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 41 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
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: 0.43% Traditional cash on cash: 2.77% Airbnb Rental Income: $2210 Traditional Rental Income: $3372 Airbnb ROI: 0.43% Traditional ROI: 2.77%
130 Spring Lane Brewster, MA OPEN HOUSE CANCELLED - ACCEPTED OFFER. Just in time for Summer 2026! Desirable north of Rt...	2 beds \| 1 baths \| 672 sq.ft.	$595,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.89% Airbnb Rental Income: $1749 Traditional Rental Income: $2058 Airbnb ROI: 0.47% Traditional ROI: 1.89%
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: 2.16% Traditional cash on cash: 7.7% Airbnb Rental Income: $2210 Traditional Rental Income: $4030 Airbnb ROI: 2.16% Traditional ROI: 7.7%
5 Maple Lane Brewster, MA Imagine yourself in the sought after Robinwood Association this summer! Start your morning...	4 beds \| 2 baths \| 1,612 sq.ft.	$715,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 3.13% Airbnb Rental Income: $2753 Traditional Rental Income: $3246 Airbnb ROI: 1.42% Traditional ROI: 3.13%
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: -0.97% Traditional cash on cash: -0.24% Airbnb Rental Income: $2210 Traditional Rental Income: $3349 Airbnb ROI: -0.97% 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: 1.09% Traditional cash on cash: 6.72% Airbnb Rental Income: $1749 Traditional Rental Income: $3490 Airbnb ROI: 1.09% Traditional ROI: 6.72%
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.	$965,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 1.96% Airbnb Rental Income: $2210 Traditional Rental Income: $3195 Airbnb ROI: 0.24% Traditional ROI: 1.96%
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: -0.36% Traditional cash on cash: 1.14% Airbnb Rental Income: $2210 Traditional Rental Income: $4000 Airbnb ROI: -0.36% 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.	$675,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.19% Airbnb Rental Income: $2753 Traditional Rental Income: $3801 Airbnb ROI: 1.49% Traditional ROI: 4.19%
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.	$1,655,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.58% Airbnb Rental Income: $2753 Traditional Rental Income: $3327 Airbnb ROI: -0.22% Traditional ROI: 0.58%
Ridgewood Drive Brewster, MA Gracing a knoll above charming and historic Rt 6A on exclusive Ridgewood Dr(Map 26-58), th...	4 beds \| 4 baths \| 2,337 sq.ft.	$1,940,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.45% Airbnb Rental Income: $2753 Traditional Rental Income: $4908 Airbnb ROI: -1.11% Traditional ROI: 0.45%
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: 1.22% Traditional cash on cash: 3.73% Airbnb Rental Income: $2210 Traditional Rental Income: $3055 Airbnb ROI: 1.22% Traditional ROI: 3.73%
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: 0.54% Traditional cash on cash: 2.88% Airbnb Rental Income: $2210 Traditional Rental Income: $3398 Airbnb ROI: 0.54% Traditional ROI: 2.88%
98 Leland Road Brewster, MA Freshly price adjusted and motivated seller! Built in 2016 and lovingly maintained by its ...	3 beds \| 2 baths \| 1,456 sq.ft.	$765,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 2.83% Airbnb Rental Income: $2210 Traditional Rental Income: $3295 Airbnb ROI: 0.53% Traditional ROI: 2.83%
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: -0.69% Traditional cash on cash: 0.47% Airbnb Rental Income: $2753 Traditional Rental Income: $4254 Airbnb ROI: -0.69% 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.	$799,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.74% Airbnb Rental Income: $2210 Traditional Rental Income: $3367 Airbnb ROI: 0.44% Traditional ROI: 2.74%
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: $2753 Traditional Rental Income: $3600 Airbnb ROI: 0.3% Traditional ROI: 1.57%
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: 0.98% Traditional cash on cash: 2.86% Airbnb Rental Income: $2753 Traditional Rental Income: $3590 Airbnb ROI: 0.98% 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: -0.21% Traditional cash on cash: 1.95% Airbnb Rental Income: $2753 Traditional Rental Income: $5457 Airbnb ROI: -0.21% 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.	$899,900	Airbnb cash on cash: 0.48% Traditional cash on cash: 2.42% Airbnb Rental Income: $2210 Traditional Rental Income: $3277 Airbnb ROI: 0.48% Traditional ROI: 2.42%
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: -0.33% Traditional cash on cash: 2.03% Airbnb Rental Income: $1749 Traditional Rental Income: $5309 Airbnb ROI: -0.33% 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.	$875,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.24% Airbnb Rental Income: $2700 Traditional Rental Income: $4155 Airbnb ROI: 0.67% Traditional ROI: 3.24%
20 Bantry Lane Brewster, MA This lovely 3-bdrm home is just 2/10 mile to the Bay and the gorgeous, private, associatio...	3 beds \| 3 baths \| 2,098 sq.ft.	$1,900,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.51% Airbnb Rental Income: $2210 Traditional Rental Income: $3689 Airbnb ROI: -0.65% Traditional ROI: 0.51%
2926 Main Street Brewster, MA Mixed Use business with Walkout Apartment just south of 6A in Historic Brewster. Offered f...	2 beds \| 2 baths \| 2,160 sq.ft.	$765,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.82% Airbnb Rental Income: $1749 Traditional Rental Income: $3072 Airbnb ROI: 0.29% Traditional ROI: 2.82%
