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 43 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
84 Anchors Aweigh Road Brewster, MA If you like like Pina Coladas... Legend has it the dunes from Rupert Holmes famous song ar...	3 beds \| 2 baths \| 654 sq.ft.	$1,095,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.01% Airbnb Rental Income: $1673 Traditional Rental Income: $2511 Airbnb ROI: -0.27% Traditional ROI: 1.01%
161 Beechtree Drive Brewster, MA Nestled in the highly sought-after Beechwood Landing neighborhood, this classic Cape home ...	3 beds \| 2 baths \| 1,834 sq.ft.	$789,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.77% Airbnb Rental Income: $1673 Traditional Rental Income: $3372 Airbnb ROI: -0.17% Traditional ROI: 2.77%
309 Great Fields Road Brewster, MA Beautifully remodeled, this unique saltbox post & beam is set on 1.41 acres of tranquility...	3 beds \| 2 baths \| 1,792 sq.ft.	$899,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.29% Airbnb Rental Income: $1673 Traditional Rental Income: $3264 Airbnb ROI: -0.17% Traditional ROI: 2.29%
62 Maple Lane Brewster, MA Due to unforeseen challenges experienced by the buyer, the property is once again availabl...	3 beds \| 3 baths \| 2,172 sq.ft.	$799,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.81% Airbnb Rental Income: $1673 Traditional Rental Income: $3302 Airbnb ROI: -0.01% Traditional ROI: 2.81%
235 Old Chatham Road Brewster, MA Property is being sold as-is. Three-bedroom home with potential to expand to up to five be...	3 beds \| 2 baths \| 1,665 sq.ft.	$459,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 7.7% Airbnb Rental Income: $1673 Traditional Rental Income: $4030 Airbnb ROI: 1.12% Traditional ROI: 7.7%
5 Maple Lane Brewster, MA Tucked on a quiet lane just off Route 6A in sought after Robinwood Association, this 4 bed...	4 beds \| 2 baths \| 1,612 sq.ft.	$749,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 2.94% Airbnb Rental Income: $1894 Traditional Rental Income: $3246 Airbnb ROI: 0.28% Traditional ROI: 2.94%
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: -1.27% Traditional cash on cash: 0.55% Airbnb Rental Income: $2568 Traditional Rental Income: $5488 Airbnb ROI: -1.27% Traditional ROI: 0.55%
232 Robbins Hill Road Brewster, MA This is an absolutely enchanting waterfront property with private stairs to your own priva...	3 beds \| 2 baths \| 1,502 sq.ft.	$2,492,000	Airbnb cash on cash: -1.16% Traditional cash on cash: -0.24% Airbnb Rental Income: $1673 Traditional Rental Income: $3349 Airbnb ROI: -1.16% Traditional ROI: -0.24%
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: 0.25% Traditional cash on cash: 6.72% Airbnb Rental Income: $1350 Traditional Rental Income: $3490 Airbnb ROI: 0.25% Traditional ROI: 6.72%
398 Lund Farm Way Brewster, MA Fully renovated and thoughtfully designed, this stunning four-bedroom, three-bathroom, 2,4...	4 beds \| 3 baths \| 2,448 sq.ft.	$1,099,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.91% Airbnb Rental Income: $1894 Traditional Rental Income: $3539 Airbnb ROI: -0.19% Traditional ROI: 1.91%
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.	$1,690,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.14% Airbnb Rental Income: $1673 Traditional Rental Income: $4000 Airbnb ROI: -0.64% Traditional ROI: 1.14%
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.	$699,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 4% Airbnb Rental Income: $1894 Traditional Rental Income: $3801 Airbnb ROI: 0.31% Traditional ROI: 4%
80 Abby Road Brewster, MA Stunning Brewster Home! Just minutes from beaches and premier golf courses, this meticulou...	4 beds \| 4 baths \| 2,859 sq.ft.	$1,695,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.54% Airbnb Rental Income: $1894 Traditional Rental Income: $3327 Airbnb ROI: -0.69% Traditional ROI: 0.54%
337 Jonathans Way Brewster, MA This Brewster salt-box cape is meticulously maintained, with all of the major systems in g...	2 beds \| 2 baths \| 1,216 sq.ft.	$629,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.91% Airbnb Rental Income: $1350 Traditional Rental Income: $2714 Airbnb ROI: -0.12% Traditional ROI: 2.91%
