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
47 Sea View Avenue, Osterville
  • Single Family
  • 7 Beds
  • 8 Baths
  • 5,593 SqFt

47 Sea View Avenue, Osterville

$13,500,000
183 Bay Street, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 5,067 SqFt

183 Bay Street, Osterville

$8,950,000
274 Carriage Road, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 5,000 SqFt

274 Carriage Road, Osterville

$8,500,000
134 Bay Road, Osterville
  • Single Family
  • 7 Beds
  • 10 Baths
  • 7,727 SqFt

134 Bay Road, Osterville

$7,999,000
250 Windswept Way, Osterville
  • Single Family
  • 6 Beds
  • 5 Baths
  • 4,235 SqFt

250 Windswept Way, Osterville

$7,495,000
206 Bay Road, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,522 SqFt

206 Bay Road, Osterville

$7,395,000
501 Eel River Road, Osterville
  • Single Family
  • 6 Beds
  • 9 Baths
  • 8,200 SqFt

501 Eel River Road, Osterville

$7,250,000
360 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 3,719 SqFt

360 Bay Road, Osterville

$6,950,000 ↓ $300,000
92 Bay Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 6,482 SqFt

92 Bay Road, Osterville

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

191 Sea View Avenue, Osterville

$5,000,000 ↓ $600,000
46 Little Island Drive, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 5,680 SqFt

46 Little Island Drive, Osterville

$4,795,000 ↓ $200,000
320 Seapuit River Road, Osterville
  • Single Family
  • 6 Beds
  • 7 Baths
  • 4,958 SqFt

320 Seapuit River Road, Osterville

$4,300,000
95 Eel River Road, Osterville
  • Single Family
  • 6 Beds
  • 5 Baths
  • 5,603 SqFt

95 Eel River Road, Osterville

$3,950,000 ↓ $300,000
94 Starboard Lane, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 4,575 SqFt

94 Starboard Lane, Osterville

$3,495,000 ↓ $255,000
285 Windswept Way, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 4,727 SqFt

285 Windswept Way, Osterville

$3,400,000
100 Eel River Road, Osterville
  • Single Family
  • 5 Beds
  • 8 Baths
  • 6,685 SqFt

100 Eel River Road, Osterville

$3,150,000 ↓ $350,000
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
30 Mayflower Lane, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 4,000 SqFt

30 Mayflower Lane, Osterville

$2,895,000
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
10 Eel River Road, Osterville
  • Single Family
  • 4 Beds
  • 6 Baths
  • 4,167 SqFt

10 Eel River Road, Osterville

$2,295,000
95 Windswept Way, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,590 SqFt

95 Windswept Way, Osterville

$1,995,000
308 Eel River Road, Osterville
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,393 SqFt

308 Eel River Road, Osterville

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

45 Hathaway Road, Osterville

$1,895,000
199 Bay Road 12, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,118 SqFt

199 Bay Road 12, Osterville

$1,499,900 ↓ $95,100
20 Grand Island Drive, Osterville
  • Single Family
  • 8 Beds
  • 5 Baths
  • 2,811 SqFt

20 Grand Island Drive, Osterville

$1,495,000
21 Windrush Lane, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,021 SqFt

21 Windrush Lane, Osterville

$1,395,000 ↓ $200,000
44 Fairwinds Drive, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,700 SqFt

44 Fairwinds Drive, Osterville

$1,195,000
280 Ice Valley Road, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 128,066 SqFt

280 Ice Valley Road, Osterville

$995,000
280 Ice Valley Road, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 2,438 SqFt

280 Ice Valley Road, Osterville

$995,000
486 Parker Road (lot 12), Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 109,667 SqFt

486 Parker Road (lot 12), Osterville

$975,000
486 Parker Road (lot 13), Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 91,860 SqFt

486 Parker Road (lot 13), Osterville

$975,000
75 Sturbridge Drive, Osterville
  • Single Family
  • 3 Beds
  • 5 Baths
  • 3,503 SqFt

75 Sturbridge Drive, Osterville

$965,000 ↓ $30,000
486 Parker Road (lot 11), Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 116,305 SqFt

486 Parker Road (lot 11), Osterville

$950,000
New
235 Wianno Circle, Osterville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,788 SqFt

235 Wianno Circle, Osterville

$925,000
New
53 Spice Lane, Osterville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,740 SqFt

53 Spice Lane, Osterville

$899,000
New
21 Cockachoiset Lane, Osterville
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,213 SqFt

21 Cockachoiset Lane, Osterville

$899,000
27 Parker Road, Osterville
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,339 SqFt

27 Parker Road, Osterville

$795,000
80 Pond Street, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,441 SqFt

80 Pond Street, Osterville

$749,000 ↓ $46,000
321 Tower Hill Road, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,400 SqFt

321 Tower Hill Road, Osterville

$735,000
716 Main Street B9, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,706 SqFt

716 Main Street B9, Osterville

$699,000 ↓ $30,000
105 Seth Goodspeed Way, Osterville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,748 SqFt

105 Seth Goodspeed Way, Osterville

$499,900 ↓ $20,000
749 Main Street H, Osterville
  • Income/Multi Family
  • 0 Beds
  • 0 Baths
  • 1,258 SqFt

749 Main Street H, Osterville

$469,000
920 Main Street Bldg 3 Unit 2, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,148 SqFt

920 Main Street Bldg 3 Unit 2, Osterville

$425,000 ↓ $12,000
39 Blossom Avenue 6b, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,188 SqFt

39 Blossom Avenue 6b, Osterville

$399,900 ↓ $10,100

Blog Posts About Osterville

Exploring Osterville Attractions

Photo: Peter Roome From boating and beaches to biking and more, there’s plenty to enjoy when it comes to exploring Osterville. The seaside village is a great place to go, whether you stay on land or head out on the water. A great way to see some of Osterville’s natural beauty is at Skunknett River Wildlife Sanctuary. The sanctuary is a good spot for birding, plus you have about 100 acres to explore by bike and foot. For swimming, beachcombing and fishing, locals know to visit Dowses ... Read More

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

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 09/18/2020. All properties are subject to prior sale, changes or withdrawal.

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