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
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.	$275,000	Airbnb cash on cash: -1.74% Traditional cash on cash: 7.29% Airbnb Rental Income: $677 Traditional Rental Income: $2716 Airbnb ROI: -1.74% Traditional ROI: 7.29%
10 Talias Trail MIDDLETOWN, CT Welcome home to 10 Talias Trail....start Spring in a new home and start "planting" new mem...	4 beds \| 3 baths \| 2,285 sq.ft.	$599,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 3.84% Airbnb Rental Income: $986 Traditional Rental Income: $3993 Airbnb ROI: -2.17% Traditional ROI: 3.84%
6 Hillside Court MIDDLETOWN, CT Welcome to this beautifully maintained Colonial that showcases modern living, featuring a ...	3 beds \| 2 baths \| 1,299 sq.ft.	$270,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 7.16% Airbnb Rental Income: $1188 Traditional Rental Income: $2661 Airbnb ROI: -0.14% Traditional ROI: 7.16%
8 Macdonough Place MIDDLETOWN, CT Eager to get a jump on the 2026 Spring Market? Better get a move to a very special in-town...	3 beds \| 2 baths \| 1,740 sq.ft.	$384,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 5.36% Airbnb Rental Income: $1188 Traditional Rental Income: $3064 Airbnb ROI: -0.92% Traditional ROI: 5.36%
404 Newfield Street MIDDLETOWN, CT Welcome to this beautiful fully updated 3-bedroom 2 full bath ranch offering the perfect b...	3 beds \| 2 baths \| 1,332 sq.ft.	$399,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 4.73% Airbnb Rental Income: $1188 Traditional Rental Income: $2834 Airbnb ROI: -0.69% Traditional ROI: 4.73%
87 Wanda Lane MIDDLETOWN, CT Set on a beautifully landscaped 0.37-acre lot in a quiet cul-de-sac setting, this spacious...	4 beds \| 3 baths \| 4,385 sq.ft.	$675,000	Airbnb cash on cash: -1.98% Traditional cash on cash: 4.15% Airbnb Rental Income: $986 Traditional Rental Income: $4488 Airbnb ROI: -1.98% Traditional ROI: 4.15%
743 Long Hill Road #A MIDDLETOWN, CT Bright, Remodeled End-Unit Townhouse in Wesleyan Hills - Move-In Ready. Discover a rare en...	2 beds \| 3 baths \| 1,569 sq.ft.	$325,000	Airbnb cash on cash: -3.23% Traditional cash on cash: 4.33% Airbnb Rental Income: $677 Traditional Rental Income: $2684 Airbnb ROI: -3.23% Traditional ROI: 4.33%
234 S Main Street #416 MIDDLETOWN, CT Welcome to 234 S Main St, Unit 416. This spacious end-unit condo offers 2 bedrooms and 2.5...	2 beds \| 3 baths \| 1,450 sq.ft.	$285,000	Airbnb cash on cash: -4.5% Traditional cash on cash: 4.16% Airbnb Rental Income: $677 Traditional Rental Income: $2702 Airbnb ROI: -4.5% Traditional ROI: 4.16%
564 Ridgewood Road MIDDLETOWN, CT This modern ranch combines quality construction with a versatile layout. The exterior feat...	4 beds \| 3 baths \| 3,136 sq.ft.	$675,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 4.45% Airbnb Rental Income: $986 Traditional Rental Income: $4422 Airbnb ROI: -1.57% Traditional ROI: 4.45%
201 College Street #5 MIDDLETOWN, CT Welcome to 201 College Street, Unit 5-an inviting 2-bedroom, 1.5-bath condo located in a h...	2 beds \| 2 baths \| 2,000 sq.ft.	$249,999	Airbnb cash on cash: -2.44% Traditional cash on cash: 7.76% Airbnb Rental Income: $677 Traditional Rental Income: $2783 Airbnb ROI: -2.44% Traditional ROI: 7.76%
57 Carriage Crossing Lane #57 MIDDLETOWN, CT Don't miss this beautifully updated, light-filled 1-bedroom, 1-bath condo-move-in ready an...	1 beds \| 1 baths \| 670 sq.ft.	$190,000	Airbnb cash on cash: -2.87% Traditional cash on cash: 3.14% Airbnb Rental Income: $737 Traditional Rental Income: $1510 Airbnb ROI: -2.87% Traditional ROI: 3.14%
64 High St MIDDLETOWN, CT 64 High St, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 1,532 sq.ft.	$299,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.74% Airbnb Rental Income: $1188 Traditional Rental Income: $2027 Airbnb ROI: -0.6% Traditional ROI: 3.74%
103 Grand St MIDDLETOWN, CT 103 Grand St, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 1,238 sq.ft.	$229,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.92% Airbnb Rental Income: $1188 Traditional Rental Income: $1839 Airbnb ROI: 0.15% Traditional ROI: 4.92%
25 Pleasant View Dr MIDDLETOWN, CT 25 Pleasant View Dr, MIDDLETOWN, CT 06457 \| Single Family Residential	3 beds \| 1 baths \| 2,030 sq.ft.	$479,900	Airbnb cash on cash: -1.54% Traditional cash on cash: 1.14% Airbnb Rental Income: $1188 Traditional Rental Income: $2004 Airbnb ROI: -1.54% Traditional ROI: 1.14%

