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.

Investment Property for Sale in Brewster, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
195 Ellis Landing Road Brewster, MA Just steps to beautiful Cape Cod Bay, sun and fun in the sand, breathtaking sunsets ... yo...	2 beds \| 1 baths \| 828 sq.ft.	$1,150,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.19% Airbnb Rental Income: $3072 Traditional Rental Income: $2064 Airbnb ROI: 0.48% Traditional ROI: 0.19%
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%
728 Great Fields Road Brewster, MA Charming three-bedroom Cape in a great Brewster location-less than a mile to Long and Seym...	3 beds \| 2 baths \| 1,266 sq.ft.	$659,900	Airbnb cash on cash: 5.55% Traditional cash on cash: 3.15% Airbnb Rental Income: $5569 Traditional Rental Income: $2973 Airbnb ROI: 5.55% Traditional ROI: 3.15%
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%
28 Middlecott Lane Brewster, MA Welcome to your dream retreat, a single-floor end unit condo nestled on the serene 6A side...	2 beds \| 2 baths \| 1,035 sq.ft.	$569,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.08% Airbnb Rental Income: $3072 Traditional Rental Income: $2610 Airbnb ROI: 1.63% Traditional ROI: 2.08%
60 Fletcher Lane unit: C #C Brewster, MA Welcome to 60-C Fletcher Lane-an inviting and updated, open concept one-bedroom condo loca...	1 beds \| 1 baths \| 579 sq.ft.	$249,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.28% Airbnb Rental Income: $3458 Traditional Rental Income: $1815 Airbnb ROI: 7.01% Traditional ROI: 3.28%
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.	$999,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.3% Airbnb Rental Income: $6080 Traditional Rental Income: $3775 Airbnb ROI: 3.49% Traditional ROI: 2.3%
92 Whiffletree Avenue Brewster, MA Discover refined coastal living in this brand-new 3,706 sq. ft. luxury home, nestled in th...	5 beds \| N/A 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 \| N/A 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%
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%
1080 Harwich Road Brewster, MA Charming 3-bedroom Custom Cape-Great Investment Opportunity Near Scenic Ponds and Bike Tra...	3 beds \| 3 baths \| 1,963 sq.ft.	$735,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 3.46% Airbnb Rental Income: $5569 Traditional Rental Income: $3599 Airbnb ROI: 4.71% Traditional ROI: 3.46%
20 Spring Lane Brewster, MA Just a half mile to Paines Creek Beach - a favorite inspiration for local artists - this d...	3 beds \| 2 baths \| 1,652 sq.ft.	$1,065,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 1.68% Airbnb Rental Income: $5569 Traditional Rental Income: $3195 Airbnb ROI: 2.95% Traditional ROI: 1.68%
80 Fletcher Lane unit: E #E Brewster, MA Beautifully updated and move-in ready, this lower level 1-bed, 1-bath condo in desirable O...	1 beds \| 1 baths \| 579 sq.ft.	$310,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 2.32% Airbnb Rental Income: $3458 Traditional Rental Income: $1774 Airbnb ROI: 5.47% Traditional ROI: 2.32%
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%
204 Timberlane Drive Brewster, MA Motivated Seller! Enjoy single floor living at its best. With a potential for a future gar...	2 beds \| 2 baths \| 1,560 sq.ft.	$749,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.4% Airbnb Rental Income: $3072 Traditional Rental Income: $3192 Airbnb ROI: 2.22% Traditional ROI: 3.4%
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%
81 Fletcher Lane unit: C #C Brewster, MA Move right into this beautifully renovated, first-floor condo in the sought-after Ocean Ed...	1 beds \| 1 baths \| 579 sq.ft.	$335,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 2% Airbnb Rental Income: $3458 Traditional Rental Income: $1777 Airbnb ROI: 4.91% Traditional ROI: 2%
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 \| N/A 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%
81 Fletcher Lane unit: I #I Brewster, MA Enjoy one level living and move right into this beautifully renovated, first-floor condo i...	1 beds \| 1 baths \| 579 sq.ft.	$325,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 2.06% Airbnb Rental Income: $3458 Traditional Rental Income: $1777 Airbnb ROI: 5.06% Traditional ROI: 2.06%
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.	$1,120,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 2.38% Airbnb Rental Income: $6080 Traditional Rental Income: $4137 Airbnb ROI: 3.1% Traditional ROI: 2.38%
62 Fletcher Lane unit: N #N Brewster, MA Move right into this beautifully renovated top-floor condo in the sought-after Ocean Edge ...	1 beds \| 1 baths \| 579 sq.ft.	$330,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 2.09% Airbnb Rental Income: $3458 Traditional Rental Income: $1778 Airbnb ROI: 5.04% Traditional ROI: 2.09%
11 Juniper Circle Brewster, MA This spacious town home is located on Cape Cod Bay in a beautifully landscaped community w...	3 beds \| 3 baths \| 2,011 sq.ft.	$1,250,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 1.63% Airbnb Rental Income: $5569 Traditional Rental Income: $3757 Airbnb ROI: 2.23% Traditional ROI: 1.63%
82 Fletcher Lane unit: I #I Brewster, MA Step into this stunningly updated top-floor condo in the desirable Ocean Edge Resort commu...	1 beds \| 1 baths \| 579 sq.ft.	$345,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 3.63% Airbnb Rental Income: $3458 Traditional Rental Income: $1765 Airbnb ROI: 6.49% Traditional ROI: 3.63%
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%
100 Fletcher Lane unit: E #E Brewster, MA Welcome to your perfect escape in the highly sought-after Ocean Edge Resort community in B...	1 beds \| 1 baths \| 579 sq.ft.	$265,000	Airbnb cash on cash: 8.79% Traditional cash on cash: 5.19% Airbnb Rental Income: $3458 Traditional Rental Income: $1794 Airbnb ROI: 8.79% Traditional ROI: 5.19%
144 Eaton Lane Brewster, MA You will fall in love with this beautiful Garden-Style 2-bedroom, 2-bath entry level condo...	2 beds \| 2 baths \| 935 sq.ft.	$449,900	Airbnb cash on cash: 3.84% Traditional cash on cash: 4.16% Airbnb Rental Income: $3072 Traditional Rental Income: $2504 Airbnb ROI: 3.84% Traditional ROI: 4.16%
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%
46 Court Way Brewster, MA Welcome to The Colony in Brewster! This 2 bedroom 2.5 bath townhouse offers 3 levels with ...	2 beds \| N/A baths \| 1,380 sq.ft.	$410,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 5.9% Airbnb Rental Income: $3072 Traditional Rental Income: $3020 Airbnb ROI: 4.22% Traditional ROI: 5.9%
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.	$1,795,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.6% Airbnb Rental Income: $6080 Traditional Rental Income: $4021 Airbnb ROI: 1.11% Traditional ROI: 0.6%
1580 Main Street Brewster, MA 1580 Main Street A/K/A ''The Captain Freeman Bangs House''. Step back in time and be engag...	4 beds \| 2 baths \| 1,872 sq.ft.	$729,900	Airbnb cash on cash: 5.4% Traditional cash on cash: 3.81% Airbnb Rental Income: $6080 Traditional Rental Income: $3801 Airbnb ROI: 5.4% Traditional ROI: 3.81%
43 Billington Lane Brewster, MA On this sunny morning, this ''A'' style townhome is bathed in natural light within the bel...	2 beds \| 2 baths \| 1,164 sq.ft.	$550,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.41% Airbnb Rental Income: $3072 Traditional Rental Income: $2677 Airbnb ROI: 2.82% Traditional ROI: 3.41%
159 Old Chatham Road Brewster, MA This Brewster home will surprise and delight you at every turn! The open main level floorp...	3 beds \| 2 baths \| 1,680 sq.ft.	$750,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 2.84% Airbnb Rental Income: $5569 Traditional Rental Income: $3157 Airbnb ROI: 4.69% Traditional ROI: 2.84%
120 Red Maple Road Brewster, MA Deerfield Estates - This traditional Colonial offers 4 bedrooms, 2.5 baths, and a private ...	4 beds \| 3 baths \| 2,502 sq.ft.	$1,100,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 1.41% Airbnb Rental Income: $6080 Traditional Rental Income: $3122 Airbnb ROI: 3.13% Traditional ROI: 1.41%

