Real Estate Investment Properties for Sale in Winooski, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
150 East Allen Street Winooski, VT Currently five contiguous residential dwellings, located in the downtown core of the city ...	N/A beds \| N/A baths \| N/A	$3,250,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.14% Airbnb Rental Income: $1966 Traditional Rental Income: $3604 Airbnb ROI: -0.57% Traditional ROI: 0.14%
102 Union Street Winooski, VT Charming Updated Farmhouse in the Heart of Winooski. This beautifully updated home blends ...	2 beds \| 1 baths \| 1,256 sq.ft.	$355,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.84% Airbnb Rental Income: $2063 Traditional Rental Income: $2340 Airbnb ROI: 1.41% Traditional ROI: 3.84%
2 Main Street Winooski, VT Welcome to this exceptional, exciting and diversified investment property! This historic 3...	4 beds \| 3 baths \| 4,611 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.95% Airbnb Rental Income: $null Traditional Rental Income: $2985 Airbnb ROI: N/A Traditional ROI: 6.95%
556 South Main Street Winooski, VT What a great way to start your home ownership! A tenant can help with the monthly expenses...	6 beds \| 2 baths \| 2,112 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.36% Airbnb Rental Income: $null Traditional Rental Income: $3632 Airbnb ROI: N/A Traditional ROI: 11.36%
10 Birge Street Winooski, VT Invest in your own home town! Full tenant roster with the easy access to laundry across t...	5 beds \| 4 baths \| 3,002 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.28% Airbnb Rental Income: $null Traditional Rental Income: $4230 Airbnb ROI: N/A Traditional ROI: 9.28%
573 South Main Street Winooski, VT Just around the corner! From the middle and high school, Oak grove elementary! Pop aroun...	2 beds \| 1 baths \| 3,312 sq.ft.	$350,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.74% Airbnb Rental Income: $2063 Traditional Rental Income: $2231 Airbnb ROI: 1.61% Traditional ROI: 3.74%
25 Cottage Street Winooski, VT Sweet neighborhood. This would be a great location for an owner to live in one unit and re...	6 beds \| 4 baths \| 3,264 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.08% Airbnb Rental Income: $null Traditional Rental Income: $4625 Airbnb ROI: N/A Traditional ROI: 10.08%
29-31 High Street Winooski, VT Location, Location, Location! In the heart of the village, on the coveted, much sought aft...	6 beds \| 3 baths \| 3,325 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $4307 Airbnb ROI: N/A Traditional ROI: 5.47%
27 St Paul Street Winooski, VT Great opportunity to own a spacious two-unit building in downtown Montpelier. The structur...	3 beds \| 2 baths \| 2,284 sq.ft.	$379,500	Airbnb cash on cash: -2.19% Traditional cash on cash: 4.98% Airbnb Rental Income: $717 Traditional Rental Income: $2964 Airbnb ROI: -2.19% Traditional ROI: 4.98%
3261 Route 30 North Winooski, VT LAKE BOMOSEEN DUPLEX - TWO HOUSES WITH INCOME: 1930 Southern house has original frame, but...	6 beds \| 5 baths \| 3,817 sq.ft.	$985,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $4758 Airbnb ROI: N/A Traditional ROI: 3.27%
72 Wood Road Winooski, VT US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. High...	3 beds \| 2 baths \| 2,334 sq.ft.	$1,300,000	Airbnb cash on cash: -2.63% Traditional cash on cash: -0.11% Airbnb Rental Income: $717 Traditional Rental Income: $3458 Airbnb ROI: -2.63% Traditional ROI: -0.11%
4722 Randolph Road Winooski, VT Incredible Rebuild or Land Opportunity with Stunning Mountain Views â Being Sold AS-IS ...	4 beds \| 2 baths \| 1,600 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.5% Airbnb Rental Income: $null Traditional Rental Income: $3149 Airbnb ROI: N/A Traditional ROI: 7.5%
2603 West Shore Road Winooski, VT Turn key two bedroom, year round cottage on the shores of Lake Champlain on the island of ...	2 beds \| 2 baths \| 1,162 sq.ft.	$475,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.64% Airbnb Rental Income: $2063 Traditional Rental Income: $2624 Airbnb ROI: 1.18% Traditional ROI: 3.64%
18 Oak Chapel Road Winooski, VT Discover the potential of this unique fixer-upper property nestled on 0.64 acres, featurin...	3 beds \| N/A baths \| 1,984 sq.ft.	$239,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 9.86% Airbnb Rental Income: $717 Traditional Rental Income: $2886 Airbnb ROI: -1.11% Traditional ROI: 9.86%
