MLS Number 42313

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 6
• Acreage 9.1

Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting. This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond and distant ocean views from almost every room and possesses a delightful mix of contemporary and modern features, such as geothermal and solar panels. The houses sit on nine acres of beautiful waterfront with 800 feet of sandy pond beach frontage. A 16’ Duxbury Dory with trailer in excellent condition included with the house, allowing you to explore the great pond and easily access Atlantic Ocean beach rights only 15 minutes away. In a private though convenient location only 12 minutes to the airport or Edgartown Village. This property may be purchased with 4 Jacobs Neck, if you need more space close-by for family and friends! Please call listing broker for details.

Listed by Deb Hancock of Hancock Real Estate

MLS Number 42130

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 7.5
• Acreage 0.3064

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. Perfect for family living or hosting guests, this home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

MLS Number 42243

• Residential
• Mls Status Active
• Bedrooms 8
• Bathroom 7.5
• Acreage 0.3282

With captivating harbor views, this generational home on North Water Street is a rare offering. The property features a 6-bedroom, 5.5-bath primary residence, with restoration work nearing completion and ongoing improvements that combine classic elegance with modern comfort. The property also includes newly constructed additions completed in Spring 2023: a 1-bedroom, 1-bath guest house and a 2-car carriage house with its own 1-bedroom, 1-bath living quarters. The private backyard oasis is perfect for relaxation and entertainment, featuring a 16' x 32' saltwater pool and spa, complete with a pool cabana. This extraordinary property is a must-see.

Listed by Erin Hegarty of Compass | Point B

MLS Number 39817

• Residential
• Mls Status Active
• Bedrooms 8
• Bathroom 7.5
• Acreage 6.6

This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive views of the South Shore. There are 5 suites all with luxurious bathrooms, closets, and private garden terraces. Additionally, there is an attached carriage house with 3 additional bedrooms, a billiards room and exercise room. The grounds offer a large, stunning pool, a 12 person Jacuzzi, outdoor kitchen, and parking courtyard. There is a high level of finish throughout, a whole house Lutron control system and advanced audio/video. Herring Creek Farm offers direct access to private South Shore beach and over 150 acres of conserved land.

Listed by Gerrett Conover of Landvest MV

MLS Number 41705

• Residential
• Mls Status Active
• Bedrooms 8
• Bathroom 7
• Acreage 3.52

An extraordinary waterfront estate on Chappaquiddick complete with 140-ft deepwater dock, 3-bedroom guesthouse, garage barn, and the unique opportunity to own your own 9-hole “links” golf course next door. The home was designed by award-winning Boston architecture firm Albert-Righter-Tittman and built by Doyle Construction - a "dream team" for the owners whose goal was to achieve a superb finished product. It is just a few minutes away but a world apart from the hustle and bustle of Edgartown village. Since completion the property has been featured in numerous magazine articles and coffee table books. The main house pays homage to the illustrious camps that dotted this shoreline a hundred years ago - grand yet welcoming. This modern interpretation allows most areas of the home to enjoy views of Nantucket Sound. Everywhere there are pleasing details such as fir floors, locust posts that support the 900 sq ft porch, and shiplap interior. The home was built to the very highest standards. There are 5 bedrooms in the main house including a primary bedroom suite on the second floor with 180-degree water views. Beneath the impeccable cosmetic details are mechanical systems that will allow any occupant to live there with all creature comforts. The basement houses a gym and steam/sauna. The home is ideal for entertaining, with its vast great room and dining table that seats 18 people. The interior spaces spill easily to the outside where the lawn stretches to the private beach which in turn yields to Nantucket Sound glistening to the horizon. The setting also provides the ideal vantage point to watch regattas featuring some of the world's finest yachts, extraordinary sunsets, and of course the legendary Edgartown July 4th firework display. These are stellar swimming waters to plunge into right off your own beach, or, if the mood takes you, somersault into from one of the two swimming platforms at the end of your own private dock. The 140-ft dock has a draft of 6 to 8 ft. In addition there are two moorings. The 990 sq ft guesthouse is privately situated and as well as a full kitchen and living area there are 3 comfortable bedrooms. The 2200 sq ft garage barn with workshop has radiant heated floors and a half bath. The house is being sold with all furniture included. There is also the opportunity to purchase the neighboring Royal & Ancient Chappaquiddick Links, a Martha's Vineyard institution.

