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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
311 Coleman Road MIDDLETOWN, CT Rare opportunity to enjoy the most beautiful sunsets from your back deck overlooking cornf...	4 beds \| 2 baths \| 1,939 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $3461 Airbnb ROI: N/A Traditional ROI: 4.39%
55 Trolley Crossing Lane #55 MIDDLETOWN, CT Price Improved! The one you have been waiting for, welcome home to 55 Trolley Crossing! Ne...	2 beds \| 2 baths \| 1,136 sq.ft.	$199,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 7.46% Airbnb Rental Income: $1560 Traditional Rental Income: $2305 Airbnb ROI: 1.14% Traditional ROI: 7.46%
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.	$600,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 7.5% Airbnb Rental Income: $1859 Traditional Rental Income: $5475 Airbnb ROI: 0.15% Traditional ROI: 7.5%
455 East Street MIDDLETOWN, CT This extraordinary center-chimney colonial blends rich history with modern elegance. Once ...	5 beds \| 3 baths \| 3,010 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $4110 Airbnb ROI: N/A Traditional ROI: 3.43%
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: 1.21% Traditional cash on cash: 6.9% Airbnb Rental Income: $1560 Traditional Rental Income: $2716 Airbnb ROI: 1.21% 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: -0.07% Traditional cash on cash: 4.62% Airbnb Rental Income: $1859 Traditional Rental Income: $3770 Airbnb ROI: -0.07% Traditional ROI: 4.62%
154 Front Street MIDDLETOWN, CT Welcome to 154 Front Street, a 2 bedroom 1.5 bath home set on a corner .2 acre lot in a fr...	2 beds \| 1 baths \| 1,103 sq.ft.	$289,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 4.77% Airbnb Rental Income: $1560 Traditional Rental Income: $2029 Airbnb ROI: 1.39% Traditional ROI: 4.77%
50 Garfield Avenue MIDDLETOWN, CT Welcome Home, Fall in love with this move in ready 3 bedroom~2 full bath Cape Cod complete...	3 beds \| 2 baths \| 1,366 sq.ft.	$389,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 1.62% Airbnb Rental Income: $1859 Traditional Rental Income: $1825 Airbnb ROI: 0.35% Traditional ROI: 1.62%
46 Rising Trail Drive #46 MIDDLETOWN, CT Buyers could not get their finanacing, BOM More than a townhouse-this is your personal ret...	2 beds \| 2 baths \| 1,680 sq.ft.	$203,500	Airbnb cash on cash: -0.3% Traditional cash on cash: 8.25% Airbnb Rental Income: $1560 Traditional Rental Income: $2762 Airbnb ROI: -0.3% Traditional ROI: 8.25%
3 Prospect Place MIDDLETOWN, CT Affordable Opportunity in a Prime Location! Perfect for first-time homebuyers, students, o...	2 beds \| 1 baths \| 735 sq.ft.	$179,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 9.41% Airbnb Rental Income: $1560 Traditional Rental Income: $2224 Airbnb ROI: 2.88% Traditional ROI: 9.41%
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.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.54% Airbnb Rental Income: $null Traditional Rental Income: $5771 Airbnb ROI: N/A Traditional ROI: 7.54%
281 George Street MIDDLETOWN, CT Welcome to 281 George Street in Middletown, a charming Ranch home offering comfort, conven...	3 beds \| 2 baths \| 1,288 sq.ft.	$324,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 5.53% Airbnb Rental Income: $1859 Traditional Rental Income: $2734 Airbnb ROI: 1.04% Traditional ROI: 5.53%
101 Mill Street MIDDLETOWN, CT Nestled on a private lot in desirable Middletown, 101 Mill Street is a stunning brick ranc...	3 beds \| 2 baths \| 1,682 sq.ft.	$335,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 6.62% Airbnb Rental Income: $1859 Traditional Rental Income: $3156 Airbnb ROI: 0.91% Traditional ROI: 6.62%
1261 Washington Street #13 MIDDLETOWN, CT Clean remodeled 2 bedroom condo for sale! Clean, conveniently located two bedroom condo wi...	2 beds \| 1 baths \| 880 sq.ft.	$167,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.43% Airbnb Rental Income: $1560 Traditional Rental Income: $1718 Airbnb ROI: 0.64% Traditional ROI: 4.43%
779 Millbrook Road MIDDLETOWN, CT Step back in time with this remarkably well-preserved 1789 four-bedroom, two-bath historic...	4 beds \| 2 baths \| 2,674 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.8% Airbnb Rental Income: $null Traditional Rental Income: $3603 Airbnb ROI: N/A Traditional ROI: 5.8%
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: -0.24% Traditional cash on cash: 3.63% Airbnb Rental Income: $1859 Traditional Rental Income: $3061 Airbnb ROI: -0.24% Traditional ROI: 3.63%
29 Talias Trail MIDDLETOWN, CT This exceptional 4-bed Cont. Colonial is perfect for your lifestyle. Built for energy-effi...	4 beds \| 3 baths \| 2,432 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $4117 Airbnb ROI: N/A Traditional ROI: 3.94%
126 Highland Avenue MIDDLETOWN, CT OPEN HOUSE CANCELLED If you're looking to start your investment portfolio, or would l...	2 beds \| 2 baths \| 1,863 sq.ft.	$259,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 7.65% Airbnb Rental Income: $1560 Traditional Rental Income: $2722 Airbnb ROI: 1.06% Traditional ROI: 7.65%
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: 0.74% Traditional cash on cash: 4.62% Airbnb Rental Income: $1859 Traditional Rental Income: $2636 Airbnb ROI: 0.74% Traditional ROI: 4.62%
11 Huber Avenue MIDDLETOWN, CT This recently-updated home is in move-in condition on a quiet dead-end street adjacent to ...	3 beds \| 1 baths \| 1,102 sq.ft.	$305,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.74% Airbnb Rental Income: $1859 Traditional Rental Income: $2059 Airbnb ROI: 1.3% Traditional ROI: 3.74%
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.	$154,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.2% Airbnb Rental Income: $1560 Traditional Rental Income: $1711 Airbnb ROI: 1.15% Traditional ROI: 5.2%
107 Cambridge Commons #107 MIDDLETOWN, CT Rare opportunity to buy a move in ready unit in the highly sought after Cambridge Commons ...	2 beds \| 3 baths \| 1,288 sq.ft.	$299,999	Airbnb cash on cash: -0.94% Traditional cash on cash: 4.17% Airbnb Rental Income: $1560 Traditional Rental Income: $2554 Airbnb ROI: -0.94% Traditional ROI: 4.17%
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: -0.46% Traditional cash on cash: 4.17% Airbnb Rental Income: $1560 Traditional Rental Income: $2074 Airbnb ROI: -0.46% Traditional ROI: 4.17%
48 Overlook Avenue MIDDLETOWN, CT This charming 5 room, 2-bedroom ranch home, ideally situated on a generous lot spanning ne...	2 beds \| 1 baths \| 1,454 sq.ft.	$299,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.58% Airbnb Rental Income: $1560 Traditional Rental Income: $2265 Airbnb ROI: 0.49% Traditional ROI: 4.58%
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: 2.06% Traditional cash on cash: 6.14% Airbnb Rental Income: $1859 Traditional Rental Income: $2323 Airbnb ROI: 2.06% Traditional ROI: 6.14%
68 Orchard Hill Lane MIDDLETOWN, CT Welcome to your peaceful retreat on a quiet Westfield cul-de-sac - where classic Colonial ...	3 beds \| 2 baths \| 2,254 sq.ft.	$435,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 4.53% Airbnb Rental Income: $1859 Traditional Rental Income: $3210 Airbnb ROI: -0.01% Traditional ROI: 4.53%