139 Stevens Road Winooski, VT Welcome to this one of a kind property on a secluded 16-acre lot. This remarkable home was...	3 beds \| 2 baths \| 1,485 sq.ft.	$300,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 8.91% Airbnb Rental Income: $717 Traditional Rental Income: $3126 Airbnb ROI: -0.71% Traditional ROI: 8.91%
3780 Danby-Pawlet Road Winooski, VT Where to start with this quintessential Vermont Get Away: 62.8 Acres of exceptionally bala...	3 beds \| 3 baths \| 3,004 sq.ft.	$1,050,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 2% Airbnb Rental Income: $717 Traditional Rental Income: $3778 Airbnb ROI: -1.45% Traditional ROI: 2%
1917 Stowe Mountain Road Winooski, VT Welcome to 1917 Stowe Mountain Rd., a sanctuary of modern elegance nestled in the breathta...	4 beds \| 3 baths \| 3,358 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $4094 Airbnb ROI: N/A Traditional ROI: 1.39%
2600 Morgan Charleston Road Winooski, VT Two homes near Echo & Seymour Lakes! Let's start with the new home offering a private livi...	3 beds \| 4 baths \| 3,476 sq.ft.	$779,900	Airbnb cash on cash: -1.59% Traditional cash on cash: 3.3% Airbnb Rental Income: $717 Traditional Rental Income: $3962 Airbnb ROI: -1.59% Traditional ROI: 3.3%
601 River Road Winooski, VT 4-unit income property in an ideal location situated next to an operating farm with huge c...	8 beds \| 4 baths \| 3,438 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.15% Airbnb Rental Income: $null Traditional Rental Income: $4364 Airbnb ROI: N/A Traditional ROI: 10.15%
89 Pearl Street Winooski, VT 3 bedroom home a short distance to schools, trails, restaurants, shops and more! Large sun...	3 beds \| 2 baths \| 1,404 sq.ft.	$224,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 11.03% Airbnb Rental Income: $717 Traditional Rental Income: $2909 Airbnb ROI: -0.76% Traditional ROI: 11.03%
3 Shannon Ridge Road Winooski, VT 3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The H...	4 beds \| 5 baths \| 5,000 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $5280 Airbnb ROI: N/A Traditional ROI: 2.74%
527 Benson Road Winooski, VT Boorn Brook Farm combines the rich character of history and the comfort of contemporary li...	5 beds \| 4 baths \| 6,998 sq.ft.	$4,975,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.72% Airbnb Rental Income: $null Traditional Rental Income: $4432 Airbnb ROI: N/A Traditional ROI: -0.72%
19 Royal Street Winooski, VT Charming North Bennington Home in a Desirable Neighborhood. Welcome to this beautifully u...	4 beds \| 1 baths \| 1,680 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $2407 Airbnb ROI: N/A Traditional ROI: 4.68%
587 VT Route 121 East Winooski, VT Step back in time without sacrificing comfort at the Woolley House, an exquisite 1818 Bric...	4 beds \| 3 baths \| 4,379 sq.ft.	$764,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $4133 Airbnb ROI: N/A Traditional ROI: 3.39%
636 Tunnel Street Winooski, VT Almost there! This owner has taken a traditional farmhouse and transformed it into an ama...	4 beds \| 3 baths \| 3,504 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $4261 Airbnb ROI: N/A Traditional ROI: 6.21%
115 Prior Road Winooski, VT Living and working in the country with privacy, wildlife, snowmobiling from your front doo...	3 beds \| 3 baths \| 2,128 sq.ft.	$795,000	Airbnb cash on cash: -1.81% Traditional cash on cash: 2.66% Airbnb Rental Income: $717 Traditional Rental Income: $3719 Airbnb ROI: -1.81% Traditional ROI: 2.66%
679 Rupert Hill Road Winooski, VT Live your BEST life here in this charming and quaint renovated farmhouse on 8 acres of pri...	4 beds \| 3 baths \| 5,295 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $4257 Airbnb ROI: N/A Traditional ROI: 2.55%
3030 Lower Road Winooski, VT CUSTOM BUILT!! This almost new Colonial offers an abundance of space. The main house inc...	5 beds \| 5 baths \| 2,683 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.84% Airbnb Rental Income: $null Traditional Rental Income: $5178 Airbnb ROI: N/A Traditional ROI: 5.84%
99 Northern Avenue Winooski, VT Donât miss this exceptional duplex offering versatility for both investors and owner-occ...	N/A beds \| N/A baths \| 1,661 sq.ft.	$259,500	Airbnb cash on cash: 3.28% Traditional cash on cash: 11.15% Airbnb Rental Income: $1966 Traditional Rental Income: $3377 Airbnb ROI: 3.28% Traditional ROI: 11.15%
2706 East Woodstock Road Winooski, VT INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Stor...	4 beds \| 4 baths \| 5,000 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $4360 Airbnb ROI: N/A Traditional ROI: 1.15%

