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
207 Woodlawn Drive #207 Seymour, CT BOM. Buyer had health issues. Amazing stand-alone, peaceful Meadow Brook Estates Condo. On...	3 beds \| 3 baths \| 2,484 sq.ft.	$625,000	Airbnb cash on cash: -2.07% Traditional cash on cash: 3.08% Airbnb Rental Income: $1172 Traditional Rental Income: $3790 Airbnb ROI: -2.07% Traditional ROI: 3.08%
94 Tomlinson Road Seymour, CT Exceptional waterfront living on 1.5 private acres in one of Seymour's most desirable neig...	3 beds \| 3 baths \| 2,729 sq.ft.	$799,900	Airbnb cash on cash: -1.55% Traditional cash on cash: 3.22% Airbnb Rental Income: $1172 Traditional Rental Income: $4339 Airbnb ROI: -1.55% Traditional ROI: 3.22%
4 Mead Farm Road Seymour, CT Agent Owned. Classic 4 bedroom, 2 and a half bath home nearing completion. This home featu...	4 beds \| 3 baths \| 3,800 sq.ft.	$889,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $4689 Airbnb ROI: N/A Traditional ROI: 4.32%
63 Micko Drive Seymour, CT This impeccably built, FULLY CUSTOMIZED 3-bed/2.5-bath townhouse showcases an exceptional ...	3 beds \| 3 baths \| 2,089 sq.ft.	$494,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 4.51% Airbnb Rental Income: $1172 Traditional Rental Income: $3628 Airbnb ROI: -1.62% Traditional ROI: 4.51%
285 S Main Street Seymour, CT Picture Sunday mornings in the family room, holiday dinners in a separate dining room, and...	5 beds \| 2 baths \| 2,310 sq.ft.	$339,988	Airbnb cash on cash: N/A Traditional cash on cash: 8.33% Airbnb Rental Income: $null Traditional Rental Income: $3634 Airbnb ROI: N/A Traditional ROI: 8.33%
38 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: -1.54% Traditional cash on cash: 4.33% Airbnb Rental Income: $1181 Traditional Rental Income: $3405 Airbnb ROI: -1.54% Traditional ROI: 4.33%
108 Buckingham Road Seymour, CT To be built. Similar to image shown. Enjoy the benefits of watching your home be built fro...	4 beds \| 3 baths \| 2,450 sq.ft.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $4265 Airbnb ROI: N/A Traditional ROI: 4.61%
59 Micko Drive Seymour, CT This impeccably built, FULLY CUSTOMIZED 3-bed/2.5-bath END-UNIT townhouse showcases EXCEPT...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -1.63% Traditional cash on cash: 4.41% Airbnb Rental Income: $1172 Traditional Rental Income: $3612 Airbnb ROI: -1.63% Traditional ROI: 4.41%
36 Micko Drive #61 Seymour, CT This impeccably built 2-bedroom, 2.5-bath townhome, featuring premium upgrades and custom ...	2 beds \| 3 baths \| 1,965 sq.ft.	$474,900	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.52% Airbnb Rental Income: $1181 Traditional Rental Income: $1710 Airbnb ROI: -1.54% Traditional ROI: 0.52%
2 Westerman Avenue Seymour, CT Welcome to 2 Westerman Avenue--- a two-family home for an investor or owner-occupants look...	4 beds \| 2 baths \| 1,800 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 4.66%
18 Buckingham Road Seymour, CT Welcome to your own private oasis, set on an expansive 2.36-acre lot with a massive, seclu...	4 beds \| 3 baths \| 2,414 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.71% Airbnb Rental Income: $null Traditional Rental Income: $4167 Airbnb ROI: N/A Traditional ROI: 4.71%
4 Bellevue Terrace Seymour, CT Welcome to 4 Bellevue Drive, a versatile 3-bedroom, 2-bathroom home situated on a fenced i...	3 beds \| 2 baths \| 1,236 sq.ft.	$325,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 5.86% Airbnb Rental Income: $1172 Traditional Rental Income: $2674 Airbnb ROI: -0.31% Traditional ROI: 5.86%
2 Edgehill Terrace Seymour, CT Your search for "one-level living" stops here!! This ranch-style has been remodeled within...	3 beds \| 1 baths \| 1,324 sq.ft.	$375,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 4.15% Airbnb Rental Income: $1172 Traditional Rental Income: $2377 Airbnb ROI: -0.36% Traditional ROI: 4.15%
14-20 George Street Seymour, CT Prime turn-key investment opportunity featuring five spacious, highly desirable 2-bedroom,...	10 beds \| 5 baths \| 3,840 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.97% Airbnb Rental Income: $null Traditional Rental Income: $7437 Airbnb ROI: N/A Traditional ROI: 6.97%
109 Davis Road Seymour, CT This Colonial style home features a distinctive two story foyer that creates an impressive...	4 beds \| 3 baths \| 3,183 sq.ft.	$739,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $4532 Airbnb ROI: N/A Traditional ROI: 3.73%
112 Maple Street Seymour, CT This ranch style home offers loads of space (over 2100 s.f. main level) and has endless po...	4 beds \| 4 baths \| 2,909 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.74% Airbnb Rental Income: $null Traditional Rental Income: $5675 Airbnb ROI: N/A Traditional ROI: 9.74%
36 Smith Street Seymour, CT Welcome to 36 Smith Street! This spacious Seymour home offers approximately 2,197 square f...	5 beds \| 3 baths \| 2,197 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $3933 Airbnb ROI: N/A Traditional ROI: 6.79%
5 Bruno Court #57 Seymour, CT This impeccably built, soon-to-be-completed 3-bed, 2.5-bath FULLY CUSTOMIZABLE townhouse o...	3 beds \| 3 baths \| 2,089 sq.ft.	$494,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 4.92% Airbnb Rental Income: $1172 Traditional Rental Income: $3815 Airbnb ROI: -1.62% Traditional ROI: 4.92%
3 Bruno Court Seymour, CT This impeccably built, soon-to-be-completed 2-bed, 3.5-bath FULLY CUSTOMIZABLE townhouse o...	2 beds \| 4 baths \| 2,089 sq.ft.	$484,900	Airbnb cash on cash: -1.57% Traditional cash on cash: 7.72% Airbnb Rental Income: $1181 Traditional Rental Income: $5009 Airbnb ROI: -1.57% Traditional ROI: 7.72%
2 Bryan Circle Seymour, CT Welcome to 2 Bryan Circle, a beautifully maintained, modern raised ranch nestled near the ...	3 beds \| 3 baths \| 1,942 sq.ft.	$500,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 4.4% Airbnb Rental Income: $1172 Traditional Rental Income: $3445 Airbnb ROI: -1.29% Traditional ROI: 4.4%
4 Elaine Drive Seymour, CT Welcome to 4 Elaine Drive, Seymour. This 3-bedroom, 1-bath ranch sits on 0.28 acres on a q...	3 beds \| 1 baths \| 960 sq.ft.	$379,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.91% Airbnb Rental Income: $1172 Traditional Rental Income: $2028 Airbnb ROI: -0.57% Traditional ROI: 2.91%
115-A Squantuck Road Seymour, CT This charming 3 bedroom, 1 bathroom ranch is nestled on a private secluded lot near the Ho...	3 beds \| 1 baths \| 1,254 sq.ft.	$315,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 4.78% Airbnb Rental Income: $1172 Traditional Rental Income: $2265 Airbnb ROI: -0.21% Traditional ROI: 4.78%
60 Birchwood Road Seymour, CT Welcome to 60 Birchwood Road! This inviting three-bedroom home features hardwood flooring ...	3 beds \| 1 baths \| 1,242 sq.ft.	$429,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.91% Airbnb Rental Income: $1172 Traditional Rental Income: $2287 Airbnb ROI: -0.82% Traditional ROI: 2.91%

