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	$12,750,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.61% Airbnb Rental Income: $3408 Traditional Rental Income: $5752 Airbnb ROI: -0.88% Traditional ROI: -0.61%
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: 0.01% Traditional cash on cash: 0.48% Airbnb Rental Income: $3408 Traditional Rental Income: $3703 Airbnb ROI: 0.01% Traditional ROI: 0.48%
124 Old Farm Road unit: 122, 116 #122, 116 Chilmark, MA An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning land...	5 beds \| N/A baths \| 3,413 sq.ft.	$4,950,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.09% Airbnb Rental Income: $4440 Traditional Rental Income: $5912 Airbnb ROI: -0.43% Traditional ROI: 0.09%
300 North Road Chilmark, MA Winding tree lined driveway off North Rd brings you to this commanding, custom designed re...	4 beds \| 4 baths \| N/A	$2,995,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 0.83% Airbnb Rental Income: $3408 Traditional Rental Income: $5631 Airbnb ROI: -0.24% Traditional ROI: 0.83%
5 Oceanview Farm Road Chilmark, MA Designed by the famous mid century architect Andrew Geller, this contemporary home is situ...	3 beds \| 2 baths \| N/A	$2,675,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.16% Airbnb Rental Income: $1723 Traditional Rental Income: $3439 Airbnb ROI: -0.72% Traditional ROI: 0.16%
18 Spruce Gate Road Chilmark, MA Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of...	5 beds \| N/A baths \| 3,700 sq.ft.	$12,500,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.89% Airbnb Rental Income: $4440 Traditional Rental Income: $3475 Airbnb ROI: -0.88% Traditional ROI: -0.89%
46 Tercel Lane Chilmark, MA Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this ...	2 beds \| 1 baths \| 716 sq.ft.	$1,650,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 0.15% Airbnb Rental Income: $4407 Traditional Rental Income: $2096 Airbnb ROI: 1.05% Traditional ROI: 0.15%
47 Quenames Road Chilmark, MA Set on a serene 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, charm, and ...	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 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: 1.3% Traditional cash on cash: 0.3% Airbnb Rental Income: $4407 Traditional Rental Income: $2020 Airbnb ROI: 1.3% Traditional ROI: 0.3%

Real Estate investment in Chilmark, MA

There are 9 properties for sale in the city of Chilmark . The median list price in Chilmark is $2,675,000 and the average price per square foot is $1,387. In December 2025, the average monthly cash on cash return in Chilmark is N/A%. The average monthly rental income in Chilmark is $3,475.

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

There are 9 investment properties available for sale in Chilmark.

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

The ROI for Short-Term is higher than the Long-Term in Chilmark with average rental income of $4,407.

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

$12,750,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $3408

Traditional Rental Income: $5752

Airbnb ROI: -0.88%

Traditional ROI: -0.61%

25 Fulling Mill Road

Chilmark, MA

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

$2,395,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $3408

Traditional Rental Income: $3703

Airbnb ROI: 0.01%

Traditional ROI: 0.48%

124 Old Farm Road unit: 122, 116 #122, 116

Chilmark, MA

5 beds | N/A baths | 3,413 sq.ft.

$4,950,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.09%

Airbnb Rental Income: $4440

Traditional Rental Income: $5912

Airbnb ROI: -0.43%

Traditional ROI: 0.09%

300 North Road

Chilmark, MA

4 beds | 4 baths | N/A

$2,995,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $3408

Traditional Rental Income: $5631

Airbnb ROI: -0.24%

Traditional ROI: 0.83%

5 Oceanview Farm Road

Chilmark, MA

3 beds | 2 baths | N/A

$2,675,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $1723

Traditional Rental Income: $3439

Airbnb ROI: -0.72%

Traditional ROI: 0.16%

18 Spruce Gate Road

Chilmark, MA

5 beds | N/A baths | 3,700 sq.ft.

$12,500,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $4440

Traditional Rental Income: $3475

Airbnb ROI: -0.88%

Traditional ROI: -0.89%

46 Tercel Lane

Chilmark, MA

2 beds | 1 baths | 716 sq.ft.

$1,650,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $4407

Traditional Rental Income: $2096

Airbnb ROI: 1.05%

Traditional ROI: 0.15%

47 Quenames Road

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%