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
180 W H Besse Cartway Brewster, MA Long Pond Waterfront. This estate-sized 2.25 acre parcel with 121 feet of private sandy be...	5 beds \| 4 baths \| 3,058 sq.ft.	$2,175,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.72% Airbnb Rental Income: $5016 Traditional Rental Income: $4682 Airbnb ROI: 0.38% Traditional ROI: 0.72%
51 Chilton Lane Brewster, MA Welcome to your new peaceful retreat on Chilton Lane! This 2-bedroom, 2-bathroom condo is ...	2 beds \| 2 baths \| 935 sq.ft.	$384,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 3.23% Airbnb Rental Income: $3802 Traditional Rental Income: $2371 Airbnb ROI: 4.92% Traditional ROI: 3.23%
17 Chilton Lane Brewster, MA Welcome to this stunning 2-bedroom, 2-bath second-floor condo in the desirable Ocean Edge ...	2 beds \| 2 baths \| 935 sq.ft.	$450,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.85% Airbnb Rental Income: $3802 Traditional Rental Income: $2478 Airbnb ROI: 4.04% Traditional ROI: 2.85%
145 Wintergreen Lane Brewster, MA Spectacular location high above Upper Mill Pond boasting waterfront views as soon as you e...	3 beds \| 3 baths \| 2,912 sq.ft.	$1,445,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.44% Airbnb Rental Income: $4388 Traditional Rental Income: $4107 Airbnb ROI: 0.97% Traditional ROI: 1.44%
86 Stone Ridge Road Brewster, MA This peaceful retreat nestled at the end of a quiet side street and surrounded by conserva...	3 beds \| 2 baths \| 1,144 sq.ft.	$699,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 2.76% Airbnb Rental Income: $4388 Traditional Rental Income: $2860 Airbnb ROI: 3.69% Traditional ROI: 2.76%
1 Howland Circle Brewster, MA Fabulous location! This end-unit, sunny and bright B-Style condo offers 3 mini-split units...	2 beds \| 2 baths \| 1,063 sq.ft.	$499,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 2.18% Airbnb Rental Income: $3802 Traditional Rental Income: $2428 Airbnb ROI: 3.36% Traditional ROI: 2.18%
243 Commons Way Brewster, MA Welcome Home ... to this delightful 2-bedroom, 1-bath Cape, perfectly situated in a vibran...	2 beds \| 1 baths \| 1,152 sq.ft.	$585,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.58% Airbnb Rental Income: $3802 Traditional Rental Income: $2316 Airbnb ROI: 3.79% Traditional ROI: 2.58%
170 Billington Lane Brewster, MA Welcome to this charming B-Style townhouse in the sought-after Ocean Edge Resort. Featurin...	2 beds \| 2 baths \| 1,063 sq.ft.	$489,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 2.59% Airbnb Rental Income: $3802 Traditional Rental Income: $2470 Airbnb ROI: 3.71% Traditional ROI: 2.59%
981 Long Pond Road Brewster, MA Brewster's Finest! Nestled deep off the road on 1.38 acres sits this abode which abuts ove...	3 beds \| 3 baths \| 1,264 sq.ft.	$860,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.2% Airbnb Rental Income: $4388 Traditional Rental Income: $3083 Airbnb ROI: 2.68% Traditional ROI: 2.2%
100 Fletcher Lane #B Brewster, MA Ocean Edge year round unit-resort living in a beautiful setting. Attention golfers! Tastef...	1 beds \| 1 baths \| 579 sq.ft.	$315,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 2.59% Airbnb Rental Income: $4031 Traditional Rental Income: $1809 Airbnb ROI: 7.19% Traditional ROI: 2.59%
103 Trevor Lane Brewster, MA This charming 2-bedroom, 1.5-bath townhome is located in the desirable Trevor Villages enc...	2 beds \| 2 baths \| 1,032 sq.ft.	$549,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.13% Airbnb Rental Income: $3802 Traditional Rental Income: $2528 Airbnb ROI: 3.01% Traditional ROI: 2.13%
229 Great Fields Road Brewster, MA Welcome to your dream home, a stunning oasis that perfectly blends comfort and luxury. Thi...	4 beds \| 5 baths \| 5,374 sq.ft.	$2,590,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 0.8% Airbnb Rental Income: $6993 Traditional Rental Income: $5373 Airbnb ROI: 0.91% Traditional ROI: 0.8%
62c Fletcher Lane Brewster, MA This freshly painted, bright and south facing top level Fletcher condo features many updat...	1 beds \| 1 baths \| 579 sq.ft.	$292,000	Airbnb cash on cash: 8.38% Traditional cash on cash: 2.94% Airbnb Rental Income: $4031 Traditional Rental Income: $1672 Airbnb ROI: 8.38% Traditional ROI: 2.94%
