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.

Investment Property for Sale in Madison, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7 Third Street Madison, CT Madison, SEASHORE! - STEAL OF THE YEAR! REDUCED! SHOWING IN NOV/DEC! Coastal living adjace...	1 beds \| 1 baths \| 441 sq.ft.	$164,900	Airbnb cash on cash: 6.06% Traditional cash on cash: 9.79% Airbnb Rental Income: $1794 Traditional Rental Income: $1893 Airbnb ROI: 6.06% Traditional ROI: 9.79%
13 Longview Terrace #13 Madison, CT At the end of Longview Terrace, privately sited with expansive marsh and river views this ...	3 beds \| 4 baths \| 3,772 sq.ft.	$799,000	Airbnb cash on cash: -2.39% Traditional cash on cash: 3.99% Airbnb Rental Income: $2035 Traditional Rental Income: $6259 Airbnb ROI: -2.39% Traditional ROI: 3.99%
75 Fairview Drive Madison, CT 3 bedroom 2 full baths close to town private road, close to Bower Park, 2 car garage attac...	3 beds \| 2 baths \| 1,419 sq.ft.	$450,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.23% Airbnb Rental Income: $2035 Traditional Rental Income: $2346 Airbnb ROI: 0.24% Traditional ROI: 2.23%
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.	$825,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 3.91% Airbnb Rental Income: $2035 Traditional Rental Income: $5533 Airbnb ROI: -1.33% Traditional ROI: 3.91%
129 Acorn Road Madison, CT A stone's throw away from the heart of Madison Village, perfectly positioned at 1.4 miles ...	4 beds \| 3 baths \| 2,698 sq.ft.	$739,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.82% Airbnb Rental Income: $2506 Traditional Rental Income: $4881 Airbnb ROI: -0.51% Traditional ROI: 3.82%
29 Circle Beach Road Madison, CT A little piece of paradise awaits you in this direct, waterfront cottage. Perfectly situat...	2 beds \| 1 baths \| 720 sq.ft.	$699,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.31% Airbnb Rental Income: $1605 Traditional Rental Income: $2332 Airbnb ROI: -1.51% Traditional ROI: 0.31%
6 1st Street Madison, CT Brand New Cottage : ) This seasonal cottage located on First Street # 6 in Young's Village...	2 beds \| 1 baths \| 612 sq.ft.	$259,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 8.05% Airbnb Rental Income: $1605 Traditional Rental Income: $2829 Airbnb ROI: 1.2% Traditional ROI: 8.05%
132 Summer Hill Road Madison, CT Welcome to your dream home, where thoughtful design meets high-end craftsmanship. This new...	4 beds \| 5 baths \| 4,637 sq.ft.	$2,375,000	Airbnb cash on cash: -2.31% Traditional cash on cash: 0.66% Airbnb Rental Income: $2506 Traditional Rental Income: $8448 Airbnb ROI: -2.31% Traditional ROI: 0.66%
33 Seaview Avenue Madison, CT Stunning one-of-a-kind residence designed by Robert Page, AIA. Set directly on coveted pri...	5 beds \| 5 baths \| 4,613 sq.ft.	$4,500,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -1.19% Airbnb Rental Income: $2567 Traditional Rental Income: $8303 Airbnb ROI: -2.71% Traditional ROI: -1.19%
64 Webster Point Road Madison, CT Spacious with amazing waterfront quality views! Sited one house from Long Island Sound on ...	4 beds \| 4 baths \| 4,010 sq.ft.	$2,295,000	Airbnb cash on cash: -2.28% Traditional cash on cash: -0.25% Airbnb Rental Income: $2506 Traditional Rental Income: $6223 Airbnb ROI: -2.28% Traditional ROI: -0.25%
7 Madrina Lane Madison, CT Location, Location, Location!! Introducing a charming and well-maintained raised ranch hom...	3 beds \| 1 baths \| 1,144 sq.ft.	$509,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.8% Airbnb Rental Income: $2035 Traditional Rental Income: $2918 Airbnb ROI: -0.16% Traditional ROI: 2.8%
66 Beaver Pond Road Madison, CT Spacious Colonial close to Town Center boasting unique first floor, handicap accessible, i...	5 beds \| 4 baths \| 4,168 sq.ft.	$995,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 3.83% Airbnb Rental Income: $2567 Traditional Rental Income: $6538 Airbnb ROI: -1.12% Traditional ROI: 3.83%
153 Middle Beach Road Madison, CT Charming beach home with full guest apartment above garage across the street from Long Isl...	4 beds \| 2 baths \| 3,083 sq.ft.	$2,400,000	Airbnb cash on cash: -2.32% Traditional cash on cash: -1.19% Airbnb Rental Income: $2506 Traditional Rental Income: $4417 Airbnb ROI: -2.32% Traditional ROI: -1.19%
20 Strawberry Hill Road Madison, CT This original owner, 1960's built, 3 bedroom, 2 bath single family residence is nestled in...	3 beds \| 2 baths \| 1,138 sq.ft.	$549,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.76% Airbnb Rental Income: $2035 Traditional Rental Income: $2596 Airbnb ROI: -0.37% Traditional ROI: 1.76%
779 Summer Hill Road Madison, CT Welcome home to this picture-perfect ranch in peaceful North Madison-where comfort, charm,...	2 beds \| 2 baths \| 1,110 sq.ft.	$435,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 2.81% Airbnb Rental Income: $1605 Traditional Rental Income: $2510 Airbnb ROI: -0.53% Traditional ROI: 2.81%
9 Old Farms Road Madison, CT Discover coastal bliss in this updated 4-bedroom, 1.5-bathroom home, spanning over 1,800 s...	4 beds \| 2 baths \| 1,828 sq.ft.	$574,900	Airbnb cash on cash: 0.24% Traditional cash on cash: 4.21% Airbnb Rental Income: $2506 Traditional Rental Income: $4029 Airbnb ROI: 0.24% Traditional ROI: 4.21%
71 Madison Springs Drive Madison, CT *** High and Best need to be in by 8 pm Sunday 11.9.2025. Welcome to 71 Madison Springs Dr...	3 beds \| 3 baths \| 3,333 sq.ft.	$899,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 1.45% Airbnb Rental Income: $2035 Traditional Rental Income: $3927 Airbnb ROI: -1.44% Traditional ROI: 1.45%
38 Sportsman Hill Road Madison, CT Welcome to an extraordinary approx 5,600 sq foot custom-built Colonial, privately sited on...	4 beds \| 4 baths \| 5,624 sq.ft.	$1,299,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.95% Airbnb Rental Income: $2506 Traditional Rental Income: $6225 Airbnb ROI: -1.63% Traditional ROI: 1.95%
35 Hotchkiss Lane Madison, CT This expanded 3 bedroom 2.5 bath Cape-style home offers 2,400+square feet of thoughtfully ...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,695,000	Airbnb cash on cash: -2.23% Traditional cash on cash: -0.19% Airbnb Rental Income: $2035 Traditional Rental Income: $4716 Airbnb ROI: -2.23% Traditional ROI: -0.19%
28 Riverside Lane Madison, CT Prepare to be captivated by this sun-soaked, updated contemporary waterfront home offering...	3 beds \| 3 baths \| 2,398 sq.ft.	$1,595,000	Airbnb cash on cash: -2.2% Traditional cash on cash: -0.08% Airbnb Rental Income: $2035 Traditional Rental Income: $4647 Airbnb ROI: -2.2% Traditional ROI: -0.08%