39 Spruce Run Drive Brewster, MA Nestled in the desirable Sheep's Landing neighborhood, with access to a private associatio...	4 beds \| 4 baths \| 3,050 sq.ft.	$1,795,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.01% Airbnb Rental Income: $1894 Traditional Rental Income: $4347 Airbnb ROI: -0.76% Traditional ROI: 1.01%
Ridgewood Drive Brewster, MA Gracing a knoll above charming and historic Rt 6A on exclusive Ridgewood Drive, this large...	4 beds \| 4 baths \| 2,778 sq.ft.	$2,330,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0% Airbnb Rental Income: $1894 Traditional Rental Income: $4908 Airbnb ROI: -1.62% Traditional ROI: 0%
61 Sheffield Road Brewster, MA An exceptional opportunity to build your dream Cape house in the heart of Brewster. This n...	3 beds \| 4 baths \| 2,396 sq.ft.	$1,199,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 2.91% Airbnb Rental Income: $1673 Traditional Rental Income: $4591 Airbnb ROI: -0.13% Traditional ROI: 2.91%
46 Trout Pond Lane Brewster, MA Spacious custom built home with 3 bedrooms, 2 full baths and room to grow on a beautiful ....	3 beds \| 2 baths \| 1,778 sq.ft.	$835,500	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.56% Airbnb Rental Income: $1673 Traditional Rental Income: $3318 Airbnb ROI: -0.16% Traditional ROI: 2.56%
236 Freemans Way Brewster, MA Discover one of Brewster's most affordable single-family opportunities at 236 Freemans Way...	3 beds \| 2 baths \| 1,376 sq.ft.	$599,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.73% Airbnb Rental Income: $1673 Traditional Rental Income: $3055 Airbnb ROI: 0.42% Traditional ROI: 3.73%
157 Jonathans Way Brewster, MA There are homes... and then there are homes you feel the moment you walk in. This is one o...	1 beds \| 2 baths \| 1,376 sq.ft.	$549,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 3.04% Airbnb Rental Income: $1082 Traditional Rental Income: $2484 Airbnb ROI: -0.42% Traditional ROI: 3.04%
279 Alden Drive Brewster, MA Beautifully renovated Brewster home offering easy one-level living with a bright, open lay...	3 beds \| 2 baths \| 1,852 sq.ft.	$799,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.88% Airbnb Rental Income: $1673 Traditional Rental Income: $3398 Airbnb ROI: -0.07% Traditional ROI: 2.88%
527 S Orleans Road Brewster, MA Just 0.7 miles to South Orleans Beach and close to Nauset Beach, this well-situated home o...	2 beds \| 2 baths \| 996 sq.ft.	$585,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.05% Airbnb Rental Income: $1350 Traditional Rental Income: $2596 Airbnb ROI: 0.01% Traditional ROI: 3.05%
98 Leland Road Brewster, MA This well maintained 10 year young easy living one level Ranch offering 3 bedrooms and 2 f...	3 beds \| 2 baths \| 1,456 sq.ft.	$799,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.67% Airbnb Rental Income: $1673 Traditional Rental Income: $3295 Airbnb ROI: -0.14% Traditional ROI: 2.67%
186 Canoe Pond Drive Brewster, MA Imagine waking up everyday to stunning views of Canoe Pond and the serene sounds of nature...	3 beds \| 3 baths \| 2,574 sq.ft.	$975,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.82% Airbnb Rental Income: $1673 Traditional Rental Income: $4118 Airbnb ROI: -0.39% Traditional ROI: 2.82%
101 Evelyn'S Drive Brewster, MA Welcome to Brewster, MA - where Cape Cod charm meets a life well-lived.Tucked away on a qu...	3 beds \| 4 baths \| 2,354 sq.ft.	$1,600,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.9% Airbnb Rental Income: $1673 Traditional Rental Income: $4558 Airbnb ROI: -0.35% Traditional ROI: 1.9%
17 Barberry Lane Brewster, MA Just steps from a sandy, private association Cape Cod Bay beach and the Brewster Flats, th...	4 beds \| 3 baths \| 2,933 sq.ft.	$2,000,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.47% Airbnb Rental Income: $1894 Traditional Rental Income: $4254 Airbnb ROI: -1.07% Traditional ROI: 0.47%
8 Marlboro Road Brewster, MA Golfers Paradise!! Come fall in love with this Custom Built Contemporary Ranch Home just o...	3 beds \| 2 baths \| 1,914 sq.ft.	$849,999	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.53% Airbnb Rental Income: $1673 Traditional Rental Income: $3367 Airbnb ROI: -0.2% Traditional ROI: 2.53%
