MLS Number 37110

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 5
• Bathroom 5

A luxurious in-town, waterfront estate overlooking Vineyard Haven Harbor - The Vineyard has always been the place to go for rest and relaxation; it is an oasis of beauty and tranquility in a vintage seaside setting. 103 Main Street offers an exquisitely designed home nestled on 1.7 acres with expansive views of the boats coming and going and yet it is right in the Village just steps from boutiques and coffee shops, restaurants and theaters. This shingle style coastal New England home, designed by respected architect Patrick Ahearn, has 6,500 sf of living space and is warm and friendly with space to accommodate everyone. The terraced pool and abundance of casual outdoor living space is private but takes full advantage of the spectacular setting. A must see!

Listed by Courtney Marek of Sandpiper Realty

MLS Number 35775

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 9
• Bathroom 7.5

Presenting one of the most outstanding real estate assets on Martha’s Vineyard. 1005 Main Street was built in 1891 and purchased in 1948 by the Singer family who have owned it since. The setting is front and center in West Chop and includes a large private beach and 210-degree views so expansive that you can enjoy sunrises and sunsets from the same chaise lounge on the deck. The views are extremely active with ferries and fishing boats passing in the distance, sailboat races, and at closer range smaller craft including perhaps your own children in a laser or kayak. There are 8 large bedrooms, 7 full baths, and a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been completely renovated between 1995 and 2005 with new insulation, HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the walkway down to it has been trod by many who have come to love this home and incomparable setting. Of course, with its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family and so it is helpful to have so much parking - eight spaces plus a two-car garage. The sea wall assures that this property will be here for future generations. Owners may apply separately for membership at the West Chop Club, which offers a wide range of amenities, including use of nearby "middle pier" for loading and unloading.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

MLS Number 36702

• Residential
• Mls Status Active
• Village Downtown
• Bedrooms 6
• Bathroom 7

This gracious, impeccably detailed, three-story air conditioned home with guest house and garage overlooks Vineyard Haven harbor towards the East Chop lighthouse, steps away from its own sandy beach and an easy stroll to downtown Vineyard Haven. Thoughtfully sited and designed, the 5,787- sf house on 1.55 acres includes four bedrooms, an expansive living and dining room, and multiple porches with spectacular water views. A graceful gambrel designed house was built in 2004 which incorporates an abundance of windows, red cedar shingles, and copper gutters. The first floor boasts an open living room with a dramatic fieldstone fireplace and a wall of French doors with views of the harbor. The gourmet kitchen adjoins a screened in porch for that perfect sunset dinner. Enjoy multiple outside sitting areas including a porch, another screened in porch and an outside kitchen and dining table on a sunny bluestone terrace. The second floor has a breathtaking master suite with an enviable master bathroom. Completing the second floor are three more bedrooms en suite and two sitting rooms. A third floor with large open spaces and sweeping views, especially from the widow's walk, will entice you for that afternoon read. Additional amenities include a full walkout basement with wet bar, an exercise room, a media room, plus a state of the art wine cellar and an elevator. This is a very special offering!

Listed by Bobbi Reed of Viewpoints

MLS Number 33535

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 8
• Bathroom 6.5

Located directly on the water with a short walk to your beach, this three-story shingle-style air conditioned home on Vineyard Sound, is an easy walk to the West Chop Club, and epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler’s pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens, open lawns, and most importantly multiple possible sites for a pool. A private path leads to the West Chop Trust’s north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come. This private community affords easy access to beaches, independence and activities for all members, and an appealing lifestyle away from the hustle and bustle of other parts of the island. We are happy to provide all the wonderful amenities available in the West Chop area.

Listed by Emily Flake of Viewpoints

MLS Number 33954

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 8
• Bathroom 6.5

Located on a winding private road, this original 1896 West Chop waterfront home was completely renovated to exacting standards in 1992. With 8 bedrooms and 6 and a half bathrooms, and a classical layout with formal and informal areas in which to relax and pass the time, this home encompasses all that this desirable location provides for family gatherings and summer memories at West Chop. A stately front entrance leads to the formal living room with adjoining separate sitting room, with fireplace, that opens to the expansive water facing porch providing active views of the Vineyard Sound and additional entertaining space to while away a lazy summer afternoon. The home offers an exceptional combination of elegant charm and modern amenities including the large gourmet kitchen breakfast room, with Wolf and Sub Zero appliances, bespoke cabinetry and a butler’s pantry that leads through to the formal dining room. The staircase leads to a large primary bedroom suite with a full bath, office and balcony overlooking the water. Three further bedrooms and 2 additional bathrooms occupy the remainder of the second floor with 4 further bedrooms and 3 baths on the third floor. The huge walk out basement was created during the renovation, and could be finished to create living space for a wine cellar, family room or gym. The home was fully air conditioned in 2019 and there is potential to add a pool. Directly in front of the property is a beautiful private conservation trust protected beach ideal for sunning, swimming, tide rides to the dock, kayaking, fishing and of course breathtaking water views and dreamy sunsets. This is a rare opportunity to buy in the heart of West Chop. Privately located, yet close to Mink Meadows Golf, the Vineyard Haven Yacht Club and conveniently close to ferry service, hospital and town center restaurants and shops. West Chop is a unique Vineyard community where families have enjoyed the fellowship of friends and neighbors for generations. See further description under "Comments/Directions" for the benefits of being part of the West Chop community in this special North Shore setting.

