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 Detached stand-alone Ranch home in sought after Kensington Acres South has been beautifull...	2 beds \| 2 baths \| 1,360 sq.ft.	$539,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 3.07% Airbnb Rental Income: $1826 Traditional Rental Income: $3114 Airbnb ROI: -0.46% Traditional ROI: 3.07%
21 Evarts Lane #21 Madison, CT The beloved Mews - This in town luxury townhouse condominium will not disappoint. Quality ...	2 beds \| 3 baths \| 2,587 sq.ft.	$1,195,000	Airbnb cash on cash: -2.01% Traditional cash on cash: -0.57% Airbnb Rental Income: $1826 Traditional Rental Income: $2931 Airbnb ROI: -2.01% Traditional ROI: -0.57%
92 Fourth Avenue Madison, CT Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal ...	2 beds \| 1 baths \| 396 sq.ft.	$149,900	Airbnb cash on cash: 6.13% Traditional cash on cash: 11.75% Airbnb Rental Income: $1826 Traditional Rental Income: $2139 Airbnb ROI: 6.13% Traditional ROI: 11.75%
132 Summer Hill Road Madison, CT PRISTINE NEW CONSTRUCTION where thoughtful design meets high end craftsmanship. This newly...	4 beds \| 5 baths \| 4,517 sq.ft.	$2,375,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.4% Airbnb Rental Income: $2461 Traditional Rental Income: $8448 Airbnb ROI: -0.59% Traditional ROI: 2.4%
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.	$2,349,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.41% Airbnb Rental Income: $2461 Traditional Rental Income: $6223 Airbnb ROI: -1.59% Traditional ROI: 0.41%
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%
40 Hull Road Madison, CT Seldom-available offering in one of Madison's premier neighborhoods. This versatile split-...	4 beds \| 3 baths \| 3,462 sq.ft.	$825,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.57% Airbnb Rental Income: $2461 Traditional Rental Income: $5409 Airbnb ROI: -0.05% Traditional ROI: 4.57%
61 Hartford Avenue Madison, CT Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed c...	3 beds \| 4 baths \| 3,306 sq.ft.	$2,495,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.43% Airbnb Rental Income: $2119 Traditional Rental Income: $5344 Airbnb ROI: -1.2% Traditional ROI: 0.43%
18 St. Francis Woods Road Madison, CT Spacious 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: 0.85% Traditional cash on cash: 5.22% Airbnb Rental Income: $2119 Traditional Rental Income: $3496 Airbnb ROI: 0.85% Traditional ROI: 5.22%
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.	$154,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 8.74% Airbnb Rental Income: $1093 Traditional Rental Income: $1719 Airbnb ROI: 1.97% Traditional ROI: 8.74%
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: -1.2% Traditional cash on cash: 1.27% Airbnb Rental Income: $2461 Traditional Rental Income: $7933 Airbnb ROI: -1.2% Traditional ROI: 1.27%
6 First 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: 3.78% Traditional cash on cash: 8.31% Airbnb Rental Income: $1826 Traditional Rental Income: $2444 Airbnb ROI: 3.78% Traditional ROI: 8.31%
34 Wildcat Springs Drive Madison, CT Modern 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: N/A Traditional cash on cash: 5.14% Airbnb Rental Income: $null Traditional Rental Income: $10007 Airbnb ROI: N/A Traditional ROI: 5.14%
11 Middle Beach Road Madison, CT WOW water views! Vintage shingle style. The charm of old Madison with modern comforts. Thi...	3 beds \| 3 baths \| 1,976 sq.ft.	$1,775,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.19% Airbnb Rental Income: $2119 Traditional Rental Income: $3910 Airbnb ROI: -1.23% Traditional ROI: 0.19%
23 Hampshire Road #23 Madison, CT Welcome to Kensington North, a highly desirable condo community in the heart of Madison. T...	2 beds \| 3 baths \| 1,728 sq.ft.	$545,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 4.08% Airbnb Rental Income: $1826 Traditional Rental Income: $3342 Airbnb ROI: 0.14% Traditional ROI: 4.08%
104 Scotland Road Madison, CT Set on what is arguably the most beautiful lot in downtown Madison. This enchanting 5-bedr...	5 beds \| 2 baths \| 2,108 sq.ft.	$769,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3970 Airbnb ROI: N/A Traditional ROI: 3.26%
50 Overbrook Road Madison, CT Welcome 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: -0.32% Traditional cash on cash: 4.61% Airbnb Rental Income: $2119 Traditional Rental Income: $5369 Airbnb ROI: -0.32% Traditional ROI: 4.61%
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.	$174,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 10.04% Airbnb Rental Income: $1826 Traditional Rental Income: $2164 Airbnb ROI: 5.05% Traditional ROI: 10.04%
880 Boston Post Road Madison, CT The historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, is coming to...	4 beds \| 4 baths \| 3,697 sq.ft.	$2,475,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 1.03% Airbnb Rental Income: $2461 Traditional Rental Income: $7152 Airbnb ROI: -1.27% Traditional ROI: 1.03%

Real Estate investment in Madison, CT

There are 23 properties for sale in the city of Madison . The median list price in Madison is $420,000 and the average price per square foot is $229. In May 2026, the average monthly cash on cash return in Madison is 3.00%. The average monthly rental income in Madison is $5,341.

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

There are 23 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 $2,119.

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.

$539,900

Airbnb cash on cash: -0.46%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $1826

Traditional Rental Income: $3114

Airbnb ROI: -0.46%

Traditional ROI: 3.07%

21 Evarts Lane #21

Madison, CT

2 beds | 3 baths | 2,587 sq.ft.

$1,195,000

Airbnb cash on cash: -2.01%

Traditional cash on cash: -0.57%

Airbnb Rental Income: $1826

Traditional Rental Income: $2931

Airbnb ROI: -2.01%

Traditional ROI: -0.57%

92 Fourth Avenue

Madison, CT

2 beds | 1 baths | 396 sq.ft.

$149,900

Airbnb cash on cash: 6.13%

Traditional cash on cash: 11.75%

Airbnb Rental Income: $1826

Traditional Rental Income: $2139

Airbnb ROI: 6.13%

Traditional ROI: 11.75%

132 Summer Hill Road

Madison, CT

4 beds | 5 baths | 4,517 sq.ft.

$2,375,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2461

Traditional Rental Income: $8448

Airbnb ROI: -0.59%

Traditional ROI: 2.4%

64 Webster Point Road

Madison, CT

4 beds | 4 baths | 4,010 sq.ft.

$2,349,000

Airbnb cash on cash: -1.59%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $2461

Traditional Rental Income: $6223

Airbnb ROI: -1.59%

Traditional ROI: 0.41%

37 Lantern Hill Road

Madison, CT

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%

40 Hull Road

Madison, CT

4 beds | 3 baths | 3,462 sq.ft.

$825,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $2461

Traditional Rental Income: $5409

Airbnb ROI: -0.05%

Traditional ROI: 4.57%

61 Hartford Avenue

Madison, CT

3 beds | 4 baths | 3,306 sq.ft.

$2,495,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $2119

Traditional Rental Income: $5344

Airbnb ROI: -1.2%