Real Estate investment in Brewster, MA

There are 63 properties for sale in the city of Brewster . The median list price in Brewster is $750,000 and the average price per square foot is $419. In November 2025, the average monthly cash on cash return in Brewster is 2.00%. The average monthly rental income in Brewster is $3,122.

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

There are 63 investment properties available for sale in Brewster.

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

The ROI for Short-Term is higher than the Long-Term in Brewster with average rental income of $5,569.

Your search for investment property begins and ends here

Investment Property for Sale in Brewster, MA

195 Ellis Landing Road

Brewster, MA

2 beds | 1 baths | 828 sq.ft.

$1,150,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $3072

Traditional Rental Income: $2064

Airbnb ROI: 0.48%

Traditional ROI: 0.19%

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%

728 Great Fields Road

Brewster, MA

3 beds | 2 baths | 1,266 sq.ft.

$659,900

Airbnb cash on cash: 5.55%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $5569

Traditional Rental Income: $2973

Airbnb ROI: 5.55%

Traditional ROI: 3.15%

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%

28 Middlecott Lane

Brewster, MA

2 beds | 2 baths | 1,035 sq.ft.

$569,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $3072

Traditional Rental Income: $2610

Airbnb ROI: 1.63%

Traditional ROI: 2.08%

60 Fletcher Lane unit: C #C

Brewster, MA

1 beds | 1 baths | 579 sq.ft.

$249,000

Airbnb cash on cash: 7.01%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $3458

Traditional Rental Income: $1815

Airbnb ROI: 7.01%

Traditional ROI: 3.28%

117 A P Newcomb Road

Brewster, MA

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

$999,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $6080

Traditional Rental Income: $3775

Airbnb ROI: 3.49%