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
21 Cockachoiset Ln Osterville, MA A new custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside...	4 beds \| 3 baths \| 3,015 sq.ft.	$2,900,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.08% Airbnb Rental Income: $2167 Traditional Rental Income: $4351 Airbnb ROI: -1.1% Traditional ROI: -0.08%
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.	$8,995,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -0.91% Airbnb Rental Income: $2096 Traditional Rental Income: $6857 Airbnb ROI: -1.54% Traditional ROI: -0.91%
162 Main Street Osterville, MA Fall in love the moment you step inside this beautifully renovated home that feels brand n...	3 beds \| 3 baths \| 2,048 sq.ft.	$1,785,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.61% Airbnb Rental Income: $1602 Traditional Rental Income: $3713 Airbnb ROI: -0.94% Traditional ROI: 0.61%
44 Seapuit Rd Osterville, MA Set on 3.4 acres and bordered by an additional 2.88 acres of protected land, this exceptio...	7 beds \| 7 baths \| 8,345 sq.ft.	$4,995,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -0.49% Airbnb Rental Income: $2096 Traditional Rental Income: $5480 Airbnb ROI: -1.34% Traditional ROI: -0.49%
71 Sand Point Osterville, MA Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coasta...	5 beds \| 5 baths \| 5,747 sq.ft.	$12,250,000	Airbnb cash on cash: -1.78% Traditional cash on cash: -1.13% Airbnb Rental Income: $2096 Traditional Rental Income: $8910 Airbnb ROI: -1.78% Traditional ROI: -1.13%
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.	$9,850,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -0.86% Airbnb Rental Income: $2096 Traditional Rental Income: $6635 Airbnb ROI: -1.42% Traditional ROI: -0.86%
177 Bayview Circle Osterville, MA Summer is in the Air! Welcome 177 Bayview Circle and Osterville Village. Enjoy sunbathing ...	3 beds \| 3 baths \| 2,050 sq.ft.	$924,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.21% Airbnb Rental Income: $1602 Traditional Rental Income: $3330 Airbnb ROI: -0.32% Traditional ROI: 2.21%
440 Grand Island Dr Osterville, MA 440 Grand Island Dr, Osterville, MA 02655 \| Single Family Residential	7 beds \| 9 baths \| 11,546 sq.ft.	$7,750,000	Airbnb cash on cash: -2.08% Traditional cash on cash: -1.19% Airbnb Rental Income: $2096 Traditional Rental Income: $7938 Airbnb ROI: -2.08% Traditional ROI: -1.19%
51 Wianno Cir Osterville, MA 51 Wianno Cir, Osterville, MA 02655 \| Single Family Residential	3 beds \| 2 baths \| 1,194 sq.ft.	$2,250,000	Airbnb cash on cash: -1.72% Traditional cash on cash: -0.87% Airbnb Rental Income: $1602 Traditional Rental Income: $2911 Airbnb ROI: -1.72% Traditional ROI: -0.87%
Lot 290 0 Indian Trl Osterville, MA Lot 290 0 Indian Trl, Osterville, MA 02655 \| Other	N/A beds \| N/A baths \| N/A	$3,125,000	Airbnb cash on cash: -3.58% Traditional cash on cash: -3.47% Airbnb Rental Income: $1774 Traditional Rental Income: $1610 Airbnb ROI: -3.58% Traditional ROI: -3.47%
30 Indian Trl Osterville, MA 30 Indian Trl, Barnstable, MA 02655 \| Other	N/A beds \| N/A baths \| N/A	$3,250,000	Airbnb cash on cash: -1.97% Traditional cash on cash: -1.86% Airbnb Rental Income: $1774 Traditional Rental Income: $1610 Airbnb ROI: -1.97% Traditional ROI: -1.86%
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: -1.27% Traditional cash on cash: 0.34% Airbnb Rental Income: $2167 Traditional Rental Income: $8486 Airbnb ROI: -1.27% Traditional ROI: 0.34%
501 Eel River Rd Osterville, MA 501 Eel River Rd, Osterville, MA 02655 \| Single Family Residential	6 beds \| 7 baths \| 8,203 sq.ft.	$9,950,000	Airbnb cash on cash: -2.07% Traditional cash on cash: -1.31% Airbnb Rental Income: $2096 Traditional Rental Income: $8535 Airbnb ROI: -2.07% Traditional ROI: -1.31%
Lot 289 Seapuit River B Rd Osterville, MA Lot 289 Seapuit River B Rd, Osterville, MA 02655 \| Other	N/A beds \| N/A baths \| N/A	$3,000,000	Airbnb cash on cash: -1.95% Traditional cash on cash: -1.91% Airbnb Rental Income: $1774 Traditional Rental Income: $1386 Airbnb ROI: -1.95% Traditional ROI: -1.91%
