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.

Single Family Homes for Sale in Middlebury, CT

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

Showing 11 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 3 Hunting Ri...	3 beds \| 2 baths \| 1,700 sq.ft.	$624,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.24% Airbnb Rental Income: $1510 Traditional Rental Income: $3079 Airbnb ROI: -0.2% Traditional ROI: 3.24%
2 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run R...	3 beds \| 3 baths \| 2,190 sq.ft.	$709,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.49% Airbnb Rental Income: $1510 Traditional Rental Income: $3576 Airbnb ROI: -0.3% Traditional ROI: 3.49%
14 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run ...	3 beds \| 2 baths \| 1,877 sq.ft.	$699,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.81% Airbnb Rental Income: $1510 Traditional Rental Income: $3337 Airbnb ROI: 0.33% Traditional ROI: 3.81%
18 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 18 Deer Run ...	3 beds \| 3 baths \| 2,190 sq.ft.	$799,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.89% Airbnb Rental Income: $1510 Traditional Rental Income: $3876 Airbnb ROI: 0.13% Traditional ROI: 3.89%
11 Upper Whittemore Road Middlebury, CT Discover your dream home at 11 Upper Whittemore Rd, a stunningly renovated Brick Ranch nes...	3 beds \| 1 baths \| 1,120 sq.ft.	$459,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.61% Airbnb Rental Income: $1510 Traditional Rental Income: $2237 Airbnb ROI: -0.11% Traditional ROI: 2.61%
10 Old Waterbury Road Waterbury, CT RARE OPPORTUNITY to find 4 units in MIDDLEBURY, CT! LOCATION! LOCATION! One parcel with (....	5 beds \| 4 baths \| 2,345 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $5655 Airbnb ROI: N/A Traditional ROI: 6.43%
152 Glenwood Avenue Waterbury, CT 2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar lea...	2 beds \| 1 baths \| 1,085 sq.ft.	$284,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 4.19% Airbnb Rental Income: $1245 Traditional Rental Income: $1890 Airbnb ROI: 0.31% Traditional ROI: 4.19%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middlebury, CT

3 Hunting Ridge Road

Middlebury, CT

3 beds | 2 baths | 1,700 sq.ft.

$624,900

Airbnb cash on cash: -0.2%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $1510

Traditional Rental Income: $3079

Airbnb ROI: -0.2%

Traditional ROI: 3.24%

2 Deer Run Road

Middlebury, CT

3 beds | 3 baths | 2,190 sq.ft.

$709,900

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1510

Traditional Rental Income: $3576

Airbnb ROI: -0.3%

Traditional ROI: 3.49%

14 Deer Run Road

Middlebury, CT

3 beds | 2 baths | 1,877 sq.ft.

$699,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1510

Traditional Rental Income: $3337

Airbnb ROI: 0.33%

Traditional ROI: 3.81%

18 Deer Run Road

Middlebury, CT

3 beds | 3 baths | 2,190 sq.ft.

$799,900

Airbnb cash on cash: 0.13%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1510

Traditional Rental Income: $3876

Airbnb ROI: 0.13%

Traditional ROI: 3.89%

11 Upper Whittemore Road

Middlebury, CT

3 beds | 1 baths | 1,120 sq.ft.

$459,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $1510

Traditional Rental Income: $2237

Airbnb ROI: -0.11%

Traditional ROI: 2.61%

10 Old Waterbury Road

Waterbury, CT

5 beds | 4 baths | 2,345 sq.ft.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.43%

Airbnb Rental Income: $null

Traditional Rental Income: $5655

Airbnb ROI: N/A

Traditional ROI: 6.43%

152 Glenwood Avenue

Waterbury, CT

2 beds | 1 baths | 1,085 sq.ft.

$284,900

Airbnb cash on cash: 0.31%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $1245

Traditional Rental Income: $1890

Airbnb ROI: 0.31%

Traditional ROI: 4.19%

Use analytics to find lucrative traditional or Airbnb properties in a matter of minutes.

No more spreadsheets, no more searching.