MLS Number 40676

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 6
• Acreage 4

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate. Nestled in a private and serene location, this magnificent property offers stunning views of the Atlantic Ocean and Chilmark Pond. Chilmark House, designed by Seattle-based architect Rick Sundberg and constructed by master builder Andrew Flake, merges contemporary amenities with Vineyard themes to create a truly unique living experience. Walking up to the front door you will see an enormous boulder that sits just inches away from the home. The massive stone was deposited on the property from a receding glacier long ago. As you enter the home, you will be greeted by tall ceilings, oak flooring, and natural light. From here, your eye will immediately be drawn to the walls of glass and ocean views. The modern kitchen is a chef's dream, featuring cherry cabinets, granite countertops, and appliances from Sub Zero, Miele, Wolf, and Scotsman. The family room off the kitchen boasts a custom fireplace and is ideal for casual gatherings. Adjacent to the kitchen and deck is a wonderful screened porch with high ceilings and ample room for dining and relaxing. The primary suite is a retreat in itself, featuring access to a private study with fireplace, two luxurious baths, deck and heated floors throughout. The second wing of the house includes three large guest bedrooms, two baths and a dressing room. The heated infinity pool is awe inspiring; a centerpiece of the home with elegant terrace and ocean views. Other outdoor features include the large kitchen garden, fruit trees and half-basketball court. A detached 3-bay garage and additional parking rounds out the main house. Set apart from the main house is the two-bedroom cottage, offering guests a private spot of their own. Chilmark House includes private south shore beach rights, accessible by boat from Chilmark Pond. This one-of-a-kind property, where the Obamas have vacationed, is the ultimate in luxury living. For a truly seamless transaction, all furniture, artwork and gym equipment is available for purchase. Please inquire for more details.

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

MLS Number 40660

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 5.5
• Acreage 4.5

OCEAN VIEW OASIS IN CHILMARK. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a day at Lucy Vincent Beach or on the boat. Pick up some local oysters and lobster rolls in Menemsha and then head home to enjoy a perfect summer sunset on the patio overlooking Menemsha Pond and the Elizabeth Islands. The home is pristine and private with many unique features that make it the perfect place from which to enjoy all that up-Island has to offer. The chef's kitchen and dining area are serene, bright, and functional. The main floor living spaces feature unparalleled Chilmark panoramas with views of South Shore beaches, Quitsa and Menemsha Ponds, and the Vineyard Sound. A stately wood-burning stone fireplace centers the living room which overlooks the expansive lap pool and stone patio area with dining space for outdoor enjoyment. The main house has 4 bedrooms and 3 1/2 baths, all with their own unique water views. The primary bedroom, on the main level, has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. This rare up-Island property also includes a secluded guest house with a well-appointed kitchen, two ensuite bedrooms, and a spacious living area with wood burning fireplace. A one-car garage on the property is a plus for storing all of your Island toys such as surfboards, beach gear, and the Island car. This Chilmark retreat also features deeded access for small boat pick-up and drop-off on Menemsha Pond, just across the way. Close to the Chilmark General store, Chilmark Tavern, Beetlebung Farm Stand, and the Chilmark Community Center for your convenience. However you like to spend your days, at the beach, by the pool, grilling with a crowd, or curled up with a good book in front of the fire, you can do it all at this one-of-a-kind Chilmark property. The co-listing agent is related to the Seller.

Listed by Tina Miller- 508-561-0042 of Compass | Point B

MLS Number 40699

• Residential
• Mls Status Active
• Bedrooms 7
• Bathroom 6
• Acreage 3

Martha's Vineyard has many fine waterfront properties but only a handful of exceptional ones. The Lee Family Compound is an exceptional 3 acre waterfront property with breathtaking unobstructed pond views from an elevated secure location, 750+ ft of pond frontage, 48 ft dock with separate mooring for easy access to Menemsha Pond and Vineyard Sound and privacy without an abutter in view - all compliment the spacious 5 bedroom 5 bath comfortable well built main house and well sited 2 bedroom 1 bath contemporary guest house. The stunning views are everywhere so 14 of the 16 rooms in both houses enjoy grand pond views. Because of the elevation -- the sunsets, moonrises, and stargazing are some of the most remarkable the island has to offer. The two home compound can house 18 comfortably and is perfect for year-round family events. Come launch your canoe, kayak or paddle board from spring to fall; swim, clam or sail from private sandy beach off the point all summer long; sunbathe on your private dock or 3 decks or on the terraced lawn overhanging the cove; and enjoy seasonal holidays by a roaring fire with extended family and loved ones. This compound is proof that a picture is worth a 1,000 words.(see Video Aerial Tour)

Listed by Robert Kenney 914-413-5223 of Tea Lane Associates

MLS Number 40627

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3.5
• Acreage 5.6

This waterfront 4 bedroom 2.5 bath quality custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and the primary bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. A large building envelope allows room for expansion should a new owner desire. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Listed by Abby Rabinovitz cell 617-429-4561 of Tea Lane Associates

MLS Number 40668

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 4.5
• Acreage 5.6

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large enclosed sun porch off the kitchen to enjoy meals and family time and is adjoined by a breakfast nook. Three (3) Bedrooms are located on the upper level. The primary bedroom is complete with a balcony to enjoy sunrises and sunsets. The 4th bedroom is on the first floor next to a full bathroom. The basement is a finished area with an additional living area. The septic system has been upgraded to allow for six bedrooms.

