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
455 East Street MIDDLETOWN, CT This extraordinary home has a rich history that includes a past life as a farm, a Christma...	5 beds \| 3 baths \| 3,010 sq.ft.	$890,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $4110 Airbnb ROI: N/A Traditional ROI: 2.74%
207 CRYSTAL LAKE RD MIDDLETOWN, CT *New Construction* 7 room, 3 bedroom, 2.5 bath Colonial built in 2024 sitting on .82 a...	3 beds \| 3 baths \| 1,988 sq.ft.	$609,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 2.79% Airbnb Rental Income: $3122 Traditional Rental Income: $3462 Airbnb ROI: 0.95% Traditional ROI: 2.79%
25 Pashley Lane MIDDLETOWN, CT Location! Location! Location! Welcome to 25 Pashley Lane, a stunning residence nestled in ...	4 beds \| 3 baths \| 2,519 sq.ft.	$629,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $4165 Airbnb ROI: N/A Traditional ROI: 4.34%
28 Afton Terrace MIDDLETOWN, CT Modern home located in a PUD. Property has been well cared for and has 3 bedrooms, 1 bathr...	3 beds \| 1 baths \| 1,580 sq.ft.	$259,900	Airbnb cash on cash: 6.99% Traditional cash on cash: 7.11% Airbnb Rental Income: $3122 Traditional Rental Income: $2441 Airbnb ROI: 6.99% Traditional ROI: 7.11%
95 Knoll Ridge Court MIDDLETOWN, CT Take a 3D Tour 24/7 or Enjoy a Video Walkthrough 24/7! Presenting a spectacular 5 BR, 4.5 ...	4 beds \| 5 baths \| 4,807 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $6093 Airbnb ROI: N/A Traditional ROI: 4.29%
20 BERLIN CT MIDDLETOWN, CT Welcome to this charming colonial style home with a traditional brick exterior. Situated o...	3 beds \| 1 baths \| N/A	$289,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 6.16% Airbnb Rental Income: $3122 Traditional Rental Income: $2356 Airbnb ROI: 6.37% Traditional ROI: 6.16%
137 Highland Avenue MIDDLETOWN, CT We're pleased to present the opportunity to acquire a sunny rare gem property in highly de...	3 beds \| 2 baths \| 2,322 sq.ft.	$349,900	Airbnb cash on cash: 3.94% Traditional cash on cash: 6.34% Airbnb Rental Income: $3122 Traditional Rental Income: $3200 Airbnb ROI: 3.94% Traditional ROI: 6.34%
39 Lorelei Circle MIDDLETOWN, CT Introducing a unique property that offers a blend of luxury and timeless charm. Step insid...	5 beds \| 4 baths \| 4,338 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.84% Airbnb Rental Income: $null Traditional Rental Income: $4983 Airbnb ROI: N/A Traditional ROI: 6.84%
111 Dekoven Drive #APT 901 MIDDLETOWN, CT Wonderful unit in the River's Edge complex with gorgeous views of the CT river and Portlan...	2 beds \| 2 baths \| 1,034 sq.ft.	$150,000	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.56% Airbnb Rental Income: $2906 Traditional Rental Income: $2012 Airbnb ROI: 7.1% Traditional ROI: 5.56%
103 TROLLEY CROSSING LANE MIDDLETOWN, CT Ranch style 4 room, 2 bedroom 1.5 bath condo. Living room w/ sliders leading to deck area ...	2 beds \| 2 baths \| 874 sq.ft.	$185,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 6.51% Airbnb Rental Income: $2906 Traditional Rental Income: $1783 Airbnb ROI: 9.06% Traditional ROI: 6.51%
15 Miller Street MIDDLETOWN, CT MOTIVATED SELLERS. Recently remodeled; new roof, hot water tank, windows, walls, doors, fl...	3 beds \| 2 baths \| 1,552 sq.ft.	$295,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 6.26% Airbnb Rental Income: $3122 Traditional Rental Income: $2695 Airbnb ROI: 5.24% Traditional ROI: 6.26%
250 Atkins Street MIDDLETOWN, CT Welcome to your dream home! This stunning brand-new construction is situated on a beautifu...	4 beds \| 3 baths \| 3,509 sq.ft.	$839,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $3945 Airbnb ROI: N/A Traditional ROI: 1.8%
122 Newfield Street #APT 2B MIDDLETOWN, CT Welcome to the exquisite 122 Newfield Street Unit 2B! Tastefully renovated 4 years ago, th...	2 beds \| 2 baths \| 1,325 sq.ft.	$328,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 3.24% Airbnb Rental Income: $2906 Traditional Rental Income: $2385 Airbnb ROI: 2.74% Traditional ROI: 3.24%
70 George Street MIDDLETOWN, CT Rare opportunity to own a spacious Ranch with a possible in-law on the lower level. Situat...	4 beds \| 3 baths \| 2,688 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.56% Airbnb Rental Income: $null Traditional Rental Income: $3992 Airbnb ROI: N/A Traditional ROI: 6.56%