Lot 288 Seapuit River Rd A Osterville, MA Lot 288 Seapuit River Rd A, Osterville, MA 02655 \| Other	N/A beds \| N/A baths \| N/A	$3,100,000	Airbnb cash on cash: -3.59% Traditional cash on cash: -3.56% Airbnb Rental Income: $1774 Traditional Rental Income: $1390 Airbnb ROI: -3.59% Traditional ROI: -3.56%
146 Scudder Rd Osterville, MA 146 Scudder Rd, Osterville, MA 02655 \| Single Family Residential	3 beds \| 4 baths \| 2,696 sq.ft.	$2,650,000	Airbnb cash on cash: -1.8% Traditional cash on cash: -0.38% Airbnb Rental Income: $1602 Traditional Rental Income: $4615 Airbnb ROI: -1.8% Traditional ROI: -0.38%
351 Swift Avenue Osterville, MA Builder/Investor Opportunity in Osterville with Expansion Potential! Charming 3-bedroom, 1...	3 beds \| 1 baths \| 1,009 sq.ft.	$744,900	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.65% Airbnb Rental Income: $1602 Traditional Rental Income: $2414 Airbnb ROI: -0.18% Traditional ROI: 1.65%
207 Crystal Lake Rd Osterville, MA 207 Crystal Lake Rd, Osterville, MA 02655 \| Single Family Residential	8 beds \| 5 baths \| 6,500 sq.ft.	$8,750,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -1.41% Airbnb Rental Income: $2096 Traditional Rental Income: $6723 Airbnb ROI: -2.04% Traditional ROI: -1.41%
414 Eel River Rd Osterville, MA 414 Eel River Rd, Osterville, MA 02655 \| Single Family Residential	10 beds \| 7 baths \| 6,905 sq.ft.	$3,499,999	Airbnb cash on cash: -1.77% Traditional cash on cash: 0.12% Airbnb Rental Income: $2096 Traditional Rental Income: $7703 Airbnb ROI: -1.77% Traditional ROI: 0.12%
414 Eel Osterville, MA 414 Eel, Osterville, MA 02655 \| Single Family Residential	10 beds \| 7 baths \| 6,905 sq.ft.	$3,499,999	Airbnb cash on cash: -1.77% Traditional cash on cash: 0.12% Airbnb Rental Income: $2096 Traditional Rental Income: $7703 Airbnb ROI: -1.77% Traditional ROI: 0.12%
34 Farm Valley Rd Osterville, MA 34 Farm Valley Rd, Osterville, MA 02655 \| Single Family Residential	3 beds \| 3 baths \| 5,008 sq.ft.	$2,950,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.85% Airbnb Rental Income: $1602 Traditional Rental Income: $4009 Airbnb ROI: -1.89% Traditional ROI: -0.85%
5 Briar Patch Road Osterville, MA South of Route 28 in Osterville village, this inviting property offers an outstanding oppo...	3 beds \| 2 baths \| 1,497 sq.ft.	$875,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.28% Airbnb Rental Income: $1602 Traditional Rental Income: $3164 Airbnb ROI: -0.19% Traditional ROI: 2.28%
60 Linden Lane Osterville, MA Nestled in the heart of Osterville Village, this 3-bedroom, 3-bath home perfectly blends c...	3 beds \| 3 baths \| 2,000 sq.ft.	$949,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.53% Airbnb Rental Income: $1602 Traditional Rental Income: $3687 Airbnb ROI: -0.34% Traditional ROI: 2.53%
31 Falling Leaf Lane Osterville, MA This beautifully updated Osterville Cape, set on a private cul-de-sac, offers move-in-read...	3 beds \| 3 baths \| 2,190 sq.ft.	$1,199,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.61% Airbnb Rental Income: $1602 Traditional Rental Income: $3678 Airbnb ROI: -0.66% Traditional ROI: 1.61%
20 Deerfield Rd Osterville, MA Property is being offered via Real Estate Auction on Friday, June 26th at 11am on-site. Th...	3 beds \| 2 baths \| 2,076 sq.ft.	$874,400	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.99% Airbnb Rental Income: $1602 Traditional Rental Income: $3368 Airbnb ROI: 0.26% Traditional ROI: 2.99%
31 Falling Leaf Ln Osterville, MA 31 Falling Leaf Ln, Osterville, MA 02655 \| Single Family Residential	3 beds \| 2 baths \| 2,190 sq.ft.	$1,199,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.67% Airbnb Rental Income: $1602 Traditional Rental Income: $3321 Airbnb ROI: -1.28% Traditional ROI: 0.67%
60 Linden Ln Osterville, MA 60 Linden Ln, Osterville, MA 02655 \| Single Family Residential	3 beds \| 3 baths \| 2,000 sq.ft.	$949,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 2.02% Airbnb Rental Income: $1602 Traditional Rental Income: $3842 Airbnb ROI: -1.03% Traditional ROI: 2.02%
