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.

Investment Property for Sale in Middlebury, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 Ridgewood Drive unit: 24 #24 Middlebury, CT Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewo...	3 beds \| 4 baths \| 2,879 sq.ft.	$574,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.03% Airbnb Rental Income: $1510 Traditional Rental Income: $2867 Airbnb ROI: -1.32% Traditional ROI: 2.03%
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%
N Benson Road unit: 64 #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%
N Benson Road unit: 55 #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%
N Benson Road unit: 53 #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%
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%
N Benson Road unit: 45 #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%
N Benson Road unit: 66 #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%
N Benson Road unit: 49 #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%
N Benson Road unit: 46 #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%
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%
N Benson Road unit: 52 #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%
N Benson Road unit: 44 #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 unit: 2 #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: -1.45% Traditional cash on cash: 5.54% Airbnb Rental Income: $1510 Traditional Rental Income: $4532 Airbnb ROI: -1.45% Traditional ROI: 5.54%
N Benson Road unit: 59 #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%
N Benson Road unit: 51 #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%
N Benson Road unit: 50 #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%
N Benson Road unit: 48 #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%
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%
N Benson Road unit: 60 #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%
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%
N Benson Road unit: 57 #57 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.	$561,271	Airbnb cash on cash: -1.86% Traditional cash on cash: 4.27% Airbnb Rental Income: $1510 Traditional Rental Income: $4286 Airbnb ROI: -1.86% Traditional ROI: 4.27%
348 Kelly Road Middlebury, CT Charming Cape Cod home ideally located just a minute from Memorial Middle School and close...	2 beds \| 1 baths \| 768 sq.ft.	$335,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.17% Airbnb Rental Income: $1028 Traditional Rental Income: $2194 Airbnb ROI: -0.68% Traditional ROI: 4.17%
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%
35 Nutmeg Road unit: Apt D1 #Apt D1 Middlebury, CT Middlebury Commons, Highly desirable 55+ community conveniently located to town center and...	1 beds \| 1 baths \| 889 sq.ft.	$229,000	Airbnb cash on cash: -1.97% Traditional cash on cash: 3.09% Airbnb Rental Income: $900 Traditional Rental Income: $1658 Airbnb ROI: -1.97% Traditional ROI: 3.09%

Real Estate investment in Middlebury, CT

There are 30 properties for sale in the city of Middlebury . The median list price in Middlebury is $558,321 and the average price per square foot is $268. In February 2026, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $4,063.

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

There are 30 investment properties available for sale in Middlebury.

In 2026, the best neighborhood to buy investment property is Middlebury.

The ROI for Long-Term is higher than the Short-Term in Middlebury with average rental income of $4,063.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, CT

24 Ridgewood Drive unit: 24 #24

Middlebury, CT

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

$574,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $1510

Traditional Rental Income: $2867

Airbnb ROI: -1.32%

Traditional ROI: 2.03%

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%

N Benson Road unit: 64 #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%

N Benson Road unit: 55 #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%

N Benson Road unit: 53 #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%

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%

N Benson Road unit: 45 #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%