Real Estate Investment Properties for Sale in Osterville, MA

Looking for investment property in Osterville, MA with high ROI ?

Explore a variety of short-term homes & houses in Osterville, MA. Invest wisely with VRBO & Osterville, 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 Osterville, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
17 Avalon Circle Osterville, MA Welcome to Osterville, where timeless elegance meets Cape Cod's coastal charm! This beauti...	3 beds \| 2 baths \| 1,316 sq.ft.	$624,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.58% Airbnb Rental Income: $4575 Traditional Rental Income: $3012 Airbnb ROI: 4.63% Traditional ROI: 3.58%
17 Ebenezer Road Osterville, MA Great 1267 sq. ft. 3 bedroom, 2 bath Cape on large lot in Osterville. First floor bedroom ...	3 beds \| 2 baths \| 1,267 sq.ft.	$539,900	Airbnb cash on cash: 5.26% Traditional cash on cash: 3.95% Airbnb Rental Income: $4575 Traditional Rental Income: $2964 Airbnb ROI: 5.26% Traditional ROI: 3.95%
25 Oyster Way Osterville, MA Located within the private, gated golf community of Oyster Harbors, in the village of Oste...	5 beds \| 5 baths \| 7,157 sq.ft.	$10,450,000	Airbnb cash on cash: -1.14% Traditional cash on cash: -1.08% Airbnb Rental Income: $6393 Traditional Rental Income: $5670 Airbnb ROI: -1.14% Traditional ROI: -1.08%
38 Beach Plum Hill Road Osterville, MA Nestled in Osterville's coveted Seapuit enclave, this EB Norris-built estate spans over tw...	5 beds \| 5 baths \| 3,802 sq.ft.	$5,444,000	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.4% Airbnb Rental Income: $6393 Traditional Rental Income: $5583 Airbnb ROI: -0.49% Traditional ROI: -0.4%
168 Garrison Lane Osterville, MA Set on highly sought-after Garrison Lane, this extraordinary residence boasts one of the m...	5 beds \| 6 baths \| 7,565 sq.ft.	$9,995,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -0.92% Airbnb Rental Income: $6393 Traditional Rental Income: $6857 Airbnb ROI: -1.11% Traditional ROI: -0.92%
64 Bay Street Osterville, MA Designed by renowned architect Ivan Bereznicki for personal use, this elegant gambrel resi...	4 beds \| 5 baths \| 2,812 sq.ft.	$2,995,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.31% Airbnb Rental Income: $5495 Traditional Rental Income: $3662 Airbnb ROI: -0.05% Traditional ROI: -0.31%
44 Seapuit Road Osterville, MA Set on 3.4 acres and bordered by an additional 2.88 acres of protected land, this exceptio...	5 beds \| 5 baths \| 8,345 sq.ft.	$5,840,000	Airbnb cash on cash: -0.63% Traditional cash on cash: -0.56% Airbnb Rental Income: $6393 Traditional Rental Income: $5480 Airbnb ROI: -0.63% Traditional ROI: -0.56%
98 Bunker Hill Road Osterville, MA Experience the epitome of bayside living at 98 Bunker Hill Road, nestled in Osterville's d...	5 beds \| 5 baths \| 4,715 sq.ft.	$2,879,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.77% Airbnb Rental Income: $6393 Traditional Rental Income: $6626 Airbnb ROI: 0.21% Traditional ROI: 0.77%
71 Sand Point Osterville, MA Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coasta...	5 beds \| 6 baths \| 5,747 sq.ft.	$12,250,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.7% Airbnb Rental Income: $6393 Traditional Rental Income: $8910 Airbnb ROI: -1.03% Traditional ROI: -0.7%
245 North Bay Road Osterville, MA Designed by renowned architect Royal Barry Wills, this magnificent Oyster Harbors residenc...	5 beds \| 6 baths \| 4,637 sq.ft.	$5,895,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0% Airbnb Rental Income: $6393 Traditional Rental Income: $8283 Airbnb ROI: -0.57% Traditional ROI: 0%
39 Tower Hill Road unit: 1C #1C Osterville, MA Your perfect year-round retreat awaits! Nestled in the heart of charming Osterville villag...	2 beds \| 2 baths \| 1,131 sq.ft.	$579,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 2.06% Airbnb Rental Income: $4681 Traditional Rental Income: $2671 Airbnb ROI: 3.99% Traditional ROI: 2.06%
14 Indian Trail Osterville, MA Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigiou...	5 beds \| 5 baths \| 3,087 sq.ft.	$10,500,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.83% Airbnb Rental Income: $6393 Traditional Rental Income: $6635 Airbnb ROI: -0.99% Traditional ROI: -0.83%
24 Indigo Lane Osterville, MA Opportunity knocks in one of Osterville's most desirable neighborhoods! This spacious 4-be...	4 beds \| 4 baths \| 3,135 sq.ft.	$1,249,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 2.83% Airbnb Rental Income: $5495 Traditional Rental Income: $5247 Airbnb ROI: 2.09% Traditional ROI: 2.83%
35 Sharon Circle Osterville, MA Tucked away on a quiet cul-de-sac in the heart of Osterville Heights, this lovingly mainta...	3 beds \| 2 baths \| 1,196 sq.ft.	$689,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 2.79% Airbnb Rental Income: $4575 Traditional Rental Income: $2928 Airbnb ROI: 3.87% Traditional ROI: 2.79%
89 Swift Avenue Osterville, MA OPPORTUNITY AWAITS! This four bedroom, two bath ranch home offers incredible potential in ...	4 beds \| 2 baths \| 2,674 sq.ft.	$1,200,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 1.59% Airbnb Rental Income: $5495 Traditional Rental Income: $3597 Airbnb ROI: 2.3% Traditional ROI: 1.59%
16 Second Avenue unit: 5A #5A Osterville, MA Tucked along picturesque Parker Road, between the Osterville Historical Museum and Wianno ...	1 beds \| 1 baths \| 720 sq.ft.	$599,500	Airbnb cash on cash: 4.63% Traditional cash on cash: 1.94% Airbnb Rental Income: $4456 Traditional Rental Income: $2015 Airbnb ROI: 4.63% Traditional ROI: 1.94%
33 Aspen Way Osterville, MA Welcome to 33 Aspen Way, a charming ranch-style home in the highly desirable village of Os...	3 beds \| 2 baths \| 1,276 sq.ft.	$679,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 3.16% Airbnb Rental Income: $4575 Traditional Rental Income: $2975 Airbnb ROI: 4.19% Traditional ROI: 3.16%
177 Bayview Circle Osterville, MA Enjoy all that Osterville has to offer! This adorable 3 bedroom, 3 bath Cape is in the per...	3 beds \| 3 baths \| 2,050 sq.ft.	$949,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 2.12% Airbnb Rental Income: $4575 Traditional Rental Income: $3330 Airbnb ROI: 2.45% Traditional ROI: 2.12%
44 Avalon Circle Osterville, MA On a quiet cul-de-sac in Osterville, this contemporary Cape blends architectural charm wit...	3 beds \| 2 baths \| 3,387 sq.ft.	$1,295,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 1.65% Airbnb Rental Income: $4575 Traditional Rental Income: $3732 Airbnb ROI: 1.56% Traditional ROI: 1.65%
77 Robbins Street Osterville, MA Lovely and spacious home in the sought-after village of Osterville. Ideally located just ....	4 beds \| 3 baths \| 2,976 sq.ft.	$1,495,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.7% Airbnb Rental Income: $5495 Traditional Rental Income: $4331 Airbnb ROI: 1.74% Traditional ROI: 1.7%
920 Main Street unit: 1 Building 2 #1 Building 2 Osterville, MA Wouldn't you just love to have one of Cape Cod's most charming Main Streets at your front ...	2 beds \| 2 baths \| 1,150 sq.ft.	$615,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 3.05% Airbnb Rental Income: $4681 Traditional Rental Income: $2685 Airbnb ROI: 4.84% Traditional ROI: 3.05%

