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 #24 Middlebury, CT Truly spectacular remodeled "Cummings" style townhouse in the sought-after Ridgewood at Mi...	3 beds \| 4 baths \| 2,879 sq.ft.	$619,900	Airbnb cash on cash: -1.28% Traditional cash on cash: 1.86% Airbnb Rental Income: $1493 Traditional Rental Income: $2867 Airbnb ROI: -1.28% Traditional ROI: 1.86%
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: -1.47% Traditional cash on cash: 2% Airbnb Rental Income: $1493 Traditional Rental Income: $3079 Airbnb ROI: -1.47% Traditional ROI: 2%
28 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting R...	4 beds \| 3 baths \| 2,466 sq.ft.	$759,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $3711 Airbnb ROI: N/A Traditional ROI: 1.98%
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.	$729,900	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.99% Airbnb Rental Income: $1493 Traditional Rental Income: $3576 Airbnb ROI: -1.71% Traditional ROI: 1.99%
11 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting R...	4 beds \| 3 baths \| 2,700 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.93%
North Benson Road #36 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.	$499,900	Airbnb cash on cash: -1.74% Traditional cash on cash: 3.74% Airbnb Rental Income: $1493 Traditional Rental Income: $3618 Airbnb ROI: -1.74% Traditional ROI: 3.74%
North Benson Road #43 Middlebury, CT An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55...	3 beds \| 3 baths \| 2,252 sq.ft.	$546,936	Airbnb cash on cash: -1.86% Traditional cash on cash: 4.33% Airbnb Rental Income: $1493 Traditional Rental Income: $4219 Airbnb ROI: -1.86% Traditional ROI: 4.33%
North Benson Road #39 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.	$505,834	Airbnb cash on cash: -1.75% Traditional cash on cash: 4.42% Airbnb Rental Income: $1493 Traditional Rental Income: $3976 Airbnb ROI: -1.75% Traditional ROI: 4.42%
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: -1.85% Traditional cash on cash: 4.37% Airbnb Rental Income: $1493 Traditional Rental Income: $4229 Airbnb ROI: -1.85% Traditional ROI: 4.37%
15 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting R...	3 beds \| 3 baths \| 2,190 sq.ft.	$794,900	Airbnb cash on cash: -1.83% Traditional cash on cash: 2.01% Airbnb Rental Income: $1493 Traditional Rental Income: $3898 Airbnb ROI: -1.83% Traditional ROI: 2.01%
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: -1.86% Traditional cash on cash: 4.61% Airbnb Rental Income: $1493 Traditional Rental Income: $4375 Airbnb ROI: -1.86% 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: -1.79% Traditional cash on cash: 4.3% Airbnb Rental Income: $1493 Traditional Rental Income: $4016 Airbnb ROI: -1.79% 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: -1.65% Traditional cash on cash: 1.85% Airbnb Rental Income: $1493 Traditional Rental Income: $3337 Airbnb ROI: -1.65% Traditional ROI: 1.85%
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: -1.81% Traditional cash on cash: 4.23% Airbnb Rental Income: $1493 Traditional Rental Income: $4018 Airbnb ROI: -1.81% 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: -1.8% Traditional cash on cash: 4.31% Airbnb Rental Income: $1493 Traditional Rental Income: $4034 Airbnb ROI: -1.8% Traditional ROI: 4.31%
11 White Birch Lane Middlebury, CT Welcome to 11 White Birch Lane - a rare opportunity to create your ideal home in one of Mi...	4 beds \| 5 baths \| 3,000 sq.ft.	$999,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.76% Airbnb Rental Income: $null Traditional Rental Income: $7429 Airbnb ROI: N/A Traditional ROI: 4.76%
1 White Birch Lane Middlebury, CT Design your dream home from the ground up at 1 White Birch Lane, a to-be-built, fully cust...	3 beds \| 3 baths \| 2,450 sq.ft.	$869,500	Airbnb cash on cash: -1.94% Traditional cash on cash: 5.24% Airbnb Rental Income: $1493 Traditional Rental Income: $6870 Airbnb ROI: -1.94% Traditional ROI: 5.24%
4 White Birch Lane Middlebury, CT Welcome to 4 White Birch Lane, a to-be-built, fully customizable 2,750 SF home offering th...	4 beds \| 4 baths \| 2,750 sq.ft.	$949,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $5397 Airbnb ROI: N/A Traditional ROI: 2.87%
7 White Birch Lane Middlebury, CT Here's your chance to build the home you've always dreamed of at 7 White Birch Lane, a to-...	4 beds \| 4 baths \| 3,325 sq.ft.	$1,099,750	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $6352 Airbnb ROI: N/A Traditional ROI: 2.99%
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: -1.82% Traditional cash on cash: 4.27% Airbnb Rental Income: $1493 Traditional Rental Income: $4091 Airbnb ROI: -1.82% 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: -1.8% Traditional cash on cash: 4.42% Airbnb Rental Income: $1493 Traditional Rental Income: $4091 Airbnb ROI: -1.8% 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: -1.83% Traditional cash on cash: 1.95% Airbnb Rental Income: $1493 Traditional Rental Income: $3876 Airbnb ROI: -1.83% Traditional ROI: 1.95%
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: -1.89% Traditional cash on cash: 4.39% Airbnb Rental Income: $1493 Traditional Rental Income: $4344 Airbnb ROI: -1.89% 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: -1.88% Traditional cash on cash: 4.46% Airbnb Rental Income: $1493 Traditional Rental Income: $4344 Airbnb ROI: -1.88% 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.	$560,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 4.51% Airbnb Rental Income: $1493 Traditional Rental Income: $4532 Airbnb ROI: -2.13% Traditional ROI: 4.51%
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: -1.91% Traditional cash on cash: 4.31% Airbnb Rental Income: $1493 Traditional Rental Income: $4358 Airbnb ROI: -1.91% 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: -1.8% Traditional cash on cash: 4.43% Airbnb Rental Income: $1493 Traditional Rental Income: $4105 Airbnb ROI: -1.8% 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: -1.76% Traditional cash on cash: 4.66% Airbnb Rental Income: $1493 Traditional Rental Income: $4117 Airbnb ROI: -1.76% Traditional ROI: 4.66%
18 Winding Trail #18 Middlebury, CT Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDRO...	3 beds \| 5 baths \| 4,051 sq.ft.	$700,000	Airbnb cash on cash: -2.53% Traditional cash on cash: 7.37% Airbnb Rental Income: $1493 Traditional Rental Income: $7518 Airbnb ROI: -2.53% Traditional ROI: 7.37%
587 Shadduck Road Middlebury, CT Welcome to 587 Shadduck Road, Middlebury, CT! This inviting two-bedroom, one-bathroom Cape...	2 beds \| 1 baths \| 1,157 sq.ft.	$389,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.42% Airbnb Rental Income: $1390 Traditional Rental Income: $2112 Airbnb ROI: -0.72% Traditional ROI: 2.42%
200 North Farm Road Middlebury, CT Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this prop...	4 beds \| 4 baths \| 3,360 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $6273 Airbnb ROI: N/A Traditional ROI: 5.17%
6 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run R...	3 beds \| 3 baths \| 2,190 sq.ft.	$810,000	Airbnb cash on cash: -1.85% Traditional cash on cash: 1.85% Airbnb Rental Income: $1493 Traditional Rental Income: $3849 Airbnb ROI: -1.85% Traditional ROI: 1.85%
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: -1.98% Traditional cash on cash: 3.98% Airbnb Rental Income: $1493 Traditional Rental Income: $4415 Airbnb ROI: -1.98% Traditional ROI: 3.98%
80 Pine Hollow Drive Middlebury, CT Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offe...	4 beds \| 4 baths \| 2,806 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $5433 Airbnb ROI: N/A Traditional ROI: 4.51%
116 Yale Avenue Middlebury, CT Tucked on a quiet street in the heart of Middlebury, this beautifully maintained Cape is w...	3 beds \| 3 baths \| 2,311 sq.ft.	$489,900	Airbnb cash on cash: -1.02% Traditional cash on cash: 4.91% Airbnb Rental Income: $1493 Traditional Rental Income: $3775 Airbnb ROI: -1.02% Traditional ROI: 4.91%
27 Winding Trail #27 Middlebury, CT Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-be...	3 beds \| 3 baths \| 2,680 sq.ft.	$565,000	Airbnb cash on cash: -2.38% Traditional cash on cash: 3.39% Airbnb Rental Income: $1493 Traditional Rental Income: $4102 Airbnb ROI: -2.38% Traditional ROI: 3.39%
115 Porter Avenue Middlebury, CT PRICED RIGHT FOR IMMEDIATE SALE! SNOOZE YOU LOSE! THIS IS "NATURES LOVERS DREAM HOME", PER...	3 beds \| 2 baths \| 1,498 sq.ft.	$399,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 5.14% Airbnb Rental Income: $1493 Traditional Rental Income: $3189 Airbnb ROI: -0.55% Traditional ROI: 5.14%

