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
38 Sanford Street Seymour, CT Charming Stucco home! Perfect one floor living! Kitchen with granite countertops and dinin...	2 beds \| 1 baths \| 1,156 sq.ft.	$270,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 5.19% Airbnb Rental Income: $1583 Traditional Rental Income: $2089 Airbnb ROI: 1.43% Traditional ROI: 5.19%
57 Bellevue Terrace Seymour, CT Welcome to your dream home in the heart of Seymour, Connecticut, a fully updated hillside ...	3 beds \| 2 baths \| 1,250 sq.ft.	$480,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.89% Airbnb Rental Income: $1704 Traditional Rental Income: $3242 Airbnb ROI: -0.59% Traditional ROI: 3.89%
77 South Main Street Seymour, CT This Well updated 3 Bedrooms 2 Full Baths, offers a comfortable leaving space, the feature...	3 beds \| 2 baths \| 1,080 sq.ft.	$389,900	Airbnb cash on cash: 0% Traditional cash on cash: 3.76% Airbnb Rental Income: $1704 Traditional Rental Income: $2608 Airbnb ROI: 0% Traditional ROI: 3.76%
154 South Benham Road Seymour, CT Welcome to 154 South Benham Road in Seymour! This spacious 4,664 sq. ft, 5-bed, 4-bath, ho...	5 beds \| 4 baths \| 4,664 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $6378 Airbnb ROI: N/A Traditional ROI: 8.1%
4 mead farm Road Seymour, CT Classic 4 bedroom, 2 and a half bath home nearing completion. This home features a large e...	4 beds \| 3 baths \| 3,800 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $4689 Airbnb ROI: N/A Traditional ROI: 2.07%
20 Argonne Terrace Seymour, CT Location! Location! Location! The 3 major points of Real Estate. This property is one stre...	3 beds \| 2 baths \| 1,183 sq.ft.	$309,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 5.78% Airbnb Rental Income: $1704 Traditional Rental Income: $2686 Airbnb ROI: 0.79% Traditional ROI: 5.78%
8 Birchwood Road Seymour, CT Picture-perfect on the outside, move-in ready on the inside, and with an incredible assuma...	3 beds \| 3 baths \| 1,552 sq.ft.	$499,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $1704 Traditional Rental Income: $3070 Airbnb ROI: -0.68% Traditional ROI: 3.26%
14 Spruce Brook Road Seymour, CT This stunning 3 bedroom, 2 bathroom ranch has been fully remodeled from top to bottom! Enj...	3 beds \| 2 baths \| 1,894 sq.ft.	$589,900	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.41% Airbnb Rental Income: $1704 Traditional Rental Income: $3141 Airbnb ROI: -1.06% Traditional ROI: 2.41%
31 Skokorat Street Seymour, CT Move right in to this "one-level living" home! This 3 BR, 1 1/2 BA ranch shows pride in ow...	3 beds \| 2 baths \| 1,296 sq.ft.	$410,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.73% Airbnb Rental Income: $1704 Traditional Rental Income: $2726 Airbnb ROI: -0.16% Traditional ROI: 3.73%
12 Deerfield Drive Seymour, CT Welcome to this charming custom ranch-style home offering space, versatility, and comfort ...	3 beds \| 2 baths \| 2,761 sq.ft.	$449,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.76% Airbnb Rental Income: $1704 Traditional Rental Income: $3406 Airbnb ROI: -0.41% Traditional ROI: 4.76%
27 Wood Street Seymour, CT Multi-family in a lovely rural neighborhood with a large side yard. The first floor is own...	4 beds \| 2 baths \| 1,778 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.63% Airbnb Rental Income: $null Traditional Rental Income: $3374 Airbnb ROI: N/A Traditional ROI: 5.63%
26 Balance Rock Road #APT 16 Seymour, CT 26 Balance Rock Road, APT #16 is the perfect entry into homeownership or real estate inves...	2 beds \| 1 baths \| 925 sq.ft.	$215,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.4% Airbnb Rental Income: $1583 Traditional Rental Income: $1752 Airbnb ROI: -0.65% Traditional ROI: 2.4%
3 Hine Street Seymour, CT This turn-key, move-in ready home was extensively renovated in 2022 and blends modern styl...	3 beds \| 1 baths \| 1,170 sq.ft.	$340,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 3.41% Airbnb Rental Income: $1704 Traditional Rental Income: $2178 Airbnb ROI: 0.45% Traditional ROI: 3.41%
43 Balance Rock Road #APT 9 Seymour, CT Two Bedroom Balance Rock Condominium, half flight up to main level living. Stylish, bright...	2 beds \| 1 baths \| 900 sq.ft.	$219,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.41% Airbnb Rental Income: $1583 Traditional Rental Income: $1766 Airbnb ROI: -0.66% Traditional ROI: 2.41%

Real Estate investment in Seymour, CT

There are 21 properties for sale in the city of Seymour . The median list price in Seymour is $419,900 and the average price per square foot is $224. In October 2025, the average monthly cash on cash return in Seymour is 4.00%. The average monthly rental income in Seymour is $3,192.

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

There are 21 investment properties available for sale in Seymour.

In 2025, the best neighborhood to buy investment property is Seymour.

The ROI for Short-Term is higher than the Long-Term in Seymour with average rental income of $1,704.

Your search for investment property begins and ends here

Investment Property for Sale in Seymour, CT

38 Sanford Street

Seymour, CT

2 beds | 1 baths | 1,156 sq.ft.

$270,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 5.19%

Airbnb Rental Income: $1583

Traditional Rental Income: $2089

Airbnb ROI: 1.43%

Traditional ROI: 5.19%

57 Bellevue Terrace

Seymour, CT

3 beds | 2 baths | 1,250 sq.ft.

$480,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1704

Traditional Rental Income: $3242

Airbnb ROI: -0.59%

Traditional ROI: 3.89%

77 South Main Street

Seymour, CT

3 beds | 2 baths | 1,080 sq.ft.

$389,900

Airbnb cash on cash: 0%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1704

Traditional Rental Income: $2608

Airbnb ROI: 0%

Traditional ROI: 3.76%

154 South Benham Road

Seymour, CT

5 beds | 4 baths | 4,664 sq.ft.

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.1%

Airbnb Rental Income: $null

Traditional Rental Income: $6378

Airbnb ROI: N/A

Traditional ROI: 8.1%

4 mead farm Road

Seymour, CT

4 beds | 3 baths | 3,800 sq.ft.

$950,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.07%

Airbnb Rental Income: $null

Traditional Rental Income: $4689

Airbnb ROI: N/A

Traditional ROI: 2.07%

20 Argonne Terrace

Seymour, CT

3 beds | 2 baths | 1,183 sq.ft.

$309,900

Airbnb cash on cash: 0.79%

Traditional cash on cash: 5.78%

Airbnb Rental Income: $1704

Traditional Rental Income: $2686

Airbnb ROI: 0.79%

Traditional ROI: 5.78%

8 Birchwood Road

Seymour, CT

3 beds | 3 baths | 1,552 sq.ft.

$499,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $1704

Traditional Rental Income: $3070

Airbnb ROI: -0.68%

Traditional ROI: 3.26%

14 Spruce Brook Road

Seymour, CT

3 beds | 2 baths | 1,894 sq.ft.

$589,900

Airbnb cash on cash: -1.06%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $1704

Traditional Rental Income: $3141

Airbnb ROI: -1.06%