Real Estate Investment Properties for Sale in Middlebury, CT

Looking for investment property in Middlebury, CT with high ROI ?

Explore a variety of short-term homes & houses in Middlebury, CT. Invest wisely with VRBO & Middlebury, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Middlebury, CT

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

Showing 18 Condo 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
24 Ridgewood Drive #24 Middlebury, CT Truly spectacular remodeled "Cummings" style townhouse in the sought-after Ridgewood at Mi...	3 beds \| 4 baths \| 2,879 sq.ft.	$599,900	Airbnb cash on cash: -1.26% Traditional cash on cash: 1.95% Airbnb Rental Income: $1510 Traditional Rental Income: $2867 Airbnb ROI: -1.26% Traditional ROI: 1.95%
North Benson Road #64 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 2,206 sq.ft.	$545,400	Airbnb cash on cash: -1.83% Traditional cash on cash: 4.37% Airbnb Rental Income: $1510 Traditional Rental Income: $4229 Airbnb ROI: -1.83% Traditional ROI: 4.37%
North Benson Road #55 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 2,462 sq.ft.	$548,828	Airbnb cash on cash: -1.83% Traditional cash on cash: 4.61% Airbnb Rental Income: $1510 Traditional Rental Income: $4375 Airbnb ROI: -1.83% Traditional ROI: 4.61%
North Benson Road #53 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$519,900	Airbnb cash on cash: -1.76% Traditional cash on cash: 4.3% Airbnb Rental Income: $1510 Traditional Rental Income: $4016 Airbnb ROI: -1.76% Traditional ROI: 4.3%
North Benson Road #45 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$525,438	Airbnb cash on cash: -1.78% Traditional cash on cash: 4.23% Airbnb Rental Income: $1510 Traditional Rental Income: $4018 Airbnb ROI: -1.78% Traditional ROI: 4.23%
North Benson Road #66 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$522,128	Airbnb cash on cash: -1.77% Traditional cash on cash: 4.31% Airbnb Rental Income: $1510 Traditional Rental Income: $4034 Airbnb ROI: -1.77% Traditional ROI: 4.31%
North Benson Road #49 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$533,416	Airbnb cash on cash: -1.8% Traditional cash on cash: 4.27% Airbnb Rental Income: $1510 Traditional Rental Income: $4091 Airbnb ROI: -1.8% Traditional ROI: 4.27%
North Benson Road #46 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$522,128	Airbnb cash on cash: -1.77% Traditional cash on cash: 4.42% Airbnb Rental Income: $1510 Traditional Rental Income: $4091 Airbnb ROI: -1.77% Traditional ROI: 4.42%
North Benson Road #52 Middlebury, CT 5 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Benson Wo...	3 beds \| 3 baths \| 2,206 sq.ft.	$560,753	Airbnb cash on cash: -1.86% Traditional cash on cash: 4.39% Airbnb Rental Income: $1510 Traditional Rental Income: $4344 Airbnb ROI: -1.86% Traditional ROI: 4.39%
North Benson Road #44 Middlebury, CT Only 3 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Bens...	3 beds \| 3 baths \| 2,252 sq.ft.	$555,888	Airbnb cash on cash: -1.85% Traditional cash on cash: 4.46% Airbnb Rental Income: $1510 Traditional Rental Income: $4344 Airbnb ROI: -1.85% Traditional ROI: 4.46%
2 Dogwood Court #2 Middlebury, CT Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the be...	3 beds \| 4 baths \| 3,103 sq.ft.	$530,000	Airbnb cash on cash: -2.05% Traditional cash on cash: 4.94% Airbnb Rental Income: $1510 Traditional Rental Income: $4532 Airbnb ROI: -2.05% Traditional ROI: 4.94%
North Benson Road #59 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 2,206 sq.ft.	$568,564	Airbnb cash on cash: -1.88% Traditional cash on cash: 4.31% Airbnb Rental Income: $1510 Traditional Rental Income: $4358 Airbnb ROI: -1.88% Traditional ROI: 4.31%
North Benson Road #51 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$523,920	Airbnb cash on cash: -1.77% Traditional cash on cash: 4.43% Airbnb Rental Income: $1510 Traditional Rental Income: $4105 Airbnb ROI: -1.77% Traditional ROI: 4.43%
North Benson Road #50 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 1,950 sq.ft.	$509,900	Airbnb cash on cash: -1.73% Traditional cash on cash: 4.66% Airbnb Rental Income: $1510 Traditional Rental Income: $4117 Airbnb ROI: -1.73% Traditional ROI: 4.66%
North Benson Road #48 Middlebury, CT Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson ...	3 beds \| 3 baths \| 2,706 sq.ft.	$603,780	Airbnb cash on cash: -1.95% Traditional cash on cash: 3.98% Airbnb Rental Income: $1510 Traditional Rental Income: $4415 Airbnb ROI: -1.95% Traditional ROI: 3.98%
North Benson Road #60 Middlebury, CT Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson ...	3 beds \| 3 baths \| 2,206 sq.ft.	$573,584	Airbnb cash on cash: -1.89% Traditional cash on cash: 4.11% Airbnb Rental Income: $1510 Traditional Rental Income: $4286 Airbnb ROI: -1.89% Traditional ROI: 4.11%

Your search for investment property begins and ends here

Condos for Sale in Middlebury, CT

24 Ridgewood Drive #24

Middlebury, CT

3 beds | 4 baths | 2,879 sq.ft.

$599,900

Airbnb cash on cash: -1.26%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $1510

Traditional Rental Income: $2867

Airbnb ROI: -1.26%

Traditional ROI: 1.95%

North Benson Road #64

Middlebury, CT

3 beds | 3 baths | 2,206 sq.ft.

$545,400

Airbnb cash on cash: -1.83%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1510

Traditional Rental Income: $4229

Airbnb ROI: -1.83%

Traditional ROI: 4.37%

North Benson Road #55

Middlebury, CT

3 beds | 3 baths | 2,462 sq.ft.

$548,828

Airbnb cash on cash: -1.83%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $1510

Traditional Rental Income: $4375

Airbnb ROI: -1.83%

Traditional ROI: 4.61%

North Benson Road #53

Middlebury, CT

3 beds | 3 baths | 1,950 sq.ft.

$519,900

Airbnb cash on cash: -1.76%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $1510

Traditional Rental Income: $4016

Airbnb ROI: -1.76%

Traditional ROI: 4.3%

North Benson Road #45

Middlebury, CT

3 beds | 3 baths | 1,950 sq.ft.

$525,438

Airbnb cash on cash: -1.78%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $1510

Traditional Rental Income: $4018

Airbnb ROI: -1.78%

Traditional ROI: 4.23%

North Benson Road #66

Middlebury, CT

3 beds | 3 baths | 1,950 sq.ft.

$522,128

Airbnb cash on cash: -1.77%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1510

Traditional Rental Income: $4034

Airbnb ROI: -1.77%

Traditional ROI: 4.31%

North Benson Road #49

Middlebury, CT

3 beds | 3 baths | 1,950 sq.ft.

$533,416

Airbnb cash on cash: -1.8%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $1510

Traditional Rental Income: $4091

Airbnb ROI: -1.8%

Traditional ROI: 4.27%

North Benson Road #46

Middlebury, CT

3 beds | 3 baths | 1,950 sq.ft.

$522,128

Airbnb cash on cash: -1.77%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $1510

Traditional Rental Income: $4091

Airbnb ROI: -1.77%