Real Estate Investment Properties for Sale in Chilmark, MA

Looking for investment property in Chilmark, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
16 Shotnaigher Lane Chilmark, MA New to market this completely renovated water view home is located in a private enclave of...	4 beds \| 4 baths \| 2,050 sq.ft.	$10,950,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.58% Airbnb Rental Income: $1729 Traditional Rental Income: $5752 Airbnb ROI: -1.02% Traditional ROI: -0.58%
25 Fulling Mill Road Chilmark, MA Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house o...	4 beds \| 3 baths \| 1,918 sq.ft.	$2,395,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.45% Airbnb Rental Income: $1729 Traditional Rental Income: $3703 Airbnb ROI: -0.66% Traditional ROI: 0.45%
308 South Road Chilmark, MA Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilm...	4 beds \| 4 baths \| 3,490 sq.ft.	$7,350,000	Airbnb cash on cash: -1.07% Traditional cash on cash: -0.16% Airbnb Rental Income: $1729 Traditional Rental Income: $7439 Airbnb ROI: -1.07% Traditional ROI: -0.16%
300 North Road Chilmark, MA Winding tree lined driveway off North Rd brings you to this commanding, custom designed re...	4 beds \| 4 baths \| 2,515 sq.ft.	$2,995,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.8% Airbnb Rental Income: $1729 Traditional Rental Income: $5631 Airbnb ROI: -0.78% Traditional ROI: 0.8%
18 Spruce Gate Road Chilmark, MA Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of...	5 beds \| 4 baths \| 3,700 sq.ft.	$12,500,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.94% Airbnb Rental Income: $2139 Traditional Rental Income: $3475 Airbnb ROI: -1.1% Traditional ROI: -0.94%
47 Quenames Road Chilmark, MA On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding ...	2 beds \| 1 baths \| 924 sq.ft.	$1,575,000	Airbnb cash on cash: -1.56% Traditional cash on cash: -0.87% Airbnb Rental Income: $1496 Traditional Rental Income: $2066 Airbnb ROI: -1.56% Traditional ROI: -0.87%
45 Quenames Road Chilmark, MA Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and ...	2 beds \| 1 baths \| 896 sq.ft.	$1,575,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.3% Airbnb Rental Income: $1496 Traditional Rental Income: $2020 Airbnb ROI: -0.36% Traditional ROI: 0.3%
43 N Slope Lane Chilmark, MA Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers th...	3 beds \| 2 baths \| 1,540 sq.ft.	$1,699,999	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.66% Airbnb Rental Income: $2337 Traditional Rental Income: $3037 Airbnb ROI: -0.15% Traditional ROI: 0.66%

Real Estate investment in Chilmark, MA

There are 8 properties for sale in the city of Chilmark . The median list price in Chilmark is $2,695,000 and the average price per square foot is $1,266. In May 2026, the average monthly cash on cash return in Chilmark is N/A%. The average monthly rental income in Chilmark is $3,589.

Chilmark, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 8 investment properties available for sale in Chilmark.

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

The ROI for Long-Term is higher than the Short-Term in Chilmark with average rental income of $3,589.

Your search for investment property begins and ends here

Investment Property for Sale in Chilmark, MA

16 Shotnaigher Lane

Chilmark, MA

4 beds | 4 baths | 2,050 sq.ft.

$10,950,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: -0.58%

Airbnb Rental Income: $1729

Traditional Rental Income: $5752

Airbnb ROI: -1.02%

Traditional ROI: -0.58%

25 Fulling Mill Road

Chilmark, MA

4 beds | 3 baths | 1,918 sq.ft.

$2,395,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $1729

Traditional Rental Income: $3703

Airbnb ROI: -0.66%

Traditional ROI: 0.45%

308 South Road

Chilmark, MA

4 beds | 4 baths | 3,490 sq.ft.

$7,350,000

Airbnb cash on cash: -1.07%

Traditional cash on cash: -0.16%

Airbnb Rental Income: $1729

Traditional Rental Income: $7439

Airbnb ROI: -1.07%

Traditional ROI: -0.16%

300 North Road

Chilmark, MA

4 beds | 4 baths | 2,515 sq.ft.

$2,995,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $1729

Traditional Rental Income: $5631

Airbnb ROI: -0.78%

Traditional ROI: 0.8%

18 Spruce Gate Road

Chilmark, MA

5 beds | 4 baths | 3,700 sq.ft.

$12,500,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $2139

Traditional Rental Income: $3475

Airbnb ROI: -1.1%

Traditional ROI: -0.94%

47 Quenames Road

Chilmark, MA

2 beds | 1 baths | 924 sq.ft.

$1,575,000

Airbnb cash on cash: -1.56%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $1496

Traditional Rental Income: $2066

Airbnb ROI: -1.56%

Traditional ROI: -0.87%

45 Quenames Road

Chilmark, MA

2 beds | 1 baths | 896 sq.ft.

$1,575,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1496

Traditional Rental Income: $2020

Airbnb ROI: -0.36%

Traditional ROI: 0.3%

43 N Slope Lane

Chilmark, MA

3 beds | 2 baths | 1,540 sq.ft.

$1,699,999

Airbnb cash on cash: -0.15%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $2337

Traditional Rental Income: $3037

Airbnb ROI: -0.15%