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.

Investment Property for Sale in Middletown, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
301 Bell Street 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.	$585,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 7.71% Airbnb Rental Income: $1388 Traditional Rental Income: $5475 Airbnb ROI: -0.54% Traditional ROI: 7.71%
59 Westfield Terrace MIDDLETOWN, CT They say love at first sight isn't real... until you walk in here." Have you ever walked i...	3 beds \| 2 baths \| 960 sq.ft.	$324,999	Airbnb cash on cash: 0.3% Traditional cash on cash: 5.36% Airbnb Rental Income: $1388 Traditional Rental Income: $2516 Airbnb ROI: 0.3% Traditional ROI: 5.36%
23 Hotchkiss Street MIDDLETOWN, CT Welcome to 23 Hotchkiss Street, where historic charm meets modern convenience in the heart...	2 beds \| 2 baths \| 1,378 sq.ft.	$300,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 6.9% Airbnb Rental Income: $1406 Traditional Rental Income: $2716 Airbnb ROI: 0.76% Traditional ROI: 6.9%
80 Elizabeth Lane MIDDLETOWN, CT Built in 2000 and beautifully reimagined, this home has been extensively remodeled to blen...	3 beds \| 3 baths \| 2,310 sq.ft.	$549,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 4.62% Airbnb Rental Income: $1388 Traditional Rental Income: $3770 Airbnb ROI: -0.83% Traditional ROI: 4.62%
50 Garfield Avenue MIDDLETOWN, CT Welcome Home, Fall in love and move in for the holidays. Stunning 3 bedroom~2 full bath Ca...	3 beds \| 2 baths \| 1,366 sq.ft.	$389,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.62% Airbnb Rental Income: $1388 Traditional Rental Income: $1825 Airbnb ROI: -0.72% Traditional ROI: 1.62%
120 Scenic View Drive MIDDLETOWN, CT Stately, custom-built Colonial nestled on a level lot with sweeping countryside views! Thi...	4 beds \| 4 baths \| 3,833 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.93% Airbnb Rental Income: $null Traditional Rental Income: $5771 Airbnb ROI: N/A Traditional ROI: 7.93%
199 Aston Lane MIDDLETOWN, CT Just steps from Wadsworth State Park and the iconic Wadsworth Mansion, this three-bedroom,...	3 beds \| 2 baths \| 1,807 sq.ft.	$469,900	Airbnb cash on cash: -1.13% Traditional cash on cash: 3.63% Airbnb Rental Income: $1388 Traditional Rental Income: $3061 Airbnb ROI: -1.13% Traditional ROI: 3.63%
105 Hawks Nest Circle MIDDLETOWN, CT Welcome to this spacious 3-bedroom, 3-bath raised ranch with great features inside and out...	3 beds \| 3 baths \| 1,176 sq.ft.	$349,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.62% Airbnb Rental Income: $1388 Traditional Rental Income: $2636 Airbnb ROI: -0.45% Traditional ROI: 4.62%
120 Chamberlain Hill Road MIDDLETOWN, CT Situated on almost 13 acres in the heart of CT, this stunning Colonial offers peace and na...	4 beds \| 5 baths \| 5,661 sq.ft.	$1,900,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.26% Airbnb Rental Income: $null Traditional Rental Income: $7839 Airbnb ROI: N/A Traditional ROI: 1.26%
56 Burgundy Hill Lane #56 MIDDLETOWN, CT Welcome to 56 Burgundy Hill Lane, Middletown! This totally renovated 2-bedroom ranch-style...	2 beds \| 1 baths \| 698 sq.ft.	$144,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 5.76% Airbnb Rental Income: $1406 Traditional Rental Income: $1711 Airbnb ROI: 0.52% Traditional ROI: 5.76%
48 Carriage Crossing Lane #8108 MIDDLETOWN, CT Welcome to this 2 Bedroom / 2 Full Bath, Move-In Ready Condo (Ground Level) - Experience s...	2 beds \| 2 baths \| 840 sq.ft.	$219,900	Airbnb cash on cash: -1.07% Traditional cash on cash: 4.17% Airbnb Rental Income: $1406 Traditional Rental Income: $2074 Airbnb ROI: -1.07% Traditional ROI: 4.17%
7 Inverness Square MIDDLETOWN, CT Welcome to 7 Inverness Square, Middletown, CT. This beautiful rare-4-bedroom, 2-bath home ...	3 beds \| 1 baths \| 1,328 sq.ft.	$249,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 6.14% Airbnb Rental Income: $1388 Traditional Rental Income: $2323 Airbnb ROI: 0.4% Traditional ROI: 6.14%
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.	$314,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 5% Airbnb Rental Income: $1388 Traditional Rental Income: $2498 Airbnb ROI: -0.16% Traditional ROI: 5%
233 Oak Ridge Drive MIDDLETOWN, CT Enjoy a complete Video Walkthrough OR take a Self-Guided 3D Tour 24/7! This move-in-ready ...	3 beds \| 2 baths \| 1,053 sq.ft.	$350,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.33% Airbnb Rental Income: $1388 Traditional Rental Income: $2541 Airbnb ROI: -0.45% Traditional ROI: 4.33%
102 Greenview Terrace MIDDLETOWN, CT Welcome to Greenview Terrace, a Riverbend Neighborhood! This three-bedroom Ranch style ho...	3 beds \| 2 baths \| 1,420 sq.ft.	$379,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 4.49% Airbnb Rental Income: $1388 Traditional Rental Income: $2829 Airbnb ROI: -0.75% Traditional ROI: 4.49%
10 Wall Street MIDDLETOWN, CT Discover this well-maintained two-family property in a quiet neighborhood, perfect for own...	4 beds \| 2 baths \| 1,941 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.23% Airbnb Rental Income: $null Traditional Rental Income: $3296 Airbnb ROI: N/A Traditional ROI: 8.23%
751 Long Hill Road #APT C MIDDLETOWN, CT Have you dreamed of living in a Showcase Townhouse? This exceptional property could be per...	2 beds \| 2 baths \| 1,339 sq.ft.	$280,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 3.91% Airbnb Rental Income: $1406 Traditional Rental Income: $2531 Airbnb ROI: -1.96% Traditional ROI: 3.91%
491 Long Hill Road MIDDLETOWN, CT Welcome home to this beautifully maintained Raised Ranch offering the perfect blend of com...	3 beds \| 2 baths \| 1,262 sq.ft.	$379,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 4.17% Airbnb Rental Income: $1388 Traditional Rental Income: $2743 Airbnb ROI: -0.82% Traditional ROI: 4.17%
3 Trolley Crossing Lane #3 MIDDLETOWN, CT Enjoy the benefit of the fully paid off special assessment valued at $15,000 for new roofi...	2 beds \| 2 baths \| 1,220 sq.ft.	$229,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 6.11% Airbnb Rental Income: $1406 Traditional Rental Income: $2442 Airbnb ROI: -0.6% Traditional ROI: 6.11%
40 Rome Avenue MIDDLETOWN, CT Great opportunity in Middletown! 40 Rome Avenue is a well-kept three-family home just minu...	5 beds \| 3 baths \| 2,870 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.27% Airbnb Rental Income: $null Traditional Rental Income: $4101 Airbnb ROI: N/A Traditional ROI: 8.27%
10 Talias Trail MIDDLETOWN, CT WOW...CHECK OUT THIS NEW PRICE!!! Welcome home to 10 Talias Trail....there is still plenty...	4 beds \| 3 baths \| 2,285 sq.ft.	$629,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3993 Airbnb ROI: N/A Traditional ROI: 3.51%
237 Boston Road MIDDLETOWN, CT Fall in love with this charming, well-maintained Cape home with attached garage located at...	2 beds \| 1 baths \| 1,154 sq.ft.	$324,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.49% Airbnb Rental Income: $1406 Traditional Rental Income: $2111 Airbnb ROI: -0.2% Traditional ROI: 3.49%

