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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
7 Third StreetMadison, CTMadison, 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%
|
75 Fairview DriveMadison, CT3 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%
|
3 Arrowhead RoadMadison, CTEmbrace 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%
|
29 Circle Beach RoadMadison, CTA 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%
|
6 1st StreetMadison, CTBrand 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%
|
132 Summer Hill RoadMadison, CTWelcome 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%
|
33 Seaview AvenueMadison, CTStunning 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%
|
64 Webster Point RoadMadison, CTSpacious 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%
|
735 Opening Hill RoadMadison, CTThis storybook Cape is a hidden treasure, offering 2,000 sq. ft. of character-filled livin... |
4 beds | 2 baths | 2,028 sq.ft. |
$675,000 |
Airbnb cash on cash: -0.26%
|
153 Middle Beach RoadMadison, CTCharming 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%
|
38 Sportsman Hill RoadMadison, CTWelcome 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%
|
35 Hotchkiss LaneMadison, CTThis 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%
|
28 Riverside LaneMadison, CTPrepare 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%
|
Real Estate investment in Madison, CT
There are 22 properties for sale in the city of Madison . The median list price in Madison is $749,000 and the average price per square foot is $303. In December 2025, the average monthly cash on cash return in Madison is 2.00%. The average monthly rental income in Madison is $4,532.