$2M - $3M

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 Compass | The O'Hanlon Group

MLS Number 41926

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 5
• Acreage 0.07

Gorgeous waterview home tucked into a corner of Vineyard Haven village. This property is a landmark thanks to its distinctive red door and the stunning flowerbeds visible to passersby. The quaint exterior disguises what greets the visitor upon entering - a sophisticated combination of traditional and modern design within a completely renovated home (most recently in 2008-2010 and then in 2019). Consider the fact that the house has four large bedrooms all with modern ensuite bathrooms PLUS an office PLUS a separate den PLUS an extra full bathroom. The primary bedroom with its private deck occupies the entire third level of the home and enjoys spectacular 120-degree harbor views of the multitude of wooden sailboats on their moorings and the ferries coming and going. This is a home for entertaining friends and family thanks to its open floor plan that opens onto a large deck. The home is located at the far end of Main Street in what is a bustling part of the village, and yet when one steps inside, the hubbub disappears as the door closes behind you. The cobbled driveway fits two cars and there is also a grassy driveway that leads to a detached two-car garage. The garage is currently configured to accommodate one car in the off-season. The other half of the garage is an art studio that could be used as is or repurposed as an office or gym. Tucked between the house and garage is a peaceful area with bluestone pavers that lead to an outdoor shower - the perfect place to rinse off after a day at the beach or out kayaking or paddle-boarding.

Listed by Wallace & Co. Sotheby's

MLS Number 42256

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 2.5
• Acreage 0.3199

Showings Available 9/14! LAGOON WATERFRONT: Charming and Updated Beachfront Cottage with Private Dock and Sweeping Lagoon Views. Experience the best of Vineyard living in this renovated waterfront cottage offering breathtaking views of the Lagoon, over 100 feet of private sandy beach frontage, and private dock. Enjoy kayaking, swimming, fishing, clamming and sunbathing right from your doorstep, and take advantage of your private 90-foot dock, perfect for every type of boating. All this, combined with stunning sunsets, makes this home truly special. Situated on a 13,000+ square foot lot, at the end of a quiet road, this lovingly maintained cottage has been in the same family for decades and serves as a quintessentially private Vineyard getaway. It features three bedrooms with two full bathrooms, plus a powder room, providing relaxed waterfront living. Inside, the modernized kitchen boasts granite counters and is adjacent to the dining room, with water views. The living room, graced by a centerpiece beach stone wood-burning fireplace, looks out to the gorgeous seaside scenery, filling the space with light and tranquility. The second-floor primary bedroom offers stunning views of the Lagoon, an oversized private deck, and an en-suite bathroom. The two guest bedrooms, one of which also enjoys water views, share a full bathroom, with efficient storage and built-in nooks throughout the house. Recent renovations include HVAC updates with AC, new electrical and plumbing, flooring, bathrooms and kitchen. Additionally, the sale could include mooring equipment for added convenience. Located just over a mile from downtown Vineyard Haven and Oak Bluffs, this home provides easy access to all the Vineyard has to offer. Relax on your private beach, boat from your private dock, enjoy exceptional sunsets, and watch the ferries come and go, all while feeling your tension drift away with the outgoing tide. This classic Vineyard home is a rare offering and not to be missed.

Listed by Sandpiper Realty

MLS Number 41916

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 1.2

27 Ocean View Farm Road is a unique house with the main living spaces designed by architect Elizabeth Carlhian in 1964 along with a connected, yet private bed and bath suite designed by architects Modigliani/Noyes in 1987. A covered breezeway between the two spaces frames the ocean views while providing cover from the weather. Taken together the house consists of 4 bedrooms and 3 baths sited high on a hill providing wide views of the Atlantic Ocean and distant views to Squibnocket and Aquinnah. Owned by the same family for over 60 years this rare offering is located on the southern side of Chilmark and is just 1.3 miles from famed Lucy Vincent Beach. The property abuts the Ocean View Preserve and provides miles of walking crosstown walking trails to Fulling Mill, Peaked Hill and beyond. Buyers will either want to renovate and restore the house to its original design or simply rebuild. The lot size is 1.2 acres which, according to Chilmark's zoning, this parcel should support a new house of 3,000 square feet by right (larger with a special permit), with 24 feet in height. Buyers will need to confirm building size and height with Chilmark’s building inspector. New construction may be able to site a house higher on the hill (25 ft. setbacks) for even more impressive views. Please note: potential buyers and their agents must be accompanied by listing broker as there are some hazards about. Call for appointment, easy to show. The property is subject to estate sale rules and is being sold in “as is” condition. Property video can be seen at this link: https://vimeo.com/manage/videos/935864342

