Real Estate Investment Properties for Sale in Middlebury, VT

Looking for investment property in Middlebury, VT with high ROI ?

Explore a variety of short-term homes & houses in Middlebury, VT. Invest wisely with VRBO & Middlebury, VT 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, VT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12 Stonegate Dr Middlebury, VT Welcome to 12 Stonegate Drive! This charming single-level home offers 2 bedrooms and 1 ful...	2 beds \| 1 baths \| 1,040 sq.ft.	$319,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.12% Airbnb Rental Income: $1662 Traditional Rental Income: $1752 Airbnb ROI: 1.27% Traditional ROI: 3.12%
53 High St Middlebury, VT Attention Buyers!! Investors, Multi-generational living, first time home buyers! HUGE P...	3 beds \| 3 baths \| 1,740 sq.ft.	$275,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 9.05% Airbnb Rental Income: $3069 Traditional Rental Income: $3355 Airbnb ROI: 5.25% Traditional ROI: 9.05%
103 Court St Middlebury, VT Opportunity Knocks in the conveniently located 5 bedroom home in Middlebury! The property ...	5 beds \| 3 baths \| 3,160 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.71% Airbnb Rental Income: $null Traditional Rental Income: $5167 Airbnb ROI: N/A Traditional ROI: 5.71%
35 Barnes Brook Rd #9.4 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	2 beds \| 1 baths \| 1,516 sq.ft.	$388,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 4.26% Airbnb Rental Income: $1662 Traditional Rental Income: $3058 Airbnb ROI: -0.85% Traditional ROI: 4.26%
39 Barnes Brook Rd #9.3 Middlebury, VT Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from...	2 beds \| 1 baths \| 1,516 sq.ft.	$585,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 1.89% Airbnb Rental Income: $1662 Traditional Rental Income: $3060 Airbnb ROI: -1.53% Traditional ROI: 1.89%
40 Brush Ln #8.3B Middlebury, VT Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from...	3 beds \| 2 baths \| 1,660 sq.ft.	$699,500	Airbnb cash on cash: 0.05% Traditional cash on cash: 1.38% Airbnb Rental Income: $3069 Traditional Rental Income: $3241 Airbnb ROI: 0.05% Traditional ROI: 1.38%
54 Brush Ln #8.4B Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	3 beds \| 2 baths \| 1,660 sq.ft.	$455,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.61% Airbnb Rental Income: $3069 Traditional Rental Income: $3219 Airbnb ROI: 1.61% Traditional ROI: 3.61%
26 Meadowlark Ln #7.5 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	2 beds \| 1 baths \| 1,538 sq.ft.	$388,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 4.23% Airbnb Rental Income: $1662 Traditional Rental Income: $3047 Airbnb ROI: -0.85% Traditional ROI: 4.23%
10 Meadowlark Ln Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	3 beds \| 2 baths \| 2,019 sq.ft.	$482,500	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.98% Airbnb Rental Income: $3069 Traditional Rental Income: $3554 Airbnb ROI: 1.36% Traditional ROI: 3.98%
30 South St Middlebury, VT This classic village home is in a great location! Situated on South St., with sidewalks on...	4 beds \| 2 baths \| 2,037 sq.ft.	$595,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.59% Airbnb Rental Income: $3566 Traditional Rental Income: $3377 Airbnb ROI: 2.52% Traditional ROI: 3.59%
68 Court St Middlebury, VT Close to town and move-in ready! If you're in the market for a house with charm, characte...	4 beds \| 2 baths \| 1,652 sq.ft.	$410,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 5.84% Airbnb Rental Income: $3566 Traditional Rental Income: $3371 Airbnb ROI: 4.3% Traditional ROI: 5.84%

Real Estate investment in Middlebury, VT

There are 23 properties for sale in the city of Middlebury . The median list price in Middlebury is $499,450 and the average price per square foot is $250. In March 2026, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $3,241.

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

There are 23 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 $3,241.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, VT

12 Stonegate Dr

Middlebury, VT

2 beds | 1 baths | 1,040 sq.ft.

$319,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $1662

Traditional Rental Income: $1752

Airbnb ROI: 1.27%

Traditional ROI: 3.12%

53 High St

Middlebury, VT

3 beds | 3 baths | 1,740 sq.ft.

$275,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 9.05%

Airbnb Rental Income: $3069

Traditional Rental Income: $3355

Airbnb ROI: 5.25%

Traditional ROI: 9.05%

103 Court St

Middlebury, VT

5 beds | 3 baths | 3,160 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.71%

Airbnb Rental Income: $null

Traditional Rental Income: $5167

Airbnb ROI: N/A

Traditional ROI: 5.71%

35 Barnes Brook Rd #9.4

Middlebury, VT

2 beds | 1 baths | 1,516 sq.ft.

$388,900

Airbnb cash on cash: -0.85%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $1662

Traditional Rental Income: $3058

Airbnb ROI: -0.85%

Traditional ROI: 4.26%

39 Barnes Brook Rd #9.3

Middlebury, VT

2 beds | 1 baths | 1,516 sq.ft.

$585,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1662

Traditional Rental Income: $3060

Airbnb ROI: -1.53%

Traditional ROI: 1.89%

40 Brush Ln #8.3B

Middlebury, VT

3 beds | 2 baths | 1,660 sq.ft.

$699,500

Airbnb cash on cash: 0.05%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $3069

Traditional Rental Income: $3241

Airbnb ROI: 0.05%

Traditional ROI: 1.38%

54 Brush Ln #8.4B

Middlebury, VT

3 beds | 2 baths | 1,660 sq.ft.

$455,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $3069

Traditional Rental Income: $3219

Airbnb ROI: 1.61%

Traditional ROI: 3.61%

26 Meadowlark Ln #7.5

Middlebury, VT

2 beds | 1 baths | 1,538 sq.ft.

$388,900

Airbnb cash on cash: -0.85%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $1662

Traditional Rental Income: $3047

Airbnb ROI: -0.85%