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
7 Third Street Madison, CT Madison, SEASHORE! - REDUCED!! Coastal living adjacent to glorious Hammonassett Beach Stat...	1 beds \| 1 baths \| 441 sq.ft.	$164,900	Airbnb cash on cash: 5.66% Traditional cash on cash: 9.39% Airbnb Rental Income: $1794 Traditional Rental Income: $1893 Airbnb ROI: 5.66% Traditional ROI: 9.39%
13 Longview Terrace unit: 13 #13 Madison, CT At the end of Longview Terrace, privately sited with expansive marsh and river views this ...	3 beds \| 4 baths \| 3,772 sq.ft.	$799,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 4.39% Airbnb Rental Income: $2035 Traditional Rental Income: $6259 Airbnb ROI: -1.99% Traditional ROI: 4.39%
75 Fairview Drive Madison, CT 3 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: 1.01% Traditional cash on cash: 3% Airbnb Rental Income: $2035 Traditional Rental Income: $2346 Airbnb ROI: 1.01% Traditional ROI: 3%
29 Circle Beach Road Madison, CT A 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: -0.28% Traditional cash on cash: 1.54% Airbnb Rental Income: $1605 Traditional Rental Income: $2332 Airbnb ROI: -0.28% Traditional ROI: 1.54%
6 1st 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: 2.31% Traditional cash on cash: 9.16% Airbnb Rental Income: $1605 Traditional Rental Income: $2829 Airbnb ROI: 2.31% Traditional ROI: 9.16%
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: -0.57% Traditional cash on cash: 2.4% Airbnb Rental Income: $2506 Traditional Rental Income: $8448 Airbnb ROI: -0.57% Traditional ROI: 2.4%
33 Seaview Avenue Madison, CT Stunning 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: -1.43% Traditional cash on cash: 0.1% Airbnb Rental Income: $2567 Traditional Rental Income: $8303 Airbnb ROI: -1.43% Traditional ROI: 0.1%
7 Madrina Lane Madison, CT Location, Location, Location!! Introducing a charming and well-maintained raised ranch hom...	3 beds \| 1 baths \| 1,144 sq.ft.	$509,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.85% Airbnb Rental Income: $2035 Traditional Rental Income: $2918 Airbnb ROI: 0.89% Traditional ROI: 3.85%
735 Opening Hill Road Madison, CT This 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: 0.35% Traditional cash on cash: 2.84% Airbnb Rental Income: $2506 Traditional Rental Income: $3466 Airbnb ROI: 0.35% Traditional ROI: 2.84%
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 \| 3,083 sq.ft.	$2,400,000	Airbnb cash on cash: -1.38% Traditional cash on cash: -0.25% Airbnb Rental Income: $2506 Traditional Rental Income: $4417 Airbnb ROI: -1.38% Traditional ROI: -0.25%
779 Summer Hill Road Madison, CT Welcome 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: 0.45% Traditional cash on cash: 3.79% Airbnb Rental Income: $1605 Traditional Rental Income: $2510 Airbnb ROI: 0.45% Traditional ROI: 3.79%
38 Sportsman Hill Road Madison, CT Welcome to an extraordinary approx 5,600 sq foot custom-built Colonial, privately sited on...	4 beds \| 4 baths \| 5,624 sq.ft.	$950,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 4.59% Airbnb Rental Income: $2506 Traditional Rental Income: $6225 Airbnb ROI: -0.3% Traditional ROI: 4.59%
35 Hotchkiss Lane Madison, CT This 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: -1.26% Traditional cash on cash: 0.77% Airbnb Rental Income: $2035 Traditional Rental Income: $4716 Airbnb ROI: -1.26% Traditional ROI: 0.77%
43 Fort Path Road Madison, CT Welcome to this adorable ranch in Madison! Stellar location! Just 1 mile from the historic...	3 beds \| 2 baths \| 1,346 sq.ft.	$540,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.41% Airbnb Rental Income: $2035 Traditional Rental Income: $3465 Airbnb ROI: 0.53% Traditional ROI: 4.41%
300 Mungertown Road Madison, CT Solidly built and ideally located, this classic Colonial offers quality, space, and everyd...	3 beds \| 3 baths \| 2,224 sq.ft.	$650,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.34% Airbnb Rental Income: $2035 Traditional Rental Income: $3637 Airbnb ROI: -0.17% Traditional ROI: 3.34%
70 High Hill Circle Madison, CT Nestled in a sought after neighborhood and privately set back from the cul-de-sac, this be...	5 beds \| 5 baths \| 4,760 sq.ft.	$1,395,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 3.92% Airbnb Rental Income: $2567 Traditional Rental Income: $8290 Airbnb ROI: -0.97% Traditional ROI: 3.92%
25 Copperstone Lane Madison, CT Welcome home to this charming 3-bedroom Cape-style Colonial, perfectly set back on a peace...	3 beds \| 3 baths \| 2,542 sq.ft.	$600,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.56% Airbnb Rental Income: $2035 Traditional Rental Income: $3919 Airbnb ROI: 0.25% Traditional ROI: 4.56%
2 Esterly Farms Road unit: 2 #2 Madison, CT Coming Soon Jan. 23rd! Photos will be loaded Jan. 29th. Available to show Jan. 30th! Welco...	1 beds \| 2 baths \| 1,344 sq.ft.	$400,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.79% Airbnb Rental Income: $1794 Traditional Rental Income: $2762 Airbnb ROI: 0.91% Traditional ROI: 4.79%

