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: 0.95% Traditional cash on cash: 4.49% Airbnb Rental Income: $1539 Traditional Rental Income: $2502 Airbnb ROI: 0.95% 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: -1.2% Traditional cash on cash: 0.47% Airbnb Rental Income: $1539 Traditional Rental Income: $3039 Airbnb ROI: -1.2% Traditional ROI: 0.47%
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: 0.34% Traditional cash on cash: 2.77% Airbnb Rental Income: $2129 Traditional Rental Income: $3372 Airbnb ROI: 0.34% Traditional ROI: 2.77%
102 Fletcher Lane #N Brewster, MA Stunningly renovated and filled with natural light, this Ocean Edge condo is truly move-in...	1 beds \| 1 baths \| 589 sq.ft.	$350,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.63% Airbnb Rental Income: $1273 Traditional Rental Income: $1782 Airbnb ROI: 0.86% Traditional ROI: 3.63%
130 Spring Lane Brewster, MA Just in time for Summer 2026! Desirable north of Rte 6A location and easy stroll to 3 Bay ...	2 beds \| 1 baths \| 672 sq.ft.	$595,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.89% Airbnb Rental Income: $1539 Traditional Rental Income: $2058 Airbnb ROI: 0.16% Traditional ROI: 1.89%
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: 0.28% Traditional cash on cash: 2.29% Airbnb Rental Income: $2129 Traditional Rental Income: $3264 Airbnb ROI: 0.28% 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: 0.5% Traditional cash on cash: 2.81% Airbnb Rental Income: $2129 Traditional Rental Income: $3302 Airbnb ROI: 0.5% 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: 2.01% Traditional cash on cash: 7.7% Airbnb Rental Income: $2129 Traditional Rental Income: $4030 Airbnb ROI: 2.01% 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.	$735,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.02% Airbnb Rental Income: $2377 Traditional Rental Income: $3246 Airbnb ROI: 0.9% Traditional ROI: 3.02%
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: -1.14% Traditional cash on cash: 0.55% Airbnb Rental Income: $2856 Traditional Rental Income: $5488 Airbnb ROI: -1.14% 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% Traditional cash on cash: -0.24% Airbnb Rental Income: $2129 Traditional Rental Income: $3349 Airbnb ROI: -1% 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: 0.65% Traditional cash on cash: 6.72% Airbnb Rental Income: $1539 Traditional Rental Income: $3490 Airbnb ROI: 0.65% 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: 0.16% Traditional cash on cash: 1.96% Airbnb Rental Income: $2129 Traditional Rental Income: $3195 Airbnb ROI: 0.16% 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: -0.4% Traditional cash on cash: 1.14% Airbnb Rental Income: $2129 Traditional Rental Income: $4000 Airbnb ROI: -0.4% 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% Traditional cash on cash: 4.19% Airbnb Rental Income: $2377 Traditional Rental Income: $3801 Airbnb ROI: 1% 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: -0.42% Traditional cash on cash: 0.58% Airbnb Rental Income: $2377 Traditional Rental Income: $3327 Airbnb ROI: -0.42% Traditional ROI: 0.58%
Ridgewood Drive Brewster, MA Gracing a knoll above charming and historic Rt 6A on exclusive Ridgewood Drive (Map 26-58)...	4 beds \| 4 baths \| 2,778 sq.ft.	$2,330,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 0% Airbnb Rental Income: $2377 Traditional Rental Income: $4908 Airbnb ROI: -1.44% Traditional ROI: 0%
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: 1.1% Traditional cash on cash: 3.73% Airbnb Rental Income: $2129 Traditional Rental Income: $3055 Airbnb ROI: 1.1% 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: 0.45% Traditional cash on cash: 2.88% Airbnb Rental Income: $2129 Traditional Rental Income: $3398 Airbnb ROI: 0.45% 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: 0.3% Traditional cash on cash: 3.05% Airbnb Rental Income: $1539 Traditional Rental Income: $2596 Airbnb ROI: 0.3% Traditional ROI: 3.05%
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: 0.43% Traditional cash on cash: 2.83% Airbnb Rental Income: $2129 Traditional Rental Income: $3295 Airbnb ROI: 0.43% Traditional ROI: 2.83%
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: 0.46% Traditional cash on cash: 3.72% Airbnb Rental Income: $1539 Traditional Rental Income: $2615 Airbnb ROI: 0.46% Traditional ROI: 3.72%
101 Fletcher Lane #L Brewster, MA Step into effortless one-level living in this beautifully renovated first-floor condo at s...	1 beds \| 1 baths \| 589 sq.ft.	$315,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 4.04% Airbnb Rental Income: $1273 Traditional Rental Income: $1746 Airbnb ROI: 1.09% Traditional ROI: 4.04%
102 Fletcher Lane #H 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.	$355,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.46% Airbnb Rental Income: $1273 Traditional Rental Income: $1745 Airbnb ROI: 0.84% Traditional ROI: 3.46%
81 Fletcher Lane #I Brewster, MA Sought after Corner Unit with one-level living in this beautifully renovated first-floor c...	1 beds \| 1 baths \| 579 sq.ft.	$325,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.81% Airbnb Rental Income: $1273 Traditional Rental Income: $1745 Airbnb ROI: 0.96% Traditional ROI: 3.81%
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: -0.85% Traditional cash on cash: 0.47% Airbnb Rental Income: $2377 Traditional Rental Income: $4254 Airbnb ROI: -0.85% Traditional ROI: 0.47%
81 Woodview Drive #81 Brewster, MA Light filled and inviting, this 2 bedroom, 1.5 bath townhouse style condo in desirable Oak...	2 beds \| 2 baths \| 1,296 sq.ft.	$419,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 5.07% Airbnb Rental Income: $1539 Traditional Rental Income: $2771 Airbnb ROI: 0.8% Traditional ROI: 5.07%
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: 0.28% Traditional cash on cash: 2.53% Airbnb Rental Income: $2129 Traditional Rental Income: $3367 Airbnb ROI: 0.28% Traditional ROI: 2.53%
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: 0.04% Traditional cash on cash: 1.57% Airbnb Rental Income: $2377 Traditional Rental Income: $3600 Airbnb ROI: 0.04% Traditional ROI: 1.57%
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: 0.56% Traditional cash on cash: 3.17% Airbnb Rental Income: $2129 Traditional Rental Income: $3405 Airbnb ROI: 0.56% Traditional ROI: 3.17%
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: 0.58% Traditional cash on cash: 2.86% Airbnb Rental Income: $2377 Traditional Rental Income: $3590 Airbnb ROI: 0.58% 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: -0.41% Traditional cash on cash: 1.95% Airbnb Rental Income: $2377 Traditional Rental Income: $5457 Airbnb ROI: -0.41% 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: 0.4% Traditional cash on cash: 2.42% Airbnb Rental Income: $2129 Traditional Rental Income: $3277 Airbnb ROI: 0.4% Traditional ROI: 2.42%
100 Fletcher Lane #G 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: 1.27% Traditional cash on cash: 4.42% Airbnb Rental Income: $1273 Traditional Rental Income: $1748 Airbnb ROI: 1.27% Traditional ROI: 4.42%
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: -0.43% Traditional cash on cash: 2.03% Airbnb Rental Income: $1539 Traditional Rental Income: $5309 Airbnb ROI: -0.43% Traditional ROI: 2.03%
27 Billington Lane #27 Brewster, MA Welcome to 27 Billington Lane at Ocean Edge! Discover the ease of coastal living in this c...	2 beds \| 2 baths \| 1,032 sq.ft.	$525,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.6% Airbnb Rental Income: $1539 Traditional Rental Income: $2606 Airbnb ROI: 0.52% Traditional ROI: 3.6%
77 Chilton Lane #77 Brewster, MA Enjoy views of Widger Hole Pond from the deck of this 2 bedroom, 2 bath second-floor condo...	2 beds \| 2 baths \| 935 sq.ft.	$429,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.67% Airbnb Rental Income: $1539 Traditional Rental Income: $2619 Airbnb ROI: 0.88% Traditional ROI: 4.67%
109 Eaton Lane #109 Brewster, MA Enjoy peaceful golf course views from this 2 bedroom, 2 bath second-floor end unit at Ocea...	2 beds \| 2 baths \| 948 sq.ft.	$409,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 4.63% Airbnb Rental Income: $1539 Traditional Rental Income: $2505 Airbnb ROI: 0.95% Traditional ROI: 4.63%
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: 0.83% Traditional cash on cash: 3.24% Airbnb Rental Income: $2856 Traditional Rental Income: $4155 Airbnb ROI: 0.83% 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: -0.69% Traditional cash on cash: 0.51% Airbnb Rental Income: $2129 Traditional Rental Income: $3689 Airbnb ROI: -0.69% Traditional ROI: 0.51%