Listed by Julianna Flanders of Flanders Real Estate

MLS Number 41047

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.6

Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark’s most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort. The interior spaces are thoughtfully designed to maximize the views and large windows let in an abundance of natural light. With most of the living area on the first floor, the spacious layout features a large living room with stone fireplace, dining room with fireplace, home office, gourmet kitchen, and 3 spacious bedrooms. The second floor features a bedroom suite with breathtaking views of Stonewall Pond and the Atlantic Ocean beyond. This Chilmark location harmoniously combines natural beauty and modern conveniences. In addition to the immediate waterfront access, the surrounding area offers a wealth of activities including boating, fishing, kayaking and paddle boarding. Don't miss your chance to make this unparalleled waterfront retreat your own.

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

MLS Number 40878

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 2.5
• Acreage 6.1

This is a true Chilmark gem with a timeless feel. Six acres with multiple dwellings, open meadows, ocean views, and private dock access on Chilmark Pond set this property apart. The well-maintained and cherished home, known as the James Allen house, dates back to 1688 embracing a deep history. Classic and comfortable, the home sits stately on this property overlooking old stonewalls lined with mature plantings. On over 6 acres, there is a detached bunk house with a half bath plus a complete two-bedroom guest house tucked in overlooking the meadow that leads towards the pond. These two houses are quite separate from each other so they can be used independently. There is a clay tennis court nestled behind hedges and stonewalls that is in pristine shape. Enjoy a quick walk to the private dock and Chilmark Pond access where one can boat across to the Atlantic Ocean beach or just enjoy life on Chilmark Pond. Easy and uncomplicated, this property has all of the amenities of Chilmark living that draw people to this end of the island.

Listed by Jill Hobby Napior 508-642-0831 of Tea Lane Associates

MLS Number 40055

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 2.5
• Acreage 4.7

Massive Atlantic Ocean views! This 4.7-acre lot with 120-degree views of the Atlantic Ocean over Keith Farm offers the ideal opportunity to create a stunning property with a main house, guesthouse and swimming pool. The current home is ready to make way for the new owner's vision. The property is just one mile to the entrance of Lucy Vincent Beach and half a mile to Beetlebung Corner. It is a mile and a half to Menemsha. The property is criss-crossed with ancient lichen-covered stone walls and has a feeling of having stepped back in time.

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

MLS Number 40760

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 2.5
• Acreage 5

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you can enjoy swimming and watching beautiful sunsets. There is also a 1 car garage with a work space.

Listed by Julianna Flanders of Flanders Real Estate

MLS Number 41240

• Residential
• Mls Status Active
• Bedrooms 3
• Bathroom 3
• Acreage 3.1

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx.

Listed by Julianna Flanders of Flanders Real Estate

MLS Number 40645

• Residential
• Mls Status Active
• Bedrooms 2
• Bathroom 3
• Acreage 4.38

Beautifully sited on over four acres, commanding views across 22+ acres of conservation land to the Middle Line Ridge beyond, a gracious drive directly off North Road brings you to this Soikkeli-built central Chilmark home with entry courtyard, cathedral ceilings, and artisan plaster interior. Sun-filled, single-floor living focused on the land: rolling lawns, perennial gardens, and exceptional stone elements. The main level, featuring a single primary suite, generous spaces for entertaining and multiple activity areas, could be furnished to accommodate a large, light-filled second and a charming smaller third bedroom with shared bath. A large finished lower-level walkout suite with rock-walled private entry, full bath and darkroom holds a myriad of possibilities.

Listed by Jessica Bradlee 508-212-9341 of Tea Lane Associates

MLS Number 40992

• Land
• Mls Status Active
• Acreage 4

CHILMARK! Hilltop Property on the highly desierable Wequobsque Road. The four-acre lot boasts one of the highest elevations on the South Shore with expansive views of the Atlantic surrounded by rolling fields. The property is located less than a mile from the town center with the conveniences of The Chilmark Store, Post Office, The Chilmark Community Center, tavern, library, Beetlebung Farm & town hall. Access to the property is a short drive along a well-maintained private road with beautiful topography, bordering stonewalls, and peaks of ocean views and distant ocean waves. If water access plays high on your list, there are multiple access points within 3 miles of the property; Quitsa Landing, Menemsha Harbor, Squibnocket & Lucy Vincent Beach! Parcel has been perked and is ready for your architect’s plans for your Chilmark dream home.

Listed by Landmarks at TODAY Real Estate