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
265 Briarwood Lane MIDDLETOWN, CT Welcome to a lifestyle that blends neighborhood charm with everyday convenience in one of ...	3 beds \| 3 baths \| 3,036 sq.ft.	$559,900	Airbnb cash on cash: -0.84% Traditional cash on cash: 4.86% Airbnb Rental Income: $1458 Traditional Rental Income: $4011 Airbnb ROI: -0.84% Traditional ROI: 4.86%
45 Willow Bee Lane MIDDLETOWN, CT Situated on a cul-de-sac in a desirable sought after neighborhood, this 3 bed 1.5 bath Col...	3 beds \| 2 baths \| 1,323 sq.ft.	$399,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.26% Airbnb Rental Income: $1458 Traditional Rental Income: $2640 Airbnb ROI: -0.05% Traditional ROI: 4.26%
26 Greenview Terrace MIDDLETOWN, CT Welcome to sought after RiverBend Community. Enter into foyer that leads to a convenient a...	4 beds \| 3 baths \| 2,600 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $3725 Airbnb ROI: N/A Traditional ROI: 4.47%
50 Garfield Avenue MIDDLETOWN, CT Completely Renovated Cape Cod with New Roof, New Siding, New Windows & New Appliances! Mov...	3 beds \| 2 baths \| 1,274 sq.ft.	$395,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 2.24% Airbnb Rental Income: $1458 Traditional Rental Income: $1825 Airbnb ROI: 0.09% Traditional ROI: 2.24%
6 Hillside Court MIDDLETOWN, CT Excellent opportunity in a quiet. Ideal for rental portfolio expansion, or owner-occupants...	3 beds \| 2 baths \| 1,299 sq.ft.	$270,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 7.16% Airbnb Rental Income: $1458 Traditional Rental Income: $2661 Airbnb ROI: 0.74% Traditional ROI: 7.16%
135 Saddle Hill Drive MIDDLETOWN, CT Some homes check the boxes. This one checks the boxes and gives you the backyard everyone ...	5 beds \| 3 baths \| 3,083 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $4196 Airbnb ROI: N/A Traditional ROI: 3.93%
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: -2.12% Traditional cash on cash: 4.16% Airbnb Rental Income: $1445 Traditional Rental Income: $2702 Airbnb ROI: -2.12% Traditional ROI: 4.16%
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: -0.27% Traditional cash on cash: 7.22% Airbnb Rental Income: $1445 Traditional Rental Income: $2783 Airbnb ROI: -0.27% Traditional ROI: 7.22%
123 Round Hill Road MIDDLETOWN, CT HIGHEST & BEST DUE BY 5 pm MONDAY 5/18 123 Round Hill Rd in Middletown is a 3-bedroom,...	3 beds \| 2 baths \| 2,064 sq.ft.	$549,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.08% Airbnb Rental Income: $1458 Traditional Rental Income: $3098 Airbnb ROI: -0.95% Traditional ROI: 3.08%
31 Burr Avenue MIDDLETOWN, CT Outstanding opportunity to own a well-maintained two-family property in one of Central Con...	2 beds \| 2 baths \| 1,470 sq.ft.	$330,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 5.76% Airbnb Rental Income: $1445 Traditional Rental Income: $2722 Airbnb ROI: 0.26% Traditional ROI: 5.76%
492 Long Hill Road MIDDLETOWN, CT Welcome home to this beautifully renovated 3-bedroom, 2-bathroom raised ranch in Wesleyan ...	3 beds \| 2 baths \| 1,536 sq.ft.	$400,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 4.4% Airbnb Rental Income: $1458 Traditional Rental Income: $2889 Airbnb ROI: -0.56% Traditional ROI: 4.4%
19 Kent Court MIDDLETOWN, CT Beautiful Colonial tucked away on a quiet cul-de-sac offering comfort, space, and modern u...	3 beds \| 2 baths \| 2,160 sq.ft.	$350,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 6.5% Airbnb Rental Income: $1458 Traditional Rental Income: $3186 Airbnb ROI: -0.07% Traditional ROI: 6.5%
656 Bartholomew Road #656 MIDDLETOWN, CT Move-in ready and meticulously maintained, this stunning home built in 2021 offers modern ...	2 beds \| 3 baths \| 1,350 sq.ft.	$399,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 5.56% Airbnb Rental Income: $1445 Traditional Rental Income: $3314 Airbnb ROI: -0.57% Traditional ROI: 5.56%
694 Millbrook Road MIDDLETOWN, CT Contemporary/Cape Cod on over a 1 acre lot, which abuts to a land trust. Large living room...	3 beds \| 2 baths \| 2,742 sq.ft.	$469,999	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.2% Airbnb Rental Income: $1458 Traditional Rental Income: $2809 Airbnb ROI: -0.86% Traditional ROI: 3.2%
791 Long Hill Road #E MIDDLETOWN, CT Here it is! The only unit on the market right now - like finding the last open seat at you...	2 beds \| 3 baths \| 1,941 sq.ft.	$329,900	Airbnb cash on cash: -0.84% Traditional cash on cash: 5.36% Airbnb Rental Income: $1445 Traditional Rental Income: $2937 Airbnb ROI: -0.84% Traditional ROI: 5.36%
17 Inverness Lane MIDDLETOWN, CT *HIGHEST AND BEST BY 12PM ON 6/10* Enjoy your tour of this thoughtfully updated unit i...	3 beds \| 1 baths \| 1,209 sq.ft.	$234,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 7.1% Airbnb Rental Income: $1458 Traditional Rental Income: $2257 Airbnb ROI: 1.55% Traditional ROI: 7.1%
56 Trolley Crossing Lane #56 MIDDLETOWN, CT Welcome to this beautifully maintained townhouse in a highly desirable location. Move-in r...	2 beds \| 2 baths \| 1,136 sq.ft.	$200,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 7.58% Airbnb Rental Income: $1445 Traditional Rental Income: $2338 Airbnb ROI: 0.61% Traditional ROI: 7.58%
46 Bretton Road MIDDLETOWN, CT Experience the perfect blend of historic charm and modern comfort in this exceptional Colo...	4 beds \| 4 baths \| 3,622 sq.ft.	$497,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $4119 Airbnb ROI: N/A Traditional ROI: 6.02%
1221 Washington Street #8 MIDDLETOWN, CT This 2-bedroom loft-style townhouse at Woodgate offers a smart, functional layout in a com...	2 beds \| 1 baths \| 845 sq.ft.	$198,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.36% Airbnb Rental Income: $1445 Traditional Rental Income: $1682 Airbnb ROI: -0.19% Traditional ROI: 3.36%
57 Ridge Road MIDDLETOWN, CT Welcome to 57 Ridge Road, where nearly 150 years of New England character meet a home that...	3 beds \| 1 baths \| 1,412 sq.ft.	$300,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 5.25% Airbnb Rental Income: $1458 Traditional Rental Income: $2356 Airbnb ROI: 0.54% Traditional ROI: 5.25%
65 Prout Hill Road MIDDLETOWN, CT Don't miss this beautifully maintained split-level home featuring numerous upgrades and ex...	3 beds \| 2 baths \| 1,654 sq.ft.	$435,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 3.56% Airbnb Rental Income: $1458 Traditional Rental Income: $2764 Airbnb ROI: -0.7% Traditional ROI: 3.56%
30 Murray Street MIDDLETOWN, CT Welcome to 30 Murray St, a charming ranch-style home offering the perfect blend of comfort...	3 beds \| 2 baths \| 1,412 sq.ft.	$399,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.92% Airbnb Rental Income: $1458 Traditional Rental Income: $2608 Airbnb ROI: -0.3% Traditional ROI: 3.92%
5 Carriage Crossing Lane #5 MIDDLETOWN, CT Welcome to 5 Carriage Crossing, a desirable first floor end-unit condo in the welcoming Ca...	2 beds \| 2 baths \| 840 sq.ft.	$220,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 6.79% Airbnb Rental Income: $1445 Traditional Rental Income: $2028 Airbnb ROI: 1.93% Traditional ROI: 6.79%