Listed by Russell Maloney Real Estate

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 Tea Lane Associates

MLS Number 42444

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 3.5
• Acreage 0.53

Welcome to 24 Dark Woods Road, a beautifully maintained 3-bedroom, 3.5-bath Contemporary Colonial nestled in an upscale, tranquil neighborhood. This spacious residence abuts acres of Sheriffs Meadow conservation land, offering miles of trails, serene pond views and peaceful privacy at the end of a quiet road, yet is just a mile from the beach and closer to Edgartown Village. This association prides itself in complementing and maintaining the natural surroundings. Step into the entryway to a sunlit, front-facing kitchen featuring granite countertops, custom cabinetry and coordinated built-in desk. The open-concept living room boasts soaring ceilings, a commodious dining area and a wall of sliders leading out to a backyard deck perfect for outdoor living and future expansion. The first-floor primary bedroom with ensuite bath, second bedroom, full bath and study, provide convenience and comfort. An open stairway leads to the second floor with a balcony overlooking the living room, where you'll discover a cozy versatile den, a large third bedroom, full bath and a bright office space. Thoughtful design elements include a central vacuum system, ample storage and energy-efficient features including solar panels and a modern heat pump system, backed by an oil heating option. Additional unfinished space on the second level as well as over the garage. The lush, irrigated yard and welcoming front hydrangea garden complete this idyllic offering. With potential for expansion to 6 bedrooms, a spacious basement, and an EV-ready garage, this home is a rare find. Offered mostly furnished, it’s ready for you to make it your own.

Listed by Seacoast Properties

MLS Number 42087

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 2.5
• Acreage 0.23

CHARMING EDGARTOWN CAPE WITH GUEST COTTAGE + POOL. Step into this stylish in-town compound, featuring a charming Main House with a nicely updated kitchen and bathrooms, accompanied by a newly constructed, coastal chic Guest Cottage -- a perfect retreat for visiting family and friends. The two homes are centered around a spacious landscaped yard and a refreshing 16x34-foot gunite pool with a bluestone terrace, creating a private oasis for relaxation and entertainment. Nestled just a short distance from town, this home offers convenient access to Edgartown Village shops and restaurants while providing a serene retreat. Inside, the open layout welcomes you with an abundance of natural light and a seamless flow between the living spaces. With its desirable features and prime location, this charming compound presents a unique opportunity to embrace the quintessential Edgartown lifestyle. Don't miss the chance to make this your enchanting new home or investment property. Furnishings are available for purchase separately, for those seeking a turn-key opportunity and effortless transition into their new Edgartown home.

Listed by Compass | Point B

MLS Number 42131

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 4.5
• Acreage 2.74

Oasis in the woods of West Tisbury! This meticulously constructed, updated and well-maintained home is set on an expansive, yet private, 2.7-acre parcel. This 6-bedroom home has three levels of living space, 2,363 square feet on the spacious first floor, 672 in the second-floor suite and 1,877 in the bright, sunlight-filled lower level, for a total of 4,912 square feet. This home abounds in gathering places, inside and outside, highlighted by additional flexible finished spaces, mature gardens, fruit trees, a sizeable patio with outdoor kitchen and a 16' X 32' inground pool that will be the focal point of your summer gatherings. There is even enough lawn for any family sports activity you can imagine! This is truly a home for all seasons. The owner designed the exterior of this home to be as low maintenance as possible. In spite of its seclusion, it is remarkably proximate to necessary destinations: 2.1 miles to Up Island Cronigs Market and 3.6 miles to the Vineyard Haven ferry dock.

Listed by Sandpiper Realty

MLS Number 42240

• Residential
• Mls Status Active
• Bedrooms 2
• Bathroom 2.5
• Acreage 0.304

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home offers convenience and charm. Don't miss the opportunity to own this fantastic property.

Listed by Donnelly + Co

MLS Number 41614

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 5
• Acreage 1.33

Waterview and waterfront property that is protected from the elements and set amongst some of the finest homes in Makonikey! Complete with fully approved plans by Moskow Linn Architects for a new 4 bedroom home with pool and 2 bed. carriage house, this private compound includes three existing dwelling structures that were originally built in 1974, 1981 and 1985. There is a northerly view of Vineyard Sound from the home site, along with ready access to an exceptionally sandy north shore beachfront (approx 100 yards from the home site via 50% ownership in 39 Beach Pebble Rd). Take the plans and build as designed or customize as you see fit! An incredible opportunity to create your dream escape in an exceptionally private and tranquil setting.

Listed by Compass | MV Team

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 Portfolio Real Estate,Inc.

MLS Number 42180

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 1.4

A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter months, wood floors, natural light and multiple levels. The living room features a contemporary Swedish woodstove and two skylights and sliding glass doors to a balcony making the space bright and cozy. The expanded primary bedroom suite is spacious and offers a private bathroom with generous jacuzzi tub. The kitchen and dining rooms open onto a large deck for entertaining that looks out over the back yard and lovely plantings. There are two guest bedrooms on the second floor separated by an open loft space currently being used as a study and sitting area. The lower level of the main house features a garage, additional storage, and a bonus room with private entrance. The studio style separate guest house offers a full bathroom and kitchen and is situated over a large barn storage space that could accommodate a vehicle or boat. The 1.4 acre property is surrounded by mature trees and abuts the historic Chilmark Cemetery, preserving the privacy and ensuring quiet neighbors. The private association barrier beach is a short walk from the house, or use the association's private beach parking. There are also kayak racks available for association residents to store their kayaks and canoes by Chilmark Pond. The main house has solar panels powering all the electric and hot water in the home and the auto charging station. The main house features a whole house water purifier, ducted heat and AC. The main and guest have separate septic systems and both septic systems have passed Title V.

Listed by Tea Lane Associates