Osterville Real Estate

Osterville is a seaside village located on Nantucket Sound in the Town of Barnstable.  The community is known for its upscale waterfront homes and exclusive private clubs.  Residents enjoy shopping and dining in the quaint business of Osterville.  Dowses Beach on East Bay Road is a popular residents-only beach and offers a sandy shoreline and the calm waters of East Bay.

Osterville Homes For Sale

198 & 227 Bridge Street, Osterville
  • Single Family
  • 9 Beds
  • 7 Baths
  • 5,516 SqFt

198 & 227 Bridge Street, Osterville

$19,500,000 ↓ $2,500,000
359 Seapuit Road, Osterville
  • Single Family
  • 6 Beds
  • 4 Baths
  • 4,076 SqFt

359 Seapuit Road, Osterville

$14,995,000
255 Eel River Road, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 7,499 SqFt

255 Eel River Road, Osterville

$11,900,000
360 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,719 SqFt

360 Bay Road, Osterville

$7,250,000
81 & 73 Oyster Way, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 7,205 SqFt

81 & 73 Oyster Way, Osterville

$6,750,000 ↑ $500,000
191 Sea View Avenue, Osterville
  • Single Family
  • 9 Beds
  • 6 Baths
  • 5,091 SqFt

191 Sea View Avenue, Osterville

$5,600,000
92 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 6,482 SqFt

92 Bay Road, Osterville

$5,500,000
150 Carriage Road, Osterville
  • Single Family
  • 8 Beds
  • 7 Baths
  • 5,134 SqFt

150 Carriage Road, Osterville

$5,295,000 ↓ $505,000
408 Wianno Avenue, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 5,915 SqFt

408 Wianno Avenue, Osterville

$5,100,000
46 Little Island Drive, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 5,680 SqFt

46 Little Island Drive, Osterville

$4,995,000
72 Bay Road, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,082 SqFt

72 Bay Road, Osterville

$4,900,000
52 Bay Road, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 65,340 SqFt

52 Bay Road, Osterville

$4,900,000
48 Oyster Way, Osterville
  • Single Family
  • 5 Beds
  • 9 Baths
  • 9,859 SqFt

48 Oyster Way, Osterville

$4,600,000
320 Seapuit River Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 4,958 SqFt

320 Seapuit River Road, Osterville

$4,300,000
629 & 656 Sea View Avenue, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 5,234 SqFt

629 & 656 Sea View Avenue, Osterville

$3,995,000 ↓ $500,000
100 Eel River Road, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 6,685 SqFt

100 Eel River Road, Osterville

$3,900,000 ↓ $1,050,000
94 Starboard Lane, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 4,575 SqFt

94 Starboard Lane, Osterville

$3,750,000
194 Eel River Road, Osterville
  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,191 SqFt

194 Eel River Road, Osterville

$3,275,000 ↓ $100,000
292 Grand Island Drive, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 4,707 SqFt

292 Grand Island Drive, Osterville

$2,995,000
142 Great Bay Road, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 4,480 SqFt

142 Great Bay Road, Osterville

$2,950,000
10 Starboard Lane, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 8,447 SqFt

10 Starboard Lane, Osterville

$2,899,000
87 Seapuit Road, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 7,829 SqFt

87 Seapuit Road, Osterville

$2,700,000
123 Pineleigh Path, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 5,287 SqFt

123 Pineleigh Path, Osterville

$2,675,000
514 Grand Island Drive, Osterville
  • Single Family
  • 7 Beds
  • 8 Baths
  • 6,618 SqFt

514 Grand Island Drive, Osterville

$2,600,000 ↓ $300,000
324 Sea View Avenue, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,809 SqFt

324 Sea View Avenue, Osterville

$2,500,000
209 Bay Street, Osterville
  • Single Family
  • 5 Beds
  • 2 Baths
  • 1,733 SqFt

209 Bay Street, Osterville

$2,500,000 ↓ $1,000,000
312 Bridge Street, Osterville
  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,692 SqFt

312 Bridge Street, Osterville

$2,450,000 ↓ $100,000
459 Wianno Avenue, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 1,860 SqFt

459 Wianno Avenue, Osterville

$2,300,000
10 Eel River Road, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 4,167 SqFt

10 Eel River Road, Osterville

$2,295,000
255 Parker Road, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 4,713 SqFt

255 Parker Road, Osterville

$2,295,000
140 Main Street, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 5,700 SqFt

140 Main Street, Osterville

$2,195,000 ↓ $100,000
352 Starboard Lane, Osterville
  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,240 SqFt

352 Starboard Lane, Osterville

$2,195,000 ↓ $100,000
570 Sea View Avenue, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,365 SqFt