Real Estate investment in Middletown, CT

There are 35 properties for sale in the city of Middletown . The median list price in Middletown is $349,819 and the average price per square foot is $216. In June 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $2,722.

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

There are 35 investment properties available for sale in Middletown.

In 2026, 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 $1,458.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

265 Briarwood Lane

MIDDLETOWN, CT

3 beds | 3 baths | 3,036 sq.ft.

$559,900

Airbnb cash on cash: -0.84%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1458

Traditional Rental Income: $4011

Airbnb ROI: -0.84%

Traditional ROI: 4.86%

45 Willow Bee Lane

MIDDLETOWN, CT

3 beds | 2 baths | 1,323 sq.ft.

$399,900

Airbnb cash on cash: -0.05%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $1458

Traditional Rental Income: $2640

Airbnb ROI: -0.05%

Traditional ROI: 4.26%

26 Greenview Terrace

MIDDLETOWN, CT

4 beds | 3 baths | 2,600 sq.ft.

$499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.47%

Airbnb Rental Income: $null

Traditional Rental Income: $3725

Airbnb ROI: N/A

Traditional ROI: 4.47%

50 Garfield Avenue

MIDDLETOWN, CT

3 beds | 2 baths | 1,274 sq.ft.

$395,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $1458

Traditional Rental Income: $1825

Airbnb ROI: 0.09%

Traditional ROI: 2.24%

6 Hillside Court

MIDDLETOWN, CT

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

$270,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 7.16%

Airbnb Rental Income: $1458

Traditional Rental Income: $2661

Airbnb ROI: 0.74%

Traditional ROI: 7.16%

135 Saddle Hill Drive

MIDDLETOWN, CT

5 beds | 3 baths | 3,083 sq.ft.

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.93%

Airbnb Rental Income: $null

Traditional Rental Income: $4196

Airbnb ROI: N/A

Traditional ROI: 3.93%

234 S Main Street #416

MIDDLETOWN, CT

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

$285,000

Airbnb cash on cash: -2.12%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $1445

Traditional Rental Income: $2702

Airbnb ROI: -2.12%

Traditional ROI: 4.16%

201 College Street #5

MIDDLETOWN, CT

2 beds | 2 baths | 2,000 sq.ft.

$249,999

Airbnb cash on cash: -0.27%

Traditional cash on cash: 7.22%

Airbnb Rental Income: $1445

Traditional Rental Income: $2783

Airbnb ROI: -0.27%