55 Bayview Drive Brewster, MA This luxurious, classic New England Cape-style home by Eastward Companies is one of a new ...	4 beds \| 6 baths \| 4,250 sq.ft.	$2,400,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 1.57% Airbnb Rental Income: $2753 Traditional Rental Income: $8550 Airbnb ROI: -1.32% Traditional ROI: 1.57%
206 Landing Drive Brewster, MA This beloved classic colonial occupies one of the best locations in Beechwood Landing Asso...	5 beds \| 4 baths \| 3,668 sq.ft.	$1,450,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.62% Airbnb Rental Income: $2700 Traditional Rental Income: $5638 Airbnb ROI: -0.04% Traditional ROI: 2.62%
210 Pine Bluff Road Brewster, MA Welcome to Brewster's Highland Association of Brewster , Inc a small peaceful neighborhood...	3 beds \| 2 baths \| 1,402 sq.ft.	$679,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 3.06% Airbnb Rental Income: $2210 Traditional Rental Income: $3130 Airbnb ROI: 0.74% Traditional ROI: 3.06%
47 Bay View Drive Brewster, MA This coastal contemporary cape style home by Eastward companies is one of a two lot Brewst...	4 beds \| 5 baths \| 4,212 sq.ft.	$2,400,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.81% Airbnb Rental Income: $2753 Traditional Rental Income: $6858 Airbnb ROI: -1.32% Traditional ROI: 0.81%
108 Wintergreen Lane Brewster, MA Serene 1.3+ acre West Brewster haven on a private way. Three bed, 2.5 bath home extensivel...	3 beds \| 3 baths \| 2,660 sq.ft.	$1,350,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.44% Airbnb Rental Income: $2210 Traditional Rental Income: $3869 Airbnb ROI: -0.32% Traditional ROI: 1.44%
988 Crowells Bog Road Brewster, MA Nature is the antidote at ''The Preserve at Sheep Pond Estates'' Sanctuary in your own 18....	3 beds \| 3 baths \| 2,427 sq.ft.	$1,425,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.32% Airbnb Rental Income: $2210 Traditional Rental Income: $3831 Airbnb ROI: -0.33% Traditional ROI: 1.32%
60 Sarah Maker Lane Brewster, MA Discover the opportunity to create your dream Cape Cod retreat in the heart of Brewster. I...	3 beds \| 2 baths \| 1,192 sq.ft.	$735,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 2.41% Airbnb Rental Income: $2210 Traditional Rental Income: $2861 Airbnb ROI: 0.64% Traditional ROI: 2.41%
160 Joe Long Road Brewster, MA Tucked away on a quiet dead-end road just steps from Nook Road, Nickerson State Park and b...	4 beds \| 2 baths \| 1,680 sq.ft.	$725,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.47% Airbnb Rental Income: $2753 Traditional Rental Income: $3518 Airbnb ROI: 1.38% Traditional ROI: 3.47%
61 & 0 Bonnie Doone Cartway Brewster, MA Opportunities like this simply do not come along. For the first time in many years, a prop...	3 beds \| 2 baths \| 1,900 sq.ft.	$1,500,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.3% Airbnb Rental Income: $2210 Traditional Rental Income: $3012 Airbnb ROI: -0.68% Traditional ROI: 0.3%
62 Bridle Path Road Brewster, MA Welcome home to this beautifully refreshed 3-bedroom, 1.5-bath ranch offering the perfect ...	3 beds \| 2 baths \| 1,152 sq.ft.	$569,900	Airbnb cash on cash: 1.31% Traditional cash on cash: 3.61% Airbnb Rental Income: $2210 Traditional Rental Income: $2875 Airbnb ROI: 1.31% Traditional ROI: 3.61%
49 Thousand Oaks Drive Brewster, MA Welcome to this exceptional, single-level retreat beautifully positioned on its lot in the...	3 beds \| 2 baths \| 1,680 sq.ft.	$750,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.81% Airbnb Rental Income: $2210 Traditional Rental Income: $3237 Airbnb ROI: 0.54% Traditional ROI: 2.81%
25 High Point Drive Brewster, MA A PRIVATE SANDY beach--one of the few on pristine, 187-acre Seymour Pond--sets this except...	5 beds \| 4 baths \| 2,927 sq.ft.	$2,100,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.34% Airbnb Rental Income: $2700 Traditional Rental Income: $5546 Airbnb ROI: -0.45% Traditional ROI: 1.34%
7 Valley Road Brewster, MA Perfectly situated between Greenland Pond and Long Pond, this beautifully maintained Colon...	4 beds \| 3 baths \| 3,043 sq.ft.	$1,299,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 1.9% Airbnb Rental Income: $2753 Traditional Rental Income: $4233 Airbnb ROI: 0.14% Traditional ROI: 1.9%
71 Compass Way Brewster, MA This spacious, immaculately kept property offers over an acre of land for the perfect blen...	4 beds \| 4 baths \| 3,426 sq.ft.	$1,425,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.65% Airbnb Rental Income: $2753 Traditional Rental Income: $5755 Airbnb ROI: -0.11% Traditional ROI: 2.65%
267 Alden Drive Brewster, MA Classic charm and modern conveniences make this spacious 2+ bdrm the perfect year round or...	2 beds \| 2 baths \| 1,638 sq.ft.	$675,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.97% Airbnb Rental Income: $1749 Traditional Rental Income: $2952 Airbnb ROI: 0.3% Traditional ROI: 2.97%
70 Doran Drive Brewster, MA Set in a private cul-de-sac in a highly desirable North of 6A location, this exceptional r...	3 beds \| 3 baths \| 2,812 sq.ft.	$1,150,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.09% Airbnb Rental Income: $2210 Traditional Rental Income: $4001 Airbnb ROI: -0.1% Traditional ROI: 2.09%

