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 42325

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 4.5
• Acreage 1.757

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges. Main house has two bedrooms, 2 1/2 baths, private office, expansive fireplaced living room, spacious kitchen/great room, oversized mudroom and large deck. Guest House over 2-car garage features two bedrooms, two full baths and lovely sitting room. LISTING AGENT IS RELATED TO OWNER. **No AC in living room of main house.

Listed by Betsy Kessler of Rutledge Properties

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 41412

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 2.5
• Acreage 0.25

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

Listed by Gerrett Conover of Landvest MV

MLS Number 42430

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3.5
• Acreage 0.76

"MARTHA'S VINEYARD PRIME LOCATION". Nestled in the prestigious Tower Ridge neighborhood off County Road, this English Tudor-style home presents a rare opportunity to own a residence in a highly sought-after private association known for its unique properties and exceptional location. Situated directly across from the renowned Farm Neck Golf Course, this property is just 2 miles from downtown Oak Bluffs and a short 10-minute drive to both Edgartown and Tisbury. Set on the most coveted 3/4-acre lot in the area, this stucco and cedar home enjoys a prime position next to a community tennis court, which sits on 8 acres of protected, private common land. The residence boasts 5 bedrooms and 3.5 bathrooms, offering ample space with nearly 3,000 square feet of living area. The property also includes a spacious 24 x 24 foot two-bay garage with an attached garage apartment, perfect for guests, family, or potential rental income. The heart of the home features an expansive 18 x 36 foot great room with soaring cathedral ceilings, fir wooden beams, and a large working fireplace. Adjacent to this space is a well-appointed kitchen with new appliances, leading into a cozy den with a second working fireplace and TV area. The backyard is bordered by 50 mature pines, cedars, and hemlocks, offering the perfect setting for a future pool and pool house. Additionally, there is a 50 x 25 foot poured cement basketball court/utility pad, a detached 12 x 18 shed with a plywood floor, and an attached 12 x 8 shed featuring a poured cement floor and its own 30-amp electrical panel. This property provides a unique chance to recreate a dream home on the island. Don’t miss this opportunity! Property being sold unfurnished, AS-IS.

Listed by Grace Hagerty of Grace Hagerty Real Estate Inc

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 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 42013

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 2
• Acreage 0.18

Immersed in the picturesque setting of Oak Bluffs on Martha's Vineyard, Fairview on Greenleaf Avenue, one of only ten homes in this coveted location, harmoniously blends historical charm with coastal serenity. This cherished family home holds a special place in the hearts of its owners, with roots tracing back to childhood memories and the family's Rochester, NY home on Fairview Crescent. Architecturally designed to echo the local gingerbread cottages, an addition seamlessly integrates with Oak Bluffs' historical aesthetic. The highlight? A rooftop deck, offering unparalleled views—the highest point on Greenleaf Ave—overlooking Lakeside Park, the rejuvenated Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound beyond. This commanding viewpoint makes Fairview the ideal spot for enjoying the annual Oak Bluffs fireworks display and glorious sunrises. For over 27 years, Fairview has been a sanctuary of family memories, lovingly maintained and enjoyed by multiple generations. It features three bedrooms and a finished basement that provides additional flexible living space. See the included photos to envision how the lower level would look with furniture and a traditional staircase. The spacious backyard and the large multipurpose building, which functions as both a shed and garage, add to the property's charm and utility. The large lot includes ample parking off of Gorham Ave. Located on a peaceful side street, Fairview enjoys proximity to the heart of Oak Bluffs' vibrant community life, including traditions like Illumination Night, concerts at the Tabernacle, and walks to Ocean Park. Yet, it offers a quiet retreat, close to all the town's amenities without being in the midst of the hustle and bustle. Noteworthy is the involvement of Island architect Jaime Weisman in the addition, ensuring thoughtful design and execution. Fairview isn't just a home; it's a gateway to a lifestyle enriched by the enchantment of Oak Bluffs, celebrated for its historic landmarks and coastal charm. It represents a rare opportunity to continue a legacy of creating memories in a setting that combines the best of Martha's Vineyard's natural beauty and cultural richness.

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