MLS Number 42039

• Residential
• Mls Status Active
• Bedrooms 8
• Bathroom 8
• Acreage 0.64

Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home, it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

MLS Number 40564

• CommercialSale
• Mls Status Active
• Bathroom 6
• Bedrooms 7
• Acreage 0.29

East Chop waterfront – Once in a lifetime, a property of this caliber becomes available, with an on-the-water East Chop location, a wide range of amenities, and multi-functional use! Uses include -- 1.) Currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 2.) Use it as a residential home or family compound, or live in a portion and rent a portion, 3.) Potential to convert to condominiums, paperwork presently in process but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 6-unit property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Private outdoor shower with dressing area. On town sewer.

Listed by Perry Patterson of MV Luxury Homes

MLS Number 40789

• Residential
• Mls Status Active
• Bedrooms 7
• Bathroom 6
• Acreage 0.29

East Chop waterfront – Once in a lifetime, a property of this caliber becomes available, with an on-the-water East Chop location, a wide range of amenities, and multi-functional use! Uses include -- 1.) Currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 2.) Use it as a residential home or family compound, or live in a portion and rent a portion, 3.) Potential to convert to condominiums, paperwork presently in process but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 6-unit property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Private outdoor shower with dressing area. On town sewer.

Listed by Perry Patterson of MV Luxury Homes

MLS Number 40762

• Land
• Mls Status Active
• Acreage 4.8

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling. Septic permits in place for two lots. Lot #1 - 147.2 (45,782sq.ft.) Permit in place for an APPROVED 6 Bedroom Septic System; Lot #2 - 147.3 - (31,320sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #3 - 147.4 - (34,824sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #4 - (52,451sq.ft.) 6 Bedroom Septic System Designed, NOT YET submitted; Lot #5 - (45,074sq.ft.) - Permit in place, APPROVED for a 4 Bedroom Septic System. Lot # 5 - May have access directly from Wapello Street. Ten (10) Bedrooms have been approved. Applications for an additional Twelve (12) Bedrooms are in process. Lot#2 - Application for 6 bedrooms. Lot#3 - Application for 6 Bedrooms. Lot #4 is undetermined at this point. Access may be allowed via Sunset Road or Eastville Avenue. Water is available via Sunset Road, at the property. Electricity is on site. Buyer is responsible for verifying any and all information on this property.

Listed by Alisan Lohan-Conway Properties

MLS Number 42664

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 0.4

This 4-bedroom / 3-bath home lies in the middle of East Chop at the highest point on the bluff offering expansive views of Vineyard Sound. The home features a large clear story living room with fireplace, a family room/kitchen also with fireplace, a huge screened porch opening up to a large deck area and a first floor bedroom with private bath. The 2nd floor offers two guest bedrooms and a master bedroom with large deck that share two baths. There are entrances on two roads, the grounds are nicely landscaped and there is a garage that could be used for a number of usages.

Listed by Gerrett Conover of Landvest MV

MLS Number 42580

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 3.5
• Acreage 0.15

This is the last undeveloped commercial property in downtown Oak Bluffs. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms. Right in the heart of Oak Bluffs a short distance to town, shops, restaurants, beaches, and ferries. With a large warp around porch the spacious home has a lot to offer. The commercial zoned land has been approved for several different situations from housing to store fronts. Come take a look at all this property has to offer.

Listed by Carleen Cordwell of Anchor Realty of Martha's Vineyard

MLS Number 40654

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 0.72

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2024 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

Listed by JoJo Lambert of Island Home Realty Inc.

MLS Number 42532

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.68

Experience the serene beauty of this 4-bedroom, 3.5-bathroom pond-front home in the Sengekontacket Community. Nestled on a hillside overlooking a freshwater pond, this home offers the perfect island retreat. Lush garden beds and wildflowers greet you as you make your way to the pond, where you can enjoy swimming or paddling. The well-appointed kitchen seamlessly connects to the dining room and deck, all with stunning pond views. The first-floor primary bedroom features a private bath and a spacious closet, with sliding doors to the back deck. Upstairs, another ensuite bedroom awaits, along with an open loft ideal for an office or a game room. The finished lower level opens to a bluestone patio with an outdoor shower and includes two bedrooms, a full bathroom, and a large laundry area. Residents of the Sengekontacket Community can take advantage of access to the dock and kayak storage on Sengekontacket Pond, as well as tennis/pickleball courts and a community clubhouse, perfect for hosting small events. Fully furnished, including kayaks and electric bikes, this property is ideal for a peaceful escape, an investment, or both. All you need is your toothbrush!