Real Estate investment in Middletown, CT

There are 25 properties for sale in the city of Middletown . The median list price in Middletown is $339,000 and the average price per square foot is $185. In December 2025, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $2,541.

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

There are 25 investment properties available for sale in Middletown.

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

The ROI for Short-Term is higher than the Long-Term in Middletown with average rental income of $1,388.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

301 Bell Street

MIDDLETOWN, CT

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

$585,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 7.71%

Airbnb Rental Income: $1388

Traditional Rental Income: $5475

Airbnb ROI: -0.54%

Traditional ROI: 7.71%

59 Westfield Terrace

MIDDLETOWN, CT

3 beds | 2 baths | 960 sq.ft.

$324,999

Airbnb cash on cash: 0.3%

Traditional cash on cash: 5.36%

Airbnb Rental Income: $1388

Traditional Rental Income: $2516

Airbnb ROI: 0.3%

Traditional ROI: 5.36%

23 Hotchkiss Street

MIDDLETOWN, CT

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

$300,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1406

Traditional Rental Income: $2716

Airbnb ROI: 0.76%

Traditional ROI: 6.9%

80 Elizabeth Lane

MIDDLETOWN, CT

3 beds | 3 baths | 2,310 sq.ft.

$549,900

Airbnb cash on cash: -0.83%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1388

Traditional Rental Income: $3770

Airbnb ROI: -0.83%

Traditional ROI: 4.62%

50 Garfield Avenue

MIDDLETOWN, CT

3 beds | 2 baths | 1,366 sq.ft.

$389,900

Airbnb cash on cash: -0.72%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1388

Traditional Rental Income: $1825

Airbnb ROI: -0.72%

Traditional ROI: 1.62%

120 Scenic View Drive

MIDDLETOWN, CT

4 beds | 4 baths | 3,833 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.93%

Airbnb Rental Income: $null

Traditional Rental Income: $5771

Airbnb ROI: N/A

Traditional ROI: 7.93%

199 Aston Lane

MIDDLETOWN, CT

3 beds | 2 baths | 1,807 sq.ft.

$469,900

Airbnb cash on cash: -1.13%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $1388

Traditional Rental Income: $3061

Airbnb ROI: -1.13%

Traditional ROI: 3.63%

105 Hawks Nest Circle

MIDDLETOWN, CT

3 beds | 3 baths | 1,176 sq.ft.

$349,900

Airbnb cash on cash: -0.45%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1388

Traditional Rental Income: $2636

Airbnb ROI: -0.45%