Real Estate investment in Middlebury, CT

There are 39 properties for sale in the city of Middlebury . The median list price in Middlebury is $560,753 and the average price per square foot is $243. In October 2025, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $4,091.

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

There are 39 investment properties available for sale in Middlebury.

In 2025, 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 $4,091.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, CT

24 Ridgewood Drive #24

Middlebury, CT

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

$619,900

Airbnb cash on cash: -1.28%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $1493

Traditional Rental Income: $2867

Airbnb ROI: -1.28%

Traditional ROI: 1.86%

3 Hunting Ridge Road

Middlebury, CT

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

$624,900

Airbnb cash on cash: -1.47%

Traditional cash on cash: 2%

Airbnb Rental Income: $1493

Traditional Rental Income: $3079

Airbnb ROI: -1.47%

Traditional ROI: 2%

28 Hunting Ridge Road

Middlebury, CT

4 beds | 3 baths | 2,466 sq.ft.

$759,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3711

Airbnb ROI: N/A

Traditional ROI: 1.98%

2 Deer Run Road

Middlebury, CT

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

$729,900

Airbnb cash on cash: -1.71%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $1493

Traditional Rental Income: $3576

Airbnb ROI: -1.71%

Traditional ROI: 1.99%

11 Hunting Ridge Road

Middlebury, CT

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

$799,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.93%

Airbnb Rental Income: $null

Traditional Rental Income: $3115

Airbnb ROI: N/A

Traditional ROI: 0.93%

North Benson Road #36

Middlebury, CT

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

$499,900

Airbnb cash on cash: -1.74%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1493

Traditional Rental Income: $3618

Airbnb ROI: -1.74%

Traditional ROI: 3.74%

North Benson Road #43

Middlebury, CT

3 beds | 3 baths | 2,252 sq.ft.

$546,936

Airbnb cash on cash: -1.86%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $1493

Traditional Rental Income: $4219

Airbnb ROI: -1.86%

Traditional ROI: 4.33%

North Benson Road #39

Middlebury, CT

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

$505,834

Airbnb cash on cash: -1.75%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $1493

Traditional Rental Income: $3976

Airbnb ROI: -1.75%