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
2019 Main St Brewster, MA 2019 Main St, Brewster, MA 02631 \| Single Family Residential	5 beds \| 5 baths \| 3,233 sq.ft.	$1,200,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.59% Airbnb Rental Income: $3059 Traditional Rental Income: $6579 Airbnb ROI: -0.19% Traditional ROI: 3.59%
52 Court Way Brewster, MA This end unit has great privacy and has been renovated from top to bottom. The Kitchen is ...	2 beds \| 1 baths \| 1,380 sq.ft.	$595,900	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.61% Airbnb Rental Income: $1987 Traditional Rental Income: $1746 Airbnb ROI: 0.1% Traditional ROI: 0.61%
37 Autumn Ct Brewster, MA Where life slows to the rhythm of nature, over 800 acres of protected Punkhorn Conservatio...	4 beds \| 3 baths \| 3,406 sq.ft.	$2,000,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.78% Airbnb Rental Income: $2753 Traditional Rental Income: $5828 Airbnb ROI: -0.22% Traditional ROI: 1.78%
3837-3839 Main St Brewster, MA Year round duplex located just 1.2 miles to Crosby Landing Beach. 4 bedrooms and 4 baths ...	4 beds \| 2 baths \| 2,188 sq.ft.	$799,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 1.92% Airbnb Rental Income: $2753 Traditional Rental Income: $2501 Airbnb ROI: 1.39% Traditional ROI: 1.92%
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: 0.61% Traditional cash on cash: 2.77% Airbnb Rental Income: $2366 Traditional Rental Income: $3372 Airbnb ROI: 0.61% Traditional ROI: 2.77%
33 Sandpiper Ln Brewster, MA A charming, move-in ready Cape home nestled on a spacious .43 acre lot in the heart of Bre...	3 beds \| 2 baths \| 1,372 sq.ft.	$799,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.48% Airbnb Rental Income: $2366 Traditional Rental Income: $3098 Airbnb ROI: 0.72% Traditional ROI: 2.48%
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: 1.56% Traditional cash on cash: 3.63% Airbnb Rental Income: $1551 Traditional Rental Income: $1782 Airbnb ROI: 1.56% Traditional ROI: 3.63%
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: 0.83% Traditional cash on cash: 1.89% Airbnb Rental Income: $1987 Traditional Rental Income: $2058 Airbnb ROI: 0.83% Traditional ROI: 1.89%
235 Old Chatham Rd 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: 2.47% Traditional cash on cash: 7.7% Airbnb Rental Income: $2366 Traditional Rental Income: $4030 Airbnb ROI: 2.47% Traditional ROI: 7.7%
147 Snow Rd Brewster, MA Immaculate Brewster beach house ready for new owners. Close to everything. Want to bike? D...	4 beds \| 3 baths \| 1,456 sq.ft.	$924,999	Airbnb cash on cash: 0.88% Traditional cash on cash: 1.8% Airbnb Rental Income: $2753 Traditional Rental Income: $2898 Airbnb ROI: 0.88% Traditional ROI: 1.8%
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 Rd 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: -0.77% Traditional cash on cash: -0.24% Airbnb Rental Income: $2753 Traditional Rental Income: $3349 Airbnb ROI: -0.77% 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: 1.59% Traditional cash on cash: 6.72% Airbnb Rental Income: $1987 Traditional Rental Income: $3490 Airbnb ROI: 1.59% 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: 0.38% Traditional cash on cash: 1.96% Airbnb Rental Income: $2366 Traditional Rental Income: $3195 Airbnb ROI: 0.38% Traditional ROI: 1.96%
410 Blueberry Pond Dr 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: -0.28% Traditional cash on cash: 1.14% Airbnb Rental Income: $2366 Traditional Rental Income: $4000 Airbnb ROI: -0.28% Traditional ROI: 1.14%
1580 Main St 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 Rd Brewster, MA Stunning Brewster Home! Just minutes from beaches and premier golf courses, this meticulou...	4 beds \| 3 baths \| 2,859 sq.ft.	$1,655,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.55% Airbnb Rental Income: $2753 Traditional Rental Income: $3327 Airbnb ROI: -0.25% Traditional ROI: 0.55%
0 Canoe Pond Dr Brewster, MA 0 Canoe Pond Dr, Brewster, MA 02631 \| Other	N/A beds \| N/A baths \| N/A	$375,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.06% Airbnb Rental Income: $1281 Traditional Rental Income: $1608 Airbnb ROI: -0.01% Traditional ROI: 2.06%
0 Ridgewood Dr Brewster, MA 0 Ridgewood Dr, Brewster, MA 02631 \| Single Family Residential	4 beds \| 3 baths \| 2,337 sq.ft.	$1,940,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.44% Airbnb Rental Income: $2753 Traditional Rental Income: $4890 Airbnb ROI: -1.11% Traditional ROI: 0.44%
0 Old Chatham Rd Brewster, MA 0 Old Chatham Rd. Rd, Brewster, MA 02631 \| Other	N/A beds \| N/A baths \| N/A	$309,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 2.25% Airbnb Rental Income: $1281 Traditional Rental Income: $1393 Airbnb ROI: 0.48% Traditional ROI: 2.25%
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%
58 Old Chatham Rd Brewster, MA 58 Old Chatham Rd, Brewster, MA 02631 \| Single Family Residential	2 beds \| 4 baths \| 2,955 sq.ft.	$1,479,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -1.02% Airbnb Rental Income: $1987 Traditional Rental Income: $1746 Airbnb ROI: -1.22% Traditional ROI: -1.02%
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.	$589,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 3.81% Airbnb Rental Income: $2366 Traditional Rental Income: $3055 Airbnb ROI: 1.5% Traditional ROI: 3.81%
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: 0.71% Traditional cash on cash: 2.88% Airbnb Rental Income: $2366 Traditional Rental Income: $3398 Airbnb ROI: 0.71% Traditional ROI: 2.88%
98 Leland Rd 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: 0.69% Traditional cash on cash: 2.81% Airbnb Rental Income: $2366 Traditional Rental Income: $3295 Airbnb ROI: 0.69% Traditional ROI: 2.81%
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: 1.26% Traditional cash on cash: 3.72% Airbnb Rental Income: $1987 Traditional Rental Income: $2615 Airbnb ROI: 1.26% 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: 1.87% Traditional cash on cash: 4.04% Airbnb Rental Income: $1551 Traditional Rental Income: $1746 Airbnb ROI: 1.87% Traditional ROI: 4.04%
102 Fletcher Ln #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: -0.56% Traditional cash on cash: 1.37% Airbnb Rental Income: $1551 Traditional Rental Income: $1745 Airbnb ROI: -0.56% Traditional ROI: 1.37%
81 Fletcher Ln #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: -0.56% Traditional cash on cash: 1.53% Airbnb Rental Income: $1551 Traditional Rental Income: $1745 Airbnb ROI: -0.56% Traditional ROI: 1.53%
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: 0.62% Traditional cash on cash: 2.74% Airbnb Rental Income: $2366 Traditional Rental Income: $3367 Airbnb ROI: 0.62% Traditional ROI: 2.74%
47 Flying Dragon Rd Brewster, MA Step into a timeless Cape Gambrel built by family for family as the perfect retreat for ma...	4 beds \| 1 baths \| 1,824 sq.ft.	$1,270,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.56% Airbnb Rental Income: $2753 Traditional Rental Income: $3600 Airbnb ROI: 0.29% Traditional ROI: 1.56%
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%
84 Alden Dr Brewster, MA Discover a rare opportunity to own a brand-new waterfront retreat in the heart of Brewster...	2 beds \| 3 baths \| 3,172 sq.ft.	$1,839,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.04% Airbnb Rental Income: $1987 Traditional Rental Income: $5309 Airbnb ROI: -0.21% Traditional ROI: 2.04%
27 Billington Ln #27 Brewster, MA Welcome to 27 Billington Lane at Ocean Edge! Discover the ease of coastal living in this c...	2 beds \| 1 baths \| 1,032 sq.ft.	$525,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.3% Airbnb Rental Income: $1987 Traditional Rental Income: $2606 Airbnb ROI: -0.02% Traditional ROI: 2.3%
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: 1.81% Traditional cash on cash: 4.67% Airbnb Rental Income: $1987 Traditional Rental Income: $2619 Airbnb ROI: 1.81% Traditional ROI: 4.67%