Real Estate investment in Winooski, VT

There are 49 properties for sale in the city of Winooski . The median list price in Winooski is $489,000 and the average price per square foot is $171. In December 2025, the average monthly cash on cash return in Winooski is 4.00%. The average monthly rental income in Winooski is $3,604.

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

There are 49 investment properties available for sale in Winooski.

In 2025, the best neighborhood to buy investment property is Winooski.

The ROI for Long-Term is higher than the Short-Term in Winooski with average rental income of $3,604.

Your search for investment property begins and ends here

Investment Property for Sale in Winooski, VT

150 East Allen Street

Winooski, VT

N/A beds | N/A baths | N/A

$3,250,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $1966

Traditional Rental Income: $3604

Airbnb ROI: -0.57%

Traditional ROI: 0.14%

102 Union Street

Winooski, VT

2 beds | 1 baths | 1,256 sq.ft.

$355,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $2063

Traditional Rental Income: $2340

Airbnb ROI: 1.41%

Traditional ROI: 3.84%

2 Main Street

Winooski, VT

4 beds | 3 baths | 4,611 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2985

Airbnb ROI: N/A

Traditional ROI: 6.95%

556 South Main Street

Winooski, VT

6 beds | 2 baths | 2,112 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.36%

Airbnb Rental Income: $null

Traditional Rental Income: $3632

Airbnb ROI: N/A

Traditional ROI: 11.36%

10 Birge Street

Winooski, VT

5 beds | 4 baths | 3,002 sq.ft.

$370,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.28%

Airbnb Rental Income: $null

Traditional Rental Income: $4230

Airbnb ROI: N/A

Traditional ROI: 9.28%

573 South Main Street

Winooski, VT

2 beds | 1 baths | 3,312 sq.ft.

$350,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2063

Traditional Rental Income: $2231

Airbnb ROI: 1.61%

Traditional ROI: 3.74%

25 Cottage Street

Winooski, VT

6 beds | 4 baths | 3,264 sq.ft.

$380,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.08%

Airbnb Rental Income: $null

Traditional Rental Income: $4625

Airbnb ROI: N/A

Traditional ROI: 10.08%

29-31 High Street

Winooski, VT

6 beds | 3 baths | 3,325 sq.ft.

$595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.47%

Airbnb Rental Income: $null

Traditional Rental Income: $4307

Airbnb ROI: N/A