Listed by Jill Napior of Tea Lane Associates

MLS Number 37396

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 7
• Bathroom 6

Elegant and refined, this exceptional estate property is sited on 1.3 acres. Located in the coveted Hatch Road neighborhood, this 2 home property boasts incredible architectural detail with all the modern amenities. As you enter the property via a winding gravel drive past an expansive lawn, you come to a setting not found so close to downtown Vineyard Haven. The main house dates back to 1900 and has been meticulously renovated and features a gourmet kitchen open to a dining room with french doors looking out to a rose garden, a spacious first floor master bedroom suite, dramatic great room with 20 foot ceilings with wood detail, and an inviting screened-in porch leading out to a private brick patio. The home features 4 additional guest bedrooms on the second floor. The guest house was designed in 2008 and built by a prominent Martha’s Vineyard builder. The wood detail includes aged lumber and the walls are warmly lined with recycled barnwood. Stunning museum quality terrazzo flooring inlaid with wood beams and terrazzo countertops are featured in the spacious great room, gourmet kitchen and dining room. Other guest house amenities include two bedrooms with en suite baths each with stunning wide plank flooring, and a spacious loft perfect for a home office. A home gym/pool house, outdoor kitchen, 2 car-garage and pool complete this rare offering.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

MLS Number 35174

• Residential
• Mls Status Active
• Village Tashmoo
• Bedrooms 6
• Bathroom 7.5

Why would you need to leave home? this extraordinary estate offers everything one needs for privacy and seclusion in a safe at home setting. Tashmoo Farm has been meticulously and tastefully restored to preserve the historic character and grandeur yet offers all of today's modern amenities. This gracious home is in pristine condition and now features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal living room, dining room, family room and home office. All new heating and A/C. The newly renovated kitchen includes 2 Sub Zero refrigerators, a Bosche dishwasher, Thermador double ovens and a five burner stove top. Many complimenting features include original moldings, 7 fireplaces, wide pine and fir floors and all new windows. A har-tru tennis court, gunite pool and a delightful pool house were added in the late 1990's. The pool house is accessible to both tennis and pool through oversized doors that lead to private patios covered by a pergola. It's is well equipped with grill area and wet bar, a changing room and full bath. Beautifully landscaped grounds with expansive lawns overlooking rolling meadows, extensive perennial gardens surrounded by stone walls offers exceptional privacy. Access to Lake Tashmoo, association dock and several walking trails. BUYER'S BROKER MUST BE PRESENT AT ALL SHOWINGS AND APPOINTMENTS.

Listed by Brenda Galligan of Karen M. Overtoom R.E.

MLS Number 37140

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 4
• Bathroom 3.5

VIEWS! VIEWS! VIEWS! Start 2021 off right with this lovely turnkey home on the water that is ready for immediate occupancy! Enjoy spectacular views from 885 square feet of decking and porch overlooking Sheriff's Meadows and the Vineyard Sound. What could be better than living space and dining outside on a pristine deck. With 120 feet of private beach, you will not find better swimming and boat activity on the island. All your amenities are here including a great outside shower, built in grill area with piped propane, mudroom to wash off the sand, and countless spaces outside to read a good book or to dine! First floor master suite with fantastic sunrises and sweeping water views. Combination kitchen and dining, inside or out, plus a living room viewing a 42 foot long deck with the Sound beyond. Upstairs, another master suite with picturesque Sheriff Meadow views, and a porch to enjoy early morning sunrises and coffee. Another 2 bedrooms and full bath plus a sitting area round out the spectacular 2nd floor. This house is ready for the discriminating buyer looking for that move-in ready home, furniture to be negotiated separately. This ideal location is near the 83 acre West Chop Woods, Mink Meadows Golf Club, the West Chop Club, and the Vineyard Haven Yacht Club. Rarely is there a waterfront in this area with such dramatic views and a total renovation. Don't miss your opportunity to have your own slice of paradise anytime you want to escape to the Vineyard or year-round living! Please call listing office for floor plans and renderings from Squash Meadow. Please view listing sheet for landscaping plans! Easy to show!

Listed by Emily Flake of Viewpoints

MLS Number 37910

• CommercialSale
• Mls Status Active
• Bathroom 1.5
• Half Baths 1
• Acreage 0.2731

Large commercial building located in the Waterfront/Commercial District of Vineyard Haven. Currently has 9 rented office spaces. Interior is in excellent condition with many "multi-year" tenants. Waterfront location on scenic Lagoon Pond and with water view over Vineyard Haven Harbor. Great location and close proximity to the ferry and everything that is downtown Vineyard Haven. Financials available upon request and with a signed confidentiality agreement. Monthly fees are based on the square footage of each unit, so the amount varies. **please do not enter building without appointment** Viewing on Sunday only and with 48 hour notice.

Listed by Doug Reece of RE/MAX on Island

MLS Number 36566

• Residential
• Mls Status Active
• Village West Chop
• Bedrooms 5
• Bathroom 3

One of a kind saltbox located in the heart of West Chop. Owned and loved by the same family since 1935, this home was erected on its current site in 1930 incorporating portions of an older (late 1700's) house which had been carefully dismantled and transported from Lambert's Cove to the current West Chop site. This is a wonderful opportunity for a new family to embrace a treasured home with peaks of water. This 5 bedroom, 3 bath home embodies simple summer life on Martha's Vineyard, rocking on the back porch, playing tag in the yard, or enjoying a morning or evening tide ride. Properties on "the Loop" rarely come on the market, this classic is not too be missed!

Listed by Emily Flake of Viewpoints