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
19 Cesars Way Osterville, MA Investors take note!!! 3BR 2BA 2 car garage, almost half acre fenced in private yard great...	3 beds \| 2 baths \| 1,204 sq.ft.	$599,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 3.91% Airbnb Rental Income: $4466 Traditional Rental Income: $3057 Airbnb ROI: 4.76% Traditional ROI: 3.91%
16 Second Avenue #5B Osterville, MA Picturesque cottage condo in the heart of Osterville Village! Offered for sale separately ...	1 beds \| 1 baths \| 760 sq.ft.	$629,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.23% Airbnb Rental Income: $2992 Traditional Rental Income: $2120 Airbnb ROI: 1.54% Traditional ROI: 1.23%
25 Milne Road Osterville, MA Welcome to this beautifully renovated 3- bedroom, 2-bathroom home that blends modern elega...	3 beds \| 2 baths \| 1,700 sq.ft.	$1,295,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.62% Airbnb Rental Income: $4466 Traditional Rental Income: $3424 Airbnb ROI: 1.71% Traditional ROI: 1.62%
42 Pond Street Osterville, MA Cape Cod living at it's finest in this luxurious, beautifully renovated home! Whether for ...	3 beds \| 3 baths \| 2,095 sq.ft.	$1,348,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 1.6% Airbnb Rental Income: $4466 Traditional Rental Income: $3875 Airbnb ROI: 1.33% Traditional ROI: 1.6%
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: -0.79% Traditional cash on cash: -1.06% Airbnb Rental Income: $10251 Traditional Rental Income: $5670 Airbnb ROI: -0.79% Traditional ROI: -1.06%
920 Main Street #4 Osterville, MA Welcome to this convenient and coastal retreat nestled in the quaint village of Osterville...	2 beds \| 2 baths \| 1,155 sq.ft.	$633,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.24% Airbnb Rental Income: $6453 Traditional Rental Income: $2542 Airbnb ROI: 5.72% Traditional ROI: 1.24%
320 Parker Road Osterville, MA Located a short stroll from Osterville Village, this shingle-style home showcases stunning...	5 beds \| 6 baths \| 5,421 sq.ft.	$3,795,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 0.25% Airbnb Rental Income: $10251 Traditional Rental Income: $6705 Airbnb ROI: 0.71% Traditional ROI: 0.25%
39 Tower Hill Road #1A Osterville, MA FIRST FLOOR, highly desirable condominium in Village Square with direct, private entrance....	2 beds \| 2 baths \| 1,159 sq.ft.	$630,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.27% Airbnb Rental Income: $6453 Traditional Rental Income: $2571 Airbnb ROI: 5.72% Traditional ROI: 1.27%
38 Beach Plum Hill Road Osterville, MA Nestled in the heart of Osterville's prestigious Seapuit community, this estate offers ove...	4 beds \| 5 baths \| 3,802 sq.ft.	$5,500,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -0.41% Airbnb Rental Income: $7319 Traditional Rental Income: $5583 Airbnb ROI: -0.34% Traditional ROI: -0.41%
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.	$11,995,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.9% Airbnb Rental Income: $10251 Traditional Rental Income: $6857 Airbnb ROI: -0.76% Traditional ROI: -0.9%
162 Main Street Osterville, MA Imagine living in a serene pondfront home, surrounded by conservation land. This treasure ...	3 beds \| 2 baths \| 1,948 sq.ft.	$1,065,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.84% Airbnb Rental Income: $4466 Traditional Rental Income: $3713 Airbnb ROI: 1.66% Traditional ROI: 1.84%
298 Starboard Lane Osterville, MA Magnificent home on Osterville's coveted Starboard Lane. Benefitting from total privacy, t...	5 beds \| 4 baths \| 3,854 sq.ft.	$2,695,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 0.74% Airbnb Rental Income: $10251 Traditional Rental Income: $5404 Airbnb ROI: 1.92% Traditional ROI: 0.74%
23 & 27 Swift Avenue Osterville, MA This beautiful Osterville residence, meticulously renovated and in turn-key condition, fea...	3 beds \| 3 baths \| 1,844 sq.ft.	$1,395,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 0.7% Airbnb Rental Income: $4466 Traditional Rental Income: $3318 Airbnb ROI: 0.87% Traditional ROI: 0.7%
16 Second Avenue #5A Osterville, MA One-of-a-kind cottage-style condo right off of Parker Road at the Aunt Tempy's Association...	1 beds \| 1 baths \| 720 sq.ft.	$649,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.09% Airbnb Rental Income: $2992 Traditional Rental Income: $2093 Airbnb ROI: 1.43% Traditional ROI: 1.09%
71 Bumps River Road Osterville, MA Located just a short distance from Osterville Village, this move-in-ready home showcases o...	3 beds \| 3 baths \| 2,693 sq.ft.	$1,830,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 0.76% Airbnb Rental Income: $4466 Traditional Rental Income: $3922 Airbnb ROI: 0.53% Traditional ROI: 0.76%
146 Wintergreen Circle Osterville, MA Discover the charm and elegance of this beautifully renovated Cape. Located near Joshua's ...	3 beds \| 2 baths \| 2,145 sq.ft.	$799,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 2.9% Airbnb Rental Income: $4466 Traditional Rental Income: $3324 Airbnb ROI: 3.18% Traditional ROI: 2.9%
55 Sunset Lane Osterville, MA Discover the potential of this delightful two-bedroom, one-bath cottage nestled in the vib...	2 beds \| 1 baths \| 560 sq.ft.	$649,900	Airbnb cash on cash: 6.64% Traditional cash on cash: 1.71% Airbnb Rental Income: $6453 Traditional Rental Income: $2198 Airbnb ROI: 6.64% Traditional ROI: 1.71%
17 Chine Way Osterville, MA Offering a beautiful combination of classic design with modern amenities, this expanded ra...	3 beds \| 3 baths \| 2,763 sq.ft.	$1,295,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 1.6% Airbnb Rental Income: $4466 Traditional Rental Income: $3844 Airbnb ROI: 1.34% Traditional ROI: 1.6%
44 Seapuit Road Osterville, MA Nestled just beyond the heart of Osterville village, this estate offers a family retreat l...	5 beds \| 5 baths \| 8,345 sq.ft.	$6,850,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.63% Airbnb Rental Income: $10251 Traditional Rental Income: $5480 Airbnb ROI: -0.17% Traditional ROI: -0.63%
33 Waterfield Road Osterville, MA Location! Location! This well-maintained, ''open floor plan'' Cape Style Home is nestled o...	3 beds \| 2 baths \| 1,544 sq.ft.	$1,050,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.73% Airbnb Rental Income: $4466 Traditional Rental Income: $3119 Airbnb ROI: 2.16% Traditional ROI: 1.73%

