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
11 Chilton Lane #11 Brewster, MA Enjoy coastal living in this thoughtfully updated Ocean Edge condo, ready for summer enjoy...	2 beds \| 2 baths \| 935 sq.ft.	$425,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.49% Airbnb Rental Income: $1435 Traditional Rental Income: $2502 Airbnb ROI: 0.73% Traditional ROI: 4.49%
9 Cockle Way Brewster, MA SEARS POINT-only one property is now available-the wait is over to Live the Cape Cod lifes...	2 beds \| 2 baths \| 1,914 sq.ft.	$1,249,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.47% Airbnb Rental Income: $1435 Traditional Rental Income: $3039 Airbnb ROI: -1.28% Traditional ROI: 0.47%
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: -1.16% Traditional cash on cash: -0.23% Airbnb Rental Income: $1651 Traditional Rental Income: $3258 Airbnb ROI: -1.16% Traditional ROI: -0.23%
424 Holly Avenue Brewster, MA This beautiful 4-bedroom, 3-bath Cape-style home in sought-after Robinwood offers comfort,...	4 beds \| 3 baths \| 2,756 sq.ft.	$925,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.24% Airbnb Rental Income: $2044 Traditional Rental Income: $4197 Airbnb ROI: 0.13% Traditional ROI: 3.24%
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: -0.19% Traditional cash on cash: 2.29% Airbnb Rental Income: $1651 Traditional Rental Income: $3264 Airbnb ROI: -0.19% Traditional ROI: 2.29%
117 A P Newcomb Road Brewster, MA Looking for the perfect Cape Cod home for 2026...117 A P Newcomb Road has arrived! 4 Bedro...	4 beds \| 3 baths \| 2,436 sq.ft.	$995,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.29% Airbnb Rental Income: $2044 Traditional Rental Income: $3775 Airbnb ROI: -0.16% 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: -0.03% Traditional cash on cash: 2.81% Airbnb Rental Income: $1651 Traditional Rental Income: $3302 Airbnb ROI: -0.03% 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: 1.08% Traditional cash on cash: 7.7% Airbnb Rental Income: $1651 Traditional Rental Income: $4030 Airbnb ROI: 1.08% 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.	$759,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.89% Airbnb Rental Income: $2044 Traditional Rental Income: $3246 Airbnb ROI: 0.44% Traditional ROI: 2.89%
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.	$2,575,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.26% Airbnb Rental Income: $1651 Traditional Rental Income: $3349 Airbnb ROI: -1.17% Traditional ROI: -0.26%
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: 0.43% Traditional cash on cash: 6.72% Airbnb Rental Income: $1435 Traditional Rental Income: $3490 Airbnb ROI: 0.43% 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: -0.07% Traditional cash on cash: 1.91% Airbnb Rental Income: $2044 Traditional Rental Income: $3539 Airbnb ROI: -0.07% 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.	$1,750,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.06% Airbnb Rental Income: $1651 Traditional Rental Income: $4000 Airbnb ROI: -0.67% Traditional ROI: 1.06%
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: -0.13% Traditional cash on cash: 2.38% Airbnb Rental Income: $2044 Traditional Rental Income: $4137 Airbnb ROI: -0.13% Traditional ROI: 2.38%
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: 0.52% Traditional cash on cash: 4.02% Airbnb Rental Income: $2044 Traditional Rental Income: $3801 Airbnb ROI: 0.52% Traditional ROI: 4.02%
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: -0.32% Traditional cash on cash: 2.83% Airbnb Rental Income: $1651 Traditional Rental Income: $3792 Airbnb ROI: -0.32% Traditional ROI: 2.83%
53 Brier Lane Brewster, MA Turnkey Cape retreat just minutes from three of Brewster's eight beautiful beaches. This t...	5 beds \| 3 baths \| 2,889 sq.ft.	$1,350,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.82% Airbnb Rental Income: $2568 Traditional Rental Income: $3116 Airbnb ROI: -0.11% Traditional ROI: 0.82%
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: -0.61% Traditional cash on cash: 0.54% Airbnb Rental Income: $2044 Traditional Rental Income: $3327 Airbnb ROI: -0.61% Traditional ROI: 0.54%
11 Juniper Circle #11 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: -0.58% Traditional cash on cash: 1.61% Airbnb Rental Income: $1651 Traditional Rental Income: $3729 Airbnb ROI: -0.58% Traditional ROI: 1.61%
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% Traditional cash on cash: 2.91% Airbnb Rental Income: $1435 Traditional Rental Income: $2714 Airbnb ROI: 0% 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: -0.69% Traditional cash on cash: 1.01% Airbnb Rental Income: $2044 Traditional Rental Income: $4347 Airbnb ROI: -0.69% 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: -1.57% Traditional cash on cash: 0% Airbnb Rental Income: $2044 Traditional Rental Income: $4908 Airbnb ROI: -1.57% 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: -0.15% Traditional cash on cash: 2.91% Airbnb Rental Income: $1651 Traditional Rental Income: $4591 Airbnb ROI: -0.15% Traditional ROI: 2.91%