Real Estate investment in Brewster, MA

There are 80 properties for sale in the city of Brewster . The median list price in Brewster is $678,094 and the average price per square foot is $363. In August 2026, the average monthly cash on cash return in Brewster is 2.00%. The average monthly rental income in Brewster is $3,244.

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

There are 80 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 $2,366.

Your search for investment property begins and ends here

Investment Property for Sale in Brewster, MA

2019 Main St

Brewster, MA

5 beds | 5 baths | 3,233 sq.ft.

$1,200,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $3059

Traditional Rental Income: $6579

Airbnb ROI: -0.19%

Traditional ROI: 3.59%

52 Court Way

Brewster, MA

2 beds | 1 baths | 1,380 sq.ft.

$595,900

Airbnb cash on cash: 0.1%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1987

Traditional Rental Income: $1746

Airbnb ROI: 0.1%

Traditional ROI: 0.61%

37 Autumn Ct

Brewster, MA

4 beds | 3 baths | 3,406 sq.ft.

$2,000,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2753

Traditional Rental Income: $5828

Airbnb ROI: -0.22%

Traditional ROI: 1.78%

3837-3839 Main St

Brewster, MA

4 beds | 2 baths | 2,188 sq.ft.

$799,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $2753

Traditional Rental Income: $2501

Airbnb ROI: 1.39%

Traditional ROI: 1.92%

161 Beechtree Drive

Brewster, MA

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

$789,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2366

Traditional Rental Income: $3372

Airbnb ROI: 0.61%

Traditional ROI: 2.77%

33 Sandpiper Ln

Brewster, MA

3 beds | 2 baths | 1,372 sq.ft.

$799,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2366

Traditional Rental Income: $3098

Airbnb ROI: 0.72%

Traditional ROI: 2.48%

102 Fletcher Lane #N

Brewster, MA

1 beds | 1 baths | 589 sq.ft.

$350,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $1551

Traditional Rental Income: $1782

Airbnb ROI: 1.56%

Traditional ROI: 3.63%

130 Spring Lane

Brewster, MA

2 beds | 1 baths | 672 sq.ft.

$595,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1987

Traditional Rental Income: $2058

Airbnb ROI: 0.83%