Real Estate investment in Osterville, MA

There are 20 properties for sale in the city of Osterville . The median list price in Osterville is $1,295,000 and the average price per square foot is $443. In December 2024, the average monthly cash on cash return in Osterville is 1.00%. The average monthly rental income in Osterville is $3,569.

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

There are 20 investment properties available for sale in Osterville.

In 2024, 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 $4,466.

Your search for investment property begins and ends here

Investment Property for Sale in Osterville, MA

19 Cesars Way

Osterville, MA

3 beds | 2 baths | 1,204 sq.ft.

$599,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $4466

Traditional Rental Income: $3057

Airbnb ROI: 4.76%

Traditional ROI: 3.91%

16 Second Avenue #5B

Osterville, MA

1 beds | 1 baths | 760 sq.ft.

$629,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2992

Traditional Rental Income: $2120

Airbnb ROI: 1.54%

Traditional ROI: 1.23%

25 Milne Road

Osterville, MA

3 beds | 2 baths | 1,700 sq.ft.

$1,295,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $4466

Traditional Rental Income: $3424

Airbnb ROI: 1.71%

Traditional ROI: 1.62%

42 Pond Street

Osterville, MA

3 beds | 3 baths | 2,095 sq.ft.

$1,348,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $4466

Traditional Rental Income: $3875

Airbnb ROI: 1.33%

Traditional ROI: 1.6%

25 Oyster Way

Osterville, MA

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

$10,450,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: -1.06%

Airbnb Rental Income: $10251

Traditional Rental Income: $5670

Airbnb ROI: -0.79%

Traditional ROI: -1.06%

920 Main Street #4

Osterville, MA

2 beds | 2 baths | 1,155 sq.ft.

$633,000

Airbnb cash on cash: 5.72%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $6453

Traditional Rental Income: $2542

Airbnb ROI: 5.72%

Traditional ROI: 1.24%

320 Parker Road

Osterville, MA

5 beds | 6 baths | 5,421 sq.ft.

$3,795,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 0.25%

Airbnb Rental Income: $10251

Traditional Rental Income: $6705

Airbnb ROI: 0.71%

Traditional ROI: 0.25%

39 Tower Hill Road #1A

Osterville, MA

2 beds | 2 baths | 1,159 sq.ft.

$630,000

Airbnb cash on cash: 5.72%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $6453

Traditional Rental Income: $2571

Airbnb ROI: 5.72%