Real Estate Investment Properties for Sale in Seymour, CT

Looking for investment property in Seymour, CT with high ROI ?

Explore a variety of short-term homes & houses in Seymour, CT. Invest wisely with VRBO & Seymour, 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 Seymour, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
41 Emma Street Seymour, CT Adorable and move-in ready, this charming 3-bedroom Cape offers the perfect blend of comfo...	3 beds \| 2 baths \| 1,421 sq.ft.	$389,900	Airbnb cash on cash: -1.25% Traditional cash on cash: 5.12% Airbnb Rental Income: $962 Traditional Rental Income: $2939 Airbnb ROI: -1.25% Traditional ROI: 5.12%
107 West Street Seymour, CT Historical home, Cape Style, Large deck leads into the kitchen and dining room which are s...	3 beds \| 1 baths \| 1,153 sq.ft.	$249,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 6.32% Airbnb Rental Income: $962 Traditional Rental Income: $2217 Airbnb ROI: -0.47% Traditional ROI: 6.32%
3 Willow Street Seymour, CT This expanded cape on cul-de-sac has plenty of room for the whole family. The home has a f...	4 beds \| 1 baths \| 1,722 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $2669 Airbnb ROI: N/A Traditional ROI: 5.28%
22 Brookfield Road Seymour, CT Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial located in the highly ...	4 beds \| 3 baths \| 3,853 sq.ft.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $4443 Airbnb ROI: N/A Traditional ROI: 3.68%
29 Moss Avenue #23 Seymour, CT Welcome to this beautifully maintained 1 bedroom, 1.5-bath condo offering comfort, space, ...	1 beds \| 2 baths \| 864 sq.ft.	$269,900	Airbnb cash on cash: -3.92% Traditional cash on cash: 3.79% Airbnb Rental Income: $298 Traditional Rental Income: $2021 Airbnb ROI: -3.92% Traditional ROI: 3.79%
387 S Main Street Seymour, CT Excellent investment opportunity in a prime location! This well maintained 4 family proper...	8 beds \| 4 baths \| 4,360 sq.ft.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $5701 Airbnb ROI: N/A Traditional ROI: 5.86%
23 Holbrook Road Seymour, CT Beautiful located home in the heart of Seymour Ct Expanded ranch offering 3 beds 2 bath Up...	3 beds \| 2 baths \| 1,744 sq.ft.	$379,900	Airbnb cash on cash: -1.22% Traditional cash on cash: 3.95% Airbnb Rental Income: $962 Traditional Rental Income: $2455 Airbnb ROI: -1.22% Traditional ROI: 3.95%
115 Roosevelt Drive Seymour, CT Just in time for summer. Direct waterfront on the Housatonic river. Dual Ranch-Style homes...	5 beds \| 2 baths \| 2,562 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $4054 Airbnb ROI: N/A Traditional ROI: 3.97%
65 Micko Drive Seymour, CT This impeccably built, soon-to-be-completed 3 Bed /2.5 Bath end-unit townhouse offers a ra...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -2.01% Traditional cash on cash: 4.46% Airbnb Rental Income: $962 Traditional Rental Income: $3635 Airbnb ROI: -2.01% Traditional ROI: 4.46%
23 Highland Avenue Seymour, CT HIGHEST & BEST SUNDAY, APRIL 26TH AT 5PM. This beautifully maintained home has been loving...	3 beds \| 2 baths \| 1,114 sq.ft.	$374,900	Airbnb cash on cash: -1.13% Traditional cash on cash: 4.24% Airbnb Rental Income: $962 Traditional Rental Income: $2501 Airbnb ROI: -1.13% Traditional ROI: 4.24%
6 Anne Avenue Seymour, CT Beautiful Ranch style home offering easy one-level living with thoughtful updates througho...	4 beds \| 2 baths \| 1,680 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $3269 Airbnb ROI: N/A Traditional ROI: 5.33%
17 Morningstar Drive Seymour, CT Welcome to 17 Morningstar Drive located in the desirable Skokorat neighborhood of Seymour!...	3 beds \| 2 baths \| 1,464 sq.ft.	$419,900	Airbnb cash on cash: -1% Traditional cash on cash: 5.06% Airbnb Rental Income: $962 Traditional Rental Income: $2997 Airbnb ROI: -1% Traditional ROI: 5.06%
46 Micko Drive Seymour, CT This impeccably built, soon-to-be-completed 2 Bed /2.5 Bath townhouse offers a rare combin...	2 beds \| 3 baths \| 1,965 sq.ft.	$474,900	Airbnb cash on cash: -2.01% Traditional cash on cash: 4.36% Airbnb Rental Income: $929 Traditional Rental Income: $3417 Airbnb ROI: -2.01% Traditional ROI: 4.36%
44 Micko Drive Seymour, CT This impeccably built, soon-to-be-completed 2 Bed /2.5 Bath townhouse offers a rare combin...	2 beds \| 3 baths \| 1,965 sq.ft.	$474,900	Airbnb cash on cash: -2.01% Traditional cash on cash: 4.33% Airbnb Rental Income: $929 Traditional Rental Income: $3404 Airbnb ROI: -2.01% Traditional ROI: 4.33%

Real Estate investment in Seymour, CT

There are 26 properties for sale in the city of Seymour . The median list price in Seymour is $389,900 and the average price per square foot is $230. In May 2026, the average monthly cash on cash return in Seymour is 4.00%. The average monthly rental income in Seymour is $3,417.

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

There are 26 investment properties available for sale in Seymour.

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

The ROI for Long-Term is higher than the Short-Term in Seymour with average rental income of $3,417.

Your search for investment property begins and ends here

Investment Property for Sale in Seymour, CT

41 Emma Street

Seymour, CT

3 beds | 2 baths | 1,421 sq.ft.

$389,900

Airbnb cash on cash: -1.25%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $962

Traditional Rental Income: $2939

Airbnb ROI: -1.25%

Traditional ROI: 5.12%

107 West Street

Seymour, CT

3 beds | 1 baths | 1,153 sq.ft.

$249,900

Airbnb cash on cash: -0.47%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $962

Traditional Rental Income: $2217

Airbnb ROI: -0.47%

Traditional ROI: 6.32%

3 Willow Street

Seymour, CT

4 beds | 1 baths | 1,722 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2669

Airbnb ROI: N/A

Traditional ROI: 5.28%

22 Brookfield Road

Seymour, CT

4 beds | 3 baths | 3,853 sq.ft.

$729,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.68%

Airbnb Rental Income: $null

Traditional Rental Income: $4443

Airbnb ROI: N/A

Traditional ROI: 3.68%

29 Moss Avenue #23

Seymour, CT

1 beds | 2 baths | 864 sq.ft.

$269,900

Airbnb cash on cash: -3.92%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $298

Traditional Rental Income: $2021

Airbnb ROI: -3.92%

Traditional ROI: 3.79%

387 S Main Street

Seymour, CT

8 beds | 4 baths | 4,360 sq.ft.

$729,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.86%

Airbnb Rental Income: $null

Traditional Rental Income: $5701

Airbnb ROI: N/A

Traditional ROI: 5.86%

23 Holbrook Road

Seymour, CT

3 beds | 2 baths | 1,744 sq.ft.

$379,900

Airbnb cash on cash: -1.22%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $962

Traditional Rental Income: $2455

Airbnb ROI: -1.22%

Traditional ROI: 3.95%

115 Roosevelt Drive

Seymour, CT

5 beds | 2 baths | 2,562 sq.ft.

$649,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.97%

Airbnb Rental Income: $null

Traditional Rental Income: $4054

Airbnb ROI: N/A