Osterville Classified Ad Listings

4 Jacobs Neck Rd. Great Potential with Pond and Beach Access ~ Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering the opportunity to create a custom main residence with a swimming pool. Owne...

210 Seapit Rd. Spacious one bedroom, one bath 2nd floor apartment with balcony off the livingroom that over looks Seapit/Waquoit Bay inlet. All utilities included EVEN Wifi and Steam TV. The apartment has it's own washer and dryer and 1 car garage for parking and storage.. 1 Bedroom. 1 Bathroom. 500 ft

75 Old Main St. Welcome to your own slice of Cape Cod paradise! Tucked away down a long, beautiful driveway, this stunning West Dennis home offers peace, privacy, and pretty views. Look out over multiple rooms onto the peaceful salt marsh and slight views of Grand Cove. Step inside to find a beautifully remodeled interior where modern luxury meets classic coastal charm. The bright, open spaces ...

7 Upland Cir. Thoughtfully updated, this stunning Nantucket-style offers an exceptional combination of comfort, style, and privacy! Tucked away on a quiet cul-de-sac, this home welcomes you with a light-filled, skylit main level featuring spacious living and dining areas, an updated kitchen and a light and bright sunroom. Luxury vinyl flooring adds a fresh, modern feel to the main level. With a...

21 First Ave. YEAR-ROUND RENTAL! This spacious 3 bedroom home offers comfortable living in a quiet Hyannisport neighborhood. The home features two separate living areas, providing flexible space for relaxing, entertaining, or working from home. A washer and dryer add everyday convenience. Ideally located close to Main Street and Craigville Beach, with easy access to local shops, restaurants, be...

10 North Road. Single Family Home for sale in West Dennis, MA for $869,900 with 2 bedrooms and 1 full bath. This 1,320 square foot home was built in 1960 on a lot size of 0.17.. Coastal charmer steps from Kelly's Pond and a short bike ride to gorgeous West Dennis beach approximately 1/2 mile away. In addition to the two upstairs bedrooms there is additional room with closet on the main floor. C...

143 Bayberry Way. Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate ...

215 Ashumet Rd. Cape Cod living at its best! Nestled on a quiet street and set on nearly 2 private acres, this beautifully updated 4 bedroom, 2.5 bath home is truly move-in ready. The stunning new kitchen features quartz countertops, new cabinetry and stainless steel appliances, complemented by all-new flooring, fresh paint and stylishly updated baths with quartz-topped vanities. First floor la...

18 Lyndale Rd. WINTER RENTAL - from October 1, 2026 to May 31, 2027. Steps to the Beach!! Beautifully Renovated and Fully Furnished 3 Bedroom, 2 FULL Bath, Ranch Home with True One-level Living. Gorgeous Master Suite with Vaulted Ceiling, Private Bath, and Generous Closet Space. Enclosed 3 Season Room, Gleaming Hardwood Floors, Central Air, Gas Heating, and Well Appointed Laundry Room. Fabulous...

555 Shootflying Hill Rd. Water views and deeded beach rights to Wequaquet Lake enhance this immaculate ranch in Centerville. Gleaming hardwood floors in livingroom and both bedrooms. Present owner has over her time replaced heating system, hot water tank, electric panel, roof and windows. Town sewer in progress so this property should be able to expand once hooked up. 2 Bedrooms. 1 Bathroom. 76...

277 Scudder Ave. Enjoy comfortable one-level living in this inviting 3 Bed / 2 Bath Ranch with custom built-ins. Bright and spacious, enhanced by cathedral ceilings, skylights, a bay window, hardwood floors, and a cozy fireplace. The kitchen-dining area opens onto a large deck overlooking a private, fenced backyard. Gas forced-air heat and central air conditioning ensure comfort in every season...

74 Long Pond Dr. Build your Cape Cod dream home on this 0.24-acre parcel ideally located on Long Pond Drive in South Yarmouth. Building plans are in hand, making it easier to bring your vision to life. Conveniently situated just off Route 28, the property offers quick access to restaurants, shopping, golf, beaches, and all the amenities that make Yarmouth a sought-after destination. Steps down ...

35 Long Hill Dr. These lots don't come available that often. Steps to the Association beach at the end of Longhill Drive. Enjoy beautiful sunsets after a day of swimming in Cape Cod Bay. With just shy of an acre of land the opportunities are endless. This lot has been engineered and cleared. Bring your ideas to begin creating your Northside Beach Home.

10 Checkerberry Ln. Welcome to this charming 3BD/2BA Cape, situated on a private 0.65-acre wooded lot with a new paved driveway, crushed seashell outfront parking, and a walkway. The interior features a lovely living room with a fireplace and wood floors. The kitchen includes an eat-in area with direct access to a large deck, ideal for entertaining. The main floor offers two bedrooms-one curren...

40 John Hall Cartway. Enjoy the Kings Way lifestyle from this spacious D-style end-unit condominium at 40 John Hall Cartway. Set on a cul-de-sac bordering the golf course's 15th green, this well-kept home offers room to relax, entertain and make it your own. Two bedrooms, two full baths and a half bath provide comfortable living, while a fireplace adds warmth and charm. Start your morning with ...

22 Country Club Ln. Prestigious Country Club Estates!!!New luxurious 3980 sq ft, 4 bedroom,3.5 bath home!!! Built by Prime Homes! Many Upgrades! Newly added 24 kw generator! Contemporary first floor living! Drive along the first fairway of the Quashnet Valley Country Club as you enter this beautiful neighborhood. Upon entering the foyer there are 3 chandeliers opening to the well-lit great room...

14 Ephriam Allen Rd. Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys views of its small kettle pond, winter waterviews and the Sanct...

35 Grayton Ave. Perfectly situated within walking distance to the beach and under a 10-minute drive to shopping, restaurants, entertainment, and Nantucket ferries, this classic Hyannis Port summer cottage offers 8 beds, 5 baths, and 3,559 sqft of timeless coastal charm. Held by the same family for over 80 years, this ''King of the Hill'' property enjoys a private setting with village views, spa...

190 Bayfront Way Unit 190. Welcome to waterfront living in FalmouthPort, where tranquil views and incredible potential come together. This B-unit condo enjoys a coveted setting directly on the water, with beautiful views from the step-down living room. This is an opportunity to create a home that truly reflects your style. The main level features an open galley kitchen overlooking the dining ar...

27 Bellavista Dr. Available for winter rental, this fully furnished Pocasset home offers comfortable one-floor living in a desirable neighborhood. Just moments from Hens Cove, you'll enjoy easy access to the water while being tucked into a quiet residential setting. Inside, the home is thoughtfully furnished with everything you need for a seasonal stay. A bright living area flows into the well-...