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
424 Quarry Road Middlebury, VT Come discover this spacious contemporary home, offering the perfect blend of country charm...	4 beds \| 3 baths \| 2,560 sq.ft.	$514,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 1.85% Airbnb Rental Income: $2347 Traditional Rental Income: $2247 Airbnb ROI: 0.85% Traditional ROI: 1.85%
95 Seminary Street Extension Middlebury, VT This updated mid-century home features new flooring and fresh interior paint. Step outside...	3 beds \| 2 baths \| 1,916 sq.ft.	$470,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.95% Airbnb Rental Income: $2530 Traditional Rental Income: $2607 Airbnb ROI: 1.39% Traditional ROI: 2.95%
39 Barnes Brook Road #9.3 Middlebury, VT Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from...	2 beds \| 2 baths \| 1,516 sq.ft.	$585,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 1.89% Airbnb Rental Income: $2561 Traditional Rental Income: $3060 Airbnb ROI: -0.16% Traditional ROI: 1.89%
40 Brush Lane #8.3B 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: 0.56% Traditional cash on cash: 3.66% Airbnb Rental Income: $2530 Traditional Rental Income: $3241 Airbnb ROI: 0.56% Traditional ROI: 3.66%
74 Brush Lane #10.5 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	3 beds \| 3 baths \| 1,938 sq.ft.	$499,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 3.5% Airbnb Rental Income: $2530 Traditional Rental Income: $3433 Airbnb ROI: 0.26% Traditional ROI: 3.5%
78 Brush Lane #10.6 Middlebury, VT Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from...	3 beds \| 3 baths \| 1,938 sq.ft.	$765,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.8% Airbnb Rental Income: $2530 Traditional Rental Income: $3433 Airbnb ROI: -0.33% Traditional ROI: 1.8%
41 Barnes Brook Road #9.2 Middlebury, VT Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from...	2 beds \| 2 baths \| 1,516 sq.ft.	$388,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.24% Airbnb Rental Income: $2561 Traditional Rental Income: $3053 Airbnb ROI: 1.21% Traditional ROI: 4.24%
2337 VT Route 7 Middlebury, VT Here is a delightful opportunity to own a simply versatile property that has been carefull...	2 beds \| 3 baths \| 1,960 sq.ft.	$489,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.34% Airbnb Rental Income: $2561 Traditional Rental Income: $3158 Airbnb ROI: 1.69% Traditional ROI: 4.34%
466 E Main Street Middlebury, VT Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills t...	4 beds \| 2 baths \| 2,684 sq.ft.	$699,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.31% Airbnb Rental Income: $2347 Traditional Rental Income: $3677 Airbnb ROI: 0.38% Traditional ROI: 3.31%
86 Brush Lane #10.7 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	3 beds \| 3 baths \| 1,938 sq.ft.	$499,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 4.19% Airbnb Rental Income: $2530 Traditional Rental Income: $3395 Airbnb ROI: 1.03% Traditional ROI: 4.19%
10 Case Street Middlebury, VT Welcome to your next home,10 Case Street, a charming 3-bedroom, 2-bath home dating back to...	3 beds \| 2 baths \| 1,455 sq.ft.	$385,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 6.64% Airbnb Rental Income: $2530 Traditional Rental Income: $3395 Airbnb ROI: 2.56% Traditional ROI: 6.64%
434 E Main Street Middlebury, VT The Middlebury River is your backyard! Lovingly held by the same family for 60 years, this...	4 beds \| 2 baths \| 2,429 sq.ft.	$420,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 3% Airbnb Rental Income: $2347 Traditional Rental Income: $2247 Airbnb ROI: 1.78% Traditional ROI: 3%

Real Estate investment in Middlebury, VT

There are 17 properties for sale in the city of Middlebury . The median list price in Middlebury is $504,698 and the average price per square foot is $242. In November 2026, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $3,395.

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

There are 17 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 $3,395.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, VT

424 Quarry Road

Middlebury, VT

4 beds | 3 baths | 2,560 sq.ft.

$514,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $2347

Traditional Rental Income: $2247

Airbnb ROI: 0.85%

Traditional ROI: 1.85%

95 Seminary Street Extension

Middlebury, VT

3 beds | 2 baths | 1,916 sq.ft.

$470,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2530

Traditional Rental Income: $2607

Airbnb ROI: 1.39%

Traditional ROI: 2.95%

39 Barnes Brook Road #9.3

Middlebury, VT

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

$585,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $2561

Traditional Rental Income: $3060

Airbnb ROI: -0.16%

Traditional ROI: 1.89%

40 Brush Lane #8.3B

Middlebury, VT

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

$455,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2530

Traditional Rental Income: $3241

Airbnb ROI: 0.56%

Traditional ROI: 3.66%

74 Brush Lane #10.5

Middlebury, VT

3 beds | 3 baths | 1,938 sq.ft.

$499,000

Airbnb cash on cash: 0.26%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $2530

Traditional Rental Income: $3433

Airbnb ROI: 0.26%

Traditional ROI: 3.5%

78 Brush Lane #10.6

Middlebury, VT

3 beds | 3 baths | 1,938 sq.ft.

$765,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2530

Traditional Rental Income: $3433

Airbnb ROI: -0.33%

Traditional ROI: 1.8%

41 Barnes Brook Road #9.2

Middlebury, VT

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

$388,900

Airbnb cash on cash: 1.21%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $2561

Traditional Rental Income: $3053

Airbnb ROI: 1.21%

Traditional ROI: 4.24%

2337 VT Route 7

Middlebury, VT

2 beds | 3 baths | 1,960 sq.ft.

$489,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $2561

Traditional Rental Income: $3158

Airbnb ROI: 1.69%