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.

W Wheatfield Twp Investment Property for Sale in Brewster, MA

Search for W Wheatfield Twp Investment Property for Sale in Brewster, Massachusetts. Browse all of Mashvisor’s W Wheatfield Twp Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 38 W Wheatfield Twp Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
37 Autumn Court Brewster, MA This spacious Cape Cod home offering 4 bedrooms, 3.5 baths, and over 3,400 sq ft of living...	4 beds \| 4 baths \| 3,406 sq.ft.	$1,098,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.65% Airbnb Rental Income: $6080 Traditional Rental Income: $5828 Airbnb ROI: 2.72% Traditional ROI: 3.65%
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%
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.	$950,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 2.11% Airbnb Rental Income: $5569 Traditional Rental Income: $3264 Airbnb ROI: 3.46% Traditional ROI: 2.11%
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: 3.48% Traditional cash on cash: 2.29% Airbnb Rental Income: $6080 Traditional Rental Income: $3775 Airbnb ROI: 3.48% Traditional ROI: 2.29%
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: 8.68% Traditional cash on cash: 7.7% Airbnb Rental Income: $5569 Traditional Rental Income: $4030 Airbnb ROI: 8.68% Traditional ROI: 7.7%
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: 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.	$1,129,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 1.84% Airbnb Rental Income: $6080 Traditional Rental Income: $3539 Airbnb ROI: 3.11% Traditional ROI: 1.84%
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 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.	$699,900	Airbnb cash on cash: 5.67% Traditional cash on cash: 4.02% Airbnb Rental Income: $6080 Traditional Rental Income: $3801 Airbnb ROI: 5.67% Traditional ROI: 4.02%
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: 3.62% Traditional cash on cash: 2.83% Airbnb Rental Income: $5569 Traditional Rental Income: $3792 Airbnb ROI: 3.62% 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: 2.49% Traditional cash on cash: 0.82% Airbnb Rental Income: $6486 Traditional Rental Income: $3116 Airbnb ROI: 2.49% 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: 1.52% Traditional cash on cash: 0.54% Airbnb Rental Income: $6080 Traditional Rental Income: $3327 Airbnb ROI: 1.52% Traditional ROI: 0.54%
274 Commons Way Brewster, MA Thoughtfully Designed 3-Bedroom Home with Spacious Kitchen & Sunlit Living Room Welcome to...	3 beds \| 3 baths \| 2,306 sq.ft.	$799,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 1.97% Airbnb Rental Income: $5569 Traditional Rental Income: $2749 Airbnb ROI: 4.26% Traditional ROI: 1.97%
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: 2.32% Traditional cash on cash: 2.91% Airbnb Rental Income: $3072 Traditional Rental Income: $2714 Airbnb ROI: 2.32% Traditional ROI: 2.91%
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%
103 Trevor Lane unit: 103 Brewster, MA Welcome to this beautifully updated 2 bedroom, 1.5 bath townhouse at Ocean Edge, offering ...	2 beds \| 2 baths \| 1,032 sq.ft.	$549,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 2.09% Airbnb Rental Income: $3072 Traditional Rental Income: $2593 Airbnb ROI: 1.65% Traditional ROI: 2.09%
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: 1.33% Traditional cash on cash: 1.01% Airbnb Rental Income: $6080 Traditional Rental Income: $4347 Airbnb ROI: 1.33% 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.	$2,430,000	Airbnb cash on cash: -0.1% Traditional cash on cash: -0.09% Airbnb Rental Income: $6080 Traditional Rental Income: $4908 Airbnb ROI: -0.1% Traditional ROI: -0.09%
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: 2.78% Traditional cash on cash: 2.91% Airbnb Rental Income: $5569 Traditional Rental Income: $4591 Airbnb ROI: 2.78% 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: 2.72% Traditional cash on cash: 2.27% Airbnb Rental Income: $5569 Traditional Rental Income: $4001 Airbnb ROI: 2.72% Traditional ROI: 2.27%
18 Juniper Circle unit: 18 Brewster, MA Professional photos upload by 3/13 afternoon. Beautifully renovated turnkey coastal retrea...	2 beds \| 2 baths \| 2,184 sq.ft.	$1,249,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -1.26% Airbnb Rental Income: $3072 Traditional Rental Income: $1746 Airbnb ROI: -0.72% Traditional ROI: -1.26%
