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
20 Eliot Avenue Chilmark, MA Waterfront home on Stonewall Pond with Ocean Views. Nestled along the serene shores of Sto...	4 beds \| 4 baths \| 3,355 sq.ft.	$6,595,000	Airbnb cash on cash: -0.71% Traditional cash on cash: -0.49% Airbnb Rental Income: $3732 Traditional Rental Income: $4274 Airbnb ROI: -0.71% Traditional ROI: -0.49%
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: -0.85% Traditional cash on cash: -0.61% Airbnb Rental Income: $3732 Traditional Rental Income: $5752 Airbnb ROI: -0.85% 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: 0.13% Traditional cash on cash: 0.48% Airbnb Rental Income: $3732 Traditional Rental Income: $3703 Airbnb ROI: 0.13% Traditional ROI: 0.48%
308 South Road Chilmark, MA Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chi...	4 beds \| 4 baths \| 3,490 sq.ft.	$7,350,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.14% Airbnb Rental Income: $3732 Traditional Rental Income: $7439 Airbnb ROI: -0.81% Traditional ROI: -0.14%
9 Beetlebung Grove Way Chilmark, MA Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of priv...	4 beds \| 3 baths \| 2,968 sq.ft.	$2,495,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.63% Airbnb Rental Income: $3732 Traditional Rental Income: $4277 Airbnb ROI: 0.05% Traditional ROI: 0.63%
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: 0.76% Traditional cash on cash: 0.09% Airbnb Rental Income: $11015 Traditional Rental Income: $5912 Airbnb ROI: 0.76% 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: -0.14% Traditional cash on cash: 0.83% Airbnb Rental Income: $3732 Traditional Rental Income: $5631 Airbnb ROI: -0.14% 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: N/A Traditional cash on cash: 0.16% Airbnb Rental Income: $null Traditional Rental Income: $3439 Airbnb ROI: N/A Traditional ROI: 0.16%
6 Tabor Hills Chilmark, MA Set on 3 acres of natural beauty, this 1968 s/f post-and-beam home offers a tranquil and i...	4 beds \| 3 baths \| 1,968 sq.ft.	$2,350,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 0.58% Airbnb Rental Income: $3732 Traditional Rental Income: $3893 Airbnb ROI: 0.14% Traditional ROI: 0.58%
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: -0.41% Traditional cash on cash: -0.89% Airbnb Rental Income: $11015 Traditional Rental Income: $3475 Airbnb ROI: -0.41% Traditional ROI: -0.89%

Real Estate investment in Chilmark, MA

There are 10 properties for sale in the city of Chilmark . The median list price in Chilmark is $3,972,500 and the average price per square foot is $1,336. In October 2025, the average monthly cash on cash return in Chilmark is N/A%. The average monthly rental income in Chilmark is $4,276.

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

There are 10 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 $3,732.

Your search for investment property begins and ends here

Investment Property for Sale in Chilmark, MA

20 Eliot Avenue

Chilmark, MA

4 beds | 4 baths | 3,355 sq.ft.

$6,595,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $3732

Traditional Rental Income: $4274

Airbnb ROI: -0.71%

Traditional ROI: -0.49%

16 Shotnaigher Lane

Chilmark, MA

4 beds | 4 baths | N/A

$12,750,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $3732

Traditional Rental Income: $5752

Airbnb ROI: -0.85%

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: 0.13%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $3732

Traditional Rental Income: $3703

Airbnb ROI: 0.13%

Traditional ROI: 0.48%

308 South Road

Chilmark, MA

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

$7,350,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $3732

Traditional Rental Income: $7439

Airbnb ROI: -0.81%

Traditional ROI: -0.14%

9 Beetlebung Grove Way

Chilmark, MA

4 beds | 3 baths | 2,968 sq.ft.

$2,495,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $3732

Traditional Rental Income: $4277

Airbnb ROI: 0.05%

Traditional ROI: 0.63%

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: 0.76%

Traditional cash on cash: 0.09%

Airbnb Rental Income: $11015

Traditional Rental Income: $5912

Airbnb ROI: 0.76%

Traditional ROI: 0.09%

300 North Road

Chilmark, MA

4 beds | 4 baths | N/A

$2,995,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $3732

Traditional Rental Income: $5631

Airbnb ROI: -0.14%

Traditional ROI: 0.83%

5 Oceanview Farm Road

Chilmark, MA

3 beds | 2 baths | N/A

$2,675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3439

Airbnb ROI: N/A