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 |
|---|---|---|---|
338 Opening Hill RoadMadison, CTExtensively updated ranch offering effortless one-level living! This charming 4-bedroom, 2... |
4 beds | 3 baths | 1,792 sq.ft. |
$589,000 |
Airbnb cash on cash: 0.47%
|
7 Third StreetMadison, CTMadison, SEASHORE! - Coastal living adjacent to Hammonassett Beach State Park! HIGH VALUE!... |
1 beds | 1 baths | 441 sq.ft. |
$172,000 |
Airbnb cash on cash: 7.14%
|
13 Longview Terrace #13Madison, CTPrivately sited at the end of Longview Terrace with expansive marsh and river views this l... |
3 beds | 4 baths | 3,772 sq.ft. |
$825,000 |
Airbnb cash on cash: -1.72%
|
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. |
$455,000 |
Airbnb cash on cash: 1.46%
|
908 Boston Post RoadMadison, CTTHE GENERAL'S RESIDENCES at Fence Creek, the perfect & rare combination of location, luxur... |
3 beds | 3 baths | 2,538 sq.ft. |
$1,395,000 |
Airbnb cash on cash: -2.48%
|
3 Arrowhead RoadMadison, CTNewly Priced! Embrace the enchantment of Shoreline Living at its finest with this sun-dren... |
3 beds | 4 baths | 2,235 sq.ft. |
$875,000 |
Airbnb cash on cash: -0.77%
|
110 Randi DriveMadison, CTA stately circular driveway ushers you into a realm of elegance & comfort. This grand & cl... |
5 beds | 5 baths | 5,779 sq.ft. |
$1,485,000 |
Airbnb cash on cash: -0.59%
|
92 Fourth AvenueMadison, CTNestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal ... |
2 beds | 1 baths | 396 sq.ft. |
$145,000 |
Airbnb cash on cash: 6.96%
|
129 Acorn RoadMadison, CTA 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: -1.13%
|
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: -0.98%
|
42 Buck Hill RoadMadison, CTThis is the Madison home you have been waiting for!! Tucked away on 1.88 acres of level l... |
4 beds | 3 baths | 3,999 sq.ft. |
$699,900 |
Airbnb cash on cash: -1.02%
|
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: 2.59%
|
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: -2.51%
|
259 Mungertown RoadMadison, CTBeautifully renovated Madison Ranch that seamlessly blends California chic with East Coast... |
3 beds | 2 baths | 2,068 sq.ft. |
$729,000 |
Airbnb cash on cash: -0.26%
|
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: -2.32%
|
64 Webster Point RoadMadison, CTGRACIOUS, SPACIOUS AND GRAND Sited one house from Long Island Sound on a quiet cul de sac... |
4 beds | 4 baths | 4,010 sq.ft. |
$2,295,000 |
Airbnb cash on cash: -2.49%
|
69 Squires RoadMadison, CTThis beautifully renovated modern home offers 2,025 sq ft of modern living with every upgr... |
3 beds | 3 baths | 2,025 sq.ft. |
$699,000 |
Airbnb cash on cash: -0.14%
|
24 Pent RoadMadison, CTFulfill your dream of having a beach cottage just steps to one of Madison's finest beaches... |
1 beds | 1 baths | 784 sq.ft. |
$450,000 |
Airbnb cash on cash: 0.29%
|
7 Madrina LaneMadison, CTLocation, Location, Location!! Introducing a charming and well-maintained raised ranch hom... |
3 beds | 1 baths | 1,144 sq.ft. |
$525,000 |
Airbnb cash on cash: 0.85%
|
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. |
$725,000 |
Airbnb cash on cash: -1.09%
|
66 Beaver Pond RoadMadison, CTSpacious 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: 0.65%
|
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: -2.51%
|
76 Squires RoadMadison, CTCome see this charming Ranch oasis in desirable Madison, where the allure of suburban tran... |
5 beds | 3 baths | 2,652 sq.ft. |
$485,000 |
Airbnb cash on cash: 4.59%
|
20 Strawberry Hill RoadMadison, CTThis 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: 0.68%
|
60 Robin Ridge DriveMadison, CTTucked away on a sought-after cul-de-sac just minutes from downtown Madison, 60 Robin Ridg... |
3 beds | 3 baths | 1,992 sq.ft. |
$599,999 |
Airbnb cash on cash: 0.36%
|
779 Summer Hill RoadMadison, CTWelcome 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: 0.31%
|
Real Estate investment in Madison, CT
There are 34 properties for sale in the city of Madison . The median list price in Madison is $699,450 and the average price per square foot is $285. In October 2025, the average monthly cash on cash return in Madison is 3.00%. The average monthly rental income in Madison is $4,469.