340 Greenland Pond Road Brewster, MA Deeded rights to private beaches on Long Pond and Greenland Pond await! This well-maintain...	3 beds \| 2 baths \| 1,968 sq.ft.	$1,095,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 1.82% Airbnb Rental Income: $1651 Traditional Rental Income: $3539 Airbnb ROI: -0.49% Traditional ROI: 1.82%
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: -0.18% Traditional cash on cash: 2.56% Airbnb Rental Income: $1651 Traditional Rental Income: $3318 Airbnb ROI: -0.18% 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: 0.39% Traditional cash on cash: 3.73% Airbnb Rental Income: $1651 Traditional Rental Income: $3055 Airbnb ROI: 0.39% Traditional ROI: 3.73%
13 Sand Dollar Lane Brewster, MA Never before on market, this happy home is finally ready to pass its keys to a new family....	2 beds \| 2 baths \| 2,437 sq.ft.	$1,075,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.29% Airbnb Rental Income: $1435 Traditional Rental Income: $2981 Airbnb ROI: -0.68% Traditional ROI: 1.29%
62 Fletcher Lane #N Brewster, MA Welcome to The Fletcher Condos within Ocean Edge Resort Community, one of Cape Cod's most ...	1 beds \| 1 baths \| 589 sq.ft.	$330,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.78% Airbnb Rental Income: $1097 Traditional Rental Income: $1736 Airbnb ROI: 0.52% Traditional ROI: 3.78%
62 Fletcher Lane #G Brewster, MA Beautifully updated and move-in ready, this top-floor 1-bed, 1-bath condo in the desirable...	1 beds \| 1 baths \| 579 sq.ft.	$350,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.49% Airbnb Rental Income: $1097 Traditional Rental Income: $1736 Airbnb ROI: 0.42% Traditional ROI: 3.49%
81 Fletcher Lane #C Brewster, MA Welcome to The Fletcher Condos within The Ocean Edge Resort Community, one of Cape Cod's m...	1 beds \| 1 baths \| 579 sq.ft.	$335,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.67% Airbnb Rental Income: $1097 Traditional Rental Income: $1736 Airbnb ROI: 0.46% Traditional ROI: 3.67%
100 Fletcher Lane #C Brewster, MA Welcome to The Fletcher Condos within Ocean Edge Resort Community, one of Cape Cod's most ...	1 beds \| 1 baths \| 579 sq.ft.	$295,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 4.39% Airbnb Rental Income: $1097 Traditional Rental Income: $1739 Airbnb ROI: 0.74% Traditional ROI: 4.39%
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: -0.39% Traditional cash on cash: 3.04% Airbnb Rental Income: $1097 Traditional Rental Income: $2484 Airbnb ROI: -0.39% Traditional ROI: 3.04%
296 Commons Way Brewster, MA Turn-key and sunny in Brewster! Highlights include a modern floor plan with soaring ceilin...	3 beds \| 2 baths \| 1,427 sq.ft.	$674,900	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.09% Airbnb Rental Income: $1651 Traditional Rental Income: $3010 Airbnb ROI: 0.2% Traditional ROI: 3.09%
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.	$849,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.65% Airbnb Rental Income: $1651 Traditional Rental Income: $3398 Airbnb ROI: -0.14% Traditional ROI: 2.65%
193 Yankee Drive Brewster, MA Easy 1-floor living in this charming, Cape-style ranch that combines comfort, convenience,...	2 beds \| 2 baths \| 1,205 sq.ft.	$650,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.75% Airbnb Rental Income: $1435 Traditional Rental Income: $2745 Airbnb ROI: -0.12% Traditional ROI: 2.75%
35 Leona Terrace Brewster, MA Prime location in Brewster! Close to the bike path, walk to Whitecaps Games plus close to ...	4 beds \| 3 baths \| 1,791 sq.ft.	$789,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.4% Airbnb Rental Income: $2044 Traditional Rental Income: $3765 Airbnb ROI: 0.34% Traditional ROI: 3.4%
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.	$615,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.85% Airbnb Rental Income: $1435 Traditional Rental Income: $2596 Airbnb ROI: 0.08% Traditional ROI: 2.85%
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: -0.16% Traditional cash on cash: 2.67% Airbnb Rental Income: $1651 Traditional Rental Income: $3295 Airbnb ROI: -0.16% Traditional ROI: 2.67%
210 Billington Lane #210 Brewster, MA Tucked away near the end of Billington Lane, this thoughtfully situated Ocean Edge condo o...	2 beds \| 2 baths \| 1,063 sq.ft.	$499,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.72% Airbnb Rental Income: $1435 Traditional Rental Income: $2615 Airbnb ROI: 0.28% Traditional ROI: 3.72%

