Osterville Classified Ad Listings

46 Lake Shore Dr. Welcome to this charming, beautifully renovated 3 bed 1 bath ranch. Ideally situated in a coveted lake community, with access to a private neighborhood beach on Jenkins Pond, known for being one of the cleanest spring fed ponds on the Cape. With pleasant sandy beaches, it is a great spot for kayaking, swimming or relaxing. The home is set on a peaceful, private and serene lot....

5 Coastline Drive. Single Family Home for sale in Mashpee, MA for $4,500,000 with 5 bedrooms and 6 full baths, 2 half baths. This 5,534 square foot home was built in 2015 on a lot size of 0.18.. Gated Seaside Neighborhood. This home is designed for entertainers and to bring people together. From the moment you enter the spacious foyer you will love the grand yet welcoming details. From coffered...

105 Whalers Walk. Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcom...

709 Old County Rd. THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and co...

23 Beetle Swamp Rd. Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you'll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures wit...

31 Butlers Cove Rd. This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft ...

12 Cockachoisett Ln. Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a ...

53 Hadrada Ln. Back on Market with Recent Improvements! Exceptional value in Centerville with newly installed flooring by a licensed contractor in the kitchen, hallway, and one bedroom. Major updates are already complete, including a newer roof, replacement windows, updated kitchen, mechanical systems, central air, garage door, patio doors, and a whole-house Generac generator. This well-maintai...

54 Buckley Rd. Discover coastal living at 54 Buckley Road in Wrinkle Point, a waterfront community with a marina and deep-water docks, community pool, clubhouse, private beaches, playground and year-round neighborhood activities. Completely renovated from the studs out (2022-2026), this 4-bedroom, 2-bath smart home offers views of West Dennis Beach. Every major system is new: Title 5 septic, 20...

82 Falling Leaf Ln. Exceptional 3-BR Family/Vacation Home in Osterville: Nestled in a well-maintained neighborhood in the desirable village of Osterville. This spacious and inviting 2116 sf 3 BR home would be an ideal primary residence or your Cape Cod getaway retreat. Beautiful hardwood floors throughout the main floor. Upstairs-2 spacious guest bedrooms and a loft/study room. This home featur...

Introducing the 1998 Boston Whaler 23 Conquest, available through Moore Yacht Sales in Groton, CT, for an asking price of $27,995. This exceptional vessel exemplifies the renowned Boston Whaler legacy with its 'Unsinkable Legend' foam-core construction, a robust deep-V hull, and a flexible layout perfect for both serious offshore fishing and enjoyable family outings. It's been upgraded with rel...

5 Atlantic Dr. Located in one of Katama's most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it's an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coa...

36 Noreast Dr. Welcome to 36 Noreast Drive, a wonderful opportunity in sought-after Sagamore Beach, just moments from the coast. Ideally situated near the beach, this property offers a great combination of location, comfort, and important recent updates. The home has been thoughtfully improved with a newer septic system, newer roof, new driveway, and new oil tank, providing peace of mind for th...

410 W Falmouth Hwy-Rte 28A Unit 9. Enjoy elevated coastal living in this exceptional three-bedroom Penthouse apartment, ideally located in the heart of West Falmouth. Offering Buzzards Bay views from two levels, this distinctive residence combines spacious interiors, outdoor living, and a highly convenient location close to the area's most desirable amenities. The residence features three bedro...

74 Coleridge Drive. Single Family Home for sale in Falmouth, MA for $1,399,000 with 5 bedrooms and 4 full baths, 1 half bath. This 3,785 square foot home was built in 1969 on a lot size of 0.36.. Welcome to 74 Coleridge Drive located in Grasmere. Newly renovated in 2026, this light-filled five-bedroom, four-and-a-half-bath home offers approximately 3,785 square feet of versatile living space in...

33 Landmark Ave. There is no place like Maushop Village! This Nantucket style Villa offers your own private sandy beach over-looking Nantucket Sound. Walk to the Popponesset Marketplace for shopping, dining, mini golf, entertainment and more. This beautiful updated Townhouse Offers an Open floor plan, upgraded stainless appliances, granite countertop, powder room, 2nd floor offers upgraded tile...

19 Essex Rd. Enjoyed by the same family since new, this 3-bedroom ranch offers an incredible opportunity for its next chapter. Situated on a quiet dead-end street, the main level features three comfortable bedrooms, hardwood floors, a tiled kitchen, and natural gas heating and cooking. Bring your creative vision to make it your own! Additional highlights include a full basement with bonus space...

25 Donegal Cir. WINTER RENTAL - Charming 2-bedroom, 1-bath home in a quiet Centerville neighborhood, just minutes from Craigville Beach. This inviting home features a spacious living room, dining area, dedicated office space, fully equipped kitchen, and dedicated laundry area. Both bedrooms offer comfortable queen beds, making the home ideal for a small family or two couples. The fully fenced p...

8 Folger Ln. Set on a quiet lane in desirable W. Dennis and just moments from the sparkling shore of West Dennis Beach with its close to 1 mile of coastline. As you enter the welcoming breezeway/sunporch the sliders lead you to the outdoor patio, an outside shower, and a shed for all the extras. The yard also has irrigation. First time offered in close to 50 years and it is in move-in ready. Wh...

40 Hidden 5 Ob Cv # 537. THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living ro...