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 o...	4 beds \| 4 baths \| N/A	$10,950,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.55% Airbnb Rental Income: $3408 Traditional Rental Income: $5752 Airbnb ROI: -0.86% Traditional ROI: -0.55%
25 Fulling Mill Rd 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: -0.03% Traditional cash on cash: 0.45% Airbnb Rental Income: $3408 Traditional Rental Income: $3703 Airbnb ROI: -0.03% Traditional ROI: 0.45%
308 South Rd 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: -0.86% Traditional cash on cash: -0.16% Airbnb Rental Income: $3408 Traditional Rental Income: $7439 Airbnb ROI: -0.86% Traditional ROI: -0.16%
124 Old Farm Road unit: 122, 116 Chilmark, MA An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning land...	5 beds \| 4 baths \| 3,413 sq.ft.	$3,950,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 0.28% Airbnb Rental Income: $4440 Traditional Rental Income: $5912 Airbnb ROI: -0.38% Traditional ROI: 0.28%
18 Spruce Gate Rd Chilmark, MA Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of...	5 beds \| 3 baths \| 3,700 sq.ft.	$12,500,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.94% Airbnb Rental Income: $4440 Traditional Rental Income: $3475 Airbnb ROI: -0.93% Traditional ROI: -0.94%
47 Quenames Rd 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: 0.09% Traditional cash on cash: -0.87% Airbnb Rental Income: $4407 Traditional Rental Income: $2066 Airbnb ROI: 0.09% Traditional ROI: -0.87%
45 Quenames Rd 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: 1.3% Traditional cash on cash: 0.3% Airbnb Rental Income: $4407 Traditional Rental Income: $2020 Airbnb ROI: 1.3% Traditional ROI: 0.3%
43 N Slope Ln 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.	$1,799,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.57% Airbnb Rental Income: $1723 Traditional Rental Income: $3037 Airbnb ROI: -0.5% Traditional ROI: 0.57%
21 & 25 Fulling Mill Rd Chilmark, MA	4 beds \| 3 baths \| 1,918 sq.ft.	$2,395,000	Airbnb cash on cash: -1.07% Traditional cash on cash: -0.67% Airbnb Rental Income: $3408 Traditional Rental Income: $3546 Airbnb ROI: -1.07% Traditional ROI: -0.67%

Real Estate investment in Chilmark, MA

There are 12 properties for sale in the city of Chilmark . The median list price in Chilmark is $2,395,000 and the average price per square foot is $1,076. In March 2026, the average monthly cash on cash return in Chilmark is N/A%. The average monthly rental income in Chilmark is $3,546.

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

There are 12 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 $3,546.

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 | N/A

$10,950,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: -0.55%

Airbnb Rental Income: $3408

Traditional Rental Income: $5752

Airbnb ROI: -0.86%

Traditional ROI: -0.55%

25 Fulling Mill Rd

Chilmark, MA

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

$2,395,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $3408

Traditional Rental Income: $3703

Airbnb ROI: -0.03%

Traditional ROI: 0.45%

308 South Rd

Chilmark, MA

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

$7,350,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: -0.16%

Airbnb Rental Income: $3408

Traditional Rental Income: $7439

Airbnb ROI: -0.86%

Traditional ROI: -0.16%

124 Old Farm Road unit: 122, 116

Chilmark, MA

5 beds | 4 baths | 3,413 sq.ft.

$3,950,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $4440

Traditional Rental Income: $5912

Airbnb ROI: -0.38%

Traditional ROI: 0.28%

18 Spruce Gate Rd

Chilmark, MA

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

$12,500,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $4440

Traditional Rental Income: $3475

Airbnb ROI: -0.93%

Traditional ROI: -0.94%

47 Quenames Rd

Chilmark, MA

2 beds | 1 baths | 924 sq.ft.

$1,575,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $4407

Traditional Rental Income: $2066

Airbnb ROI: 0.09%

Traditional ROI: -0.87%

45 Quenames Rd

Chilmark, MA

2 beds | 1 baths | 896 sq.ft.

$1,575,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $4407

Traditional Rental Income: $2020

Airbnb ROI: 1.3%

Traditional ROI: 0.3%

43 N Slope Ln

Chilmark, MA

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

$1,799,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $1723

Traditional Rental Income: $3037

Airbnb ROI: -0.5%