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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
110 Sarahs Way Middlebury, VT Set on just under half an acre in one of Vermont's most beloved college towns, this though...	4 beds \| 2 baths \| 2,032 sq.ft.	$460,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.93% Airbnb Rental Income: $2419 Traditional Rental Income: $3255 Airbnb ROI: 1.62% Traditional ROI: 4.93%
31 Evergreen Lane Middlebury, VT Discover this stunning end-unit condominium nestled in one of Middlebury's most charming n...	2 beds \| 2 baths \| 1,397 sq.ft.	$380,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 3.51% Airbnb Rental Income: $1445 Traditional Rental Income: $2690 Airbnb ROI: -1.19% Traditional ROI: 3.51%
442 East Main Street Middlebury, VT This inviting home offers a bright, comfortable layout designed for easy everyday living. ...	4 beds \| 2 baths \| 1,815 sq.ft.	$449,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.73% Airbnb Rental Income: $2419 Traditional Rental Income: $2664 Airbnb ROI: 1.74% Traditional ROI: 3.73%
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.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.35% Airbnb Rental Income: $null Traditional Rental Income: $5167 Airbnb ROI: N/A Traditional ROI: 6.35%
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: -1.34% Traditional cash on cash: 4.26% Airbnb Rental Income: $1445 Traditional Rental Income: $3058 Airbnb ROI: -1.34% 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: -1.86% Traditional cash on cash: 1.89% Airbnb Rental Income: $1445 Traditional Rental Income: $3060 Airbnb ROI: -1.86% Traditional ROI: 1.89%
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: -1.24% Traditional cash on cash: 1.38% Airbnb Rental Income: $2060 Traditional Rental Income: $3241 Airbnb ROI: -1.24% 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: -0.36% Traditional cash on cash: 3.61% Airbnb Rental Income: $2060 Traditional Rental Income: $3219 Airbnb ROI: -0.36% Traditional ROI: 3.61%
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.	$595,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.59% Airbnb Rental Income: $2419 Traditional Rental Income: $3377 Airbnb ROI: 0.8% Traditional ROI: 3.59%
74 Brush Lane #10.5 Middlebury, VT Special pricing for qualified buyers! Down payment and closing cost assistance of up to $4...	3 beds \| 3 baths \| 1,938 sq.ft.	$540,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 3.73% Airbnb Rental Income: $1445 Traditional Rental Income: $3433 Airbnb ROI: -1.06% Traditional ROI: 3.73%
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: -1.59% Traditional cash on cash: 1.8% Airbnb Rental Income: $1445 Traditional Rental Income: $3433 Airbnb ROI: -1.59% Traditional ROI: 1.8%
7 Evergreen Lane Middlebury, VT Easy condo living can be just the right fit for someone that doesn't want to shovel, mow t...	2 beds \| 2 baths \| 1,440 sq.ft.	$299,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 4.69% Airbnb Rental Income: $1445 Traditional Rental Income: $2649 Airbnb ROI: -1.11% Traditional ROI: 4.69%

Real Estate investment in Middlebury, VT

There are 21 properties for sale in the city of Middlebury . The median list price in Middlebury is $529,950 and the average price per square foot is $260. In May 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 21 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

110 Sarahs Way

Middlebury, VT

4 beds | 2 baths | 2,032 sq.ft.

$460,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $2419

Traditional Rental Income: $3255

Airbnb ROI: 1.62%

Traditional ROI: 4.93%

31 Evergreen Lane

Middlebury, VT

2 beds | 2 baths | 1,397 sq.ft.

$380,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $1445

Traditional Rental Income: $2690

Airbnb ROI: -1.19%

Traditional ROI: 3.51%

442 East Main Street

Middlebury, VT

4 beds | 2 baths | 1,815 sq.ft.

$449,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $2419

Traditional Rental Income: $2664

Airbnb ROI: 1.74%

Traditional ROI: 3.73%

103 Court Street

Middlebury, VT

5 beds | 4 baths | 3,160 sq.ft.

$570,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.35%

Airbnb Rental Income: $null

Traditional Rental Income: $5167

Airbnb ROI: N/A

Traditional ROI: 6.35%

35 Barnes Brook Road #9.4

Middlebury, VT

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

$388,900

Airbnb cash on cash: -1.34%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $1445

Traditional Rental Income: $3058

Airbnb ROI: -1.34%

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: -1.86%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1445

Traditional Rental Income: $3060

Airbnb ROI: -1.86%

Traditional ROI: 1.89%

40 Brush Lane #8.3B

Middlebury, VT

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

$699,500

Airbnb cash on cash: -1.24%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $2060

Traditional Rental Income: $3241

Airbnb ROI: -1.24%

Traditional ROI: 1.38%

54 Brush Lane #8.4B

Middlebury, VT

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

$455,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $2060

Traditional Rental Income: $3219

Airbnb ROI: -0.36%