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
3 Winding Trail #3 Middlebury, CT Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewoo...	3 beds \| 3 baths \| 3,179 sq.ft.	$559,900	Airbnb cash on cash: -1.83% Traditional cash on cash: 3.59% Airbnb Rental Income: $1216 Traditional Rental Income: $3659 Airbnb ROI: -1.83% Traditional ROI: 3.59%
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: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $3711 Airbnb ROI: N/A Traditional ROI: 3.93%
397 White Deer Rock Road Middlebury, CT Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bun...	3 beds \| 3 baths \| 3,863 sq.ft.	$2,195,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.3% Airbnb Rental Income: $1216 Traditional Rental Income: $2900 Airbnb ROI: -1.32% Traditional ROI: -0.3%
N 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: -2.31% Traditional cash on cash: 4.37% Airbnb Rental Income: $1216 Traditional Rental Income: $4229 Airbnb ROI: -2.31% 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.	$834,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 3.24% Airbnb Rental Income: $1216 Traditional Rental Income: $3898 Airbnb ROI: -0.72% Traditional ROI: 3.24%
N 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: -2.31% Traditional cash on cash: 4.61% Airbnb Rental Income: $1216 Traditional Rental Income: $4375 Airbnb ROI: -2.31% Traditional ROI: 4.61%
N 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: -2.27% Traditional cash on cash: 4.3% Airbnb Rental Income: $1216 Traditional Rental Income: $4016 Airbnb ROI: -2.27% Traditional ROI: 4.3%
N 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: -2.27% Traditional cash on cash: 4.23% Airbnb Rental Income: $1216 Traditional Rental Income: $4018 Airbnb ROI: -2.27% Traditional ROI: 4.23%
N 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: -2.29% Traditional cash on cash: 4.27% Airbnb Rental Income: $1216 Traditional Rental Income: $4091 Airbnb ROI: -2.29% Traditional ROI: 4.27%
N 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: -2.27% Traditional cash on cash: 4.42% Airbnb Rental Income: $1216 Traditional Rental Income: $4091 Airbnb ROI: -2.27% Traditional ROI: 4.42%
N 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: -2.33% Traditional cash on cash: 4.39% Airbnb Rental Income: $1216 Traditional Rental Income: $4344 Airbnb ROI: -2.33% Traditional ROI: 4.39%
N 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: -2.32% Traditional cash on cash: 4.46% Airbnb Rental Income: $1216 Traditional Rental Income: $4344 Airbnb ROI: -2.32% Traditional ROI: 4.46%
N 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: -2.34% Traditional cash on cash: 4.31% Airbnb Rental Income: $1216 Traditional Rental Income: $4358 Airbnb ROI: -2.34% Traditional ROI: 4.31%
N 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: -2.27% Traditional cash on cash: 4.43% Airbnb Rental Income: $1216 Traditional Rental Income: $4105 Airbnb ROI: -2.27% Traditional ROI: 4.43%
N 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: -2.25% Traditional cash on cash: 4.66% Airbnb Rental Income: $1216 Traditional Rental Income: $4117 Airbnb ROI: -2.25% Traditional ROI: 4.66%
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.	$849,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 3.57% Airbnb Rental Income: $1216 Traditional Rental Income: $3849 Airbnb ROI: -0.25% Traditional ROI: 3.57%
N 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: -2.39% Traditional cash on cash: 3.98% Airbnb Rental Income: $1216 Traditional Rental Income: $4415 Airbnb ROI: -2.39% 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.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.08% Airbnb Rental Income: $null Traditional Rental Income: $5433 Airbnb ROI: N/A Traditional ROI: 5.08%
N 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: -2.35% Traditional cash on cash: 4.11% Airbnb Rental Income: $1216 Traditional Rental Income: $4286 Airbnb ROI: -2.35% Traditional ROI: 4.11%
N Benson Road #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: -2.33% Traditional cash on cash: 4.27% Airbnb Rental Income: $1216 Traditional Rental Income: $4286 Airbnb ROI: -2.33% Traditional ROI: 4.27%
152 Glenwood Avenue Middlebury, 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.	$224,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 5.55% Airbnb Rental Income: $993 Traditional Rental Income: $1890 Airbnb ROI: -0.33% Traditional ROI: 5.55%
19 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 19 Deer Run ...	4 beds \| 3 baths \| 3,100 sq.ft.	$900,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $1082 Airbnb ROI: N/A Traditional ROI: 0.02%
24 Ridgewood Drive #24 Middlebury, CT Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewo...	3 beds \| 4 baths \| 2,879 sq.ft.	$554,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 5.43% Airbnb Rental Income: $1216 Traditional Rental Income: $4129 Airbnb ROI: -0.95% Traditional ROI: 5.43%
N Benson Road #62 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: -1.69% Traditional cash on cash: 4.15% Airbnb Rental Income: $1216 Traditional Rental Income: $3799 Airbnb ROI: -1.69% Traditional ROI: 4.15%
20 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting R...	3 beds \| 2 baths \| 1,877 sq.ft.	$774,900	Airbnb cash on cash: -2.11% Traditional cash on cash: 1.3% Airbnb Rental Income: $1216 Traditional Rental Income: $3289 Airbnb ROI: -2.11% Traditional ROI: 1.3%
36 Highridge Road #36 Middlebury, CT Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most de...	3 beds \| 3 baths \| 1,997 sq.ft.	$585,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.97% Airbnb Rental Income: $1216 Traditional Rental Income: $3551 Airbnb ROI: -1.03% Traditional ROI: 3.97%
408 Breakneck Hill Road Middlebury, CT Charm abounds in this remodeled classic cape with 2 car garage, central air, and massive 1...	2 beds \| 3 baths \| 1,848 sq.ft.	$625,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 3.27% Airbnb Rental Income: $993 Traditional Rental Income: $3402 Airbnb ROI: -1.46% Traditional ROI: 3.27%
851 South Street Middlebury, CT Welcome to this beautifully updated home which offers modern comfort, high-end finishes & ...	5 beds \| 3 baths \| 3,301 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.08% Airbnb Rental Income: $null Traditional Rental Income: $4890 Airbnb ROI: N/A Traditional ROI: 3.08%
N Benson Road #65 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.	$573,572	Airbnb cash on cash: -1.76% Traditional cash on cash: 3.82% Airbnb Rental Income: $1216 Traditional Rental Income: $3810 Airbnb ROI: -1.76% Traditional ROI: 3.82%
168 N Farm Road Middlebury, CT Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath...	4 beds \| 4 baths \| 3,302 sq.ft.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.58% Airbnb Rental Income: $null Traditional Rental Income: $6352 Airbnb ROI: N/A Traditional ROI: 6.58%
8 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run R...	3 beds \| 3 baths \| 2,450 sq.ft.	$839,900	Airbnb cash on cash: -2.19% Traditional cash on cash: 1.9% Airbnb Rental Income: $1216 Traditional Rental Income: $4023 Airbnb ROI: -2.19% Traditional ROI: 1.9%
36 Independence Circle #36 Middlebury, CT Welcome to this impressive 3,512-square-foot Colonial offering 10 spacious rooms 4 bedroom...	4 beds \| 4 baths \| 3,512 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.02% Airbnb Rental Income: $null Traditional Rental Income: $6085 Airbnb ROI: N/A Traditional ROI: 7.02%
N Benson Road #56 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.	$572,000	Airbnb cash on cash: -1.75% Traditional cash on cash: 3.84% Airbnb Rental Income: $1216 Traditional Rental Income: $3811 Airbnb ROI: -1.75% Traditional ROI: 3.84%

