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
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%
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%
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%
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%
16 North Street Madison, CT Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in D...	1 beds \| 1 baths \| 476 sq.ft.	$149,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 9.06% Airbnb Rental Income: $1536 Traditional Rental Income: $1719 Airbnb ROI: 4.66% Traditional ROI: 9.06%
32 North Street Madison, CT 32 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: 6.66% Traditional cash on cash: 10.69% Airbnb Rental Income: $2063 Traditional Rental Income: $2164 Airbnb ROI: 6.66% Traditional ROI: 10.69%
55 Island Avenue Madison, CT A rare offering in one of Madison's coveted shoreline neighborhoods, this custom-built Cap...	4 beds \| 3 baths \| 3,046 sq.ft.	$1,400,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.44% Airbnb Rental Income: $2261 Traditional Rental Income: $5082 Airbnb ROI: -1.17% Traditional ROI: 1.44%
351 Bartlett Drive Madison, CT Beautifully 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% Traditional cash on cash: 4.59% Airbnb Rental Income: $2261 Traditional Rental Income: $6375 Airbnb ROI: -0.46% Traditional ROI: 4.59%
86A E Wharf Road Madison, CT Rare opportunity to own in one of Madison's most coveted shoreline locations. Just steps f...	3 beds \| 2 baths \| 1,824 sq.ft.	$1,300,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.48% Airbnb Rental Income: $2491 Traditional Rental Income: $3649 Airbnb ROI: -0.98% Traditional ROI: 0.48%
97 E Wharf Road Madison, CT If 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: -0.72% Traditional cash on cash: 0.56% Airbnb Rental Income: $2491 Traditional Rental Income: $3469 Airbnb ROI: -0.72% Traditional ROI: 0.56%
221 Duck Hole Road Madison, 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: 1.34% Traditional cash on cash: 4.65% Airbnb Rental Income: $2491 Traditional Rental Income: $3636 Airbnb ROI: 1.34% Traditional ROI: 4.65%
86 Nursery Lane Madison, CT ABSOLUTELY 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: -0.57% Traditional cash on cash: 4.63% Airbnb Rental Income: $2261 Traditional Rental Income: $6222 Airbnb ROI: -0.57% Traditional ROI: 4.63%
476 Summer Hill Road Madison, CT This turnkey, sun-filled Colonial situated south of Route 80 in Madison perfectly blends m...	4 beds \| 3 baths \| 2,057 sq.ft.	$650,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 4.11% Airbnb Rental Income: $2261 Traditional Rental Income: $3845 Airbnb ROI: 0.56% Traditional ROI: 4.11%
32 Liberty Street Madison, CT Rare 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: -0.52% Traditional cash on cash: 0.91% Airbnb Rental Income: $2491 Traditional Rental Income: $3624 Airbnb ROI: -0.52% Traditional ROI: 0.91%
21 Centre Village Drive #21 Madison, CT Beautifully updated two-bedroom townhouse in Centre Village. One of only four 2-bedroom un...	2 beds \| 3 baths \| 1,498 sq.ft.	$625,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.42% Airbnb Rental Income: $2063 Traditional Rental Income: $3258 Airbnb ROI: 0.46% Traditional ROI: 3.42%
320 Summer Hill Road Madison, CT ** NOTICE: Multiple-offer situation - Sellers request that the Highest & Best Offer be sub...	4 beds \| 3 baths \| 2,536 sq.ft.	$675,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 4.29% Airbnb Rental Income: $2261 Traditional Rental Income: $4217 Airbnb ROI: 0.28% Traditional ROI: 4.29%
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%
12 W Sussex Place #12 Madison, CT Welcome to easy, low-maintenance living in this beautifully maintained 2-bedroom 1.5 bath ...	2 beds \| 2 baths \| 2,096 sq.ft.	$479,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.5% Airbnb Rental Income: $2063 Traditional Rental Income: $2719 Airbnb ROI: 0.84% Traditional ROI: 3.5%
31 Martleshamheath Lane Madison, CT Nestled on a secluded 1.89-acre wooded lot in the desirable seaside town of Madison, this ...	3 beds \| 4 baths \| 3,225 sq.ft.	$699,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 6.03% Airbnb Rental Income: $2491 Traditional Rental Income: $5454 Airbnb ROI: 0.56% Traditional ROI: 6.03%
17 Linden Ln Madison, CT 17 Linden Ln, Madison, CT 06443 \| Single Family Residential	2 beds \| 1 baths \| 852 sq.ft.	$850,000	Airbnb cash on cash: -1.31% Traditional cash on cash: -0.8% Airbnb Rental Income: $2063 Traditional Rental Income: $1939 Airbnb ROI: -1.31% Traditional ROI: -0.8%

Real Estate investment in Madison, CT

There are 42 properties for sale in the city of Madison . The median list price in Madison is $449,000 and the average price per square foot is $241. In August 2026, the average monthly cash on cash return in Madison is 3.00%. The average monthly rental income in Madison is $4,407.

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

There are 42 investment properties available for sale in Madison.

In 2026, the best neighborhood to buy investment property is Madison.

The ROI for Short-Term is higher than the Long-Term in Madison with average rental income of $2,261.

Your search for investment property begins and ends here

Investment Property 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%

81 Legend Hill Road #81

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%

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%

98 Bishop Lane

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%

26 Bassett Lane

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%

24 Indigo Trail

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%

3 Arrowhead Road

Madison, CT

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%