Real Estate investment in Madison, CT

There are 27 properties for sale in the city of Madison . The median list price in Madison is $799,000 and the average price per square foot is $307. In December 2025, the average monthly cash on cash return in Madison is 2.00%. The average monthly rental income in Madison is $4,539.

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

There are 27 investment properties available for sale in Madison.

In 2025, 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 $4,539.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, CT

7 Third Street

Madison, CT

1 beds | 1 baths | 441 sq.ft.

$164,900

Airbnb cash on cash: 6.06%

Traditional cash on cash: 9.79%

Airbnb Rental Income: $1794

Traditional Rental Income: $1893

Airbnb ROI: 6.06%

Traditional ROI: 9.79%

13 Longview Terrace #13

Madison, CT

3 beds | 4 baths | 3,772 sq.ft.

$799,000

Airbnb cash on cash: -2.39%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $2035

Traditional Rental Income: $6259

Airbnb ROI: -2.39%

Traditional ROI: 3.99%

75 Fairview Drive

Madison, CT

3 beds | 2 baths | 1,419 sq.ft.

$450,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $2035

Traditional Rental Income: $2346

Airbnb ROI: 0.24%

Traditional ROI: 2.23%

3 Arrowhead Road

Madison, CT

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

$825,000

Airbnb cash on cash: -1.33%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $2035

Traditional Rental Income: $5533

Airbnb ROI: -1.33%

Traditional ROI: 3.91%

129 Acorn Road

Madison, CT

4 beds | 3 baths | 2,698 sq.ft.

$739,900

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $2506

Traditional Rental Income: $4881

Airbnb ROI: -0.51%

Traditional ROI: 3.82%

29 Circle Beach Road

Madison, CT

2 beds | 1 baths | 720 sq.ft.

$699,000

Airbnb cash on cash: -1.51%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $1605

Traditional Rental Income: $2332

Airbnb ROI: -1.51%

Traditional ROI: 0.31%

6 1st Street

Madison, CT

2 beds | 1 baths | 612 sq.ft.

$259,900

Airbnb cash on cash: 1.2%

Traditional cash on cash: 8.05%

Airbnb Rental Income: $1605

Traditional Rental Income: $2829

Airbnb ROI: 1.2%

Traditional ROI: 8.05%

132 Summer Hill Road

Madison, CT

4 beds | 5 baths | 4,637 sq.ft.

$2,375,000

Airbnb cash on cash: -2.31%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $2506

Traditional Rental Income: $8448

Airbnb ROI: -2.31%