92 Whiffletree Avenue Brewster, MA New construction in a lovely West Brewster setting with filtered pond views and nature bou...	5 beds \| 5 baths \| 3,706 sq.ft.	$2,395,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.2% Airbnb Rental Income: $5016 Traditional Rental Income: $5488 Airbnb ROI: -0.47% Traditional ROI: 0.2%
88 Whiffletree Avenue Brewster, MA New construction in a lovely West Brewster setting with filtered pond views and nature bou...	5 beds \| 5 baths \| 3,891 sq.ft.	$2,559,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.05% Airbnb Rental Income: $5016 Traditional Rental Income: $5495 Airbnb ROI: -0.58% Traditional ROI: 0.05%
2750 Main Street Brewster, MA Welcome to 2750 Main St, a charming residence nestled in the heart of Brewster, a sought-a...	5 beds \| 2 baths \| 2,707 sq.ft.	$4,200,000	Airbnb cash on cash: -0.16% Traditional cash on cash: -0.19% Airbnb Rental Income: $5016 Traditional Rental Income: $3882 Airbnb ROI: -0.16% Traditional ROI: -0.19%
120 Alden Drive Brewster, MA This stunning, fully renovated Brewster home, located on a quiet road just steps from hist...	3 beds \| 4 baths \| 2,786 sq.ft.	$1,399,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.11% Airbnb Rental Income: $4388 Traditional Rental Income: $3402 Airbnb ROI: 1.16% Traditional ROI: 1.11%
15 Vesper Pond Drive Brewster, MA This new luxury Eastward Home currently under construction enjoys a private, natural setti...	4 beds \| 5 baths \| 3,850 sq.ft.	$2,400,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 0.18% Airbnb Rental Income: $6993 Traditional Rental Income: $5436 Airbnb ROI: 0.27% Traditional ROI: 0.18%
79 Freemans Way Brewster, MA So many possibilities for expansion on this 1.48-acre level lot! With a custom 6-bedroom s...	4 beds \| 2 baths \| 1,956 sq.ft.	$775,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 2.97% Airbnb Rental Income: $6993 Traditional Rental Income: $3411 Airbnb ROI: 6.05% Traditional ROI: 2.97%
22 Harmony Lane Brewster, MA Price improvement! Nestled in a serene setting, this 3 bedroom, 2 bath Cape ranch offers s...	3 beds \| 2 baths \| 1,192 sq.ft.	$689,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.12% Airbnb Rental Income: $4388 Traditional Rental Income: $3097 Airbnb ROI: 3.7% Traditional ROI: 3.12%
249 A P Newcomb Road Brewster, MA Opportunity! This charmer in West Brewster has so much to offer, including a fantastic loc...	3 beds \| 2 baths \| 1,393 sq.ft.	$599,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 3.74% Airbnb Rental Income: $4388 Traditional Rental Income: $3154 Airbnb ROI: 4.3% Traditional ROI: 3.74%
674 Great Fields Rd Road Brewster, MA Welcome to this classic Cape Cod home brimming with potential! Set on 1.53 picturesque acr...	2 beds \| 3 baths \| 1,916 sq.ft.	$674,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 3.1% Airbnb Rental Income: $3802 Traditional Rental Income: $3114 Airbnb ROI: 2.88% Traditional ROI: 3.1%
153 Tower Hill Circle Brewster, MA Spacious updated 4 bedroom 2 full bath Cape in quiet Brewster neighborhood less than 1/4 ...	4 beds \| 2 baths \| 1,764 sq.ft.	$728,888	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.31% Airbnb Rental Income: $6993 Traditional Rental Income: $3356 Airbnb ROI: 6.67% Traditional ROI: 3.31%
86 Spring Lane Brewster, MA Situated north of the historic Route 6A and just 0.8 miles from the serene Paines Creek Be...	3 beds \| 2 baths \| 1,512 sq.ft.	$850,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.32% Airbnb Rental Income: $4388 Traditional Rental Income: $3128 Airbnb ROI: 2.75% Traditional ROI: 2.32%
25 Beach Plum Lane Brewster, MA Welcome to this charming 2-bed, 1-bath ranch home, complete with a bonus room perfect for ...	2 beds \| 1 baths \| 1,032 sq.ft.	$599,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 3.17% Airbnb Rental Income: $3802 Traditional Rental Income: $2712 Airbnb ROI: 3.65% Traditional ROI: 3.17%
925 Crowells Bog Road Brewster, MA This well appointed, expanded cape is situated on the corner of Crowell's Bog and Newport ...	3 beds \| 2 baths \| 1,683 sq.ft.	$675,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 3.53% Airbnb Rental Income: $4388 Traditional Rental Income: $3390 Airbnb ROI: 3.66% Traditional ROI: 3.53%
