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
53 Chilton Lane Brewster, MA Enjoy the scenic pond view from the living room and main bedroom of this condo! In fact, i...	2 beds \| 2 baths \| 935 sq.ft.	$389,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.64% Airbnb Rental Income: $3072 Traditional Rental Income: $2594 Airbnb ROI: 3.03% Traditional ROI: 3.64%
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%
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.	$275,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 2.88% Airbnb Rental Income: $3458 Traditional Rental Income: $1815 Airbnb ROI: 6.27% Traditional ROI: 2.88%
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%
232 Eaton Lane Brewster, MA Recently remodeled Ocean Edge Condo, ready for your summer enjoyment! This 2 bedroom, 2 ba...	2 beds \| 2 baths \| 935 sq.ft.	$417,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.29% Airbnb Rental Income: $3072 Traditional Rental Income: $2478 Airbnb ROI: 3.02% Traditional ROI: 3.29%
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%
93 Chilton Lane Brewster, MA This beautifully updated 2-bed, 2-bath second-floor condo in Ocean Edge offers comfort and...	2 beds \| 2 baths \| 935 sq.ft.	$409,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.04% Airbnb Rental Income: $3072 Traditional Rental Income: $2458 Airbnb ROI: 2.82% Traditional ROI: 3.04%
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%
101 Fletcher Lane unit: G #G Brewster, MA Welcome to your serene escape at the Villages at Ocean Edge, where this charming one-bedro...	1 beds \| 1 baths \| 579 sq.ft.	$279,000	Airbnb cash on cash: 6.1% Traditional cash on cash: 2.75% Airbnb Rental Income: $3458 Traditional Rental Income: $1810 Airbnb ROI: 6.1% Traditional ROI: 2.75%
146 Crescent Lane Brewster, MA Welcome to The Colony! This spacious 2-bedroom, 2.5-bath condo offers 1,380 sq ft of comfo...	2 beds \| 3 baths \| 1,380 sq.ft.	$438,500	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.04% Airbnb Rental Income: $3072 Traditional Rental Income: $2997 Airbnb ROI: 2.51% Traditional ROI: 4.04%
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%
81 Fletcher Lane unit: J #J Brewster, MA Move right into this beautifully renovated, first-floor condo in the sought-after Ocean Ed...	1 beds \| 1 baths \| 589 sq.ft.	$320,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 2.17% Airbnb Rental Income: $3458 Traditional Rental Income: $1774 Airbnb ROI: 5.23% Traditional ROI: 2.17%
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%
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%
18 Juniper Circle Brewster, MA Coastal luxury in Brewster's coveted Sears Point. Welcome to 18 Juniper Circle, a spacious...	2 beds \| 2 baths \| 2,184 sq.ft.	$1,075,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.51% Airbnb Rental Income: $3072 Traditional Rental Income: $3521 Airbnb ROI: -0.64% Traditional ROI: 0.51%
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%
104 Chestnut Circle Brewster, MA Offering privacy, peace, and plenty of space, this end unit with walk out basement is the ...	2 beds \| 2 baths \| 1,380 sq.ft.	$499,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.07% Airbnb Rental Income: $3072 Traditional Rental Income: $2853 Airbnb ROI: 2.04% Traditional ROI: 3.07%
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%
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%
158 Billington Lane Brewster, MA Charming B-Style Townhome at Ocean Edge Resort Lovingly maintained by the original owners,...	2 beds \| 2 baths \| 1,063 sq.ft.	$595,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 2.02% Airbnb Rental Income: $3072 Traditional Rental Income: $2580 Airbnb ROI: 1.65% Traditional ROI: 2.02%
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%
228 Eaton Lane Brewster, MA Discover a rare opportunity to own a beautifully updated, entry-level end unit in the popu...	2 beds \| 2 baths \| 948 sq.ft.	$399,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 3.5% Airbnb Rental Income: $3072 Traditional Rental Income: $2489 Airbnb ROI: 3.18% Traditional ROI: 3.5%

Real Estate investment in Brewster, MA

There are 59 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 $417. In September 2025, the average monthly cash on cash return in Brewster is 2.00%. The average monthly rental income in Brewster is $3,232.

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

There are 59 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

53 Chilton Lane

Brewster, MA

2 beds | 2 baths | 935 sq.ft.

$389,500

Airbnb cash on cash: 3.03%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3072

Traditional Rental Income: $2594

Airbnb ROI: 3.03%

Traditional ROI: 3.64%

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%

60 Fletcher Lane unit: C #C

Brewster, MA

1 beds | 1 baths | 579 sq.ft.

$275,000

Airbnb cash on cash: 6.27%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $3458

Traditional Rental Income: $1815

Airbnb ROI: 6.27%

Traditional ROI: 2.88%

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%

232 Eaton Lane

Brewster, MA

2 beds | 2 baths | 935 sq.ft.

$417,000

Airbnb cash on cash: 3.02%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $3072

Traditional Rental Income: $2478

Airbnb ROI: 3.02%