$2M - $3M

MLS Number 32104

• Residential
• Square Feet 1625
• Bedrooms 5
• Bathroom 2
• Half Bath 1

In-town charmer. This 5-bedroom Victorian is located on a quiet street of multimillion-dollar homes, and represents an opportunity for the buyer seeking entrée into one of the island's most distinguished neighborhoods. Tucked away from all the hustle and bustle of village living yet it is an easy stroll to Edgartown Harbor, shopping, restaurants, and Fuller Street Beach. With one-third of an acre of land, there are plenty of options for the future owner, whether it involves a major renovation and/or addition, swimming pool, or new construction. Experience village living in one of New England's most charming communities.

Listed by Wallace & Co. Sotheby's

MLS Number 25297

• Residential
• Square Feet 1927
• Bedrooms 5
• Bathroom 2
• Half Bath 1

Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).

Listed by Russell Maloney Real Estate

MLS Number 31993

• Residential
• Square Feet 5534
• Bedrooms 7
• Bathroom 6
• Acreage 0.657

Majestic single family water view home plus guest house in the heart of the William Street Historic District with superb Bracketed-Italianate style, known as the Captain Benjamin Cromwell House and later the Clough House. This commanding period home with perfectly proportioned cross gable and cupola, is year-round, impeccably renovated and maintained, and in move-in condition. Amenities include 6 bedrooms, 5 baths, oil heat, a/c,1100+/- s.f. third floor loft, cupola, and cabin/guest house with studio bedroom, kitchenette, full bath,a/c, Rinnai heat, 2 car garage, outside shower, and original out house on .66 manicured grounds. As the captain of the Island Line transportation service between New Bedford, the Vineyard, and Nantucket with his steam-powered side-wheelers, the Eagle's Wing and later the Monohansett, this property was an emblem of Captain Cromwell's success and enhanced by its prominent physical setting with surrounding ornate caste iron fencing. The architecture, water views, spacious front veranda approximately 440 s.f., interior spaces with 9' and 10' ceilings, crown molding, gleaming antique wood floors, horse hair plaster, and history will captivate the attention of the most discerning buyer. The original village of Holmes Hole became the town of Vineyard Haven in 1871 and later the town of Tisbury. William Street was the second street originally laid out by the village in approximately 1831. The William Street Historic District is unique in that it has consistently maintained its look with its historic 19th century homes. Truly a rare, in-town opportunity with access to the park, deep water dock, beach, harbor, and clay tennis courts only steps away. In summary, this property needs to be seen to be fully appreciated. Please read floor descriptions for more details.

Listed by Viewpoints

MLS Number 33807

• Residential
• Square Feet 2325
• Bedrooms 4
• Bathroom 3
• Half Bath 2

Close to downtown on a quiet side street, this 2,325-SF house with water views and magical morning light is steps away from a secluded beach overlooking the town's outer harbor. With three en-suite bedrooms upstairs and a downstairs den, first-floor and upper decks facing the water, and proximity to the Vineyard Haven Yacht Club and West Chop, this architect-designed contemporary offers comfortable and convenient summer living. The open floor plan flows around a floor-to-ceiling central fireplace, with expansive windows and plenty of built-in storage. The .20-acre corner lot features mature landscaping and a large sunny lawn with a field stone wall. Other amenities in this beautifully renovated home include a spacious garage, central air, unfinished basement, and an airy, light-filled mudroom.