44 Howland Circle Brewster, MA Your Ocean Edge escape awaits at 44 Howland Circle. This bright two-bedroom, two-full-bath...	2 beds \| 2 baths \| 1,063 sq.ft.	$529,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 2.52% Airbnb Rental Income: $3802 Traditional Rental Income: $2680 Airbnb ROI: 3.13% Traditional ROI: 2.52%
55 Leona Terrace Brewster, MA This lovingly maintained ranch is a testament to quality and care. Boasting beautiful oak ...	3 beds \| 2 baths \| 1,192 sq.ft.	$775,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.73% Airbnb Rental Income: $4388 Traditional Rental Income: $3126 Airbnb ROI: 3.21% Traditional ROI: 2.73%
60 Ocean Street Extension #9 Brewster, MA Revel in stunning and panoramic views of Cape Cod Bay and the Brewster flats from this Wat...	3 beds \| 2 baths \| 1,450 sq.ft.	$2,299,000	Airbnb cash on cash: -2.56% Traditional cash on cash: -2.61% Airbnb Rental Income: $4388 Traditional Rental Income: $3369 Airbnb ROI: -2.56% Traditional ROI: -2.61%
232 Robbins Hill Road Brewster, MA RARE OPPORTUNITY to own two homes on more than half an acre of private beachfront property...	3 beds \| 2 baths \| 1,502 sq.ft.	$2,999,900	Airbnb cash on cash: -0.29% Traditional cash on cash: -0.33% Airbnb Rental Income: $4388 Traditional Rental Income: $3349 Airbnb ROI: -0.29% Traditional ROI: -0.33%
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.	$443,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 6.4% Airbnb Rental Income: $3802 Traditional Rental Income: $3490 Airbnb ROI: 5.16% Traditional ROI: 6.4%
298 Cranview Road Brewster, MA Brand New Septic System. If you like quiet and privacy, off the road, this is the locatio...	3 beds \| 3 baths \| 2,206 sq.ft.	$955,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 2.73% Airbnb Rental Income: $4388 Traditional Rental Income: $3908 Airbnb ROI: 2.24% Traditional ROI: 2.73%
84 Seamans Lane Brewster, MA Escape to tranquility in this charming 3-bedroom, 2-bath home nestled on a double lot tota...	3 beds \| 2 baths \| 1,512 sq.ft.	$799,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.73% Airbnb Rental Income: $4388 Traditional Rental Income: $3302 Airbnb ROI: 2.95% Traditional ROI: 2.73%
180 Lower Road Brewster, MA Fresh to the market in a magical Bayside, ''North of 6-A'', location. This sweet, Mid-Cent...	2 beds \| 2 baths \| 832 sq.ft.	$622,500	Airbnb cash on cash: 3.41% Traditional cash on cash: 2.68% Airbnb Rental Income: $3802 Traditional Rental Income: $2560 Airbnb ROI: 3.41% Traditional ROI: 2.68%
86 Eaton Lane Brewster, MA Ocean Edge is the ultimate in Cape resort style living. This one owner, 2 bedroom, 2 bath...	2 beds \| 2 baths \| 935 sq.ft.	$399,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 3.69% Airbnb Rental Income: $3802 Traditional Rental Income: $2477 Airbnb ROI: 5.03% Traditional ROI: 3.69%
2016 Main Street Brewster, MA Consider this bit of Old Cape Cod, in the heart of Brewster Village. ''The Homeport'' is o...	3 beds \| 2 baths \| 1,888 sq.ft.	$672,500	Airbnb cash on cash: 3.82% Traditional cash on cash: 4.28% Airbnb Rental Income: $4388 Traditional Rental Income: $3753 Airbnb ROI: 3.82% Traditional ROI: 4.28%
12 Woodview Drive Brewster, MA Welcome to Oakwood Village in Brewster! Townhouse condo with 2 bedrooms 1.5 baths end uni...	2 beds \| 2 baths \| 1,152 sq.ft.	$419,900	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.73% Airbnb Rental Income: $3802 Traditional Rental Income: $2665 Airbnb ROI: 4.53% Traditional ROI: 3.73%
76 Tracy Lane Brewster, MA Brewster Ease! Discover your dream retreat in this lovingly maintained Brewster home, perf...	3 beds \| 2 baths \| 1,568 sq.ft.	$750,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 2.69% Airbnb Rental Income: $4388 Traditional Rental Income: $3116 Airbnb ROI: 3.2% Traditional ROI: 2.69%
21 Ocean Street Brewster, MA MORE PHOTOS COMING! The wait for your cottage on ''The Landing'' in Brewster is over! Si...	3 beds \| 1 baths \| 816 sq.ft.	$1,225,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 0.48% Airbnb Rental Income: $4388 Traditional Rental Income: $2552 Airbnb ROI: 1.28% Traditional ROI: 0.48%
61 Puritan Drive Brewster, MA Discover the charm of Cape Cod living at 61 Puritan Drive in Brewster! This inviting ranch...	3 beds \| 1 baths \| 1,040 sq.ft.	$650,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.35% Airbnb Rental Income: $4388 Traditional Rental Income: $2446 Airbnb ROI: 4.03% Traditional ROI: 2.35%