Real Estate investment in Brewster, MA

There are 60 properties for sale in the city of Brewster . The median list price in Brewster is $589,695 and the average price per square foot is $322. In June 2026, the average monthly cash on cash return in Brewster is 3.00%. The average monthly rental income in Brewster is $3,286.

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

There are 60 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 $2,129.

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: 0.95%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $1539

Traditional Rental Income: $2502

Airbnb ROI: 0.95%

Traditional ROI: 4.49%

9 Cockle Way

Brewster, MA

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

$1,249,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $1539

Traditional Rental Income: $3039

Airbnb ROI: -1.2%

Traditional ROI: 0.47%

161 Beechtree Drive

Brewster, MA

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

$789,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2129

Traditional Rental Income: $3372

Airbnb ROI: 0.34%

Traditional ROI: 2.77%

102 Fletcher Lane #N

Brewster, MA

1 beds | 1 baths | 589 sq.ft.

$350,000

Airbnb cash on cash: 0.86%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $1273

Traditional Rental Income: $1782

Airbnb ROI: 0.86%

Traditional ROI: 3.63%

130 Spring Lane

Brewster, MA

2 beds | 1 baths | 672 sq.ft.

$595,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1539

Traditional Rental Income: $2058

Airbnb ROI: 0.16%

Traditional ROI: 1.89%

309 Great Fields Road

Brewster, MA

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

$899,000

Airbnb cash on cash: 0.28%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2129

Traditional Rental Income: $3264

Airbnb ROI: 0.28%

Traditional ROI: 2.29%

62 Maple Lane

Brewster, MA

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

$799,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $2129

Traditional Rental Income: $3302

Airbnb ROI: 0.5%

Traditional ROI: 2.81%

235 Old Chatham Road

Brewster, MA

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

$459,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $2129

Traditional Rental Income: $4030

Airbnb ROI: 2.01%