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 |
|---|---|---|---|
6 Ladshaw Drive #6Madison, CTPrivacy & 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%
|
34 Canborne Way #34Madison, CTNestled 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%
|
60 Bradley Corners RoadMadison, CTHighest 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%
|
15 Hampshire Road #15Madison, CTOne-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%
|
26 Bassett LaneMadison, CTCompletely 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%
|
24 Indigo TrlMadison, CTLuxury 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%
|
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. |
$875,000 |
Airbnb cash on cash: -0.52%
|
37 Lantern Hill RoadMadison, CTAn 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%
|
61 Hartford AvenueMadison, CTOwn 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%
|
18 St. Francis Woods RoadMadison, CTSpacious 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%
|
16 North StreetMadison, CTEscape 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%
|
34 Wildcat Springs DriveMadison, CTModern 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%
|
50 Overbrook RoadMadison, CTWelcome to a beautiful Cape Cod-Contemporary retreat that perfectly blends modern updates ... |
3 beds | 4 baths | 3,766 sq.ft. |
$825,000 |
Airbnb cash on cash: -0.42%
|
85 Fawn Brook CircleMadison, CTA Shoreline Masterpiece: Custom Cape Cod Living on 1.10 Private Acres Welcome to 85 Fawn B... |
4 beds | 3 baths | 2,976 sq.ft. |
$925,000 |
Airbnb cash on cash: -0.12%
|
32 North StreetMadison, CT32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this... |
2 beds | 1 baths | 592 sq.ft. |
$164,900 |
Airbnb cash on cash: 6.94%
|
880 Boston Post RoadMadison, CTThe historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, has come to ... |
4 beds | 4 baths | 3,697 sq.ft. |
$2,295,000 |
Airbnb cash on cash: -1.37%
|
81A Middle Beach RoadMadison, CTNEW PRICE. Set back from Middle Beach Rd and sited 25' above sea level (so no flood insura... |
4 beds | 3 baths | 3,321 sq.ft. |
$2,495,000 |
Airbnb cash on cash: -1.31%
|
50 East StreetMadison, CTLOCATION ~ 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%
|
351 Bartlett DriveMadison, CTBeautifully sited on a fabulous private lot in the highly sought-after Neck River Farms Ne... |
4 beds | 4 baths | 4,015 sq.ft. |
$995,000 |
Airbnb cash on cash: -0.46%
|
17-D Yankee Glen Drive #17DMadison, CTMOVE IN READY! Welcome home to 17 Yankee Glen Drive, a beautifully maintained and thoughtf... |
2 beds | 3 baths | 1,434 sq.ft. |
$475,000 |
Airbnb cash on cash: 1.21%
|
97 E Wharf RoadMadison, CTIf you've ever strolled down East Wharf, you've likely noticed this charming home. Just a ... |
3 beds | 3 baths | 1,293 sq.ft. |
$1,325,000 |
Airbnb cash on cash: -1.04%
|
221 Duck Hole RoadMadison, CT**PLEASE SUBMIT ANY OFFERS BY 12PM TUESDAY 6/16** Nestled in a serene woodland setting, th... |
3 beds | 3 baths | 2,068 sq.ft. |
$565,000 |
Airbnb cash on cash: 0.6%
|
86 Nursery LaneMadison, CTABSOLUTELY STUNNING is the only way to describe this immaculate 4+ bedroom Colonial, perfe... |
4 beds | 4 baths | 4,250 sq.ft. |
$935,000 |
Airbnb cash on cash: -0.56%
|
52 E Wharf RoadMadison, CTWelcome to the highly desirable East Wharf area, where this Shingle-Style residence is sur... |
5 beds | 3 baths | 2,920 sq.ft. |
$1,985,000 |
Airbnb cash on cash: -1.3%
|
53 Summer Hill RoadMadison, CTWake up to pure tranquility in this stunning 4-bedroom, 2.5-bath contemporary home. Perfec... |
4 beds | 3 baths | 2,024 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.19%
|
32 Liberty StreetMadison, CTRare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situat... |
3 beds | 3 baths | 1,188 sq.ft. |
$1,299,000 |
Airbnb cash on cash: -0.85%
|
Real Estate investment in Madison, CT
There are 35 properties for sale in the city of Madison . The median list price in Madison is $439,000 and the average price per square foot is $239. In June 2026, the average monthly cash on cash return in Madison is 3.00%. The average monthly rental income in Madison is $4,574.