ranch-style unit d...	2 beds \| 2 baths \| 1,280 sq.ft.	$485,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.9% Airbnb Rental Income: $2117 Traditional Rental Income: $2996 Airbnb ROI: -0.23% Traditional ROI: 2.9%
60 Bradley Corners Road Madison , CT Highest and best offers are due by Tuesday, May 26th at 5:00 PM. Welcome home to 60 Bradle...	4 beds \| 3 baths \| 1,984 sq.ft.	$625,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.1% Airbnb Rental Income: $2266 Traditional Rental Income: $3833 Airbnb ROI: 0.44% Traditional ROI: 4.1%
15 Hampshire Road #15 Madison , CT One-level living at its best. A pristine two-bedroom residence situated directly across fr...	2 beds \| 2 baths \| 1,280 sq.ft.	$615,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.4% Airbnb Rental Income: $2117 Traditional Rental Income: $3076 Airbnb ROI: -0.21% Traditional ROI: 2.4%
26 Bassett Lane Madison , CT Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights...	3 beds \| 4 baths \| 2,160 sq.ft.	$2,149,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.45% Airbnb Rental Income: $2023 Traditional Rental Income: $5953 Airbnb ROI: -0.79% Traditional ROI: 1.45%
3 Arrowhead Road Madison , CT Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at ...	3 beds \| 4 baths \| 2,160 sq.ft.	$875,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.43% Airbnb Rental Income: $2023 Traditional Rental Income: $5533 Airbnb ROI: -0.52% Traditional ROI: 4.43%
37 Lantern Hill Road Madison , CT An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town ...	5 beds \| 6 baths \| 7,139 sq.ft.	$2,875,000	Airbnb cash on cash: -1.81% Traditional cash on cash: -0.23% Airbnb Rental Income: $2120 Traditional Rental Income: $5799 Airbnb ROI: -1.81% Traditional ROI: -0.23%
61 Hartford Avenue Madison , CT Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed c...	3 beds \| 4 baths \| 3,306 sq.ft.	$2,295,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.55% Airbnb Rental Income: $2023 Traditional Rental Income: $5344 Airbnb ROI: -1.26% Traditional ROI: 0.55%
18 St. Francis Woods Road Madison , CT Spacious Split-level home with deck, open porch and patio overlooking large, level lot. Th...	3 beds \| 3 baths \| 1,824 sq.ft.	$469,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 5.22% Airbnb Rental Income: $2023 Traditional Rental Income: $3496 Airbnb ROI: 0.67% Traditional ROI: 5.22%
16 North Street Madison , CT Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in D...	1 beds \| 1 baths \| 476 sq.ft.	$154,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 8.74% Airbnb Rental Income: $1245 Traditional Rental Income: $1719 Airbnb ROI: 2.83% Traditional ROI: 8.74%
34 Wildcat Springs Drive Madison , CT Modern Charm Meets Effortless Comfort in Desirable Neighborhood Step into a bright, beauti...	5 beds \| 6 baths \| 5,380 sq.ft.	$1,495,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.14% Airbnb Rental Income: $2120 Traditional Rental Income: $10007 Airbnb ROI: -0.93% Traditional ROI: 5.14%

Your search for investment property begins and ends here

Single Family Homes for Sale in Madison, CT

24 Indigo Trl

Madison, CT

4 beds | 5 baths | 6,194 sq.ft.

$2,650,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 1.52%

Airbnb Rental Income: $2266

Traditional Rental Income: $8549

Airbnb ROI: -1.27%

Traditional ROI: 1.52%

50 East Street

Madison, CT

2 beds | 1 baths | 480 sq.ft.

$200,000

Airbnb cash on cash: 5.77%

Traditional cash on cash: 9.25%

Airbnb Rental Income: $2117

Traditional Rental Income: $2236

Airbnb ROI: 5.77%

Traditional ROI: 9.25%

Other Investment Properties for Sale in Madison

Madison , CT

2 beds | 2 baths | 1,360 sq.ft.

$499,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $2117

Traditional Rental Income: $3114

Airbnb ROI: 0.1%

Traditional ROI: 3.4%

Madison , CT

2 beds | 2 baths | 1,280 sq.ft.

$485,900

Airbnb cash on cash: -0.23%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2117

Traditional Rental Income: $2996

Airbnb ROI: -0.23%

Traditional ROI: 2.9%

Madison , CT

4 beds | 3 baths | 1,984 sq.ft.

$625,000

Airbnb cash on cash: 0.44%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2266

Traditional Rental Income: $3833

Airbnb ROI: 0.44%

Traditional ROI: 4.1%

Madison , CT

2 beds | 2 baths | 1,280 sq.ft.

$615,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2117

Traditional Rental Income: $3076

Airbnb ROI: -0.21%

Traditional ROI: 2.4%

Madison , CT

3 beds | 4 baths | 2,160 sq.ft.

$2,149,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $2023

Traditional Rental Income: $5953

Airbnb ROI: -0.79%

Traditional ROI: 1.45%

Madison , CT

3 beds | 4 baths | 2,160 sq.ft.

$875,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $2023

Traditional Rental Income: $5533

Airbnb ROI: -0.52%

Traditional ROI: 4.43%

Madison , CT

5 beds | 6 baths | 7,139 sq.ft.

$2,875,000

Airbnb cash on cash: -1.81%