Real Estate Investment Properties for Sale in Brewster, MA

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

Explore a variety of short-term homes & houses in Brewster, MA. Invest wisely with VRBO & Brewster, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Brewster, MA

Search for Single Family Residential for Sale in Brewster, Massachusetts. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 37 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
663 Crowells Bog Road Brewster, MA Expanded 4 bedroom Cape-style home ideally located between Sheep Pond and Long Pond in Bre...	4 beds \| 4 baths \| 3,738 sq.ft.	$1,589,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.01% Airbnb Rental Income: $6080 Traditional Rental Income: $5430 Airbnb ROI: 1.63% Traditional ROI: 2.01%
240 Robbins Hill Road Brewster, MA Bayfront Brewster- Located in one of Brewsters premier bay locations. The residence offers...	3 beds \| 2 baths \| 1,418 sq.ft.	$2,395,000	Airbnb cash on cash: 0.31% Traditional cash on cash: -0.23% Airbnb Rental Income: $5569 Traditional Rental Income: $3258 Airbnb ROI: 0.31% Traditional ROI: -0.23%
19 Burning Bush Way Brewster, MA There's something undeniably charming about this home! Perhaps it's the wide-open floor pl...	2 beds \| 2 baths \| 2,034 sq.ft.	$750,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 2.61% Airbnb Rental Income: $3072 Traditional Rental Income: $3074 Airbnb ROI: 1.6% Traditional ROI: 2.61%
167 Ambergris Circle Brewster, MA Welcome to 167 Ambergris Circle, tucked into the heart of the sought-after Salt Works neig...	3 beds \| 3 baths \| 2,001 sq.ft.	$1,625,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.78% Airbnb Rental Income: $5569 Traditional Rental Income: $3538 Airbnb ROI: 1.39% Traditional ROI: 0.78%
221 Greenland Pond Road Brewster, MA Tucked away in the woods of Brewster, this inviting 3-bedroom, 2-bath Cape offers the perf...	3 beds \| 2 baths \| 1,471 sq.ft.	$795,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 2.47% Airbnb Rental Income: $5569 Traditional Rental Income: $3161 Airbnb ROI: 4.21% Traditional ROI: 2.47%
117 A P Newcomb Road Brewster, MA Welcome to 117 A P Newcomb Road in historic Brewster. This spacious 4-bedroom, 3-bathroom ...	4 beds \| 3 baths \| 2,436 sq.ft.	$1,030,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 2.2% Airbnb Rental Income: $6080 Traditional Rental Income: $3775 Airbnb ROI: 3.35% Traditional ROI: 2.2%
9 Park Lane Brewster, MA Beautifully Maintained 4 Bed, 3 Bath Home Near Breakwater Beach! This spacious and well-ke...	4 beds \| 3 baths \| 2,306 sq.ft.	$799,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.31% Airbnb Rental Income: $6080 Traditional Rental Income: $3698 Airbnb ROI: 4.89% Traditional ROI: 3.31%
92 Whiffletree Avenue Brewster, MA Discover refined coastal living in this brand-new 3,706 sq. ft. luxury home, nestled in th...	5 beds \| 5 baths \| 3,706 sq.ft.	$2,095,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 0.55% Airbnb Rental Income: $6486 Traditional Rental Income: $5488 Airbnb ROI: 0.41% Traditional ROI: 0.55%
88 Whiffletree Avenue Brewster, MA This Brand-New Luxury Home in picturesque West Brewster is 3,891 sq. ft. with 5 bedroom, 4...	5 beds \| 5 baths \| 3,891 sq.ft.	$2,195,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.38% Airbnb Rental Income: $6486 Traditional Rental Income: $5495 Airbnb ROI: 1.24% Traditional ROI: 1.38%
3937 Main Street Brewster, MA Potential abounds with this Main Street/Route 6a mixed use property with great visibility ...	2 beds \| 3 baths \| 3,692 sq.ft.	$889,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 2.47% Airbnb Rental Income: $3072 Traditional Rental Income: $3366 Airbnb ROI: 1.26% Traditional ROI: 2.47%
232 Robbins Hill Road Brewster, MA RARE OPPORTUNITY to own two homes on more than half an acre of private beachfront property...	3 beds \| 2 baths \| 1,502 sq.ft.	$2,595,000	Airbnb cash on cash: 0.19% Traditional cash on cash: -0.27% Airbnb Rental Income: $5569 Traditional Rental Income: $3349 Airbnb ROI: 0.19% Traditional ROI: -0.27%
