Osterville Classified Ad Listings

12 Lower County Rd. Year-round 1-bedroom waterfront rental in Dennis Port overlooking Swan River. Unit is approximately 400 sq. ft. Enjoy peaceful water views, a private deck and access to the shared dock-an ideal setting for kayaking, paddleboarding or simply relaxing by the water. Bright, efficient interior with updated windows/doors and off-street parking. Convenient to Dennis Port beaches, ...

235 Edgewater Dr W. This is a weekly summer rental at $6000 per week. Escape to this perfect waterfront Cape Cod summer rental getaway that has been newly renovated. Enjoy beautiful water views and a private dock with direct access to Vineyard Sound--no bridges required--this home is a boater's paradise. Dock your boat at the deep-water dock and soak in breathtaking sunsets from the west-facing...

25 Oyster Way. Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously lands...

3 Elizabeth Rd. Location, lifestyle, and convenience come together in this comfortable home, tucked into a quiet, well-established Pocasset neighborhood just a half mile from Hen Cove. Launch a boat or kayak from the public boat ramp, tie up at the dinghy dock, go for a swim, cast a line, or simply head to the water to enjoy a beautiful Cape Cod sunset. Area marinas, restaurants, and the privat...

27 Island Inn Rd Unit 9C. Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-...

68 Gold Leaf Ln Unit 68. "Wow!!" is all I can say, and so will you, when you see this stunning end unit at wonderful Windchime! This is possibly the nicest unit that's come on the market for a long time. The location within Windchime is the best, adjacent to the greenery and trails of town conservation land. But that's just the beginning. The light from the windows everywhere, including high tr...

66 Tern Ln. Awaken to the gentle shimmer of Lake Wequaquet, one of Cape Cod's largest lakes-perfect for an early morning swim or casting a line in the quiet calm.From the moment you arrive, this classic Cape home captures your heart. Its sweeping stone porch feels at one with the natural landscape, offering a timeless welcome. Inside, the soft glow of mahogany floors is complemented by detailed...

72 Hathaway Rd. Discover the charm of Wianno in this beautifully renovated four-bedroom, three-bath home, walking distance to Osterville Village, beaches, and the best of Cape Cod living. With deeded access to Eel River and lovely views overlooking the Wianno golf course, this inviting property offers a rare combination of location, comfort, and lifestyle. Thoughtfully designed for easy one-lev...

19 Morse Ed St # 333. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street and Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, offic...

53 Bar Neck Rd Unit B. Enjoy your winter overlooking Great Harbor! This beautifully updated 2-bedroom, 1.5- bath apartment welcomes you to Woods Hole. It features modern finishes throughout, an in-unit washer and dryer, and convenient off-street parking. Ideally located close to local science institutions, bike paths, and downtown Woods Hole and Falmouth.. 2 Bedrooms. 2 Bathroom. 1700 ft

70 Cape Dr Apt 5B. YEAR ROUND RENTAL Welcome to this beautifully updated 2-bedroom, 1-bath condo in the desirable Pheasant Run community, just minutes from Mashpee Commons and close to shopping, restaurants, beaches, golf, and everyday conveniences. This bright and inviting unit features upgraded wood-look vinyl flooring, white shaker kitchen cabinets, and stainless steel appliances, creating a...

31 Susan Ruth Rd. In a village along Nantucket Sound, Dennis Port features warm-water beaches that are considered among Cape Cod's most desirable for swimming and windsurfing. If you are looking for a Cape Cod cottage, you found it. Situated a short walk from the waterfront of Haigis Beach. Heated Sunporch with panoramic view of the outdoor space.. Here's what makes it special: Two bedrooms One...

172 Irving Ave. Set in the heart of Hyannis Port with commanding views of the harbor and Nantucket Sound, this magnificent shingle-style residence offers Cape Cod living at its finest. Boasting an unrivaled location just a stone's throw from the beach and yacht club, a spacious wraparound porch welcomes you on approach, ideal for entertaining or relaxing amidst gentle sea breezes and a breathta...

16 2nd Ave Unit 4. LIKE-NEW IN OSTERVILLE'S COVETED WIANNO AREA! Rare opportunity to own a free-standing condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. The light-filled interior features soaring ceili...

32 Edgartown-West Tisbury Rd. A Rare Offering in West Tisbury - Over 19 Acres of Opportunity with approvals in place for a six lot subdivision. An exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally si...

23 Highview Ave. Welcome to this charming, updated ranch in the desirable Briarwood/John's Pond Association of Mashpee! Cathedral ceilings create a bright, open feel, while the updated kitchen with all new appliances makes this home move-in ready. A finished outbuilding connected by a breezeway adds valuable flexible living space - ideal as a home office, den, gym, hobby room, or guest overflow...

51 Spinnaker Ln. Welcome to 51 Spinnaker Lane, where privacy, style and versatility come together in sought-after Pocasset Woods. This isn't just a house-It's the backdrop to your next great chapter! Granite steps, a manicured lawn and seasonal plantings create beautiful curb appeal, while conservation land surrounds you w/ privacy, and miles of trails to explore. Inside, the inviting layout fl...

119 Whitehall Way. Fantastic curb appeal for this charming quintessential Cape! Located in a lovely well kept neighborhood on a quiet and private partial cul-de-sac street. This 4 bedroom, 3 bath home has been lovingly cared for over decades by the same family. It boasts an updated kitchen with granite counters and large, eat-in island. 1st floor primary suite. 2nd floor large bedroom and bath ...

Introducing the 1997 Viking 47 Convertible "Alibi" the epitome of luxury in mid-size sportfishing. Built on Viking's renowned modified-V hull, Alibi promises a smooth ride and exceptional stability, making her perfect for both serious fishing tournaments and leisurely coastal voyages. Equipped with twin 800 HP MAN D2848LE403 diesel engines, she boasts impressive cruising speeds and reliable per...

179 Pineleigh Path. Overlooking the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. The kitchen is tailored for both everyday living and entertaining,...