Real Estate Investment Properties for Sale in Charleston, VT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
849 Mount Bess Road Charleston, VT Own a breathtaking slice of Vermont with Mount Bess Farmâ1,606+/- acres of pristine land...	3 beds \| 3 baths \| 2,487 sq.ft.	$4,750,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -0.71% Airbnb Rental Income: $1025 Traditional Rental Income: $3106 Airbnb ROI: -1.26% Traditional ROI: -0.71%
100 Derby Gore Road Charleston, VT This stunning single family log home located at 100 Derby Gore Road in Derby, VT was built...	3 beds \| 3 baths \| 1,904 sq.ft.	$545,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 4.65% Airbnb Rental Income: $1025 Traditional Rental Income: $3399 Airbnb ROI: -0.72% Traditional ROI: 4.65%
Investment Properties for Sale in Other Cities of Vermont
30 Water Street Jamaica , VT Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in...	3 beds \| 1 baths \| 636 sq.ft.	$215,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 7.94% Airbnb Rental Income: $2267 Traditional Rental Income: $2036 Airbnb ROI: 6.29% Traditional ROI: 7.94%
41 Two Brook Drive Wilmington , VT Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Sn...	4 beds \| 5 baths \| 3,420 sq.ft.	$979,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 5% Airbnb Rental Income: $2046 Traditional Rental Income: $6604 Airbnb ROI: -0.59% Traditional ROI: 5%
22 Lower Howes Road #A89 Wilmington , VT Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirabl...	3 beds \| 2 baths \| 2,100 sq.ft.	$524,999	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.1% Airbnb Rental Income: $2025 Traditional Rental Income: $3232 Airbnb ROI: 0.57% Traditional ROI: 4.1%
153 Westminster Road Putney , VT Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. additi...	4 beds \| 3 baths \| 3,104 sq.ft.	$695,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.6% Airbnb Rental Income: $2644 Traditional Rental Income: $4103 Airbnb ROI: 0.38% Traditional ROI: 3.6%
2769 Cloudland Road Pomfret , VT Breathtaking long range views of Killington Peak and Saskadena 6 greet you as you wind you...	4 beds \| 4 baths \| 3,485 sq.ft.	$3,400,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.32% Airbnb Rental Income: $2544 Traditional Rental Income: $5488 Airbnb ROI: -0.81% Traditional ROI: 0.32%
225 Spectacle Pond Road 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: 0.09% Traditional cash on cash: 3.02% Airbnb Rental Income: $1903 Traditional Rental Income: $2959 Airbnb ROI: 0.09% Traditional ROI: 3.02%
16 Nutmeg Lane Dover , VT Step into this warm, inviting home, and you may never want to leave. Tucked away on a priv...	3 beds \| 2 baths \| 2,000 sq.ft.	$529,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.78% Airbnb Rental Income: $1460 Traditional Rental Income: $3247 Airbnb ROI: -0.71% Traditional ROI: 3.78%
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.	$480,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.41% Airbnb Rental Income: $1460 Traditional Rental Income: $3189 Airbnb ROI: -0.4% Traditional ROI: 4.41%
320 Old Bow Road Weathersfield , VT Spacious Country Retreat with Stunning Views! Experience the perfect blend of space, priva...	4 beds \| 5 baths \| 4,009 sq.ft.	$997,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $6647 Airbnb ROI: N/A Traditional ROI: 5.05%
6 Pheasant Run Road Fairfax , VT Tucked in a quiet and desirable Fairfax neighborhood, this home has been beautifully maint...	3 beds \| 3 baths \| 2,468 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.73%
3 Church Street Brandon , VT * OPEN HOUSE-September 21st from 2:00-4:00 * Enjoy the charm of small-town living with th...	3 beds \| 2 baths \| 1,195 sq.ft.	$270,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 9.97% Airbnb Rental Income: $2018 Traditional Rental Income: $3186 Airbnb ROI: 3.32% Traditional ROI: 9.97%
8 Hillside Acres Vergennes , VT Discover this beautifully reimagined 3-bedroom, 1.5-bath home in a peaceful country-style ...	3 beds \| 2 baths \| 1,505 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $3062 Airbnb ROI: N/A Traditional ROI: 6.16%
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: 3.6% Traditional cash on cash: 3.94% Airbnb Rental Income: $4251 Traditional Rental Income: $3543 Airbnb ROI: 3.6% Traditional ROI: 3.94%

Real Estate investment in Charleston, VT

There are 2 properties for sale in the city of Charleston . The median list price in Charleston is $2,647,500 and the average price per square foot is $1,206. In November 2025, the average monthly cash on cash return in Charleston is 2.00%. The average monthly rental income in Charleston is $3,253.

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

There are 2 investment properties available for sale in Charleston.

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

The ROI for Long-Term is higher than the Short-Term in Charleston with average rental income of $3,253.

Your search for investment property begins and ends here

Investment Property for Sale in Charleston, VT

849 Mount Bess Road

Charleston, VT

3 beds | 3 baths | 2,487 sq.ft.

$4,750,000

Airbnb cash on cash: -1.26%

Traditional cash on cash: -0.71%

Airbnb Rental Income: $1025

Traditional Rental Income: $3106

Airbnb ROI: -1.26%

Traditional ROI: -0.71%

100 Derby Gore Road

Charleston, VT

3 beds | 3 baths | 1,904 sq.ft.

$545,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $1025

Traditional Rental Income: $3399

Airbnb ROI: -0.72%

Traditional ROI: 4.65%

Investment Properties for Sale in Other Cities of Vermont

Jamaica , VT

3 beds | 1 baths | 636 sq.ft.

$215,000

Airbnb cash on cash: 6.29%

Traditional cash on cash: 7.94%

Airbnb Rental Income: $2267

Traditional Rental Income: $2036

Airbnb ROI: 6.29%

Traditional ROI: 7.94%

Wilmington , VT

4 beds | 5 baths | 3,420 sq.ft.

$979,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 5%

Airbnb Rental Income: $2046

Traditional Rental Income: $6604

Airbnb ROI: -0.59%

Traditional ROI: 5%

Wilmington , VT

3 beds | 2 baths | 2,100 sq.ft.

$524,999

Airbnb cash on cash: 0.57%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2025

Traditional Rental Income: $3232

Airbnb ROI: 0.57%

Traditional ROI: 4.1%

Putney , VT

4 beds | 3 baths | 3,104 sq.ft.

$695,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2644

Traditional Rental Income: $4103

Airbnb ROI: 0.38%

Traditional ROI: 3.6%

Pomfret , VT

4 beds | 4 baths | 3,485 sq.ft.

$3,400,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $2544

Traditional Rental Income: $5488

Airbnb ROI: -0.81%

Traditional ROI: 0.32%

Brighton , VT

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

$569,900

Airbnb cash on cash: 0.09%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1903

Traditional Rental Income: $2959

Airbnb ROI: 0.09%

Traditional ROI: 3.02%

Dover , VT

3 beds | 2 baths | 2,000 sq.ft.

$529,000

Airbnb cash on cash: -0.71%