Real Estate Investment Properties for Sale in Pittsfield, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1114 Hawk Mountain Rd Pittsfield, VT This thoughtfully reimagined four-bedroom Hawk home showcases the signature elements of Ro...	4 beds \| 1 baths \| 1,380 sq.ft.	$629,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.46% Airbnb Rental Income: $1717 Traditional Rental Income: $3158 Airbnb ROI: 0.2% Traditional ROI: 3.46%
57 Tweed River Dr Pittsfield, VT 57 Tweed River Dr, Pittsfield, VT 05762 \| Single Family Residential	5 beds \| 4 baths \| 4,575 sq.ft.	$3,900,000	Airbnb cash on cash: -2.55% Traditional cash on cash: N/A Airbnb Rental Income: $1824 Traditional Rental Income: $0 Airbnb ROI: -2.55% Traditional ROI: N/A
681 S Hill Rd Pittsfield, VT 681 S Hill Rd, Pittsfield, VT 05762 \| Single Family Residential	3 beds \| 4 baths \| 4,671 sq.ft.	$2,150,000	Airbnb cash on cash: -2.47% Traditional cash on cash: -0.61% Airbnb Rental Income: $1342 Traditional Rental Income: $4637 Airbnb ROI: -2.47% Traditional ROI: -0.61%
360 Liberty Hill Rd Pittsfield, VT 360 Liberty Hill Rd, Pittsfield, VT 05762 \| Other	N/A beds \| N/A baths \| N/A	$80,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.35% Airbnb Rental Income: $null Traditional Rental Income: $1052 Airbnb ROI: N/A Traditional ROI: 9.35%
Investment Properties for Sale in Other Cities of Vermont
303 Winding Way Killington , VT Nestled at the top of a quiet dead-end road, this 4-bedroom single-family home sits on a g...	4 beds \| 3 baths \| 1,750 sq.ft.	$599,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.75% Airbnb Rental Income: $1963 Traditional Rental Income: $3417 Airbnb ROI: 0.22% Traditional ROI: 3.75%
133 E Mountain Rd #3A1 Killington , VT 2-Bedroom, 2-Bath Unit in Mountain Green â Building 3 Welcome to this inviting 2-bedroom...	2 beds \| 2 baths \| 913 sq.ft.	$238,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 3.48% Airbnb Rental Income: $1259 Traditional Rental Income: $2286 Airbnb ROI: -2.86% Traditional ROI: 3.48%
41 Two Brook Dr Wilmington , VT Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Sn...	4 beds \| 3 baths \| 3,420 sq.ft.	$898,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 5.54% Airbnb Rental Income: $1976 Traditional Rental Income: $6604 Airbnb ROI: -0.62% Traditional ROI: 5.54%
225 Spectacle Pond Rd Brighton , VT Discover year-round lakeside living with this inviting 3-bedroom, 2-bath home on the shore...	2 beds \| 2 baths \| 2,358 sq.ft.	$569,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.02% Airbnb Rental Income: $1916 Traditional Rental Income: $2959 Airbnb ROI: 0.11% Traditional ROI: 3.02%
24 Antler Loop Dover , VT This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a pictu...	3 beds \| 2 baths \| 1,943 sq.ft.	$470,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.56% Airbnb Rental Income: $1369 Traditional Rental Income: $3189 Airbnb ROI: -0.52% Traditional ROI: 4.56%
1576 RIPLEY ROAD Waterbury , VT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2.5 baths \| 2,305 sq.ft.	$597,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 3.94% Airbnb Rental Income: $4294 Traditional Rental Income: $3543 Airbnb ROI: 3.66% Traditional ROI: 3.94%
1422 Cabot Rd Woodbury , VT Country contemporary home features 4 beds,1-1/2 baths. A main level bedroom,half bath and ...	4 beds \| 1 baths \| 1,530 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 6.22%

Real Estate investment in Pittsfield, VT

There are 4 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $279,900 and the average price per square foot is $152. In February 2026, the average monthly cash on cash return in Pittsfield is 6.00%. The average monthly rental income in Pittsfield is $1,052.

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

There are 4 investment properties available for sale in Pittsfield.

In 2026, the best neighborhood to buy investment property is Pittsfield.

The ROI for Long-Term is higher than the Short-Term in Pittsfield with average rental income of $1,052.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, VT

1114 Hawk Mountain Rd

Pittsfield, VT

4 beds | 1 baths | 1,380 sq.ft.

$629,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1717

Traditional Rental Income: $3158

Airbnb ROI: 0.2%

Traditional ROI: 3.46%

57 Tweed River Dr

Pittsfield, VT

5 beds | 4 baths | 4,575 sq.ft.

$3,900,000

Airbnb cash on cash: -2.55%

Traditional cash on cash: N/A

Airbnb Rental Income: $1824

Traditional Rental Income: $0

Airbnb ROI: -2.55%

Traditional ROI: N/A

681 S Hill Rd

Pittsfield, VT

3 beds | 4 baths | 4,671 sq.ft.

$2,150,000

Airbnb cash on cash: -2.47%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $1342

Traditional Rental Income: $4637

Airbnb ROI: -2.47%

Traditional ROI: -0.61%

360 Liberty Hill Rd

Pittsfield, VT

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

$80,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.35%

Airbnb Rental Income: $null

Traditional Rental Income: $1052

Airbnb ROI: N/A

Traditional ROI: 9.35%

Investment Properties for Sale in Other Cities of Vermont

303 Winding Way

Killington , VT

4 beds | 3 baths | 1,750 sq.ft.

$599,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1963

Traditional Rental Income: $3417

Airbnb ROI: 0.22%

Traditional ROI: 3.75%

133 E Mountain Rd #3A1

Killington , VT

2 beds | 2 baths | 913 sq.ft.

$238,000

Airbnb cash on cash: -2.86%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $1259

Traditional Rental Income: $2286

Airbnb ROI: -2.86%

Traditional ROI: 3.48%

41 Two Brook Dr

Wilmington , VT

4 beds | 3 baths | 3,420 sq.ft.

$898,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1976

Traditional Rental Income: $6604

Airbnb ROI: -0.62%

Traditional ROI: 5.54%

225 Spectacle Pond Rd

Brighton , VT

2 beds | 2 baths | 2,358 sq.ft.

$569,900

Airbnb cash on cash: 0.11%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1916

Traditional Rental Income: $2959