Real Estate Investments for Sale in Chilmark, MA With High ROI

Are you looking for a vacation rental in Chilmark, MA? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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
27 Ocean View Farm Road Chilmark, MA 27 Ocean View Farm Road is a unique house with the main living spaces designed by architec...	4 beds \| 3 baths \| 2,450 sq.ft.	$2,750,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 0.42% Airbnb Rental Income: $11786 Traditional Rental Income: $4232 Airbnb ROI: 2.54% Traditional ROI: 0.42%
64 Squibnocket Farm Road Chilmark, MA Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This ...	4 beds \| 5 baths \| 3,705 sq.ft.	$16,500,000	Airbnb cash on cash: -0.5% Traditional cash on cash: -0.69% Airbnb Rental Income: $11786 Traditional Rental Income: $6715 Airbnb ROI: -0.5% Traditional ROI: -0.69%
Investment Properties for Sale in Other Cities of Massachusetts
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,599,000	Airbnb cash on cash: 1% Traditional cash on cash: 0.86% Airbnb Rental Income: $8120 Traditional Rental Income: $6236 Airbnb ROI: 1% Traditional ROI: 0.86%
717 Beechmont St Boston , MA She's perched atop Metropolitan Hill (Bostonâs 2nd highest point), has stunning views of...	3 beds \| 2 baths \| 1,440 sq.ft.	$675,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.34% Airbnb Rental Income: $4843 Traditional Rental Income: $4000 Airbnb ROI: 4.1% Traditional ROI: 4.34%
357 Commercial St #725 Boston , MA Experience the pinnacle of Boston living in this stunning condo, a sanctuary of luxury per...	2 beds \| 2 baths \| 1,524 sq.ft.	$1,650,000	Airbnb cash on cash: 0.72% Traditional cash on cash: -0.35% Airbnb Rental Income: $6793 Traditional Rental Income: $3835 Airbnb ROI: 0.72% Traditional ROI: -0.35%
4 Rabbit Run Eastham , MA Waterview Splendor! Panoramic views with contemporary flare and coastal charm make this di...	4 beds \| 5 baths \| 3,250 sq.ft.	$1,995,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.37% Airbnb Rental Income: $4780 Traditional Rental Income: $5465 Airbnb ROI: 0.47% Traditional ROI: 1.37%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 3 baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.24% Airbnb Rental Income: $5616 Traditional Rental Income: $3577 Airbnb ROI: 0.68% Traditional ROI: 0.24%
15 Shannon Road Harwich , MA This ranch is full of charm but needs some upgrades and tlc. It is in walking distance to ...	2 beds \| 2 baths \| 1,124 sq.ft.	$338,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 7.34% Airbnb Rental Income: $2951 Traditional Rental Income: $3001 Airbnb ROI: 5.04% Traditional ROI: 7.34%
239 Chatham Road Harwich , MA 239 Chatham Road is under a mile to Red River Beach and has room for all your guests! This...	4 beds \| 3 baths \| 2,290 sq.ft.	$850,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 2.95% Airbnb Rental Income: $5650 Traditional Rental Income: $3748 Airbnb ROI: 3.92% Traditional ROI: 2.95%
3 Seagull Lane Harwich , MA This home is full of possibility! It has lots of Old World charm but tastefully updated wi...	4 beds \| 2 baths \| 2,218 sq.ft.	$799,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 2.59% Airbnb Rental Income: $5650 Traditional Rental Income: $3102 Airbnb ROI: 4.5% Traditional ROI: 2.59%
18 Uncle Vicks Way Orleans , MA Welcome to Orleans! From Nauset Beach to Skaket Beach, from Town Cove to Pleasant Bay, C...	3 beds \| 2 baths \| 1,515 sq.ft.	$775,000	Airbnb cash on cash: 6% Traditional cash on cash: 2.86% Airbnb Rental Income: $6807 Traditional Rental Income: $3216 Airbnb ROI: 6% Traditional ROI: 2.86%
22 Felicity Lane Osterville , MA Welcome to 22 Felicity Lane...a beautifully built Archibald home that exudes elegance and ...	3 beds \| 3 baths \| 2,923 sq.ft.	$1,395,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.34% Airbnb Rental Income: $3924 Traditional Rental Income: $3743 Airbnb ROI: 0.83% Traditional ROI: 1.34%
90 Woodland St Natick , MA This spectacular estate is neatly sited on 1.5 acres, comprised of two parcels of perfectl...	4 beds \| 4 baths \| 4,500 sq.ft.	$1,299,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.66% Airbnb Rental Income: $5570 Traditional Rental Income: $5993 Airbnb ROI: 1.39% Traditional ROI: 2.66%
34 Horizon Drive Chatham , MA Deeded Access to stunning Lover's Lake, only a 3-minute walk! Welcome to 34 Horizon Drive,...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,075,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 2.1% Airbnb Rental Income: $6195 Traditional Rental Income: $3558 Airbnb ROI: 3.52% Traditional ROI: 2.1%
30 Bradford Lane Eastham , MA 30 Bradford Lane is a rare Cape Cod gem, perfectly blending comfort, space, and charm. Ima...	3 beds \| 4 baths \| 2,946 sq.ft.	$1,095,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 2.91% Airbnb Rental Income: $5616 Traditional Rental Income: $4788 Airbnb ROI: 2.62% Traditional ROI: 2.91%
33 The Heights Mashpee , MA Incredible opportunity to own a one of a kind double lot with spectacular golf, pond and c...	4 beds \| 6 baths \| 5,830 sq.ft.	$3,500,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 1.05% Airbnb Rental Income: $7559 Traditional Rental Income: $8052 Airbnb ROI: 0.45% Traditional ROI: 1.05%
372 W Main St Plainfield , MA Looking for nature, comfort, and just minutes from the Berkshires? This 1830's property ha...	3 beds \| 1 baths \| 1,774 sq.ft.	$310,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.03% Airbnb Rental Income: $3461 Traditional Rental Income: $2093 Airbnb ROI: 7.09% Traditional ROI: 5.03%

