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
25 Oyster Way Osterville, MA Located within the private, gated golf community of Oyster Harbors, in the village of Oste...	5 beds \| 4 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%
168 Garrison Lane Osterville, MA Nestled amid beautifully landscaped grounds, this exceptional 7,500+/- square foot residen...	5 beds \| 6 baths \| 7,565 sq.ft.	$9,995,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.92% Airbnb Rental Income: $6393 Traditional Rental Income: $6857 Airbnb ROI: -1.1% Traditional ROI: -0.92%
98 Bunker Hill Road Osterville, MA Experience the epitome of bayside living at 98 Bunker Hill Road, nestled in Osterville's d...	5 beds \| 4 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: -1.43% Traditional cash on cash: -1.1% Airbnb Rental Income: $6393 Traditional Rental Income: $8910 Airbnb ROI: -1.43% Traditional ROI: -1.1%
14 Indian Trail Osterville, MA Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigiou...	5 beds \| 4 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%
89 Swift Avenue Osterville, MA Spacious Osterville ranch offering 2,674 sq ft of single-level living with an excellent fl...	4 beds \| 2 baths \| 2,674 sq.ft.	$1,175,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.64% Airbnb Rental Income: $5495 Traditional Rental Income: $3597 Airbnb ROI: 2.37% Traditional ROI: 1.64%
77 Robbins Street Osterville, MA Must see this ideally located, spacious home just .03 miles to shops and restaurants and l...	4 beds \| 2 baths \| 2,976 sq.ft.	$1,349,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 1.99% Airbnb Rental Income: $5495 Traditional Rental Income: $4331 Airbnb ROI: 2.04% Traditional ROI: 1.99%
369 Bumps River Road Osterville, MA Welcome to your new home in the highly sought-after village of Osterville! This charming 3...	3 beds \| 2 baths \| 1,152 sq.ft.	$680,000	Airbnb cash on cash: 4% Traditional cash on cash: 2.83% Airbnb Rental Income: $4575 Traditional Rental Income: $2880 Airbnb ROI: 4% Traditional ROI: 2.83%
40 Waterfield Road Osterville, MA Your love affair will begin as you pull into the crushed stone, horseshoe drive w/ cobbles...	4 beds \| 2 baths \| 1,775 sq.ft.	$1,115,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 1.86% Airbnb Rental Income: $5495 Traditional Rental Income: $3553 Airbnb ROI: 2.67% Traditional ROI: 1.86%
30 Deerfield Rd. Osterville, MA Property is being offered via Estate Auction on Friday, January 16th at 11am on-site. The ...	3 beds \| 2 baths \| 1,937 sq.ft.	$766,100	Airbnb cash on cash: 3.91% Traditional cash on cash: 3.5% Airbnb Rental Income: $4575 Traditional Rental Income: $3330 Airbnb ROI: 3.91% Traditional ROI: 3.5%
280 Ice Valley Road Osterville, MA Set on an exceptionally oversized 2.94-acre corner parcel within Osterville's highly sough...	4 beds \| 6 baths \| 3,557 sq.ft.	$4,595,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.46% Airbnb Rental Income: $5495 Traditional Rental Income: $8486 Airbnb ROI: -0.5% Traditional ROI: 0.46%
39 Blossom Avenue unit: Apt 4 #Apt 4 Osterville, MA Welcome to 39 Blossom Ave, Unit 4, a charming, lovingly cared-for condo located in the hea...	2 beds \| 2 baths \| 1,320 sq.ft.	$599,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.04% Airbnb Rental Income: $4681 Traditional Rental Income: $2766 Airbnb ROI: 3.73% Traditional ROI: 2.04%
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.	$588,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 1.99% Airbnb Rental Income: $4456 Traditional Rental Income: $2015 Airbnb ROI: 4.74% Traditional ROI: 1.99%
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%
3040 Falmouth Road unit: H #H Osterville, MA All utilities-heat and electric-are covered by the monthly fee (except cable), making this...	2 beds \| 1 baths \| 594 sq.ft.	$349,500	Airbnb cash on cash: 9.85% Traditional cash on cash: 4.61% Airbnb Rental Income: $4681 Traditional Rental Income: $1993 Airbnb ROI: 9.85% Traditional ROI: 4.61%
123 Tower Hill Road Osterville, MA With a prime in-town location, this 3-bedroom, 1.5-bath Osterville Cape offers the perfect...	3 beds \| 2 baths \| 1,136 sq.ft.	$789,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 1.79% Airbnb Rental Income: $4575 Traditional Rental Income: $2581 Airbnb ROI: 3.2% Traditional ROI: 1.79%
33 Sunset Lane Osterville, MA A rare find in the village of Osterville! Discover a truly exceptional opportunity in the ...	3 beds \| 2 baths \| 1,686 sq.ft.	$1,599,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 0.39% Airbnb Rental Income: $4575 Traditional Rental Income: $3154 Airbnb ROI: 0.71% Traditional ROI: 0.39%
30 Pond Street Osterville, MA Attention contractors, developers, and homeowners with a vision! Full acre lot less than 1...	3 beds \| 1 baths \| 974 sq.ft.	$675,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 1.98% Airbnb Rental Income: $4575 Traditional Rental Income: $2346 Airbnb ROI: 4.01% Traditional ROI: 1.98%
29 Oak Ridge Road Osterville, MA Step into this classic Osterville Cape, offering a comfortable pragmatic and spacious floo...	3 beds \| 2 baths \| 2,602 sq.ft.	$1,595,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.74% Airbnb Rental Income: $4575 Traditional Rental Income: $3330 Airbnb ROI: 0.94% Traditional ROI: 0.74%

Real Estate investment in Osterville, MA

There are 19 properties for sale in the city of Osterville . The median list price in Osterville is $1,175,000 and the average price per square foot is $425. In January 2026, the average monthly cash on cash return in Osterville is 2.00%. The average monthly rental income in Osterville is $3,330.

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

There are 19 investment properties available for sale in Osterville.

In 2026, 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 $4,681.

Your search for investment property begins and ends here

Investment Property for Sale in Osterville, MA

25 Oyster Way

Osterville, MA

5 beds | 4 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%

168 Garrison Lane

Osterville, MA

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

$9,995,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.92%

Airbnb Rental Income: $6393

Traditional Rental Income: $6857

Airbnb ROI: -1.1%

Traditional ROI: -0.92%

98 Bunker Hill Road

Osterville, MA

5 beds | 4 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

5 beds | 6 baths | 5,747 sq.ft.

$12,250,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: -1.1%

Airbnb Rental Income: $6393

Traditional Rental Income: $8910

Airbnb ROI: -1.43%

Traditional ROI: -1.1%

14 Indian Trail

Osterville, MA

5 beds | 4 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%

89 Swift Avenue

Osterville, MA

4 beds | 2 baths | 2,674 sq.ft.

$1,175,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 1.64%

Airbnb Rental Income: $5495

Traditional Rental Income: $3597

Airbnb ROI: 2.37%

Traditional ROI: 1.64%

77 Robbins Street

Osterville, MA

4 beds | 2 baths | 2,976 sq.ft.

$1,349,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $5495

Traditional Rental Income: $4331

Airbnb ROI: 2.04%

Traditional ROI: 1.99%

369 Bumps River Road

Osterville, MA

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

$680,000

Airbnb cash on cash: 4%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $4575

Traditional Rental Income: $2880

Airbnb ROI: 4%