Real Estate Investment Properties for Sale in Middletown, CT

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

Explore a variety of short-term homes & houses in Middletown, CT. Invest wisely with VRBO & Middletown, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Middletown, CT

Search for Single Family Residential for Sale in Middletown, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 27 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
301 Bell St MIDDLETOWN, CT Take a 3D Tour or Enjoy a Video Walkthrough 24/7! This striking double A-Frame, with iconi...	3 beds \| 4 baths \| 3,853 sq.ft.	$575,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 7.26% Airbnb Rental Income: $1388 Traditional Rental Income: $5475 Airbnb ROI: -1.13% Traditional ROI: 7.26%
23 Hotchkiss St MIDDLETOWN, CT Welcome to 23 Hotchkiss Street, where historic charm meets modern convenience in the heart...	2 beds \| 1 baths \| 1,378 sq.ft.	$300,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 6.61% Airbnb Rental Income: $1406 Traditional Rental Income: $2716 Airbnb ROI: 0.48% Traditional ROI: 6.61%
95 Training Hill Rd MIDDLETOWN, CT GORGEOUS RANCH HOME FEATURING 4 BEDROOMS.INTERIOR HAS AN OPEN FLOOR PLAN WITH FLOWING ROOM...	3 beds \| 2 baths \| 1,537 sq.ft.	$409,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 4.39% Airbnb Rental Income: $1388 Traditional Rental Income: $2695 Airbnb ROI: -0.1% Traditional ROI: 4.39%
3 Huber Manor MIDDLETOWN, CT Wesleyan University area Ranch on a cul-de-sac. A nice sized living room with inviting atm...	3 beds \| 2 baths \| 1,444 sq.ft.	$300,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 7.06% Airbnb Rental Income: $1388 Traditional Rental Income: $2903 Airbnb ROI: 0.21% Traditional ROI: 7.06%
63 Millbrook Rd MIDDLETOWN, CT Step into modern elegance with this contemporary 3 bedroom, 2 bath home. Clean lines and l...	4 beds \| 2 baths \| 1,963 sq.ft.	$434,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 2.7%
347 Farm Hill Road MIDDLETOWN, CT This charming brick ranch offers so much potential! The spacious, sun-filled living room f...	3 beds \| 1 baths \| 1,974 sq.ft.	$275,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.83% Airbnb Rental Income: $1388 Traditional Rental Income: $2498 Airbnb ROI: -0.07% Traditional ROI: 5.83%
672 Laurel Grove Rd MIDDLETOWN, CT 672 Laurel Grove Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 2,579 sq.ft.	$559,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 1.8% Airbnb Rental Income: $1388 Traditional Rental Income: $2666 Airbnb ROI: -1.45% Traditional ROI: 1.8%
Lot 5 Nathan Hale Rd MIDDLETOWN, CT Lot 5 Nathan Hale Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,500 sq.ft.	$499,900	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.8% Airbnb Rental Income: $1388 Traditional Rental Income: $2863 Airbnb ROI: -1.25% Traditional ROI: 2.8%
175 Lincoln St MIDDLETOWN, CT 175 Lincoln St, MIDDLETOWN, CT 06457 \| Single Family Residential	4 beds \| 1 baths \| 2,005 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2184 Airbnb ROI: N/A Traditional ROI: 3.73%
42 Saybrook Rd MIDDLETOWN, CT 42 Saybrook Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	4 beds \| 2 baths \| 1,704 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 6.1%
5 Lorraine Ter MIDDLETOWN, CT 5 Lorraine Ter, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,934 sq.ft.	$409,100	Airbnb cash on cash: -0.84% Traditional cash on cash: 3.73% Airbnb Rental Income: $1388 Traditional Rental Income: $2719 Airbnb ROI: -0.84% Traditional ROI: 3.73%
145 Webster Ln #2-41 MIDDLETOWN, CT 145 Webster Ln #2-41, MIDDLETOWN, CT 06457 \| Single Family Residential	2 beds \| 2 baths \| 1,555 sq.ft.	$629,900	Airbnb cash on cash: -2.27% Traditional cash on cash: 0.5% Airbnb Rental Income: $1406 Traditional Rental Income: $2613 Airbnb ROI: -2.27% Traditional ROI: 0.5%
565 High St MIDDLETOWN, CT 565 High St, MIDDLETOWN, CT 06457 \| Single Family Residential	N/A beds \| N/A baths \| 2,192 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $1011 Airbnb ROI: N/A Traditional ROI: 0.43%
146 Liberty St MIDDLETOWN, CT 146 Liberty St, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 1,340 sq.ft.	$249,609	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.96% Airbnb Rental Income: $1388 Traditional Rental Income: $1910 Airbnb ROI: -0.19% Traditional ROI: 2.96%
Lot 3 Coleman Rd MIDDLETOWN, CT Lot 3 Coleman Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	4 beds \| 2 baths \| 2,006 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $3368 Airbnb ROI: N/A Traditional ROI: 2.28%
Lot 4 Nathan Hale Rd MIDDLETOWN, CT Lot 4 Nathan Hale Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,761 sq.ft.	$574,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.34% Airbnb Rental Income: $1388 Traditional Rental Income: $3026 Airbnb ROI: -1.49% Traditional ROI: 2.34%
Lot 3 Nathan Hale Rd MIDDLETOWN, CT Lot 3 Nathan Hale Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,761 sq.ft.	$574,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.34% Airbnb Rental Income: $1388 Traditional Rental Income: $3026 Airbnb ROI: -1.49% Traditional ROI: 2.34%
Lot 1 Nathan Hale Rd MIDDLETOWN, CT Lot 1 Nathan Hale Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,761 sq.ft.	$549,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 2.59% Airbnb Rental Income: $1388 Traditional Rental Income: $3026 Airbnb ROI: -1.42% Traditional ROI: 2.59%
Lot 2 Nathan Hale Rd MIDDLETOWN, CT Lot 2 Nathan Hale Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,761 sq.ft.	$574,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.34% Airbnb Rental Income: $1388 Traditional Rental Income: $3026 Airbnb ROI: -1.49% Traditional ROI: 2.34%
137 Webster Ln #2-42 MIDDLETOWN, CT 137 Webster Ln #2-42, MIDDLETOWN, CT 06457 \| Single Family Residential	2 beds \| 2 baths \| 1,430 sq.ft.	$549,900	Airbnb cash on cash: -2.15% Traditional cash on cash: 0.94% Airbnb Rental Income: $1406 Traditional Rental Income: $2572 Airbnb ROI: -2.15% Traditional ROI: 0.94%
183 Aston Ln MIDDLETOWN, CT 183 Aston Ln, MIDDLETOWN, CT 06457 \| Single Family Residential	5 beds \| 2 baths \| 2,908 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3193 Airbnb ROI: N/A Traditional ROI: 3.51%
50 Cedar St MIDDLETOWN, CT 50 Cedar St, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 2 baths \| 1,440 sq.ft.	$379,900	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.91% Airbnb Rental Income: $1388 Traditional Rental Income: $2598 Airbnb ROI: -0.66% Traditional ROI: 3.91%
208 Highmeadow Ln MIDDLETOWN, CT 208 Highmeadow Ln, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 3 baths \| 3,576 sq.ft.	$525,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 3.73% Airbnb Rental Income: $1388 Traditional Rental Income: $3453 Airbnb ROI: -1.34% Traditional ROI: 3.73%
82 Westfield Ter MIDDLETOWN, CT 82 Westfield Ter, MIDDLETOWN, CT 06457 \| Single Family Residential	2 beds \| 1 baths \| 1,090 sq.ft.	$414,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.49% Airbnb Rental Income: $1406 Traditional Rental Income: $1496 Airbnb ROI: -0.83% Traditional ROI: 0.49%
72 Glendale Ave MIDDLETOWN, CT 72 Glendale Ave, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 1,462 sq.ft.	$300,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.83% Airbnb Rental Income: $1388 Traditional Rental Income: $2054 Airbnb ROI: -0.01% Traditional ROI: 3.83%
104 Boston Rd MIDDLETOWN, CT 104 Boston Rd, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 1,050 sq.ft.	$349,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 2.75% Airbnb Rental Income: $1388 Traditional Rental Income: $2019 Airbnb ROI: -0.45% Traditional ROI: 2.75%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, CT