Real Estate investment in Middletown, CT

There are 17 properties for sale in the city of Middletown . The median list price in Middletown is $379,450 and the average price per square foot is $233. In May 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,702.

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

There are 17 investment properties available for sale in Middletown.

In 2026, the best neighborhood to buy investment property is MIDDLETOWN.

The ROI for Long-Term is higher than the Short-Term in Middletown with average rental income of $2,702.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

23 Hotchkiss Street

MIDDLETOWN, CT

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

$275,000

Airbnb cash on cash: -1.74%

Traditional cash on cash: 7.29%

Airbnb Rental Income: $677

Traditional Rental Income: $2716

Airbnb ROI: -1.74%

Traditional ROI: 7.29%

10 Talias Trail

MIDDLETOWN, CT

4 beds | 3 baths | 2,285 sq.ft.

$599,000

Airbnb cash on cash: -2.17%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $986

Traditional Rental Income: $3993

Airbnb ROI: -2.17%

Traditional ROI: 3.84%

6 Hillside Court

MIDDLETOWN, CT

3 beds | 2 baths | 1,299 sq.ft.

$270,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 7.16%

Airbnb Rental Income: $1188

Traditional Rental Income: $2661

Airbnb ROI: -0.14%

Traditional ROI: 7.16%

8 Macdonough Place

MIDDLETOWN, CT

3 beds | 2 baths | 1,740 sq.ft.

$384,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 5.36%

Airbnb Rental Income: $1188

Traditional Rental Income: $3064

Airbnb ROI: -0.92%

Traditional ROI: 5.36%

404 Newfield Street

MIDDLETOWN, CT

3 beds | 2 baths | 1,332 sq.ft.

$399,900

Airbnb cash on cash: -0.69%

Traditional cash on cash: 4.73%

Airbnb Rental Income: $1188

Traditional Rental Income: $2834

Airbnb ROI: -0.69%

Traditional ROI: 4.73%

87 Wanda Lane

MIDDLETOWN, CT

4 beds | 3 baths | 4,385 sq.ft.

$675,000

Airbnb cash on cash: -1.98%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $986

Traditional Rental Income: $4488

Airbnb ROI: -1.98%

Traditional ROI: 4.15%

743 Long Hill Road #A

MIDDLETOWN, CT

2 beds | 3 baths | 1,569 sq.ft.

$325,000

Airbnb cash on cash: -3.23%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $677

Traditional Rental Income: $2684

Airbnb ROI: -3.23%

Traditional ROI: 4.33%

234 S Main Street #416

MIDDLETOWN, CT

2 beds | 3 baths | 1,450 sq.ft.

$285,000

Airbnb cash on cash: -4.5%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $677

Traditional Rental Income: $2702

Airbnb ROI: -4.5%