255 Bayberry Way Osterville, MA 255 Bayberry Way, Osterville, MA 02655 \| Single Family Residential	7 beds \| 6 baths \| 4,896 sq.ft.	$7,900,000	Airbnb cash on cash: -2.02% Traditional cash on cash: -1.11% Airbnb Rental Income: $2096 Traditional Rental Income: $8264 Airbnb ROI: -2.02% Traditional ROI: -1.11%
39 Tower Hill Road #Apt 15B Osterville, MA RARE opportunity for a gorgeous first floor unit in Osterville's desirable Village Square....	2 beds \| 2 baths \| 1,260 sq.ft.	$719,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 1.43% Airbnb Rental Income: $1218 Traditional Rental Income: $2776 Airbnb ROI: -1.48% Traditional ROI: 1.43%
441 Old Mill Road Osterville, MA Osterville opportunity! Situated on 1.4 acres and abutting conservation land, this 2-bedro...	2 beds \| 2 baths \| 1,144 sq.ft.	$810,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.9% Airbnb Rental Income: $1218 Traditional Rental Income: $2702 Airbnb ROI: -0.58% Traditional ROI: 1.9%
21 Cockachoisett Lane Osterville, MA A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Cro...	4 beds \| 4 baths \| 3,015 sq.ft.	$2,900,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.32% Airbnb Rental Income: $2167 Traditional Rental Income: $5724 Airbnb ROI: -1.21% Traditional ROI: 0.32%
93 Oyster Way Osterville, MA Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal e...	4 beds \| 4 baths \| 4,964 sq.ft.	$4,795,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.52% Airbnb Rental Income: $2167 Traditional Rental Income: $5305 Airbnb ROI: -1.35% Traditional ROI: -0.52%
955 Main St Osterville, MA 955 Main St, Osterville, MA 02655 \| Single Family Residential	3 beds \| 2 baths \| 1,764 sq.ft.	$1,579,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -0.08% Airbnb Rental Income: $1602 Traditional Rental Income: $3233 Airbnb ROI: -1.51% Traditional ROI: -0.08%
153 Hickory Hill Circle Osterville, MA This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect...	4 beds \| 3 baths \| 2,585 sq.ft.	$899,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.78% Airbnb Rental Income: $2167 Traditional Rental Income: $4506 Airbnb ROI: 0.33% Traditional ROI: 3.78%
170 Sturbridge Drive Osterville, MA Discover the charm and convenience of this lovingly maintained ranch-style home, perfectly...	2 beds \| 3 baths \| 1,992 sq.ft.	$1,150,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.28% Airbnb Rental Income: $1218 Traditional Rental Income: $3190 Airbnb ROI: -0.93% Traditional ROI: 1.28%
153 Hickory Hill Circke Osterville, MA 153 Hickory Hill Circke, Osterville, MA 02655 \| Single Family Residential	4 beds \| 2 baths \| 2,585 sq.ft.	$899,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.08% Airbnb Rental Income: $2167 Traditional Rental Income: $3694 Airbnb ROI: -0.4% Traditional ROI: 2.08%
81 Osterville W Barnstable Road Osterville, MA This elegant Cape-style residence offers a refined retreat just minutes from everything Os...	3 beds \| 3 baths \| 3,084 sq.ft.	$1,950,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.5% Airbnb Rental Income: $1602 Traditional Rental Income: $3900 Airbnb ROI: -1.02% Traditional ROI: 0.5%
30 Cockachoisett Lane Osterville, MA Defined by its water views, generous grounds, and multiple outdoor living spaces, 30 Cocka...	4 beds \| 5 baths \| 4,241 sq.ft.	$3,900,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.77% Airbnb Rental Income: $2167 Traditional Rental Income: $6514 Airbnb ROI: -0.58% Traditional ROI: 0.77%
12 Cockachoisett Lane Osterville, MA Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages alo...	3 beds \| 3 baths \| 3,178 sq.ft.	$2,950,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.38% Airbnb Rental Income: $1602 Traditional Rental Income: $3898 Airbnb ROI: -0.62% Traditional ROI: 0.38%
12 Cockachoiset Lane Osterville, MA Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages alo...	3 beds \| 3 baths \| 3,178 sq.ft.	$2,950,000	Airbnb cash on cash: -1.41% Traditional cash on cash: -0.41% Airbnb Rental Income: $1602 Traditional Rental Income: $3872 Airbnb ROI: -1.41% Traditional ROI: -0.41%

