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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9 West Street #D Winooski, VT OPEN HOUSE SAT 10/11/25 11:00 to 1:00 Discover easy living in this smart and stylish tw...	2 beds \| 1 baths \| 848 sq.ft.	$249,900	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.98% Airbnb Rental Income: $2103 Traditional Rental Income: $1906 Airbnb ROI: 2.53% Traditional ROI: 3.98%
150 Franklin Street Winooski, VT Absolutely charming home conveniently located near everything that Winooski has to offer. ...	3 beds \| 2 baths \| 1,400 sq.ft.	$499,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 3.25% Airbnb Rental Income: $898 Traditional Rental Income: $2871 Airbnb ROI: -1.7% Traditional ROI: 3.25%
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: -0.58% Traditional cash on cash: 0.14% Airbnb Rental Income: $1955 Traditional Rental Income: $3604 Airbnb ROI: -0.58% 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.	$367,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.68% Airbnb Rental Income: $2103 Traditional Rental Income: $2340 Airbnb ROI: 1.43% Traditional ROI: 3.68%
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: 1.71% Traditional cash on cash: 3.74% Airbnb Rental Income: $2103 Traditional Rental Income: $2231 Airbnb ROI: 1.71% Traditional ROI: 3.74%
60 Winooski Falls Way #1404 Winooski, VT Stunning Penthouse with Panoramic Views of the Winooski River!!! Welcome to luxury living ...	2 beds \| 2 baths \| 1,760 sq.ft.	$735,000	Airbnb cash on cash: -2.52% Traditional cash on cash: -0.34% Airbnb Rental Income: $2103 Traditional Rental Income: $3055 Airbnb ROI: -2.52% Traditional ROI: -0.34%
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%
133 East Mountain Road #3B15 Winooski, VT Spread out in this spacious 900 sq foot, end unit located in the main building which house...	1 beds \| 1 baths \| 900 sq.ft.	$110,000	Airbnb cash on cash: -4.94% Traditional cash on cash: 5.56% Airbnb Rental Income: $1156 Traditional Rental Income: $1893 Airbnb ROI: -4.94% Traditional ROI: 5.56%
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: -1.77% Traditional cash on cash: 4.98% Airbnb Rental Income: $898 Traditional Rental Income: $2964 Airbnb ROI: -1.77% Traditional ROI: 4.98%
81 Trombley Road Winooski, VT This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready ...	3 beds \| 2 baths \| 1,232 sq.ft.	$275,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 7.23% Airbnb Rental Income: $898 Traditional Rental Income: $2712 Airbnb ROI: -1.07% Traditional ROI: 7.23%
16 Mott South Street Winooski, VT Imagine awakening every day to the sound of waves crashing on your own beautiful, private ...	3 beds \| 2 baths \| 2,243 sq.ft.	$875,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 2% Airbnb Rental Income: $898 Traditional Rental Income: $3483 Airbnb ROI: -1.59% Traditional ROI: 2%
99 VT Route 14 Winooski, VT Situated directly on the picturesque shores of Sabin Pond, this property has breathtaking ...	1 beds \| 1 baths \| 1,080 sq.ft.	$279,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.97% Airbnb Rental Income: $1156 Traditional Rental Income: $1924 Airbnb ROI: 0.6% Traditional ROI: 4.97%
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: -2.5% Traditional cash on cash: -0.11% Airbnb Rental Income: $898 Traditional Rental Income: $3458 Airbnb ROI: -2.5% Traditional ROI: -0.11%
26 Dorman Road Winooski, VT Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestl...	4 beds \| 2 baths \| 1,248 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.98% Airbnb Rental Income: $null Traditional Rental Income: $2993 Airbnb ROI: N/A Traditional ROI: 7.98%
644 Trailview Drive Winooski, VT Nestled between two of Killington's most iconic trails, this five-bedroom contemporary off...	5 beds \| 5 baths \| 4,316 sq.ft.	$2,225,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.14% Airbnb Rental Income: $null Traditional Rental Income: $6433 Airbnb ROI: N/A Traditional ROI: 1.14%
3732 VT Route 30 Winooski, VT Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take o...	9 beds \| 9 baths \| 5,480 sq.ft.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $6207 Airbnb ROI: N/A Traditional ROI: 4.56%
121 Dover Hill Road Winooski, VT Highly motivated sellers. Ideal for remote workers or second-home buyers, this Vermont ret...	3 beds \| 2 baths \| 3,000 sq.ft.	$549,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 5.25% Airbnb Rental Income: $898 Traditional Rental Income: $3840 Airbnb ROI: -1.14% Traditional ROI: 5.25%
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.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $3149 Airbnb ROI: N/A Traditional ROI: 7.09%
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.	$499,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.42% Airbnb Rental Income: $2103 Traditional Rental Income: $2624 Airbnb ROI: 1.15% Traditional ROI: 3.42%
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: -0.44% Traditional cash on cash: 9.86% Airbnb Rental Income: $898 Traditional Rental Income: $2886 Airbnb ROI: -0.44% Traditional ROI: 9.86%
63 Cooper Hill Road Winooski, VT New Price Improvement!!! Welcome to the original Cooper family homestead, a timeless treas...	3 beds \| 3 baths \| 2,494 sq.ft.	$489,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 4.05% Airbnb Rental Income: $898 Traditional Rental Income: $3053 Airbnb ROI: -1.4% Traditional ROI: 4.05%
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: -0.18% Traditional cash on cash: 8.91% Airbnb Rental Income: $898 Traditional Rental Income: $3126 Airbnb ROI: -0.18% 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: -1.26% Traditional cash on cash: 2.04% Airbnb Rental Income: $898 Traditional Rental Income: $3778 Airbnb ROI: -1.26% Traditional ROI: 2.04%
25B Boulder Ridge Drive #B Winooski, VT This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed ...	4 beds \| 4 baths \| 3,100 sq.ft.	$875,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $3727 Airbnb ROI: N/A Traditional ROI: 0.99%
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%
732 Under the Mountain Road Winooski, VT Welcome to "Fairmount," a beautiful historic home with unrivaled panoramic views and an ex...	5 beds \| 4 baths \| 3,516 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.31% Airbnb Rental Income: $null Traditional Rental Income: $4463 Airbnb ROI: N/A Traditional ROI: 1.31%

Real Estate investment in Winooski, VT

There are 81 properties for sale in the city of Winooski . The median list price in Winooski is $495,000 and the average price per square foot is $200. In November 2025, the average monthly cash on cash return in Winooski is 5.00%. The average monthly rental income in Winooski is $3,343.

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

There are 81 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 $3,343.

Your search for investment property begins and ends here

Investment Property for Sale in Winooski, VT

9 West Street #D

Winooski, VT

2 beds | 1 baths | 848 sq.ft.

$249,900

Airbnb cash on cash: 2.53%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $2103

Traditional Rental Income: $1906

Airbnb ROI: 2.53%

Traditional ROI: 3.98%

150 Franklin Street

Winooski, VT

3 beds | 2 baths | 1,400 sq.ft.

$499,000

Airbnb cash on cash: -1.7%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $898

Traditional Rental Income: $2871

Airbnb ROI: -1.7%

Traditional ROI: 3.25%

150 East Allen Street

Winooski, VT

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

$3,250,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $1955

Traditional Rental Income: $3604

Airbnb ROI: -0.58%

Traditional ROI: 0.14%

102 Union Street

Winooski, VT

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

$367,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $2103

Traditional Rental Income: $2340

Airbnb ROI: 1.43%

Traditional ROI: 3.68%

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: 1.71%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2103

Traditional Rental Income: $2231

Airbnb ROI: 1.71%