Listed by Viewpoints

MLS Number 32289

• Land
• Village Sengy
• Acreage 9.1

SPLENDOR ON SENGEKONTACKET. Once part of the 240-acre Amoz Smith Farm, this gorgeous estate-sized property abuts Felix Neck Wildlife Sanctuary -- and shares a legacy to Felix Neck as previous owners, Lucia and George Moffett, gifted roughly 200 acres of land that make up Felix Neck Wildlife Sanctuary today. Perched on a gentle knoll, the property enjoys superlative views across meadowlands to Sengekontacket Pond and Nantucket Sound beyond. A protective easement provides a footpath that leads to the shores of Sengekontacket Pond, providing direct water access and opportunities for kayaking, canoeing, paddleboarding, shellfishing and more. Since the property is surrounded by conservation land, there are also miles of nature trails that are ideal for exploring by foot. Bring your creative vision to fruition in this most special and private setting surrounded by water, meadow and woodlands. This special offering is made up of four combined parcels (including 11, 12 and 20 Moffett Way, totaling 9.1 acres). There is currently a Main House and Guest House on the property, which can be renovated and/or replaced by new construction. Buyers can also use the current Guest House while a new home is designed and built on the property. This is a perfect opportunity for a conservation-minded buyer who would welcome the opportunity to become a steward of this most special property.

Listed by Point B Realty LLC

MLS Number 31443

• Land
• Village South Shore
• Acreage 6.2

Set beautifully on the southwest part of Kanomika, a prominent peninsula on the Edgartown Great Pond, this prime waterfront parcel is the ideal place to create your dream residence. With over 6 acres and approximately 500' feet of waterfront, the property includes one of the most sandy stretches on the Pond and a southwesterly orientation which provides rare potential for sunsets and spectacular water views toward Swan Neck and dunes in the distance. Launch a boat to enjoy beach on the Atlantic, or swim or sun along your own private shoreline. Perfectly located on the waterfront, the property includes access to a shared tennis court as part of Kanomika - a private neighborhood with protective covenants and waterfront lots of 4 acres or more. Convenient to downtown and Katama, the area is characterized primarily by forest and gently sloping topography and the approach, off Meetinghouse Road, crosses a sprawling meadow that is under conservation. Bring your architect or builder and express what home on the Vineyard means for you in this most pristine and natural locale.

Listed by Wallace & Co. Sotheby's

MLS Number 33171

• Residential
• Village North
• Square Feet 4000
• Bedrooms 4
• Bathroom 3

No detail was forgotten in this meticulously maintained Post and Beam custom home down Flanders Lane. A peaceful setting where you can hear the Menemsha bell chiming in the distance. With four spacious bedrooms, 2 of which are master bedrooms, gracious living areas, beautiful outdoor spaces and deeded rights to 200' of Menemsha Pond frontage, this home is a rare find. From the Alaskan cedar shake roof, to the soapstone kitchen counters and sink, the level of quality and craftsmanship is supreme. The finish work of the oversized living room with huge brick fireplace is an ideal resting place for those chilly winter evenings. The cozy TV/Dining area off the kitchen serves as the perfect entertaining space that can spill out onto the stone patio. A brand new 18 x 36 gunnite heated saltwater in-ground pool currently being added to this unique gem of a property, will enhance the already well maintained and beautiful landscapes and gardens surrounding this home. A must see property, too many details and qualities to list. An unparalleled find! View the House tour: https://my.matterport.com/show/?m=ytJREnUVwRg

Listed by Flanders Real Estate

MLS Number 34377

• Land
• Village Downtown
• Acreage 2.8

Nestled on a quiet lane in one of Edgartown's most distinguished enclaves just half a mile to the village, this 2.8 acre lot off Planting Field Way offers the opportunity to build a dream compound with house, guesthouse and pool. There are charming second story views of Nantucket Sound over conservation land owned by Sheriffs Meadow. The existing house and garage on the property are usable but will inevitably make way for improvements commensurate with the value of the land in this area of multimillion dollar homes.