737 Thousand Oaks Drive Brewster, MA 3 bedroom ranch per field card with a 2 bedroom layout just waiting to be finished. Come a...	2 beds \| 2 baths \| 1,302 sq.ft.	$420,850	Airbnb cash on cash: 3.89% Traditional cash on cash: 6.72% Airbnb Rental Income: $3072 Traditional Rental Income: $3490 Airbnb ROI: 3.89% Traditional ROI: 6.72%
55 Wayside Drive Brewster, MA Welcome to this inviting traditional Cape style home, featuring a delightful sunroom for a...	3 beds \| 2 baths \| 1,274 sq.ft.	$675,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 2.88% Airbnb Rental Income: $5569 Traditional Rental Income: $2913 Airbnb ROI: 5.32% Traditional ROI: 2.88%
2241 Main Street Brewster, MA Step back in time and experience the character and charm of this historic antique home, id...	3 beds \| 2 baths \| 1,655 sq.ft.	$799,999	Airbnb cash on cash: 4.38% Traditional cash on cash: 2.69% Airbnb Rental Income: $5569 Traditional Rental Income: $3192 Airbnb ROI: 4.38% Traditional ROI: 2.69%
21 High Point Drive Brewster, MA Rare waterfront gem perched on 1.3 acres overlooking serene Seymour Pond. With sparkling w...	3 beds \| 3 baths \| 1,737 sq.ft.	$1,195,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 1.66% Airbnb Rental Income: $5569 Traditional Rental Income: $3740 Airbnb ROI: 2.3% Traditional ROI: 1.66%
272 Sheep Pond Drive Brewster, MA Enjoy deeded rights to 2 ass'n beaches, direct access to Sheep Pond and beautiful water vi...	3 beds \| 2 baths \| 1,764 sq.ft.	$849,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.55% Airbnb Rental Income: $5569 Traditional Rental Income: $3605 Airbnb ROI: 3.62% Traditional ROI: 2.55%
38 Captain Baker Road Brewster, MA Imagine golden hour from a 50-foot deck overlooking Cape Cod's largest body of fresh, warm...	5 beds \| 7 baths \| 6,435 sq.ft.	$3,595,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 1.15% Airbnb Rental Income: $6486 Traditional Rental Income: $8873 Airbnb ROI: 0.06% Traditional ROI: 1.15%
204 Timberlane Drive Brewster, MA Enjoy single floor living at its best. This newly constructed 3 bedroom 2 bath ranch style...	2 beds \| 2 baths \| 1,560 sq.ft.	$789,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.18% Airbnb Rental Income: $3072 Traditional Rental Income: $3192 Airbnb ROI: 2.06% Traditional ROI: 3.18%
33 Rogers Road Brewster, MA This lovely and immaculate Cape checks all the boxes! 2 large and comfortable bedrooms ups...	2 beds \| 2 baths \| 2,024 sq.ft.	$875,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.94% Airbnb Rental Income: $3072 Traditional Rental Income: $3056 Airbnb ROI: 1.1% Traditional ROI: 1.94%
43 Owl Pond Road Brewster, MA Welcome to a home that truly has it all-space, style, and a setting that makes every day f...	4 beds \| 3 baths \| 2,877 sq.ft.	$1,199,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.14% Airbnb Rental Income: $6080 Traditional Rental Income: $4160 Airbnb ROI: 2.79% Traditional ROI: 2.14%
126 Bittersweet Drive Brewster, MA 3BR, 2BA Cape located at the end of a quiet cul-de-sac near Cape Cod Bay beaches, the CC B...	3 beds \| 2 baths \| 1,867 sq.ft.	$895,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 2.18% Airbnb Rental Income: $5569 Traditional Rental Income: $3285 Airbnb ROI: 3.58% Traditional ROI: 2.18%
410 Blueberry Pond Drive Brewster, MA Completed in 2023, this newly built, fully electric home blends elevated design, sustainab...	3 beds \| 3 baths \| 2,471 sq.ft.	$1,825,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 0.98% Airbnb Rental Income: $5569 Traditional Rental Income: $4000 Airbnb ROI: 1.25% Traditional ROI: 0.98%
26 Newport Road Brewster, MA Five bedrooms and deeded rights to Sheep Pond combine for an excellent income opportunity!...	5 beds \| 2 baths \| 1,344 sq.ft.	$729,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 3.26% Airbnb Rental Income: $6486 Traditional Rental Income: $3367 Airbnb ROI: 5.98% Traditional ROI: 3.26%
181 Stony Brook Road Brewster, MA Discover the charm of a classic Cape Cod style home on the northside. This traditional hom...	3 beds \| 2 baths \| 1,620 sq.ft.	$749,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 2.73% Airbnb Rental Income: $5569 Traditional Rental Income: $3168 Airbnb ROI: 4.57% Traditional ROI: 2.73%
