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
7 East Farm Road Middlebury, CT Come enjoy a unique, elegant, old-world experience designed with artful accents and archit...	4 beds \| 7 baths \| 9,981 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $9301 Airbnb ROI: N/A Traditional ROI: 3.61%
106 Periwinkle Drive #17 Middlebury, CT Debating between a house or a condo? Benson Woods (over 55 community) offers the best of b...	2 beds \| 2 baths \| 1,854 sq.ft.	$459,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.31% Airbnb Rental Income: $2340 Traditional Rental Income: $3004 Airbnb ROI: 1.42% Traditional ROI: 4.31%
108 Periwinkle Drive #18 Middlebury, CT Debating between a house or a condo? Benson Woods (over 55 community) offers the best of b...	2 beds \| 2 baths \| 2,384 sq.ft.	$499,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $3279 Airbnb ROI: 1.23% Traditional ROI: 4.48%
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: 2.61% Traditional cash on cash: 2% Airbnb Rental Income: $4351 Traditional Rental Income: $3079 Airbnb ROI: 2.61% 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.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.85% Airbnb Rental Income: $null Traditional Rental Income: $3711 Airbnb ROI: N/A Traditional ROI: 1.85%
401 Chestnut Circle #75 Middlebury, CT Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a priva...	2 beds \| 2 baths \| 2,292 sq.ft.	$660,500	Airbnb cash on cash: -1.34% Traditional cash on cash: 0.93% Airbnb Rental Income: $2340 Traditional Rental Income: $3161 Airbnb ROI: -1.34% Traditional ROI: 0.93%
403 Chestnut Circle #76 Middlebury, CT Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a priva...	2 beds \| 2 baths \| 2,292 sq.ft.	$665,600	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.9% Airbnb Rental Income: $2340 Traditional Rental Income: $3161 Airbnb ROI: -1.35% Traditional ROI: 0.9%
405 Chestnut Circle #77 Middlebury, CT Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a priva...	2 beds \| 2 baths \| 2,292 sq.ft.	$649,500	Airbnb cash on cash: -1.31% Traditional cash on cash: 1% Airbnb Rental Income: $2340 Traditional Rental Income: $3161 Airbnb ROI: -1.31% Traditional ROI: 1%
409 Chestnut Circle #79 Middlebury, CT Construction is now underway on the final homesite in the highly sought-after Phase 3 of C...	2 beds \| 3 baths \| 2,292 sq.ft.	$699,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 0.89% Airbnb Rental Income: $2340 Traditional Rental Income: $3270 Airbnb ROI: -1.42% Traditional ROI: 0.89%
407 Chestnut Circle #78 Middlebury, CT Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a priva...	2 beds \| 2 baths \| 2,292 sq.ft.	$655,500	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.97% Airbnb Rental Income: $2340 Traditional Rental Income: $3161 Airbnb ROI: -1.32% Traditional ROI: 0.97%
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: 1.79% Traditional cash on cash: 1.99% Airbnb Rental Income: $4351 Traditional Rental Income: $3576 Airbnb ROI: 1.79% Traditional ROI: 1.99%
17 Deer Run Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 17 Deer Run ...	4 beds \| 3 baths \| 2,466 sq.ft.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.85% Airbnb Rental Income: $null Traditional Rental Income: $3711 Airbnb ROI: N/A Traditional ROI: 1.85%
23 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates.23 Hunting Ri...	4 beds \| 3 baths \| 2,700 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $3821 Airbnb ROI: N/A Traditional ROI: 1.88%
593 Park Road Extension Middlebury, CT This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn w...	4 beds \| 4 baths \| 4,496 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.44% Airbnb Rental Income: $null Traditional Rental Income: $4772 Airbnb ROI: N/A Traditional ROI: 1.44%
39 Ridgewood Drive #39 Middlebury, CT Experience luxury living in this stunning 2100+ SqFt Portman ELITE end unit home in the pr...	3 beds \| 3 baths \| 2,122 sq.ft.	$560,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.89% Airbnb Rental Income: $4351 Traditional Rental Income: $3726 Airbnb ROI: 2.34% Traditional ROI: 2.89%
18 Hunting Ridge Road Middlebury, CT Welcome home to Middlebury's newest 23 lot subdivision- Hunting Ridge Estates. This home i...	4 beds \| 3 baths \| 2,700 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $3769 Airbnb ROI: N/A Traditional ROI: 1.81%
191 Ridgewood Drive #191 Middlebury, CT DON'T PAY EXTRA FOR NEW BUILD! Welcome to this rare newer luxury home nestled in sought af...	3 beds \| 3 baths \| 2,658 sq.ft.	$639,995	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.51% Airbnb Rental Income: $4351 Traditional Rental Income: $3927 Airbnb ROI: 1.68% Traditional ROI: 2.51%
36 Aveline Avenue Middlebury, CT Minutes off of 84, this gorgeous ranch is located on Middlebury's Aveline Ave. This sprawl...	4 beds \| 1 baths \| 1,782 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $2710 Airbnb ROI: N/A Traditional ROI: 1.88%
1232 Straits Turnpike Middlebury, CT MIDDLEBURY! A "ONCE IN A LIFETIME" OPPORTUNITY TO OWN IN A HIGHLY SOUGHT AFTER SUBURBAN CO...	2 beds \| 2 baths \| 1,708 sq.ft.	$269,900	Airbnb cash on cash: 3.45% Traditional cash on cash: 7.54% Airbnb Rental Income: $2340 Traditional Rental Income: $2803 Airbnb ROI: 3.45% Traditional ROI: 7.54%
89 Tyler Crossing Middlebury, CT Discover this elegant colonial-style home in Middlebury, set on 1.4 serene acres. With 4 b...	4 beds \| 3 baths \| 2,704 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $3919 Airbnb ROI: N/A Traditional ROI: 3.71%
6 Colonial Court #6 Middlebury, CT This gorgeous home with exceptional curb appeal, located on a quiet cul de sac in a great ...	3 beds \| 3 baths \| 2,950 sq.ft.	$689,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.41% Airbnb Rental Income: $4351 Traditional Rental Income: $3859 Airbnb ROI: 1.75% Traditional ROI: 2.41%
23 Ridgewood Drive #23 Middlebury, CT Experience luxury living Middlebury with this maintenance-free luxury condo at Ridgewood! ...	2 beds \| 3 baths \| 1,963 sq.ft.	$445,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.87% Airbnb Rental Income: $2340 Traditional Rental Income: $3492 Airbnb ROI: -0.29% Traditional ROI: 3.87%
15 Lakeview Drive Middlebury, CT Custom built by Harlamon Homes this newly constructed colonial is unsurpassed in quality, ...	4 beds \| 3 baths \| 2,800 sq.ft.	$689,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $3903 Airbnb ROI: N/A Traditional ROI: 2.8%
115 Periwinkle Drive #115 Middlebury, CT Enjoy a lifestyle of relaxed sophistication in this captivating home located in an adult c...	2 beds \| 3 baths \| 3,276 sq.ft.	$625,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 0.95% Airbnb Rental Income: $2340 Traditional Rental Income: $3026 Airbnb ROI: -1.22% Traditional ROI: 0.95%
11 Hunting Ridge Road Middlebury, CT Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting R...	3 beds \| 2 baths \| 1,850 sq.ft.	$699,000	Airbnb cash on cash: 2% Traditional cash on cash: 1.51% Airbnb Rental Income: $4351 Traditional Rental Income: $3115 Airbnb ROI: 2% Traditional ROI: 1.51%
203 Tower Road Middlebury, CT Discover the perfect blend of timeless charm and serene natural beauty in this elegant col...	4 beds \| 3 baths \| 2,572 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $3861 Airbnb ROI: N/A Traditional ROI: 3.83%
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: 3.36% Traditional cash on cash: 3.74% Airbnb Rental Income: $4351 Traditional Rental Income: $3618 Airbnb ROI: 3.36% Traditional ROI: 3.74%
North Benson Road #37 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: 3.23% Traditional cash on cash: 3.61% Airbnb Rental Income: $4351 Traditional Rental Income: $3618 Airbnb ROI: 3.23% Traditional ROI: 3.61%
111 Periwinkle Drive #111 Middlebury, CT This bright and sunny home in the desirable 55+ community of Benson Woods combines country...	2 beds \| 3 baths \| 2,476 sq.ft.	$590,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.5% Airbnb Rental Income: $2340 Traditional Rental Income: $2090 Airbnb ROI: -1.1% Traditional ROI: -0.5%