Listed by Wallace & Co. Sotheby's

MLS Number 34588

• Residential
• Square Feet 4332
• Bedrooms 5
• Bathroom 4
• Half Bath 2

Rare Opportunity to Own One of The Nicest Winterized Homes in Chilmark. This House Has It All, And Could Either Be a Great Income Property Or a Great Place to Call Home. 5 Bedrooms, 4 Full Bathrooms (Jacuzzi in master bathroom), 2 Half Bathrooms, Chef's Kitchen (Thermador Gas Oven/Range, Sub-Zero Refrigerator/Freezer, Dishwasher, Microwave), Breakfast Bar, Huge Living Room, Reclaimed Wood Beams and Columns, Vaulted Ceilings, Laundry Room, Insulated Garage, Finished Basement with Movie Theater, Arcade (Billiards, Jukebox, Pinball, Darts, Video Games), Home Office, Wine Cellar, and very large Walk-In Cedar Closet, Tennis Court, Bocce Court, Outdoor Jacuzzi, Steam Room/Spa, Massive Deck w/ Large Viking Gas Grill, 2 Outdoor Showers (if you go to MV with your family during the summer, you realize how valuable it is to have 2 outdoor showers), Roof Deck, Stone Walls Around Yard & Tennis Court, and a Beautiful Landscape, equipped with Irrigation/Sprinkler System and Shed for Storage. Furniture Negotiable

Listed by Douglas Elliman MV

MLS Number 33749

• Residential
• Village Chappy
• Square Feet 3230
• Bedrooms 4
• Bathroom 2

Tucked between the calm waters of the bay and the Atlantic Ocean, under the guard of the Cape Poge Lighthouse, rests a retreat like no other. Lovingly restored and meticulously maintained, the three bedroom main house and one bedroom boathouse offer all the amenities one would expect, but not necessarily anticipate, from off the grid living. The ideal lifestyle choice for water sport and outdoor enthusiasts alike; with boating, kayaking, kite surfing, and shell-fishing at your doorstep, or for those seeking refuge and relaxation from the bustle of everyday life. Protected by the surrounding 500 acres of conservation, and accessed only over sand or by sea, this truly is the greatest escape.

Listed by Sandpiper Realty

MLS Number 33279

• Residential
• Village North
• Square Feet 4136
• Bedrooms 4
• Bathroom 4

This stunning new 3 bedroom 3.5 bath custom home and 1 bedroom 1 bath guest cottage are sited on 2.9 private acres with water views out to the Vineyard Sound. Both are beautifully designed and built with great attention to quality and detail. Relax on the roof deck from the main house and take in spectacular views of the Vineyard Sound and the Elizabeth Islands. This is a home which feels close to the natural beauty around it. Large windows on the main level offer distant views of rolling hills out to the water and soft sunlight infuses the spacious great room, the heart of the home. Here, the gourmet kitchen flows gracefully into the living/ dining area anchored by a beautifully crafted stone fireplace. An expansive deck and screen porch off the great room extend the living space. Several steps up from the great room is a luxurious master bedroom suite with a steam shower and its own deck with private outdoor shower. The light filled lower walk out level has two more bedrooms, each with their own bath, separate stone patio and individual outdoor shower. The lower level also has a separate office and a large family room. This is a fabulous home with wonderful spaces for socializing and entertaining as well as private areas for time alone or quiet conversation. Just a five minute drive to Aquinnah beaches, this exceptional property is ready to move right in. Furnishings are available separately.

Listed by Tea Lane Associates

MLS Number 33703

• Residential
• Village Downtown
• Square Feet 4304
• Bedrooms 5
• Bathroom 5

NEW CONSTRUCTION, 4,304 sq. feet of custom designed living in the Jordan Way neighborhood, approximately 1/10th of a mile to Edgartown Historic District. The open floor plan features an open kitchen, dining and living room with a fireplace that overlooks the outdoor area. The first floor features a mudroom with laundry, home office and first floor master suite. The second floor has three bedrooms all with private baths. Added to this property is a detached two car garage with a downstairs half bath, and a full bath and guest bedroom upstairs. Professional landscaping adds to the character of this property. Listing price includes a credit of $15,000 towards completion of the second floor master closet and second floor guest bedroom to the far right so that buyer can have input on closet design; or buyer can elect to take a $15,000 credit and work with an independent closet company.

Listed by Vineyard Village Realty