Your search for investment property begins and ends here

Single Family Homes for Sale in Brewster, MA

161 Beechtree Drive

Brewster, MA

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

$789,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2210

Traditional Rental Income: $3372

Airbnb ROI: 0.43%

Traditional ROI: 2.77%

130 Spring Lane

Brewster, MA

2 beds | 1 baths | 672 sq.ft.

$595,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1749

Traditional Rental Income: $2058

Airbnb ROI: 0.47%

Traditional ROI: 1.89%

235 Old Chatham Road

Brewster, MA

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

$459,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $2210

Traditional Rental Income: $4030

Airbnb ROI: 2.16%

Traditional ROI: 7.7%

5 Maple Lane

Brewster, MA

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

$715,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $2753

Traditional Rental Income: $3246

Airbnb ROI: 1.42%

Traditional ROI: 3.13%

232 Robbins Hill Road

Brewster, MA

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

$2,492,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $2210

Traditional Rental Income: $3349

Airbnb ROI: -0.97%

Traditional ROI: -0.24%

737 Thousand Oaks Drive

Brewster, MA

2 beds | 2 baths | 1,302 sq.ft.

$420,850

Airbnb cash on cash: 1.09%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $1749

Traditional Rental Income: $3490

Airbnb ROI: 1.09%

Traditional ROI: 6.72%

20 Spring Lane

Brewster, MA

3 beds | 2 baths | 1,652 sq.ft.

$965,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $2210

Traditional Rental Income: $3195

Airbnb ROI: 0.24%

Traditional ROI: 1.96%

410 Blueberry Pond Drive

Brewster, MA

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

$1,690,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $2210

Traditional Rental Income: $4000

Airbnb ROI: -0.36%