1193 Randolph Road MIDDLETOWN, CT Welcome to this beautifully maintained Cape Cod-style home, set on over 1 acre of private ...	4 beds \| 2 baths \| 1,929 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $3150 Airbnb ROI: N/A Traditional ROI: 3.43%
379 East Street MIDDLETOWN, CT Home sweet home! This immaculately maintained 3600+ sq ft Colonial Farmhouse features a pe...	4 beds \| 3 baths \| 3,652 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $4037 Airbnb ROI: N/A Traditional ROI: 3.92%
25 Evergreen Avenue MIDDLETOWN, CT Welcome to this charming 3 bedroom, 1 1/2 bath colonial style home. As you walk up to the ...	3 beds \| 2 baths \| 1,314 sq.ft.	$299,900	Airbnb cash on cash: 5.1% Traditional cash on cash: 6.5% Airbnb Rental Income: $3122 Traditional Rental Income: $2807 Airbnb ROI: 5.1% Traditional ROI: 6.5%
3 Avon Court MIDDLETOWN, CT Welcome to 3 Avon Court! First time available since it was built in 1980, this charming si...	3 beds \| 1 baths \| 1,084 sq.ft.	$299,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 3.95% Airbnb Rental Income: $3122 Traditional Rental Income: $2114 Airbnb ROI: 5.01% Traditional ROI: 3.95%
138 Trolley Crossing Lane #138 MIDDLETOWN, CT Why rent when you can own this 2-bedroom bath and a half condominium. Located on the groun...	2 beds \| 2 baths \| 860 sq.ft.	$159,000	Airbnb cash on cash: 8.3% Traditional cash on cash: 6.29% Airbnb Rental Income: $2906 Traditional Rental Income: $1927 Airbnb ROI: 8.3% Traditional ROI: 6.29%
21 In Town Terrace #21 MIDDLETOWN, CT This beautifully updated, detached 3-level townhome offers the perfect blend of privacy & ...	3 beds \| 3 baths \| 1,620 sq.ft.	$320,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 6.22% Airbnb Rental Income: $3122 Traditional Rental Income: $3298 Airbnb ROI: 3.28% Traditional ROI: 6.22%
2 Forest Glen Circle #3 MIDDLETOWN, CT This inviting first-floor 2-bedroom condo is perfect for both entertaining and relaxing. T...	2 beds \| 1 baths \| 930 sq.ft.	$224,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 3.35% Airbnb Rental Income: $2906 Traditional Rental Income: $1801 Airbnb ROI: 5.39% Traditional ROI: 3.35%
37 Roberts Street MIDDLETOWN, CT Enjoy this well-maintained 2-story colonial featuring 3 bedrooms and 1.5 baths. On the mai...	3 beds \| 2 baths \| 1,248 sq.ft.	$319,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 5.46% Airbnb Rental Income: $3122 Traditional Rental Income: $2672 Airbnb ROI: 4.6% Traditional ROI: 5.46%
10 Portland Street MIDDLETOWN, CT Attention investors and buyers looking for a multi-family home or multi generational livin...	4 beds \| 2 baths \| 1,540 sq.ft.	$298,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.04% Airbnb Rental Income: $null Traditional Rental Income: $2940 Airbnb ROI: N/A Traditional ROI: 7.04%
2 Lakeside Avenue MIDDLETOWN, CT This stunning over 2000 square foot colonial home, located at the end of a private cul-de-...	3 beds \| 3 baths \| 2,223 sq.ft.	$429,900	Airbnb cash on cash: 2.64% Traditional cash on cash: 5.62% Airbnb Rental Income: $3122 Traditional Rental Income: $3612 Airbnb ROI: 2.64% Traditional ROI: 5.62%
675 Newfield Street #APT 14 MIDDLETOWN, CT Spacious end unit with 2-bedrooms, 1 1/2-bathrooms, centrally located in small quaint comp...	2 beds \| 2 baths \| 1,292 sq.ft.	$229,900	Airbnb cash on cash: 5.33% Traditional cash on cash: 6.61% Airbnb Rental Income: $2906 Traditional Rental Income: $2511 Airbnb ROI: 5.33% Traditional ROI: 6.61%
121 Hunting Hill Avenue MIDDLETOWN, CT The Hetzell-Hotchkiss House, circa 1864 is a large stately brick colonial in South Farms. ...	4 beds \| 2 baths \| 3,063 sq.ft.	$406,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.4% Airbnb Rental Income: $null Traditional Rental Income: $3714 Airbnb ROI: N/A Traditional ROI: 6.4%
119 Schuyler Avenue MIDDLETOWN, CT PRICE REDUCTION Nestled on a tranquil dead-end street, this charming 1920s home featur...	3 beds \| 1 baths \| 1,344 sq.ft.	$289,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 5.13% Airbnb Rental Income: $3122 Traditional Rental Income: $2336 Airbnb ROI: 5.41% Traditional ROI: 5.13%
12 Poinsettia Street MIDDLETOWN, CT Welcome to your new home nestled on a serene cul-de-sac just minutes from Wesleyan Univers...	3 beds \| 2 baths \| 2,697 sq.ft.	$459,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 4.82% Airbnb Rental Income: $3122 Traditional Rental Income: $3509 Airbnb ROI: 2.27% Traditional ROI: 4.82%