570 Sea View Avenue, Osterville

$2,150,000 ↓ $245,000
247 Crystal Lake Road, Osterville
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,372 SqFt

247 Crystal Lake Road, Osterville

$2,100,000 ↓ $200,000
95 Windswept Way, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,590 SqFt

95 Windswept Way, Osterville

$1,995,000
163 Pineleigh Path, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,750 SqFt

163 Pineleigh Path, Osterville

$1,950,000
45 Hathaway Road, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,901 SqFt

45 Hathaway Road, Osterville

$1,895,000
140 Pineleigh Path, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,909 SqFt

140 Pineleigh Path, Osterville

$1,750,000
195 Crystal Lake Road, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,796 SqFt

195 Crystal Lake Road, Osterville

$1,750,000
421 Grand Island Drive, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 4,242 SqFt

421 Grand Island Drive, Osterville

$1,650,000 ↓ $145,000
199 Bay Road 12, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,118 SqFt

199 Bay Road 12, Osterville

$1,595,000 ↓ $100,000
81 Farm Valley Road, Osterville
  • Single Family
  • 4 Beds
  • 7 Baths
  • 3,534 SqFt

81 Farm Valley Road, Osterville

$1,495,000 ↓ $4,000
60 Smoke Valley Road, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,462 SqFt

60 Smoke Valley Road, Osterville

$1,395,000
21 Windrush Lane, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,021 SqFt

21 Windrush Lane, Osterville

$1,395,000 ↓ $200,000
10 Barnard Road, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,311 SqFt

10 Barnard Road, Osterville

$1,350,000
158 Swift Avenue, Osterville
  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,108 SqFt

158 Swift Avenue, Osterville

$1,350,000 ↓ $100,000
95 Wianno Circle, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,000 SqFt

95 Wianno Circle, Osterville

$1,190,000
11 Oak Ridge Road, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,132 SqFt

11 Oak Ridge Road, Osterville

$1,190,000

Blog Posts About Osterville

Osterville-- Mid Cape Upscale Living

Described by some as an upscale Mid Cape village, Osterville is a fantastic place to live and visit. Ocean views, waterfront homes and a quaint downtown all come together to make this such a desirable location. Whether you spend your afternoons out on the water, out on the beach or strolling through one of Osterville’s galleries and boutiques, the village has plenty to offer. From upscale shopping on Main Street to its sand and water, the location proves a great place for everything f... Read More

Osterville Parks: Hidden Gems on the Cape

Photo: Elizabeth McClay From its tranquil ponds and beaches to its small lake and local businesses, Osterville is a favorite of Cape Cod visitors and locals alike. Especially popular during the summer months, Osterville is known for its beautiful homes and its equally beautiful natural scenery. As one of Barnstable’s seven villages, Osterville sits on Nantucket Sound. The residential area offers access to a small business district, plus beaches, ponds and some true delights. If you’re ... Read More

Exploring Osterville Village

Blending the natural beauty of Cape Cod with the appeal of a small town setting, Osterville Village presents the enjoyment of seaside elegance. Right on Nantucket Sound, the village is a prime location for fun on the beach or on the water. Popular during the summer months, it’s common to find out-of-towners with second homes in Osterville. There are also two private country clubs in the village, each with its own golf course, tennis courts and private beach. In addition, you’ll find s... Read More

Wianno Club: Osterville Historic Landmark

With a rich history dating back to the late 1800s, the Wianno Club is a true Osterville historic landmark. Now the site of frequent gatherings, celebrations and even weddings, the club celebrates more than a century overlooking Nantucket Sound and even has a spot on the National Register of Historic Places.The Cotocheset House, now the main clubhouse of the Wianno Club, sits on land once purchased by Plymouth settlers from the Native Americans, later used as the site of a grand summer h... Read More

Oyster Harbors: Luxury on Nantucket Sound

 Home to some of the most expensive properties on Cape Cod, Oyster Harbors offers pure luxury for those searching for an estate on Nantucket Sound. The home of billionaires and philanthropists, the gated, waterfront community features its own golf course and extreme privacy. Formerly known as Grand Island, the location became the setting for the summer homes of prominent Boston families around the turn-of-the-century. The 1920s ushered in a new offering, with construction of the stylish ... Read More

Cape Cod img src Islands Association of Realtors LogoThe data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than ROBERT PAUL PROPERTIES are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor ROBERT PAUL PROPERTIES shall be responsible for any typographical errors, misinformation or misprints and shall be held totally harmless. This site was last updated 07/04/2020. All properties are subject to prior sale, changes or withdrawal.

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