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: 0.17% Traditional cash on cash: 5.12% Airbnb Rental Income: $1584 Traditional Rental Income: $2939 Airbnb ROI: 0.17% Traditional ROI: 5.12%
208 Bungay Road Seymour, CT Charming ranch-style home on nearly 2 private acres with major upgrades already completed!...	2 beds \| 2 baths \| 1,546 sq.ft.	$459,900	Airbnb cash on cash: -1.27% Traditional cash on cash: 3.94% Airbnb Rental Income: $1048 Traditional Rental Income: $2927 Airbnb ROI: -1.27% Traditional ROI: 3.94%
3 Roosevelt Dr Seymour, CT 3 Roosevelt Dr, Seymour, CT 06483 \| Single Family Residential	2 beds \| 1 baths \| 1,431 sq.ft.	$599,900	Airbnb cash on cash: -2.07% Traditional cash on cash: -0.47% Airbnb Rental Income: $1048 Traditional Rental Income: $1579 Airbnb ROI: -2.07% Traditional ROI: -0.47%
48 Micko Drive Seymour, CT This impeccably built, soon-to-be-completed 2 Bed/2.5 Bath townhouse offers a rare combina...	2 beds \| 3 baths \| 1,965 sq.ft.	$474,900	Airbnb cash on cash: -2.44% Traditional cash on cash: 3.7% Airbnb Rental Income: $1048 Traditional Rental Income: $3411 Airbnb ROI: -2.44% Traditional ROI: 3.7%
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 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: 0.34% Traditional cash on cash: 4.24% Airbnb Rental Income: $1584 Traditional Rental Income: $2501 Airbnb ROI: 0.34% Traditional ROI: 4.24%
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: -1.79% Traditional cash on cash: 4.33% Airbnb Rental Income: $1048 Traditional Rental Income: $3404 Airbnb ROI: -1.79% Traditional ROI: 4.33%
31 Smith Street Seymour, CT Welcome home to this spacious Colonial full of potential! Add your personal touches and up...	5 beds \| 2 baths \| 1,785 sq.ft.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.49% Airbnb Rental Income: $null Traditional Rental Income: $3345 Airbnb ROI: N/A Traditional ROI: 8.49%
9 Rosko Street Seymour, CT HIGHLY MOTIVATED SELLERS!! Sellers are offering a credit at closing towards updating the k...	2 beds \| 2 baths \| 1,710 sq.ft.	$345,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 5.84% Airbnb Rental Income: $1048 Traditional Rental Income: $2872 Airbnb ROI: -0.91% Traditional ROI: 5.84%
40 Church Street Seymour, CT Bring the whole family-and the extended family too! This completely remodeled grand Coloni...	4 beds \| 3 baths \| 2,639 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $4150 Airbnb ROI: N/A Traditional ROI: 4.33%
63 Micko Drive Seymour, CT This impeccably built, soon-to-be-completed 3 Bed /2.5 Bath townhouse offers a rare combin...	3 beds \| 3 baths \| 2,089 sq.ft.	$494,900	Airbnb cash on cash: -0.88% Traditional cash on cash: 4.51% Airbnb Rental Income: $1584 Traditional Rental Income: $3628 Airbnb ROI: -0.88% Traditional ROI: 4.51%
2 Whippoorwill Lane Seymour, CT Welcome home! This home has been lovingly cared for by the same owner for the past 34 year...	3 beds \| 1 baths \| 1,172 sq.ft.	$315,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 4.49% Airbnb Rental Income: $1584 Traditional Rental Income: $2186 Airbnb ROI: 0.93% Traditional ROI: 4.49%

Real Estate investment in Seymour, CT

There are 24 properties for sale in the city of Seymour . The median list price in Seymour is $389,450 and the average price per square foot is $236. In June 2026, the average monthly cash on cash return in Seymour is 4.00%. The average monthly rental income in Seymour is $3,411.

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

There are 24 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 $3,411.

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: 0.17%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1584

Traditional Rental Income: $2939

Airbnb ROI: 0.17%

Traditional ROI: 5.12%

208 Bungay Road

Seymour, CT

2 beds | 2 baths | 1,546 sq.ft.

$459,900

Airbnb cash on cash: -1.27%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1048

Traditional Rental Income: $2927

Airbnb ROI: -1.27%

Traditional ROI: 3.94%

3 Roosevelt Dr

Seymour, CT

2 beds | 1 baths | 1,431 sq.ft.

$599,900

Airbnb cash on cash: -2.07%

Traditional cash on cash: -0.47%

Airbnb Rental Income: $1048

Traditional Rental Income: $1579

Airbnb ROI: -2.07%

Traditional ROI: -0.47%

48 Micko Drive

Seymour, CT

2 beds | 3 baths | 1,965 sq.ft.

$474,900

Airbnb cash on cash: -2.44%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1048

Traditional Rental Income: $3411

Airbnb ROI: -2.44%

Traditional ROI: 3.7%

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 Highland Avenue

Seymour, CT

3 beds | 2 baths | 1,114 sq.ft.

$374,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1584

Traditional Rental Income: $2501

Airbnb ROI: 0.34%

Traditional ROI: 4.24%

44 Micko Drive

Seymour, CT

2 beds | 3 baths | 1,965 sq.ft.

$474,900

Airbnb cash on cash: -1.79%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $1048

Traditional Rental Income: $3404

Airbnb ROI: -1.79%

Traditional ROI: 4.33%

31 Smith Street

Seymour, CT

5 beds | 2 baths | 1,785 sq.ft.

$310,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3345

Airbnb ROI: N/A