Real Estate investment in Osterville, MA

There are 52 properties for sale in the city of Osterville . The median list price in Osterville is $2,450,000 and the average price per square foot is $705. In May 2026, the average monthly cash on cash return in Osterville is N/A%. The average monthly rental income in Osterville is $3,885.

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

There are 52 investment properties available for sale in Osterville.

In 2026, the best neighborhood to buy investment property is Osterville.

The ROI for Long-Term is higher than the Short-Term in Osterville with average rental income of $3,885.

Your search for investment property begins and ends here

Investment Property for Sale in Osterville, MA

21 Cockachoiset Ln

Osterville, MA

4 beds | 3 baths | 3,015 sq.ft.

$2,900,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $2167

Traditional Rental Income: $4351

Airbnb ROI: -1.1%

Traditional ROI: -0.08%

168 Garrison Lane

Osterville, MA

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

$8,995,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: -0.91%

Airbnb Rental Income: $2096

Traditional Rental Income: $6857

Airbnb ROI: -1.54%

Traditional ROI: -0.91%

162 Main Street

Osterville, MA

3 beds | 3 baths | 2,048 sq.ft.

$1,785,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1602

Traditional Rental Income: $3713

Airbnb ROI: -0.94%

Traditional ROI: 0.61%

44 Seapuit Rd

Osterville, MA

7 beds | 7 baths | 8,345 sq.ft.

$4,995,000

Airbnb cash on cash: -1.34%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $2096

Traditional Rental Income: $5480

Airbnb ROI: -1.34%

Traditional ROI: -0.49%

71 Sand Point

Osterville, MA

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

$12,250,000

Airbnb cash on cash: -1.78%

Traditional cash on cash: -1.13%

Airbnb Rental Income: $2096

Traditional Rental Income: $8910

Airbnb ROI: -1.78%

Traditional ROI: -1.13%

14 Indian Trail

Osterville, MA

5 beds | 4 baths | 3,087 sq.ft.

$9,850,000

Airbnb cash on cash: -1.42%

Traditional cash on cash: -0.86%

Airbnb Rental Income: $2096

Traditional Rental Income: $6635

Airbnb ROI: -1.42%

Traditional ROI: -0.86%

177 Bayview Circle

Osterville, MA

3 beds | 3 baths | 2,050 sq.ft.

$924,900

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1602

Traditional Rental Income: $3330

Airbnb ROI: -0.32%

Traditional ROI: 2.21%

440 Grand Island Dr

Osterville, MA

7 beds | 9 baths | 11,546 sq.ft.

$7,750,000

Airbnb cash on cash: -2.08%

Traditional cash on cash: -1.19%

Airbnb Rental Income: $2096

Traditional Rental Income: $7938

Airbnb ROI: -2.08%