Real Estate investment in Osterville, MA

There are 21 properties for sale in the city of Osterville . The median list price in Osterville is $1,272,000 and the average price per square foot is $389. In September 2025, the average monthly cash on cash return in Osterville is 2.00%. The average monthly rental income in Osterville is $3,697.

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

There are 21 investment properties available for sale in Osterville.

In 2025, the best neighborhood to buy investment property is Osterville.

The ROI for Short-Term is higher than the Long-Term in Osterville with average rental income of $5,495.

Your search for investment property begins and ends here

Investment Property for Sale in Osterville, MA

17 Avalon Circle

Osterville, MA

3 beds | 2 baths | 1,316 sq.ft.

$624,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $4575

Traditional Rental Income: $3012

Airbnb ROI: 4.63%

Traditional ROI: 3.58%

17 Ebenezer Road

Osterville, MA

3 beds | 2 baths | 1,267 sq.ft.

$539,900

Airbnb cash on cash: 5.26%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $4575

Traditional Rental Income: $2964

Airbnb ROI: 5.26%

Traditional ROI: 3.95%

25 Oyster Way

Osterville, MA

5 beds | 5 baths | 7,157 sq.ft.

$10,450,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: -1.08%

Airbnb Rental Income: $6393

Traditional Rental Income: $5670

Airbnb ROI: -1.14%

Traditional ROI: -1.08%

38 Beach Plum Hill Road

Osterville, MA

5 beds | 5 baths | 3,802 sq.ft.

$5,444,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: -0.4%

Airbnb Rental Income: $6393

Traditional Rental Income: $5583

Airbnb ROI: -0.49%

Traditional ROI: -0.4%

168 Garrison Lane

Osterville, MA

5 beds | 6 baths | 7,565 sq.ft.

$9,995,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: -0.92%

Airbnb Rental Income: $6393

Traditional Rental Income: $6857

Airbnb ROI: -1.11%

Traditional ROI: -0.92%

64 Bay Street

Osterville, MA

4 beds | 5 baths | 2,812 sq.ft.

$2,995,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $5495

Traditional Rental Income: $3662

Airbnb ROI: -0.05%

Traditional ROI: -0.31%

44 Seapuit Road

Osterville, MA

5 beds | 5 baths | 8,345 sq.ft.

$5,840,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: -0.56%

Airbnb Rental Income: $6393

Traditional Rental Income: $5480

Airbnb ROI: -0.63%

Traditional ROI: -0.56%

98 Bunker Hill Road

Osterville, MA

5 beds | 5 baths | 4,715 sq.ft.

$2,879,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $6393

Traditional Rental Income: $6626

Airbnb ROI: 0.21%