958 Long Pond Road Brewster, MA Three Lots Totaling 3+ Acres in Brewster! An exceptional opportunity awaits with this uniq...	4 beds \| 3 baths \| 2,440 sq.ft.	$1,200,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.16% Airbnb Rental Income: $6080 Traditional Rental Income: $4137 Airbnb ROI: 2.82% Traditional ROI: 2.16%
40 Horseshoe Way Brewster, MA This charming ranch-style home offers 1 floor living in the heart of Brewster! More rooms ...	3 beds \| 2 baths \| 1,672 sq.ft.	$699,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 3.18% Airbnb Rental Income: $5569 Traditional Rental Income: $3232 Airbnb ROI: 5.05% Traditional ROI: 3.18%
133 Horseshoe Way Brewster, MA Welcome to this beautifully renovated three-bedroom classic 1970s Cape, ideally located in...	3 beds \| 2 baths \| 1,764 sq.ft.	$829,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 2.66% Airbnb Rental Income: $5569 Traditional Rental Income: $3326 Airbnb ROI: 4.12% Traditional ROI: 2.66%
262 Sheep Pond Drive Brewster, MA Welcome to 262 Sheep Pond Drive, where stunning pond views and a beautifully designed home...	3 beds \| 4 baths \| 3,272 sq.ft.	$1,750,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 1.4% Airbnb Rental Income: $5569 Traditional Rental Income: $4979 Airbnb ROI: 1.08% Traditional ROI: 1.4%
418 Massasoit Trail Brewster, MA Commanding 2.99 acres with extensive frontage on Seymour Pond, this rare Brewster offering...	2 beds \| 2 baths \| 1,681 sq.ft.	$995,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 1.88% Airbnb Rental Income: $3072 Traditional Rental Income: $3263 Airbnb ROI: 0.91% Traditional ROI: 1.88%
37 Oliver Road Brewster, MA Set on over 5 acres of privacy in a peaceful Brewster location, this exceptional property ...	4 beds \| 4 baths \| 3,937 sq.ft.	$2,695,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 0.89% Airbnb Rental Income: $6080 Traditional Rental Income: $5822 Airbnb ROI: 0.51% Traditional ROI: 0.89%
153 Red Fawn Road Brewster, MA Hike right into Nickerson State Park! Pretty, access path is 2/10 mile across the street! ...	4 beds \| 2 baths \| 1,582 sq.ft.	$689,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.64% Airbnb Rental Income: $6080 Traditional Rental Income: $3474 Airbnb ROI: 5.83% Traditional ROI: 3.64%
55 Carlton Circle Brewster, MA Brewster Prime & coveted MUST SEE cul de sac location positioned between Sheep and Long po...	4 beds \| 3 baths \| 2,784 sq.ft.	$1,329,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 1.98% Airbnb Rental Income: $6080 Traditional Rental Income: $4550 Airbnb ROI: 2.25% Traditional ROI: 1.98%
236 Yankee Drive Brewster, MA A charming ranch offering 1-floor living plus central AC and gas hot air heat for year-rou...	3 beds \| 2 baths \| 1,713 sq.ft.	$725,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 2.99% Airbnb Rental Income: $5569 Traditional Rental Income: $3240 Airbnb ROI: 4.78% Traditional ROI: 2.99%
62 Eldridge Road Brewster, MA Welcome to this gracious 2,880 sf home on a quiet country lane north of 6A in a prime loca...	4 beds \| 3 baths \| 2,880 sq.ft.	$1,195,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 2.17% Airbnb Rental Income: $6080 Traditional Rental Income: $4248 Airbnb ROI: 2.73% Traditional ROI: 2.17%
33 Captain William Arthur Road Brewster, MA An exceptionally rare offering where coastal charm meets comfort in the highly desired She...	3 beds \| 1 baths \| 1,800 sq.ft.	$740,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 2.31% Airbnb Rental Income: $5569 Traditional Rental Income: $2761 Airbnb ROI: 4.76% Traditional ROI: 2.31%
242 Sheep Pond Drive Brewster, MA ''The Best View of Sheep Pond.'' That's what the neighbors say-and once you see it, you'll...	5 beds \| 2 baths \| 2,599 sq.ft.	$1,300,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.68% Airbnb Rental Income: $6486 Traditional Rental Income: $4002 Airbnb ROI: 2.69% Traditional ROI: 1.68%
166 Highland Moors Drive Brewster, MA In one of Brewster's most desirable locations, this treasured home is perched above Namska...	4 beds \| 3 baths \| 2,509 sq.ft.	$1,950,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 0.47% Airbnb Rental Income: $6080 Traditional Rental Income: $4021 Airbnb ROI: 0.95% Traditional ROI: 0.47%