Real Estate investment in Middletown, CT

There are 33 properties for sale in the city of Middletown . The median list price in Middletown is $329,950 and the average price per square foot is $177. In October 2025, 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 33 investment properties available for sale in Middletown.

In 2025, 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 $2,722.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CT

311 Coleman Road

MIDDLETOWN, CT

4 beds | 2 baths | 1,939 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.39%

Airbnb Rental Income: $null

Traditional Rental Income: $3461

Airbnb ROI: N/A

Traditional ROI: 4.39%

55 Trolley Crossing Lane #55

MIDDLETOWN, CT

2 beds | 2 baths | 1,136 sq.ft.

$199,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 7.46%

Airbnb Rental Income: $1560

Traditional Rental Income: $2305

Airbnb ROI: 1.14%

Traditional ROI: 7.46%

301 Bell Street

MIDDLETOWN, CT

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

$600,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $1859

Traditional Rental Income: $5475

Airbnb ROI: 0.15%

Traditional ROI: 7.5%

455 East Street

MIDDLETOWN, CT

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

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.43%

Airbnb Rental Income: $null

Traditional Rental Income: $4110

Airbnb ROI: N/A

Traditional ROI: 3.43%

23 Hotchkiss Street

MIDDLETOWN, CT

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

$300,000

Airbnb cash on cash: 1.21%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1560

Traditional Rental Income: $2716

Airbnb ROI: 1.21%

Traditional ROI: 6.9%

80 Elizabeth Lane

MIDDLETOWN, CT

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

$549,900

Airbnb cash on cash: -0.07%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1859

Traditional Rental Income: $3770

Airbnb ROI: -0.07%

Traditional ROI: 4.62%

154 Front Street

MIDDLETOWN, CT

2 beds | 1 baths | 1,103 sq.ft.

$289,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1560

Traditional Rental Income: $2029

Airbnb ROI: 1.39%

Traditional ROI: 4.77%

50 Garfield Avenue

MIDDLETOWN, CT

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

$389,900

Airbnb cash on cash: 0.35%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1859

Traditional Rental Income: $1825

Airbnb ROI: 0.35%