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

186 Windswept Way, Osterville
  • Single Family
  • 8 Beds
  • 8 Baths
  • 10,063 SqFt

186 Windswept Way, Osterville

$18,800,000
198 & 227 Bridge Street, Osterville
  • Single Family
  • 9 Beds
  • 7 Baths
  • 5,516 SqFt

198 & 227 Bridge Street, Osterville

$16,900,000 ↓ $1,100,000
48 Oyster Way, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 9,859 SqFt

48 Oyster Way, Osterville

$5,800,000
83 Bunker Hill Road, Osterville
  • Single Family
  • 5 Beds
  • 7 Baths
  • 5,721 SqFt

83 Bunker Hill Road, Osterville

$3,650,000 ↓ $300,000
405 Bridge Street, Osterville
  • Single Family
  • 5 Beds
  • 6 Baths
  • 6,768 SqFt

405 Bridge Street, Osterville

$3,500,000 ↓ $495,000
473 Grand Island Drive, Osterville
  • Single Family
  • 6 Beds
  • 6 Baths
  • 7,126 SqFt

473 Grand Island Drive, Osterville

$3,495,000 ↑ $600,000
21 Indian Trail, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 93,218 SqFt

21 Indian Trail, Osterville

$3,495,000
131 Garrison Lane, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,966 SqFt

131 Garrison Lane, Osterville

$2,950,000 ↓ $345,000
30 Indian Trail, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 106,722 SqFt

30 Indian Trail, Osterville

$2,700,000
Lot 288 Seapuit River Road, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 100,188 SqFt

Lot 288 Seapuit River Road, Osterville

$2,600,000
New
65 Starboard Lane, Osterville
  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,684 SqFt

65 Starboard Lane, Osterville

$2,599,900
Lot 290 Indian Trail, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 87,556 SqFt

Lot 290 Indian Trail, Osterville

$2,500,000
Lot 289 Seapuit River Road, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 90,605 SqFt

Lot 289 Seapuit River Road, Osterville

$2,500,000
242 Washington Avenue, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 73,616 SqFt

242 Washington Avenue, Osterville

$2,100,000
174 Wianno Avenue, Osterville
  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,597 SqFt

174 Wianno Avenue, Osterville

$1,999,000 ↓ $196,000
271 Pineleigh Path, Osterville
  • Lots and Land
  • 0 Beds
  • 0 Baths
  • 43,560 SqFt

271 Pineleigh Path, Osterville

$1,650,000
1336 Main Street, Osterville
  • Income/Multi Family
  • 0 Beds
  • 0 Baths
  • 7,781 SqFt

1336 Main Street, Osterville

$1,450,000
12 Fire Station Road, Osterville
  • Single Family
  • 3 Beds
  • 6 Baths
  • 4,269 SqFt

12 Fire Station Road, Osterville

$1,395,000 ↓ $200,000
New
60 Smoke Valley Road, Osterville
  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,462 SqFt

60 Smoke Valley Road, Osterville

$1,295,000
New
118 Bayview Circle, Osterville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,344 SqFt

118 Bayview Circle, Osterville

$749,000
174 Tanglewood Drive, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,860 SqFt

174 Tanglewood Drive, Osterville

$749,000 ↓ $50,000
192 Tanglewood Drive, Osterville
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,500 SqFt

192 Tanglewood Drive, Osterville

$569,900 ↓ $20,000
933 Main Street 1, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,216 SqFt

933 Main Street 1, Osterville

$549,000
182 Pond Street, Osterville
  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,478 SqFt

182 Pond Street, Osterville

$499,000
28 Flowing Pond Circle, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,085 SqFt

28 Flowing Pond Circle, Osterville

$459,900
727 Main Street D2, Osterville
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,201 SqFt

727 Main Street D2, Osterville

$449,000 ↓ $10,000

Blog Posts About Osterville

The Most Exclusive Areas on the Cape

With dozens of beaches, hundreds of charming shops and some beautiful homes, it’s hard to point out just one great location on the Cape. However, some of the most exclusive areas of Cape Cod are appreciated for their extreme luxury and privacy. Chatham Chatham is said to offer one of the Cape’s most scenic golf courses. Eastward Ho Country Club dates back to the 1920s and is known today for its ultra-exclusive membership. It’s not easy to become a member and the dress code at the go... Read More

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

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 09/18/2021. All properties are subject to prior sale, changes or withdrawal.

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