295 Greenland Pond Road Brewster, MA Welcome to Beechwood Landing! This charming, move-in ready ranch is perfect as a year roun...	3 beds \| 3 baths \| 3,000 sq.ft.	$1,150,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 2.1% Airbnb Rental Income: $1673 Traditional Rental Income: $3929 Airbnb ROI: -0.45% Traditional ROI: 2.1%
47 Flying Dragon Road Brewster, MA Step into a timeless Cape Gambrel built by family for family as the perfect retreat for ma...	4 beds \| 2 baths \| 1,824 sq.ft.	$1,270,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.57% Airbnb Rental Income: $1894 Traditional Rental Income: $3600 Airbnb ROI: -0.3% Traditional ROI: 1.57%
98 Sheep Pond Drive Brewster, MA Nestled in the sought-after Sheep Pond Beach Association neighborhood, this quintessential...	3 beds \| 2 baths \| 1,344 sq.ft.	$689,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.03% Airbnb Rental Income: $1673 Traditional Rental Income: $3062 Airbnb ROI: 0.14% Traditional ROI: 3.03%
147 Brook Trail Road Brewster, MA 147 Brook Trail offers a practical and comfortable entry into Brewster living that include...	3 beds \| 2 baths \| 1,983 sq.ft.	$749,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $1673 Traditional Rental Income: $3405 Airbnb ROI: 0.02% Traditional ROI: 3.17%
182 Ambergris Circle Brewster, MA There is only one word to describe this home: Stunning! Custom Built in 1998 & renovated b...	3 beds \| 3 baths \| 3,403 sq.ft.	$2,200,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.26% Airbnb Rental Income: $1673 Traditional Rental Income: $3822 Airbnb ROI: -1.02% Traditional ROI: 0.26%
10 Park Lane Brewster, MA A meticulously maintained and beautifully renovated gem in the heart of Brewster! This hom...	4 beds \| 2 baths \| 2,079 sq.ft.	$850,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.86% Airbnb Rental Income: $1894 Traditional Rental Income: $3590 Airbnb ROI: 0.08% Traditional ROI: 2.86%
72 Winstead Road Brewster, MA A masterfully crafted custom residence, impeccably maintained with many updates. This exce...	4 beds \| 4 baths \| 3,021 sq.ft.	$1,675,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.95% Airbnb Rental Income: $1894 Traditional Rental Income: $5457 Airbnb ROI: -0.67% Traditional ROI: 1.95%
1066 Millstone Rd Brewster, MA This cape style ranch has been fully renovated from top to bottom and is only minutes from...	3 beds \| 2 baths \| 1,633 sq.ft.	$910,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.38% Airbnb Rental Income: $1673 Traditional Rental Income: $3277 Airbnb ROI: -0.06% Traditional ROI: 2.38%
84 Alden Drive Brewster, MA Discover a rare opportunity to own a brand-new waterfront retreat in the heart of Brewster...	2 beds \| 4 baths \| 3,172 sq.ft.	$1,849,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.03% Airbnb Rental Income: $1350 Traditional Rental Income: $5309 Airbnb ROI: -0.52% Traditional ROI: 2.03%
38 Bittersweet Drive Brewster, MA Fantastic opportunity to own a home on a cul-de-sac north of Route 6A in Brewster. Large 5...	5 beds \| 3 baths \| 2,295 sq.ft.	$949,900	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.9% Airbnb Rental Income: $2568 Traditional Rental Income: $4155 Airbnb ROI: 0.41% Traditional ROI: 2.9%
16 Cedar Lane Brewster, MA Tucked beside the natural beauty of Nickerson State Park, 16 Cedar Lane offers a rare Brew...	2 beds \| 1 baths \| 1,040 sq.ft.	$550,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.61% Airbnb Rental Income: $1350 Traditional Rental Income: $2265 Airbnb ROI: 0.03% Traditional ROI: 2.61%
20 Bantry Lane Brewster, MA Set in the coveted Kings Grant neighborhood, this lovely home offers wonderful privacy and...	3 beds \| 3 baths \| 2,098 sq.ft.	$1,900,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.51% Airbnb Rental Income: $1673 Traditional Rental Income: $3689 Airbnb ROI: -0.9% Traditional ROI: 0.51%
2926 Main Street Brewster, MA Just south of 6A in Historic Brewster. Offered for the first time in close to 25 years- Mu...	2 beds \| 2 baths \| 2,160 sq.ft.	$765,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 2.82% Airbnb Rental Income: $1350 Traditional Rental Income: $3072 Airbnb ROI: -0.18% Traditional ROI: 2.82%

