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
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.	$649,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 3.22% Airbnb Rental Income: $5569 Traditional Rental Income: $2973 Airbnb ROI: 5.66% Traditional ROI: 3.22%
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%
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%
92 Whiffletree Avenue Brewster, MA Discover refined coastal living in this brand-new 3,706 sq. ft. luxury home, nestled in th...	5 beds \| 4 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%
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%
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.	$1,199,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 1.72% Airbnb Rental Income: $6080 Traditional Rental Income: $3539 Airbnb ROI: 2.92% Traditional ROI: 1.72%
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.	$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%
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%
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.	$255,000	Airbnb cash on cash: 9.17% Traditional cash on cash: 5.43% Airbnb Rental Income: $3458 Traditional Rental Income: $1794 Airbnb ROI: 9.17% Traditional ROI: 5.43%
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%
120 Red Maple Road Brewster, MA Deerfield Estates - This traditional Colonial offers 4 bedrooms, 2.5 baths, and a private ...	4 beds \| 2 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%
16 Commons Way Brewster, MA Welcome to this ranch style home in the heart of Brewster. Just off Millstone Road, it off...	3 beds \| 2 baths \| 1,838 sq.ft.	$719,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.35% Airbnb Rental Income: $5569 Traditional Rental Income: $3366 Airbnb ROI: 4.97% Traditional ROI: 3.35%
102 Wildwood Road Brewster, MA This charming Cape-style home, set on a private .51 acre lot, offers a delightful blend of...	3 beds \| 2 baths \| 2,812 sq.ft.	$889,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.84% Airbnb Rental Income: $5569 Traditional Rental Income: $3792 Airbnb ROI: 3.63% Traditional ROI: 2.84%
25 Black Duck Cartway Brewster, MA Captivating grand waterfront Country Log home is nestled in the Punkhorn Parklands on 4.8 ...	3 beds \| 3 baths \| 3,250 sq.ft.	$2,349,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 0.48% Airbnb Rental Income: $5569 Traditional Rental Income: $4387 Airbnb ROI: 0.51% Traditional ROI: 0.48%
42 Landing Lane unit: 42 #42 Brewster, MA Sea Pines Condominiums! Association amenities in this well-run condo complex are included ...	2 beds \| 2 baths \| 1,516 sq.ft.	$630,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.12% Airbnb Rental Income: $3072 Traditional Rental Income: $2947 Airbnb ROI: 2.14% Traditional ROI: 3.12%
274 Commons Way Brewster, MA Thoughtfully Designed 3-Bedroom Home with Spacious Kitchen & Sunlit Living Room Welcome to...	3 beds \| 2 baths \| 2,306 sq.ft.	$849,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 1.8% Airbnb Rental Income: $5569 Traditional Rental Income: $2749 Airbnb ROI: 3.95% Traditional ROI: 1.8%
104 Howland Circle unit: 104 #104 Brewster, MA Wonderful, updated, fully furnished and B-style townhome in Howland Village with a great r...	2 beds \| 2 baths \| 1,063 sq.ft.	$575,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.08% Airbnb Rental Income: $3072 Traditional Rental Income: $2592 Airbnb ROI: 2.67% Traditional ROI: 3.08%
78 Eaton Lane unit: 78 #78 Brewster, MA Welcome to your serene second-level garden condominium, where modern elegance meets comfor...	2 beds \| 2 baths \| 935 sq.ft.	$399,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 6.34% Airbnb Rental Income: $3072 Traditional Rental Income: $3069 Airbnb ROI: 4.48% Traditional ROI: 6.34%
52 Bettys Lane Brewster, MA You can not beat this location in Brewster! Enjoy serene pond views of Black Pond and Long...	3 beds \| 2 baths \| 2,317 sq.ft.	$895,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 2.42% Airbnb Rental Income: $5569 Traditional Rental Income: $3392 Airbnb ROI: 3.7% Traditional ROI: 2.42%