88 Woodview Drive unit: 88-H Brewster, MA A beautifully updated end unit that perfectly combines modern comfort with unbeatable conv...	2 beds \| 2 baths \| 1,297 sq.ft.	$495,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 2.86% Airbnb Rental Income: $3072 Traditional Rental Income: $2755 Airbnb ROI: 2.03% Traditional ROI: 2.86%
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: 4.02% Traditional cash on cash: 2.56% Airbnb Rental Income: $5569 Traditional Rental Income: $3318 Airbnb ROI: 4.02% Traditional ROI: 2.56%
81 Fletcher Lane unit: H Brewster, MA Beautifully transformed main-level, no-stairs 1-bedroom, 1-bath condo in the highly desira...	1 beds \| 1 baths \| 579 sq.ft.	$329,000	Airbnb cash on cash: 6.81% Traditional cash on cash: 4.01% Airbnb Rental Income: $3458 Traditional Rental Income: $1825 Airbnb ROI: 6.81% Traditional ROI: 4.01%
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.	$610,000	Airbnb cash on cash: 6.1% Traditional cash on cash: 3.64% Airbnb Rental Income: $5569 Traditional Rental Income: $3055 Airbnb ROI: 6.1% Traditional ROI: 3.64%
48 Middlecott Lane unit: 48 Brewster, MA Welcome to this lovely loft-style patio home in the sought-after Middlecott Village. Thoug...	2 beds \| 2 baths \| 1,190 sq.ft.	$659,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 1.1% Airbnb Rental Income: $3072 Traditional Rental Income: $1746 Airbnb ROI: 2.11% Traditional ROI: 1.1%
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: 0.06% Airbnb Rental Income: $3072 Traditional Rental Income: $1746 Airbnb ROI: 0.68% Traditional ROI: 0.06%
62 Fletcher Lane unit: 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: 6.87% Traditional cash on cash: 3.78% Airbnb Rental Income: $3458 Traditional Rental Income: $1736 Airbnb ROI: 6.87% Traditional ROI: 3.78%
62 Fletcher Lane unit: 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: 6.4% Traditional cash on cash: 3.49% Airbnb Rental Income: $3458 Traditional Rental Income: $1736 Airbnb ROI: 6.4% Traditional ROI: 3.49%
81 Fletcher Lane unit: 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: 6.7% Traditional cash on cash: 3.95% Airbnb Rental Income: $3458 Traditional Rental Income: $1825 Airbnb ROI: 6.7% Traditional ROI: 3.95%
100 Fletcher Lane unit: 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: 7.82% Traditional cash on cash: 4.7% Airbnb Rental Income: $3458 Traditional Rental Income: $1825 Airbnb ROI: 7.82% Traditional ROI: 4.7%
9 Cockle Way unit: 9 Brewster, MA Live the Cape Cod lifestyle you've always imagined--without compromise--in Sears Point, Br...	2 beds \| 2 baths \| 1,914 sq.ft.	$1,249,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.06% Airbnb Rental Income: $3072 Traditional Rental Income: $3028 Airbnb ROI: 0.49% Traditional ROI: 1.06%
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: 3.44% Traditional cash on cash: 1.75% Airbnb Rental Income: $3458 Traditional Rental Income: $1825 Airbnb ROI: 3.44% Traditional ROI: 1.75%
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: 5.38% Traditional cash on cash: 3.09% Airbnb Rental Income: $5569 Traditional Rental Income: $3010 Airbnb ROI: 5.38% Traditional ROI: 3.09%

Your search for investment property begins and ends here

W Wheatfield Twp Investment Property for Sale in Brewster, MA

37 Autumn Court

Brewster, MA

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

$1,098,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $6080

Traditional Rental Income: $5828

Airbnb ROI: 2.72%

Traditional ROI: 3.65%

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%

309 Great Fields Road

Brewster, MA

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

$950,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5569

Traditional Rental Income: $3264

Airbnb ROI: 3.46%

Traditional ROI: 2.11%

117 A P Newcomb Road

Brewster, MA

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

$995,000

Airbnb cash on cash: 3.48%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $6080

Traditional Rental Income: $3775

Airbnb ROI: 3.48%

Traditional ROI: 2.29%

235 Old Chatham Road

Brewster, MA

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

$459,000

Airbnb cash on cash: 8.68%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $5569

Traditional Rental Income: $4030

Airbnb ROI: 8.68%

Traditional ROI: 7.7%

92 Whiffletree Avenue

Brewster, MA

5 beds | 5 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.

$1,129,000

Airbnb cash on cash: 3.11%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $6080

Traditional Rental Income: $3539

Airbnb ROI: 3.11%