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.

Condos for Sale in Madison, CT

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

Showing 4 Condo 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
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.	$487,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.51% Airbnb Rental Income: $2063 Traditional Rental Income: $3114 Airbnb ROI: 0.03% Traditional ROI: 3.51%
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: -0.32% Traditional cash on cash: 2.9% Airbnb Rental Income: $2063 Traditional Rental Income: $2996 Airbnb ROI: -0.32% Traditional ROI: 2.9%
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: -0.29% Traditional cash on cash: 2.4% Airbnb Rental Income: $2063 Traditional Rental Income: $3076 Airbnb ROI: -0.29% Traditional ROI: 2.4%
23 Aylesbury Circle #23 Madison, CT Rare opportunity to own an exceptionally beautiful, turnkey Windermere home overlooking th...	3 beds \| 3 baths \| 1,476 sq.ft.	$875,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.97% Airbnb Rental Income: $2491 Traditional Rental Income: $3462 Airbnb ROI: 0.04% Traditional ROI: 1.97%
Other Investment Properties for Sale in Madison
81 Legend Hill Road #81 Madison , CT Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It b...	2 beds \| 3 baths \| 2,604 sq.ft.	$665,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 1.71% Airbnb Rental Income: $2063 Traditional Rental Income: $3233 Airbnb ROI: -1.04% Traditional ROI: 1.71%
98 Bishop Lane Madison , CT Set gracefully on a beautifully landscaped property framed by classic New England stone wa...	4 beds \| 3 baths \| 2,303 sq.ft.	$899,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.27% Airbnb Rental Income: $2261 Traditional Rental Income: $4538 Airbnb ROI: -0.13% Traditional ROI: 3.27%
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.	$1,950,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 1.7% Airbnb Rental Income: $2491 Traditional Rental Income: $5953 Airbnb ROI: -0.55% Traditional ROI: 1.7%
24 Indigo Trail Madison , CT Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian cust...	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: $2261 Traditional Rental Income: $8549 Airbnb ROI: -1.27% Traditional ROI: 1.52%
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: -0.04% Traditional cash on cash: 4.43% Airbnb Rental Income: $2491 Traditional Rental Income: $5533 Airbnb ROI: -0.04% Traditional ROI: 4.43%
64 Webster Point Road Madison , CT NEW PRICE BELOW RECENT APPRAISAL. One house from L.I. Sound on a quiet Webster Point Road ...	4 beds \| 4 baths \| 4,010 sq.ft.	$2,195,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 0.51% Airbnb Rental Income: $2261 Traditional Rental Income: $6223 Airbnb ROI: -1.72% Traditional ROI: 0.51%
153 Middle Beach Rd Madison , CT Charming beach home with full guest apartment above garage across the street from Long Isl...	4 beds \| 2 baths \| 2,251 sq.ft.	$2,150,000	Airbnb cash on cash: -1.53% Traditional cash on cash: -0.17% Airbnb Rental Income: $2261 Traditional Rental Income: $4417 Airbnb ROI: -1.53% Traditional ROI: -0.17%
30 Meeting House Ln Madison , CT 30 Meeting House Ln, Madison, CT 06443 \| Single Family Residential	5 beds \| 3 baths \| 3,912 sq.ft.	$1,695,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.13% Airbnb Rental Income: $null Traditional Rental Income: $4812 Airbnb ROI: N/A Traditional ROI: -0.13%
92 Scotland Ave Madison , CT 92 Scotland Ave, Madison, CT 06443 \| Single Family Residential	5 beds \| 4 baths \| 4,143 sq.ft.	$2,300,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.35% Airbnb Rental Income: $null Traditional Rental Income: $6027 Airbnb ROI: N/A Traditional ROI: -0.35%
31 Stony Lane Lot 1 Rd Madison , CT 31 Stony Lane Lot 1 Rd, Madison, CT 06443 \| Single Family Residential	4 beds \| 3 baths \| 3,200 sq.ft.	$1,790,000	Airbnb cash on cash: -2.17% Traditional cash on cash: -0.22% Airbnb Rental Income: $2261 Traditional Rental Income: $4924 Airbnb ROI: -2.17% Traditional ROI: -0.22%
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: N/A Traditional cash on cash: -0.23% Airbnb Rental Income: $null Traditional Rental Income: $5799 Airbnb ROI: N/A Traditional ROI: -0.23%

Your search for investment property begins and ends here

Condos for Sale in Madison, CT

6 Ladshaw Drive #6

Madison, CT

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

$487,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2063

Traditional Rental Income: $3114

Airbnb ROI: 0.03%

Traditional ROI: 3.51%

34 Canborne Way #34

Madison, CT

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

$485,900

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2063

Traditional Rental Income: $2996

Airbnb ROI: -0.32%

Traditional ROI: 2.9%

15 Hampshire Road #15

Madison, CT

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

$615,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2063

Traditional Rental Income: $3076

Airbnb ROI: -0.29%

Traditional ROI: 2.4%

23 Aylesbury Circle #23

Madison, CT

3 beds | 3 baths | 1,476 sq.ft.

$875,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $2491

Traditional Rental Income: $3462

Airbnb ROI: 0.04%

Traditional ROI: 1.97%

Other Investment Properties for Sale in Madison

Madison , CT

2 beds | 3 baths | 2,604 sq.ft.

$665,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $2063

Traditional Rental Income: $3233

Airbnb ROI: -1.04%

Traditional ROI: 1.71%

Madison , CT

4 beds | 3 baths | 2,303 sq.ft.

$899,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $2261

Traditional Rental Income: $4538

Airbnb ROI: -0.13%

Traditional ROI: 3.27%

Madison , CT

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

$1,950,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $2491

Traditional Rental Income: $5953

Airbnb ROI: -0.55%

Traditional ROI: 1.7%

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: $2261

Traditional Rental Income: $8549

Airbnb ROI: -1.27%

Traditional ROI: 1.52%

Madison , CT

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