Real Estate investment in Chilmark, MA

There are 2 properties for sale in the city of Chilmark . The median list price in Chilmark is $9,625,000 and the average price per square foot is $3,127. In September 2024, the average monthly cash on cash return in Chilmark is N/A%. The average monthly rental income in Chilmark is $5,474.

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

There are 2 investment properties available for sale in Chilmark.

In 2024, 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 $5,474.

Your search for investment property begins and ends here

Investment Property for Sale in Chilmark, MA

27 Ocean View Farm Road

Chilmark, MA

4 beds | 3 baths | 2,450 sq.ft.

$2,750,000

Airbnb cash on cash: 2.54%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $11786

Traditional Rental Income: $4232

Airbnb ROI: 2.54%

Traditional ROI: 0.42%

64 Squibnocket Farm Road

Chilmark, MA

4 beds | 5 baths | 3,705 sq.ft.

$16,500,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: -0.69%

Airbnb Rental Income: $11786

Traditional Rental Income: $6715

Airbnb ROI: -0.5%

Traditional ROI: -0.69%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,599,000

Airbnb cash on cash: 1%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $8120

Traditional Rental Income: $6236

Airbnb ROI: 1%

Traditional ROI: 0.86%

Boston , MA

3 beds | 2 baths | 1,440 sq.ft.

$675,000

Airbnb cash on cash: 4.1%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $4843

Traditional Rental Income: $4000

Airbnb ROI: 4.1%

Traditional ROI: 4.34%

Boston , MA

2 beds | 2 baths | 1,524 sq.ft.

$1,650,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: -0.35%

Airbnb Rental Income: $6793

Traditional Rental Income: $3835

Airbnb ROI: 0.72%

Traditional ROI: -0.35%

Eastham , MA

4 beds | 5 baths | 3,250 sq.ft.

$1,995,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $4780

Traditional Rental Income: $5465

Airbnb ROI: 0.47%

Traditional ROI: 1.37%

Eastham , MA

3 beds | 3 baths | 1,662 sq.ft.

$2,195,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 0.24%

Airbnb Rental Income: $5616

Traditional Rental Income: $3577

Airbnb ROI: 0.68%

Traditional ROI: 0.24%

Harwich , MA

2 beds | 2 baths | 1,124 sq.ft.

$338,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 7.34%

Airbnb Rental Income: $2951

Traditional Rental Income: $3001

Airbnb ROI: 5.04%

Traditional ROI: 7.34%

Harwich , MA

4 beds | 3 baths | 2,290 sq.ft.

$850,000

Airbnb cash on cash: 3.92%