Real Estate investment in Middlebury, CT

There are 39 properties for sale in the city of Middlebury . The median list price in Middlebury is $569,900 and the average price per square foot is $240. In June 2026, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $4,021.

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

There are 39 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 $4,021.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, CT

3 Winding Trail #3

Middlebury, CT

3 beds | 3 baths | 3,179 sq.ft.

$559,900

Airbnb cash on cash: -1.83%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $1216

Traditional Rental Income: $3659

Airbnb ROI: -1.83%

Traditional ROI: 3.59%

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: 3.93%

Airbnb Rental Income: $null

Traditional Rental Income: $3711

Airbnb ROI: N/A

Traditional ROI: 3.93%

397 White Deer Rock Road

Middlebury, CT

3 beds | 3 baths | 3,863 sq.ft.

$2,195,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: -0.3%

Airbnb Rental Income: $1216

Traditional Rental Income: $2900

Airbnb ROI: -1.32%

Traditional ROI: -0.3%

N Benson Road #64

Middlebury, CT

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

$545,400

Airbnb cash on cash: -2.31%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1216

Traditional Rental Income: $4229

Airbnb ROI: -2.31%

Traditional ROI: 4.37%

15 Hunting Ridge Road

Middlebury, CT

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

$834,900

Airbnb cash on cash: -0.72%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $1216

Traditional Rental Income: $3898

Airbnb ROI: -0.72%

Traditional ROI: 3.24%

N Benson Road #55

Middlebury, CT

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

$548,828

Airbnb cash on cash: -2.31%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $1216

Traditional Rental Income: $4375

Airbnb ROI: -2.31%

Traditional ROI: 4.61%

N Benson Road #53

Middlebury, CT

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

$519,900

Airbnb cash on cash: -2.27%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $1216

Traditional Rental Income: $4016

Airbnb ROI: -2.27%

Traditional ROI: 4.3%

N Benson Road #45

Middlebury, CT

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

$525,438

Airbnb cash on cash: -2.27%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $1216

Traditional Rental Income: $4018

Airbnb ROI: -2.27%