23 Landing Lane unit: 23 #23 Brewster, MA Discover coastal living at its finest in this true one-bedroom condo tucked just off sceni...	1 beds \| 1 baths \| 942 sq.ft.	$459,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.71% Airbnb Rental Income: $3458 Traditional Rental Income: $1955 Airbnb ROI: 4.43% Traditional ROI: 2.71%
63 Trevor Lane unit: 63 #63 Brewster, MA Welcome to 63 Trevor Lane, a ''C'' style townhome in Ocean Edge Resort. This property has ...	2 beds \| 2 baths \| 1,032 sq.ft.	$482,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 4.03% Airbnb Rental Income: $3072 Traditional Rental Income: $2608 Airbnb ROI: 3.5% Traditional ROI: 4.03%
127 Eaton Lane unit: 127 #127 Brewster, MA Beautifully updated 1st floor condo at Ocean Edge, being offered fully furnished and ready...	2 beds \| 2 baths \| 935 sq.ft.	$454,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 4.03% Airbnb Rental Income: $3072 Traditional Rental Income: $2460 Airbnb ROI: 3.82% Traditional ROI: 4.03%
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.	$650,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.78% Airbnb Rental Income: $3072 Traditional Rental Income: $2714 Airbnb ROI: 2.22% Traditional ROI: 2.78%
77 Hazel Lane Brewster, MA Tucked along a quiet lane in desirable Brewster, this expansive Colonial-style home offers...	4 beds \| 4 baths \| 3,064 sq.ft.	$999,500	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.67% Airbnb Rental Income: $6080 Traditional Rental Income: $5134 Airbnb ROI: 3.39% Traditional ROI: 3.67%
184 Barons Way Brewster, MA This charming four-bedroom, two-bath home offers exceptional flexibility with two bedrooms...	4 beds \| 2 baths \| 2,252 sq.ft.	$793,900	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.04% Airbnb Rental Income: $6080 Traditional Rental Income: $3510 Airbnb ROI: 4.89% Traditional ROI: 3.04%
87 N Pond Drive Brewster, MA Set on the peaceful shores of Blueberry Pond, this private pond front retreat offers rare ...	4 beds \| 4 baths \| 2,481 sq.ft.	$1,649,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 1.96% Airbnb Rental Income: $6080 Traditional Rental Income: $5305 Airbnb ROI: 1.68% Traditional ROI: 1.96%
14 Howland Circle unit: 14 #14 Brewster, MA Welcome to this inviting A-style townhome at Ocean Edge offering two bedrooms, two baths, ...	2 beds \| 2 baths \| 1,164 sq.ft.	$585,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 3.07% Airbnb Rental Income: $3072 Traditional Rental Income: $2647 Airbnb ROI: 2.57% Traditional ROI: 3.07%

Real Estate investment in Brewster, MA

There are 28 properties for sale in the city of Brewster . The median list price in Brewster is $719,000 and the average price per square foot is $417. In February 2026, the average monthly cash on cash return in Brewster is 3.00%. The average monthly rental income in Brewster is $3,159.

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

There are 28 investment properties available for sale in Brewster.

In 2026, 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

728 Great Fields Road

Brewster, MA

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

$649,000

Airbnb cash on cash: 5.66%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $5569

Traditional Rental Income: $2973

Airbnb ROI: 5.66%

Traditional ROI: 3.22%

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%

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%

92 Whiffletree Avenue

Brewster, MA

5 beds | 4 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%

737 Thousand Oaks Drive

Brewster, MA

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%

398 Lund Farm Way

Brewster, MA

4 beds | 3 baths | 2,448 sq.ft.

$1,199,000

Airbnb cash on cash: 2.92%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $6080

Traditional Rental Income: $3539

Airbnb ROI: 2.92%

Traditional ROI: 1.72%

20 Spring Lane

Brewster, MA

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%

958 Long Pond Road

Brewster, MA

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%