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
182 Rising Trail Dr #182 MIDDLETOWN, CT Well cared for condo in a large complex with many amenities to enjoy. The current owner l...	3 beds \| 1 baths \| 1,232 sq.ft.	$259,900	Airbnb cash on cash: -0.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $1388 Traditional Rental Income: $1754 Airbnb ROI: -0.49% Traditional ROI: 2.72%
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%
201 College St #26 MIDDLETOWN, CT Hamlin Court, formerly the old Central School in Middletown. Re-imagined in 1980 into 28 ...	1 beds \| 1 baths \| 740 sq.ft.	$179,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 4.35% Airbnb Rental Income: $1267 Traditional Rental Income: $1400 Airbnb ROI: 1.23% Traditional ROI: 4.35%
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%
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: -0.06% Traditional cash on cash: 2.29% Airbnb Rental Income: $1388 Traditional Rental Income: $1825 Airbnb ROI: -0.06% Traditional ROI: 2.29%
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: 7.56% Airbnb Rental Income: $null Traditional Rental Income: $5771 Airbnb ROI: N/A Traditional ROI: 7.56%
56 Burgundy Hill Ln #56 MIDDLETOWN, CT Welcome to 56 Burgundy Hill Lane, Middletown! This totally renovated 2-bedroom ranch-style...	2 beds \| 1 baths \| 698 sq.ft.	$140,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 6.79% Airbnb Rental Income: $1406 Traditional Rental Income: $1711 Airbnb ROI: 1.37% Traditional ROI: 6.79%
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%
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: 8.56% Airbnb Rental Income: $null Traditional Rental Income: $3296 Airbnb ROI: N/A Traditional ROI: 8.56%
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.	$369,900	Airbnb cash on cash: -0.39% Traditional cash on cash: 4.72% Airbnb Rental Income: $1388 Traditional Rental Income: $2743 Airbnb ROI: -0.39% Traditional ROI: 4.72%
44 Trailside Crossing MIDDLETOWN, CT Tucked away on a quiet cul-de-sac, this beautifully maintained colonial offers serene priv...	4 beds \| 3 baths \| 2,356 sq.ft.	$605,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.08% Airbnb Rental Income: $null Traditional Rental Income: $3956 Airbnb ROI: N/A Traditional ROI: 4.08%
581 High Street MIDDLETOWN, CT Welcome to this updated, energy-efficient home, located just minutes from Wesleyan Univers...	3 beds \| 1 baths \| 1,057 sq.ft.	$280,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 4.09% Airbnb Rental Income: $1388 Traditional Rental Income: $2072 Airbnb ROI: -0.1% Traditional ROI: 4.09%
163 Cynthia Lane unit: Apt A4 #Apt A4 MIDDLETOWN, CT Highest and Best By Tuesday Jan 6th at 8pm Discover easy, low-maintenance living in this w...	2 beds \| 1 baths \| 930 sq.ft.	$199,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.71% Airbnb Rental Income: $1406 Traditional Rental Income: $1796 Airbnb ROI: -0.58% Traditional ROI: 3.71%
565 Newfield St Apt 34 MIDDLETOWN, CT There's something immediately comforting about a home that gives you room to breathe-and t...	2 beds \| 2 baths \| 1,544 sq.ft.	$279,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 4.76% Airbnb Rental Income: $1406 Traditional Rental Income: $2617 Airbnb ROI: -1.45% Traditional ROI: 4.76%
285 Carriage Crossing Ln #285 MIDDLETOWN, CT Spectacular 1 Bed, 1 Bath Condo available for sale in the desirable Carriage Crossing comp...	1 beds \| 1 baths \| 670 sq.ft.	$159,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 4.65% Airbnb Rental Income: $1267 Traditional Rental Income: $1630 Airbnb ROI: -0.34% Traditional ROI: 4.65%
180 Carriage Crossing Ln #180 MIDDLETOWN, CT 180 Carriage Crossing Ln #180, MIDDLETOWN, CT 06457 \| Condo/Coop	2 beds \| 2 baths \| 866 sq.ft.	$190,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 3.55% Airbnb Rental Income: $1406 Traditional Rental Income: $1761 Airbnb ROI: -0.76% Traditional ROI: 3.55%
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%
94 Cynthia Ln #D-5 MIDDLETOWN, CT 94 Cynthia Ln #D-5, MIDDLETOWN, CT 06457 \| Condo/Coop	2 beds \| 1 baths \| 930 sq.ft.	$215,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.1% Airbnb Rental Income: $1406 Traditional Rental Income: $1377 Airbnb ROI: -0.75% Traditional ROI: 1.1%
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%
Mountain Laurel Dr MIDDLETOWN, CT Mountain Laurel Dr, MIDDLETOWN, CT 06457 \| Other	N/A beds \| N/A baths \| N/A	$129,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $883 Airbnb ROI: N/A Traditional ROI: 3.28%
Lot 2 Coleman Rd MIDDLETOWN, CT Lot 2 Coleman Rd, MIDDLETOWN, CT 06457 \| Other	N/A beds \| N/A baths \| N/A	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $883 Airbnb ROI: N/A Traditional ROI: 2.11%
Country Club Rd and Massa Tom Rd Rd E MIDDLETOWN, CT Country Club Rd and Massa Tom Rd Rd E, MIDDLETOWN, CT 06457 \| Other	N/A beds \| N/A baths \| 3,000 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.2% Airbnb Rental Income: $null Traditional Rental Income: $1131 Airbnb ROI: N/A Traditional ROI: -2.2%
0 Bell St MIDDLETOWN, CT 0 Bell St, MIDDLETOWN, CT 06457 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $883 Airbnb ROI: N/A Traditional ROI: 5.06%
0 Middle St MIDDLETOWN, CT 0 Middle St, MIDDLETOWN, CT 06457 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.71% Airbnb Rental Income: $null Traditional Rental Income: $883 Airbnb ROI: N/A Traditional ROI: -0.71%
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%

Real Estate investment in Middletown, CT

There are 50 properties for sale in the city of Middletown . The median list price in Middletown is $369,900 and the average price per square foot is $227. In February 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,482.

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

There are 50 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 $2,482.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

182 Rising Trail Dr #182

MIDDLETOWN, CT

3 beds | 1 baths | 1,232 sq.ft.

$259,900

Airbnb cash on cash: -0.49%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1388

Traditional Rental Income: $1754

Airbnb ROI: -0.49%

Traditional ROI: 2.72%

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%

201 College St #26

MIDDLETOWN, CT

1 beds | 1 baths | 740 sq.ft.

$179,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $1267

Traditional Rental Income: $1400

Airbnb ROI: 1.23%

Traditional ROI: 4.35%

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%

50 Garfield Avenue

MIDDLETOWN, CT

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

$389,900

Airbnb cash on cash: -0.06%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1388

Traditional Rental Income: $1825

Airbnb ROI: -0.06%