Real Estate investment in Brewster, MA

There are 52 properties for sale in the city of Brewster . The median list price in Brewster is $673,700 and the average price per square foot is $408. In December 2024, the average monthly cash on cash return in Brewster is 3.00%. The average monthly rental income in Brewster is $3,090.

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

There are 52 investment properties available for sale in Brewster.

In 2024, 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 $4,388.

Your search for investment property begins and ends here

Investment Property for Sale in Brewster, MA

180 W H Besse Cartway

Brewster, MA

5 beds | 4 baths | 3,058 sq.ft.

$2,175,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $5016

Traditional Rental Income: $4682

Airbnb ROI: 0.38%

Traditional ROI: 0.72%

51 Chilton Lane

Brewster, MA

2 beds | 2 baths | 935 sq.ft.

$384,900

Airbnb cash on cash: 4.92%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $3802

Traditional Rental Income: $2371

Airbnb ROI: 4.92%

Traditional ROI: 3.23%

17 Chilton Lane

Brewster, MA

2 beds | 2 baths | 935 sq.ft.

$450,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3802

Traditional Rental Income: $2478

Airbnb ROI: 4.04%

Traditional ROI: 2.85%

145 Wintergreen Lane

Brewster, MA

3 beds | 3 baths | 2,912 sq.ft.

$1,445,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 1.44%

Airbnb Rental Income: $4388

Traditional Rental Income: $4107

Airbnb ROI: 0.97%

Traditional ROI: 1.44%

86 Stone Ridge Road

Brewster, MA

3 beds | 2 baths | 1,144 sq.ft.

$699,000

Airbnb cash on cash: 3.69%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $4388

Traditional Rental Income: $2860

Airbnb ROI: 3.69%

Traditional ROI: 2.76%

1 Howland Circle

Brewster, MA

2 beds | 2 baths | 1,063 sq.ft.

$499,000

Airbnb cash on cash: 3.36%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $3802

Traditional Rental Income: $2428

Airbnb ROI: 3.36%

Traditional ROI: 2.18%

243 Commons Way

Brewster, MA

2 beds | 1 baths | 1,152 sq.ft.

$585,000

Airbnb cash on cash: 3.79%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $3802

Traditional Rental Income: $2316

Airbnb ROI: 3.79%

Traditional ROI: 2.58%

170 Billington Lane

Brewster, MA

2 beds | 2 baths | 1,063 sq.ft.

$489,000

Airbnb cash on cash: 3.71%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $3802

Traditional Rental Income: $2470

Airbnb ROI: 3.71%