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.

Sugarloaf Investment Property for Sale in Middletown, CT

Search for Sugarloaf Investment Property for Sale in Middletown, Connecticut. Browse all of Mashvisor’s Sugarloaf Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 31 Sugarloaf Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$585,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 7.71% Airbnb Rental Income: $1388 Traditional Rental Income: $5475 Airbnb ROI: -0.54% Traditional ROI: 7.71%
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%
59 Westfield Terrace MIDDLETOWN, CT SPOILER ALERT!!: You're about to fall in love. Have you ever walked into a home and instan...	3 beds \| 2 baths \| 960 sq.ft.	$360,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.75% Airbnb Rental Income: $1388 Traditional Rental Income: $2516 Airbnb ROI: 0.17% Traditional ROI: 4.75%
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: 0.76% Traditional cash on cash: 6.9% Airbnb Rental Income: $1406 Traditional Rental Income: $2716 Airbnb ROI: 0.76% 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: -0.83% Traditional cash on cash: 4.62% Airbnb Rental Income: $1388 Traditional Rental Income: $3770 Airbnb ROI: -0.83% 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: 0.92% Traditional cash on cash: 4.77% Airbnb Rental Income: $1406 Traditional Rental Income: $2029 Airbnb ROI: 0.92% 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: -0.72% Traditional cash on cash: 1.62% Airbnb Rental Income: $1388 Traditional Rental Income: $1825 Airbnb ROI: -0.72% Traditional ROI: 1.62%
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: 7.93% Airbnb Rental Income: $null Traditional Rental Income: $5771 Airbnb ROI: N/A Traditional ROI: 7.93%
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: -0.25% Traditional cash on cash: 5.53% Airbnb Rental Income: $1388 Traditional Rental Income: $2734 Airbnb ROI: -0.25% 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: -0.33% Traditional cash on cash: 6.62% Airbnb Rental Income: $1388 Traditional Rental Income: $3156 Airbnb ROI: -0.33% Traditional ROI: 6.62%
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: -1.13% Traditional cash on cash: 3.63% Airbnb Rental Income: $1388 Traditional Rental Income: $3061 Airbnb ROI: -1.13% Traditional ROI: 3.63%
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: 0.53% Traditional cash on cash: 7.65% Airbnb Rental Income: $1406 Traditional Rental Income: $2722 Airbnb ROI: 0.53% 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: -0.45% Traditional cash on cash: 4.62% Airbnb Rental Income: $1388 Traditional Rental Income: $2636 Airbnb ROI: -0.45% 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: -0.07% Traditional cash on cash: 3.74% Airbnb Rental Income: $1388 Traditional Rental Income: $2059 Airbnb ROI: -0.07% 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.	$144,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 5.76% Airbnb Rental Income: $1406 Traditional Rental Income: $1711 Airbnb ROI: 0.52% Traditional ROI: 5.76%
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: -1.39% Traditional cash on cash: 4.17% Airbnb Rental Income: $1406 Traditional Rental Income: $2554 Airbnb ROI: -1.39% 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: -1.07% Traditional cash on cash: 4.17% Airbnb Rental Income: $1406 Traditional Rental Income: $2074 Airbnb ROI: -1.07% 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: 0.04% Traditional cash on cash: 4.58% Airbnb Rental Income: $1406 Traditional Rental Income: $2265 Airbnb ROI: 0.04% 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: 0.4% Traditional cash on cash: 6.14% Airbnb Rental Income: $1388 Traditional Rental Income: $2323 Airbnb ROI: 0.4% Traditional ROI: 6.14%
64 Victoria Heights MIDDLETOWN, CT Welcome Home to this stunning custom brick ranch, perfectly nestled in a neighborhood of l...	4 beds \| 2 baths \| 1,902 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.12% Airbnb Rental Income: $null Traditional Rental Income: $3527 Airbnb ROI: N/A Traditional ROI: 5.12%
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.	$314,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 5% Airbnb Rental Income: $1388 Traditional Rental Income: $2498 Airbnb ROI: -0.16% Traditional ROI: 5%

Your search for investment property begins and ends here

Sugarloaf Investment Property for Sale in Middletown, CT

301 Bell Street

MIDDLETOWN, CT

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

$585,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 7.71%

Airbnb Rental Income: $1388

Traditional Rental Income: $5475

Airbnb ROI: -0.54%

Traditional ROI: 7.71%

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%

59 Westfield Terrace

MIDDLETOWN, CT

3 beds | 2 baths | 960 sq.ft.

$360,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $1388

Traditional Rental Income: $2516

Airbnb ROI: 0.17%

Traditional ROI: 4.75%

23 Hotchkiss Street

MIDDLETOWN, CT

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

$300,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1406

Traditional Rental Income: $2716

Airbnb ROI: 0.76%

Traditional ROI: 6.9%

80 Elizabeth Lane

MIDDLETOWN, CT

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

$549,900

Airbnb cash on cash: -0.83%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1388

Traditional Rental Income: $3770

Airbnb ROI: -0.83%

Traditional ROI: 4.62%

154 Front Street

MIDDLETOWN, CT

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

$289,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1406

Traditional Rental Income: $2029

Airbnb ROI: 0.92%

Traditional ROI: 4.77%

50 Garfield Avenue

MIDDLETOWN, CT

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

$389,900

Airbnb cash on cash: -0.72%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1388

Traditional Rental Income: $1825

Airbnb ROI: -0.72%

Traditional ROI: 1.62%

120 Scenic View Drive

MIDDLETOWN, CT

4 beds | 4 baths | 3,833 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.93%

Airbnb Rental Income: $null

Traditional Rental Income: $5771

Airbnb ROI: N/A