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
70 Maple Street #205 Middlebury, VT Located in the heart of Middlebury - walking distance to shopping, restaurants and events-...	3 beds \| 3 baths \| 1,653 sq.ft.	$850,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 0.05% Airbnb Rental Income: $3069 Traditional Rental Income: $3271 Airbnb ROI: -1.09% Traditional ROI: 0.05%
86 Ossie Road Middlebury, VT Quaint, village home-many recent improvements: rain gutters, Northern Bsmt system, new app...	3 beds \| 2 baths \| 1,673 sq.ft.	$417,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.8% Airbnb Rental Income: $3069 Traditional Rental Income: $2513 Airbnb ROI: 3.43% Traditional ROI: 3.8%
118 Three Mile Bridge Road Middlebury, VT This classic 1820 colonial blends historical charm with everyday practicality on a level o...	3 beds \| 2 baths \| 2,232 sq.ft.	$389,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 5.12% Airbnb Rental Income: $3069 Traditional Rental Income: $2821 Airbnb ROI: 3.88% Traditional ROI: 5.12%
53 High Street Middlebury, VT Investment Opportunity!! What was once a barn in the early 1900's is now 2 apartments. Th...	3 beds \| 3 baths \| 1,740 sq.ft.	$325,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 7.53% Airbnb Rental Income: $3069 Traditional Rental Income: $3355 Airbnb ROI: 4.3% Traditional ROI: 7.53%
103 Court Street Middlebury, VT Opportunity Knocks in the conveniently located 5 bedroom home in Middlebury! The property ...	5 beds \| 4 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%
200 Butternut Ridge Drive Middlebury, VT This lovely home is really only about 4 years old. The current owner purchased the propert...	3 beds \| 3 baths \| 2,174 sq.ft.	$460,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 4.98% Airbnb Rental Income: $3069 Traditional Rental Income: $3247 Airbnb ROI: 2.94% Traditional ROI: 4.98%
35 Barnes Brook Road #9.4 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	2 beds \| 2 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 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: -1.53% Traditional cash on cash: 1.89% Airbnb Rental Income: $1662 Traditional Rental Income: $3060 Airbnb ROI: -1.53% Traditional ROI: 1.89%
30 Mountain View Lane Middlebury, VT Great house on a corner lot in a Middlebury neighborhood that's close to town! The first ...	4 beds \| 3 baths \| 1,760 sq.ft.	$499,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 4.66% Airbnb Rental Income: $3566 Traditional Rental Income: $3490 Airbnb ROI: 3.14% Traditional ROI: 4.66%
10 Brush Lane #8.1B 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.	$482,500	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.29% Airbnb Rental Income: $3069 Traditional Rental Income: $3241 Airbnb ROI: 1.36% Traditional ROI: 3.29%
40 Brush Lane #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%
28 Brush Lane #8.2A Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	2 beds \| 2 baths \| 1,434 sq.ft.	$426,300	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.52% Airbnb Rental Income: $1662 Traditional Rental Income: $3009 Airbnb ROI: -1.02% Traditional ROI: 3.52%
54 Brush Lane #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.	$482,500	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.24% Airbnb Rental Income: $3069 Traditional Rental Income: $3219 Airbnb ROI: 1.36% Traditional ROI: 3.24%
26 Meadowlark Lane #7.5 Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	2 beds \| 2 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 Lane Middlebury, VT Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welco...	3 beds \| 3 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%
42 Lower Plains Road Middlebury, VT Enjoy living in a peaceful, secluded home with a horse barn, surrounded by more than 38 ac...	4 beds \| 3 baths \| 1,875 sq.ft.	$399,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 5.73% Airbnb Rental Income: $3566 Traditional Rental Income: $3568 Airbnb ROI: 3.63% Traditional ROI: 5.73%
23 Brookside Drive Middlebury, VT PRICE REDUCED FOR A GREAT VALUE IN MIDDLEBURY! ENERGY CONSCIOUS, NICELY MAINTAINED, IN-TOW...	2 beds \| 2 baths \| 1,884 sq.ft.	$409,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.65% Airbnb Rental Income: $1662 Traditional Rental Income: $2882 Airbnb ROI: 0.25% Traditional ROI: 4.65%
68 Court Street 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 31 properties for sale in the city of Middlebury . The median list price in Middlebury is $426,300 and the average price per square foot is $232. In December 2025, the average monthly cash on cash return in Middlebury is 4.00%. The average monthly rental income in Middlebury is $3,219.

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

There are 31 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 $3,219.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, VT

70 Maple Street #205

Middlebury, VT

3 beds | 3 baths | 1,653 sq.ft.

$850,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $3069

Traditional Rental Income: $3271

Airbnb ROI: -1.09%

Traditional ROI: 0.05%

86 Ossie Road

Middlebury, VT

3 beds | 2 baths | 1,673 sq.ft.

$417,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3069

Traditional Rental Income: $2513

Airbnb ROI: 3.43%

Traditional ROI: 3.8%

118 Three Mile Bridge Road

Middlebury, VT

3 beds | 2 baths | 2,232 sq.ft.

$389,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $3069

Traditional Rental Income: $2821

Airbnb ROI: 3.88%

Traditional ROI: 5.12%

53 High Street

Middlebury, VT

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

$325,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 7.53%

Airbnb Rental Income: $3069

Traditional Rental Income: $3355

Airbnb ROI: 4.3%

Traditional ROI: 7.53%

103 Court Street

Middlebury, VT

5 beds | 4 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%

200 Butternut Ridge Drive

Middlebury, VT

3 beds | 3 baths | 2,174 sq.ft.

$460,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $3069

Traditional Rental Income: $3247

Airbnb ROI: 2.94%

Traditional ROI: 4.98%

35 Barnes Brook Road #9.4

Middlebury, VT

2 beds | 2 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 Road #9.3

Middlebury, VT

2 beds | 2 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%