Your search for investment property begins and ends here

Single Family Homes for Sale in Brewster, MA

84 Anchors Aweigh Road

Brewster, MA

3 beds | 2 baths | 654 sq.ft.

$1,095,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $1673

Traditional Rental Income: $2511

Airbnb ROI: -0.27%

Traditional ROI: 1.01%

161 Beechtree Drive

Brewster, MA

3 beds | 2 baths | 1,834 sq.ft.

$789,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $1673

Traditional Rental Income: $3372

Airbnb ROI: -0.17%

Traditional ROI: 2.77%

309 Great Fields Road

Brewster, MA

3 beds | 2 baths | 1,792 sq.ft.

$899,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1673

Traditional Rental Income: $3264

Airbnb ROI: -0.17%

Traditional ROI: 2.29%

62 Maple Lane

Brewster, MA

3 beds | 3 baths | 2,172 sq.ft.

$799,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $1673

Traditional Rental Income: $3302

Airbnb ROI: -0.01%

Traditional ROI: 2.81%

235 Old Chatham Road

Brewster, MA

3 beds | 2 baths | 1,665 sq.ft.

$459,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $1673

Traditional Rental Income: $4030

Airbnb ROI: 1.12%

Traditional ROI: 7.7%

5 Maple Lane

Brewster, MA

4 beds | 2 baths | 1,612 sq.ft.

$749,900

Airbnb cash on cash: 0.28%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $1894

Traditional Rental Income: $3246

Airbnb ROI: 0.28%

Traditional ROI: 2.94%

92 Whiffletree Avenue

Brewster, MA

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

$2,095,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $2568

Traditional Rental Income: $5488

Airbnb ROI: -1.27%

Traditional ROI: 0.55%

232 Robbins Hill Road

Brewster, MA

3 beds | 2 baths | 1,502 sq.ft.

$2,492,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $1673

Traditional Rental Income: $3349

Airbnb ROI: -1.16%