Real Estate investment in Madison, CT

There are 19 properties for sale in the city of Madison . The median list price in Madison is $419,950 and the average price per square foot is $228. In February 2026, the average monthly cash on cash return in Madison is 4.00%. The average monthly rental income in Madison is $3,919.

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

There are 19 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 $2,035.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, CT

7 Third Street

Madison, CT

1 beds | 1 baths | 441 sq.ft.

$164,900

Airbnb cash on cash: 5.66%

Traditional cash on cash: 9.39%

Airbnb Rental Income: $1794

Traditional Rental Income: $1893

Airbnb ROI: 5.66%

Traditional ROI: 9.39%

13 Longview Terrace unit: 13 #13

Madison, CT

3 beds | 4 baths | 3,772 sq.ft.

$799,000

Airbnb cash on cash: -1.99%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $2035

Traditional Rental Income: $6259

Airbnb ROI: -1.99%

Traditional ROI: 4.39%

75 Fairview Drive

Madison, CT

3 beds | 2 baths | 1,419 sq.ft.

$450,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 3%

Airbnb Rental Income: $2035

Traditional Rental Income: $2346

Airbnb ROI: 1.01%

Traditional ROI: 3%

29 Circle Beach Road

Madison, CT

2 beds | 1 baths | 720 sq.ft.

$699,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $1605

Traditional Rental Income: $2332

Airbnb ROI: -0.28%

Traditional ROI: 1.54%

6 1st Street

Madison, CT

2 beds | 1 baths | 612 sq.ft.

$259,900

Airbnb cash on cash: 2.31%

Traditional cash on cash: 9.16%

Airbnb Rental Income: $1605

Traditional Rental Income: $2829

Airbnb ROI: 2.31%

Traditional ROI: 9.16%

132 Summer Hill Road

Madison, CT

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

$2,375,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2506

Traditional Rental Income: $8448

Airbnb ROI: -0.57%

Traditional ROI: 2.4%

33 Seaview Avenue

Madison, CT

5 beds | 5 baths | 4,613 sq.ft.

$4,500,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2567

Traditional Rental Income: $8303

Airbnb ROI: -1.43%

Traditional ROI: 0.1%

7 Madrina Lane

Madison, CT

3 beds | 1 baths | 1,144 sq.ft.

$509,900

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $2035

Traditional Rental Income: $2918

Airbnb ROI: 0.89%