Real Estate investment in Seymour, CT

There are 30 properties for sale in the city of Seymour . The median list price in Seymour is $393,500 and the average price per square foot is $231. In November 2026, the average monthly cash on cash return in Seymour is 4.00%. The average monthly rental income in Seymour is $3,612.

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

There are 30 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 $3,612.

Your search for investment property begins and ends here

Investment Property for Sale in Seymour, CT

207 Woodlawn Drive #207

Seymour, CT

3 beds | 3 baths | 2,484 sq.ft.

$625,000

Airbnb cash on cash: -2.07%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1172

Traditional Rental Income: $3790

Airbnb ROI: -2.07%

Traditional ROI: 3.08%

94 Tomlinson Road

Seymour, CT

3 beds | 3 baths | 2,729 sq.ft.

$799,900

Airbnb cash on cash: -1.55%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1172

Traditional Rental Income: $4339

Airbnb ROI: -1.55%

Traditional ROI: 3.22%

4 Mead Farm Road

Seymour, CT

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

$889,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $4689

Airbnb ROI: N/A

Traditional ROI: 4.32%

63 Micko Drive

Seymour, CT

3 beds | 3 baths | 2,089 sq.ft.

$494,900

Airbnb cash on cash: -1.62%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1172

Traditional Rental Income: $3628

Airbnb ROI: -1.62%

Traditional ROI: 4.51%

285 S Main Street

Seymour, CT

5 beds | 2 baths | 2,310 sq.ft.

$339,988

Airbnb cash on cash: N/A

Traditional cash on cash: 8.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3634

Airbnb ROI: N/A

Traditional ROI: 8.33%

38 Micko Drive

Seymour, CT

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

$474,900

Airbnb cash on cash: -1.54%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $1181

Traditional Rental Income: $3405

Airbnb ROI: -1.54%

Traditional ROI: 4.33%

108 Buckingham Road

Seymour, CT

4 beds | 3 baths | 2,450 sq.ft.

$789,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $4265

Airbnb ROI: N/A

Traditional ROI: 4.61%

59 Micko Drive

Seymour, CT

3 beds | 3 baths | 2,089 sq.ft.

$499,900

Airbnb cash on cash: -1.63%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1172

Traditional Rental Income: $3612

Airbnb ROI: -1.63%