Real Estate investment in Brewster, MA

There are 65 properties for sale in the city of Brewster . The median list price in Brewster is $842,250 and the average price per square foot is $468. In May 2026, the average monthly cash on cash return in Brewster is 3.00%. The average monthly rental income in Brewster is $3,302.

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

There are 65 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 $1,651.

Your search for investment property begins and ends here

Investment Property for Sale in Brewster, MA

11 Chilton Lane #11

Brewster, MA

2 beds | 2 baths | 935 sq.ft.

$425,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $1435

Traditional Rental Income: $2502

Airbnb ROI: 0.73%

Traditional ROI: 4.49%

9 Cockle Way

Brewster, MA

2 beds | 2 baths | 1,914 sq.ft.

$1,249,000

Airbnb cash on cash: -1.28%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $1435

Traditional Rental Income: $3039

Airbnb ROI: -1.28%

Traditional ROI: 0.47%

240 Robbins Hill Road

Brewster, MA

3 beds | 2 baths | 1,418 sq.ft.

$2,395,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $1651

Traditional Rental Income: $3258

Airbnb ROI: -1.16%

Traditional ROI: -0.23%

424 Holly Avenue

Brewster, MA

4 beds | 3 baths | 2,756 sq.ft.

$925,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $2044

Traditional Rental Income: $4197

Airbnb ROI: 0.13%

Traditional ROI: 3.24%

309 Great Fields Road

Brewster, MA

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

$899,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1651

Traditional Rental Income: $3264

Airbnb ROI: -0.19%

Traditional ROI: 2.29%

117 A P Newcomb Road

Brewster, MA

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

$995,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2044

Traditional Rental Income: $3775

Airbnb ROI: -0.16%

Traditional ROI: 2.29%

62 Maple Lane

Brewster, MA

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

$799,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $1651

Traditional Rental Income: $3302

Airbnb ROI: -0.03%

Traditional ROI: 2.81%

235 Old Chatham Road

Brewster, MA

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

$459,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $1651

Traditional Rental Income: $4030

Airbnb ROI: 1.08%