Real Estate investment in Middletown, CT

There are 28 properties for sale in the city of Middletown . The median list price in Middletown is $319,950 and the average price per square foot is $158. In December 2024, the average monthly cash on cash return in Middletown is 6.00%. The average monthly rental income in Middletown is $3,019.

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

There are 28 investment properties available for sale in Middletown.

In 2024, 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 $3,019.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

455 East Street

MIDDLETOWN, CT

5 beds | 3 baths | 3,010 sq.ft.

$890,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.74%

Airbnb Rental Income: $null

Traditional Rental Income: $4110

Airbnb ROI: N/A

Traditional ROI: 2.74%

207 CRYSTAL LAKE RD

MIDDLETOWN, CT

3 beds | 3 baths | 1,988 sq.ft.

$609,900

Airbnb cash on cash: 0.95%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $3122

Traditional Rental Income: $3462

Airbnb ROI: 0.95%

Traditional ROI: 2.79%

25 Pashley Lane

MIDDLETOWN, CT

4 beds | 3 baths | 2,519 sq.ft.

$629,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.34%

Airbnb Rental Income: $null

Traditional Rental Income: $4165

Airbnb ROI: N/A

Traditional ROI: 4.34%

28 Afton Terrace

MIDDLETOWN, CT

3 beds | 1 baths | 1,580 sq.ft.

$259,900

Airbnb cash on cash: 6.99%

Traditional cash on cash: 7.11%

Airbnb Rental Income: $3122

Traditional Rental Income: $2441

Airbnb ROI: 6.99%

Traditional ROI: 7.11%

95 Knoll Ridge Court

MIDDLETOWN, CT

4 beds | 5 baths | 4,807 sq.ft.

$925,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.29%

Airbnb Rental Income: $null

Traditional Rental Income: $6093

Airbnb ROI: N/A

Traditional ROI: 4.29%

20 BERLIN CT

MIDDLETOWN, CT

3 beds | 1 baths | N/A

$289,900

Airbnb cash on cash: 6.37%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $3122

Traditional Rental Income: $2356

Airbnb ROI: 6.37%

Traditional ROI: 6.16%

137 Highland Avenue

MIDDLETOWN, CT

3 beds | 2 baths | 2,322 sq.ft.

$349,900

Airbnb cash on cash: 3.94%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $3122

Traditional Rental Income: $3200

Airbnb ROI: 3.94%

Traditional ROI: 6.34%

39 Lorelei Circle

MIDDLETOWN, CT

5 beds | 4 baths | 4,338 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.84%

Airbnb Rental Income: $null

Traditional Rental Income: $4983

Airbnb ROI: N/A