Osterville Classified Ad Listings

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,...

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 ...

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...

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...

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...

67 Lakefield Rd. Welcome home to this classic Cape Cod residence full of warmth and charm! This inviting home offers comfortable one-floor living and ample flexible space in the finished basement. Step inside to a welcoming entry room adjacent to the bright, sun-filled vaulted family room complete with dual skylights and a ceiling fan. The newly updated eat-in kitchen offers ample cabinet stora...

378 Ames Way. Welcome to this charming 2-bedroom half cape set on a beautiful, level.38-acre lot in Centerville. Offering a wonderful combination of comfort, privacy. This inviting home abuts more than 7 acres of conservation land, providing a peaceful surroundings and a sense of space that is hard to find. Filled with natural light this home has a large, updated kitchen offers plenty of room f...

Really well kept 2015 Sailfish 320WAC! G&S Maintained Since New!!! Pride of Ownership is apparent in this one. Boat is turn-key and ready for new adventures. Enormous 'Dance Floor' Open Cockpit. Spacious Cabin w/Enclosed Head & Shower, Galley, Mid-Birth, TV and More! Large and Comfortable Enclosed Helm w/Wrap-Around Glass and Wipers, Passenger Lounge, Bolstered Helm Seat, ShorePower, AC, Garmin...

33 Horsefoot Rd. There are still places on Cape Cod that almost no one knows are there. Tucked within one of West Dennis's oldest enclaves, Horsefoot Road is a tiny one-lane offshoot that reaches out into Bass River. There's no through traffic and nowhere to go--except to the river. With the marsh on one side and Bass River on the other, this almost-hidden little street feels hugged by water. A...

27 Oregon Rd. Welcome to this charming 4-bedroom, 2-full-bath home located in desirable Mashpee! Offering 1,550 square feet of living space, this home is full of potential and ready for your personal touch. The 1st floor features beautiful oak flooring and a cozy wood-burning fireplace, creating a warm and inviting atmosphere. There are 2 bedrooms and a full bathroom on this level. the 2nd floo...

15 Twenty First St N. Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island's best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken liv...

27 7th St N. 27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers a...

46 Buttonwood Farm T111 Rd W Unit 1. THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Insi...

487 Lamberts Cove Rd. This sweet four-bedroom home has fantastic energy and captures the effortless feeling of summer on Martha's Vineyard. Set high on 2.4 acres along beloved Lamberts Cove Road, the property is just a short walk to Ice House, Lamberts Cove Beach, and Seth's Pond. Designed for easy enjoyment, the home offers a warm and welcoming kitchen filled with sunshine, a spacious living r...

14 Trapps Pond Rd. Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming ...

126 Old Colony Dr. This property is located in the fantastic 'Old Colony Estates' neighborhood. Very short walk to the ballfields at Heritage Park, the Mashpee Dog Park, the Mashpee Pickleball Park, and the Playground. This 5-bedroom, 2-bathroom Cape Cod style home is perfect for a large family. The 1st floor features an open kitchen and dining area, a large living room with a fireplace, two be...

50 Rivers Edge Rd. A contemporary masterpiece of industrial elegance, this custom-built residence envelops you in warmth, sophistication, and effortless comfort. A true Architectural Gem on the Child's River, it offers direct water access to Waquoit Bay and a coveted lifestyle within the exclusive River's Edge Association. Designed for refined living, the flowing open floor plan blends striking...

31 Jasons Ln. Beautifully renovated and thoughtfully designed by an Osterville builder, this custom ranch offers the ease of one-level living with the elevated finishes of a designer home including 3 beds with a large master suite and 3 full baths each one has its own unique design. The light-filled interior features a cathedral shiplap ceiling, Phillip Jeffries wallcoverings, extensive marble,...

19 Floodtide Ln. Stunning Bayside Builders "The Villager" a one level much desired open floor plan featuring a Great room with cathedral ceilings, custom built-ins, gas fireplace, spacious dining area with direct access to deck and private serene yard. Gleaming hardwood floors throughout, first floor laundry, 2 car garage, TOWN SEWER. Large primary bedroom ensuite has walk-in closet and cathedr...

31 Katharyn Michael Rd. Nestled in the heart of Yarmouth Port, 31 Katharyn Michael Road offers a perfect blend of Cape Cod charm and easy, low-maintenance living. This bright and airy condo at The Gardens was designed for both relaxation and effortless entertaining. There is plenty of room to unwind after a day spent exploring the nearby bay-side beaches or the local boutiques and eateries that...