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%
110 Charles Avenue Middlebury, VT Move-in ready and nicely renovated. Welcome to this beautifully updated Middlebury home, ...	4 beds \| 2 baths \| 1,520 sq.ft.	$400,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 6.02% Airbnb Rental Income: $3566 Traditional Rental Income: $3252 Airbnb ROI: 4.76% Traditional ROI: 6.02%
52 School House Hill Road Middlebury, VT Discover peace, privacy, and convenience in this inviting 3-bedroom home set on 2.88 sceni...	3 beds \| 2 baths \| 1,830 sq.ft.	$329,000	Airbnb cash on cash: 4.92% Traditional cash on cash: 7.56% Airbnb Rental Income: $3069 Traditional Rental Income: $3184 Airbnb ROI: 4.92% Traditional ROI: 7.56%
12 Stonegate Drive 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%
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%
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%
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.	$455,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.66% Airbnb Rental Income: $3069 Traditional Rental Income: $3241 Airbnb ROI: 1.61% Traditional ROI: 3.66%
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%
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.	$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 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%
30 South Street 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.	$630,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.34% Airbnb Rental Income: $3566 Traditional Rental Income: $3377 Airbnb ROI: 2.33% Traditional ROI: 3.34%
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 30 properties for sale in the city of Middlebury . The median list price in Middlebury is $482,500 and the average price per square foot is $262. In January 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 30 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

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%

110 Charles Avenue

Middlebury, VT

4 beds | 2 baths | 1,520 sq.ft.

$400,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $3566

Traditional Rental Income: $3252

Airbnb ROI: 4.76%

Traditional ROI: 6.02%

52 School House Hill Road

Middlebury, VT

3 beds | 2 baths | 1,830 sq.ft.

$329,000

Airbnb cash on cash: 4.92%

Traditional cash on cash: 7.56%

Airbnb Rental Income: $3069

Traditional Rental Income: $3184

Airbnb ROI: 4.92%

Traditional ROI: 7.56%

12 Stonegate Drive

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%

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%

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%