Your search for investment property begins and ends here

Single Family Homes for Sale in Brewster, MA

663 Crowells Bog Road

Brewster, MA

4 beds | 4 baths | 3,738 sq.ft.

$1,589,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 2.01%

Airbnb Rental Income: $6080

Traditional Rental Income: $5430

Airbnb ROI: 1.63%

Traditional ROI: 2.01%

240 Robbins Hill Road

Brewster, MA

3 beds | 2 baths | 1,418 sq.ft.

$2,395,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $5569

Traditional Rental Income: $3258

Airbnb ROI: 0.31%

Traditional ROI: -0.23%

19 Burning Bush Way

Brewster, MA

2 beds | 2 baths | 2,034 sq.ft.

$750,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $3072

Traditional Rental Income: $3074

Airbnb ROI: 1.6%

Traditional ROI: 2.61%

167 Ambergris Circle

Brewster, MA

3 beds | 3 baths | 2,001 sq.ft.

$1,625,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $5569

Traditional Rental Income: $3538

Airbnb ROI: 1.39%

Traditional ROI: 0.78%

221 Greenland Pond Road

Brewster, MA

3 beds | 2 baths | 1,471 sq.ft.

$795,000

Airbnb cash on cash: 4.21%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $5569

Traditional Rental Income: $3161

Airbnb ROI: 4.21%

Traditional ROI: 2.47%

117 A P Newcomb Road

Brewster, MA

4 beds | 3 baths | 2,436 sq.ft.

$1,030,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $6080

Traditional Rental Income: $3775

Airbnb ROI: 3.35%

Traditional ROI: 2.2%

9 Park Lane

Brewster, MA

4 beds | 3 baths | 2,306 sq.ft.

$799,000

Airbnb cash on cash: 4.89%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $6080

Traditional Rental Income: $3698

Airbnb ROI: 4.89%

Traditional ROI: 3.31%

92 Whiffletree Avenue

Brewster, MA

5 beds | 5 baths | 3,706 sq.ft.

$2,095,000

Airbnb cash on cash: 0.41%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $6486

Traditional Rental Income: $5488

Airbnb ROI: 0.41%