Listed by Cassie Courtney of Wallace & Co. Sotheby's

MLS Number 42425

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 2
• Acreage 0.29

OAK BLUFFS BEACHFRONT WITH DOCK - Completed in 2024, this fully renovated three-bedroom, two-bath cottage offers sweeping views of Vineyard Haven Harbor, with private dock and an additional abutting parcel for extra privacy and expanded water frontage. The home seamlessly blends modern upgrades with classic Vineyard charm. In the living room, a large picture window perfectly frames panoramic views of the harbor, setting the tone for this coastal retreat. The space features original wood floors, beadboard walls, and a cozy gas fireplace set against a real stone chimney wall. Flowing seamlessly from the living room, the dining area offers the perfect setting for memorable meals, accompanied by stunning water views. Adjacent to the living room is a sunroom, ideal for relaxing while enjoying sunsets over West Chop. The fully updated cook's kitchen is a chef's delight with new appliances, double ovens, a gas stove, butcher block countertops, and a farmhouse sink. The layout comfortably seats six, creating the perfect space for guests to relax and chat while the chef works their magic. The first-floor bedroom opens to an expansive Ipe hardwood deck with seating for eight, a propane gas grill hookup, and a custom outdoor shower. Upstairs, two additional bedrooms feature designer Annie Selke wallpaper, beadboard accents, and refinished original floors, creating cozy, inviting spaces. Both bathrooms are thoughtfully updated with designer tiles, ceramic floors, and luxury finishes. A new mudroom and laundry room with ample storage makes this property both practical and picturesque. Additional recent upgrades include new shingles, shutters, plumbing, electrical, insulation, mini-split heating and cooling systems, new driveway and landscaping. For pet owners, this home is fully equipped with dog doors and a fully fenced-in yard, making it ideal for those who want to bring their furry friends along. With every detail meticulously attended to, this pristine property is truly move-in ready. All the work has been done, allowing the next owner to immediately enjoy the carefree coastal lifestyle and all the beauty that this exceptional Vineyard location has to offer.

Listed by Jen O'Hanlon of Compass | The O'Hanlon Group

MLS Number 42244

• CommercialSale
• Mls Status Active
• Bathroom 4
• Bedrooms 4
• Acreage 0.12

Historic classic Victorian located at the gateway to the Oak Bluffs Business district & adjacent to the historic Martha’s Vineyard Camp Meeting Association. The layout offers incredible opportunities for a business and would also be ideal for a live/work situation or seasonal rental. With its large welcoming front porch and inviting secret garden for hosting family, friends and customers, this property has been cherished by many over the years. For nearly 25 years, Oak Bluffs’ institution Good Dog Goods has operated out of the first floor and 2nd floor office space and been the main tenant. There is also a one-bedroom apartment, including a balcony with commanding views over Circuit Avenue is the perfect spot for people watching. This amazing business opportunity is looking for the next entrepreneurial spirit to take the reins and steward a true gem of a property.

Listed by Kyle Neyer of Tea Lane Associates

MLS Number 42351

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 4
• Acreage 0.12

Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district & adjacent to the historic Martha’s Vineyard Camp Meeting Association. Create a single-family home or convert to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities for a business and would also be ideal for a live/work situation or seasonal rental. With its large welcoming front porch and inviting secret garden for hosting family, friends and customers, this property has been cherished by many over the years. For nearly 25 years, Oak Bluffs’ institution Good Dog Goods has operated out of the first floor and 2nd floor office space and been the main tenant. There is also a one-bedroom apartment, including a balcony with commanding views over Circuit Avenue is the perfect spot for people watching. This amazing home is looking for the next entrepreneurial spirit to take the reins and steward a true gem of a property.

Listed by Kyle Neyer of Tea Lane Associates

MLS Number 42441

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.89

Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and hand-cut stone propane fireplace, a kitchen featuring granite countertops, Wolf range, and an undercounter wine cooler. A casual dining area at one end of the kitchen, and inviting living room offer the perfect space to entertain. Rounding out the first floor, the primary bedroom has a large walk-in closet, soaking tub, and bay window looking out over the backyard. The second first floor bedroom is currently being used as a TV room. The second level has two sizable ensuite bedrooms with ample closet space and skylights. Highlights of the home include radiant heat, hardwood floors, firepit, large yard and plenty of room for expansion. Even more opportunity for expansion is found in the partially finished lower level. A future office, media room, or workout area awaits. The two car garage is large and has additional space above offering options for additional guest quarters. Meadow View Farms is quiet and private with walking trails and association tennis. The property has mature plantings and is close to both the bike path and over 200 acres of conservation land with hiking trails. Title 5 inspection passed for a 5 bedroom septic. This home is move in ready and is perfect for year-round living. This home would also make a desirable summer vacation retreat.

Listed by Brian C. Smith of Portfolio Real Estate,Inc.