Real Estate investment in Middlebury, CT

There are 29 properties for sale in the city of Middlebury . The median list price in Middlebury is $649,500 and the average price per square foot is $244. In November 2024, the average monthly cash on cash return in Middlebury is 2.00%. The average monthly rental income in Middlebury is $3,576.

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

There are 29 investment properties available for sale in Middlebury.

In 2024, 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 $3,576.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, CT

7 East Farm Road

Middlebury, CT

4 beds | 7 baths | 9,981 sq.ft.

$1,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.61%

Airbnb Rental Income: $null

Traditional Rental Income: $9301

Airbnb ROI: N/A

Traditional ROI: 3.61%

106 Periwinkle Drive #17

Middlebury, CT

2 beds | 2 baths | 1,854 sq.ft.

$459,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2340

Traditional Rental Income: $3004

Airbnb ROI: 1.42%

Traditional ROI: 4.31%

108 Periwinkle Drive #18

Middlebury, CT

2 beds | 2 baths | 2,384 sq.ft.

$499,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $2340

Traditional Rental Income: $3279

Airbnb ROI: 1.23%

Traditional ROI: 4.48%

3 Hunting Ridge Road

Middlebury, CT

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

$624,900

Airbnb cash on cash: 2.61%

Traditional cash on cash: 2%

Airbnb Rental Income: $4351

Traditional Rental Income: $3079

Airbnb ROI: 2.61%

Traditional ROI: 2%

28 Hunting Ridge Road

Middlebury, CT

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

$779,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3711

Airbnb ROI: N/A

Traditional ROI: 1.85%

401 Chestnut Circle #75

Middlebury, CT

2 beds | 2 baths | 2,292 sq.ft.

$660,500

Airbnb cash on cash: -1.34%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $2340

Traditional Rental Income: $3161

Airbnb ROI: -1.34%

Traditional ROI: 0.93%

403 Chestnut Circle #76

Middlebury, CT

2 beds | 2 baths | 2,292 sq.ft.

$665,600

Airbnb cash on cash: -1.35%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $2340

Traditional Rental Income: $3161

Airbnb ROI: -1.35%

Traditional ROI: 0.9%

405 Chestnut Circle #77

Middlebury, CT

2 beds | 2 baths | 2,292 sq.ft.

$649,500

Airbnb cash on cash: -1.31%

Traditional cash on cash: 1%

Airbnb Rental Income: $2340

Traditional Rental Income: $3161

Airbnb ROI: -1.31%