301 Bell St

MIDDLETOWN, CT

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

$575,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 7.26%

Airbnb Rental Income: $1388

Traditional Rental Income: $5475

Airbnb ROI: -1.13%

Traditional ROI: 7.26%

23 Hotchkiss St

MIDDLETOWN, CT

2 beds | 1 baths | 1,378 sq.ft.

$300,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 6.61%

Airbnb Rental Income: $1406

Traditional Rental Income: $2716

Airbnb ROI: 0.48%

Traditional ROI: 6.61%

95 Training Hill Rd

MIDDLETOWN, CT

3 beds | 2 baths | 1,537 sq.ft.

$409,900

Airbnb cash on cash: -0.1%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $1388

Traditional Rental Income: $2695

Airbnb ROI: -0.1%

Traditional ROI: 4.39%

3 Huber Manor

MIDDLETOWN, CT

3 beds | 2 baths | 1,444 sq.ft.

$300,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 7.06%

Airbnb Rental Income: $1388

Traditional Rental Income: $2903

Airbnb ROI: 0.21%

Traditional ROI: 7.06%

63 Millbrook Rd

MIDDLETOWN, CT

4 beds | 2 baths | 1,963 sq.ft.

$434,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2465

Airbnb ROI: N/A

Traditional ROI: 2.7%

347 Farm Hill Road

MIDDLETOWN, CT

3 beds | 1 baths | 1,974 sq.ft.

$275,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 5.83%

Airbnb Rental Income: $1388

Traditional Rental Income: $2498

Airbnb ROI: -0.07%

Traditional ROI: 5.83%

672 Laurel Grove Rd

MIDDLETOWN, CT

3 beds | 2 baths | 2,579 sq.ft.

$559,000

Airbnb cash on cash: -1.45%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $1388

Traditional Rental Income: $2666

Airbnb ROI: -1.45%

Traditional ROI: 1.8%

Lot 5 Nathan Hale Rd

MIDDLETOWN, CT

3 beds | 2 baths | 1,500 sq.ft.

$499,900

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $1388

Traditional Rental Income: $2863

Airbnb ROI: -1.25%