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

MLS Number 41236

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 4.5
• Acreage 35.2

Spectacular 35 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1 1/2 mile wide main pond and barrier beach to the ocean beyond. The handful of well pruned trees on the property enhance the water views. The sophisticated and charming quality house was built by Andrew Flake, arguably the finest Vineyard builder over the last 40 years. Mark Hutker created an innovative design with an arc shape nautical theme so every room faces the water. The 3 second floor bedrooms enjoy large balconies and the first floor primary bedroom opens to a nice deck and quiet garden sanctuary. The handmade luxury kitchen cabinetry and extensive woodworking were done by Smallbone, a British Company noted for time honored design and craftsmanship. Adding to this estate, reflecting decades of careful planning and development, is a lovely private pool and pool house, 4 room guest suite over the garage with large deck, two stone wall enclosed specimen fruit tree meadows, a large field circled by a grand stone wall, a idyllic lily pond and two miles of private trails. Last but not least, are 14+ subdividable acres. Keep boats and small craft on your mooring at waters edge for a short trip to the 3,000 ft Boldwater private beach. Boldwater is 38 homesites on 450 acres with 150 acres of conservation and abuts approx. 1,500 acres of conservation lands and a few large estates. A most remarkable rural area convenient to town and the airport. (** The 20.8 acre 32 Boldwater Road waterfront property can be purchased without the abutting 14+ acres at 3 Jacobs Neck Road for $8,550,000)

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

MLS Number 41887

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 7.5
• Acreage 16.4

CASUAL ELEGANCE ON KATAMA BAY. Welcome to 25 Lelands Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappaquiddick. This magnificent home, nestled at the end of a private winding drive on 16.4 private acres, offers over 7,200 square feet of living space, designed for the ultimate luxury of spending treasured time with family and friends. As you step inside, you'll be greeted by the warmth of four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork and built-ins, a spacious screened porch and more! The rooftop widow's walk provides breathtaking 360-degree views, while the sparkling blue waters of Katama Bay can be seen and enjoyed from most every room in the house This welcoming retreat features six bedrooms, all with en suite baths, including an exquisite three-room Owner's Suite with en suite bath, adjoining den/office, sweeping water views, and a private second-floor deck. Additionally, there is a three-room Family Suite on the second floor, complete with its own private living area and kitchenette. The combined screened and covered porch, which extends nearly the full length of the home and overlooks Katama Bay, is a defining feature of the property, providing ample space for al fresco summer meals, reading, playing games, or simply soaking in the brilliant evening sunsets. With over 320 feet of frontage on Katama Bay, this home offers ample opportunities for sailing, boating, paddleboarding, fishing, and clamming. Embrace the tranquility of life on Chappy, surrounded by sand dunes, tidal ponds and grassland habitats, with access to miles of unspoiled beaches and nature trails. There is an attached 3-bay garage for storing all your recreational gear including your island car, watercraft, bicycles, beach equipment and fishing gear! The home was designed by architect Patrick Ahearn and is being offered turnkey, including hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, adding objects and vibrant colors that delight the eye in every room. Enjoy this beautiful property as-is or bring your own design style and create your signature coastal haven. Discover the perfect blend of casual elegance and serene waterfront living at this stunning Chappy waterfront retreat on Katama Bay.

Listed by Wendy Harman of Compass | Point B

MLS Number 41159

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 6
• Acreage 0.24

43 Peases Point Way South is where warmth and style meet sophistication, creating a truly one-of-a-kind living experience in the heart of Edgartown Village. Once you step through the gated arbor, you are welcomed by a lovely courtyard, creating the first of many unexpected and special moments carefully planned to provide the utmost privacy and tranquility, whether indoors or out. The Patrick Ahearn-designed home, just a short stroll away from Main Street shops, restaurants and the scenic Edgartown harbor, is elevated by its exceptional interior finishes and distinctive floor plan. Unparalleled luxury is carried through all levels of living, including an awe-inspiring outdoor space anchored by a remarkable salt water pool with a sunken fire pit and unique custom glass wall feature. Perfectly curated and luxurious furnishings only further enhance each space, making a turn-key opportunity possible. Recently completed, this phenomenal property has set a new elite standard.

Listed by Katherine Donahue of Sandpiper Realty

MLS Number 41086

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 6
• Acreage 4.8

This waterfront Edgartown Great Pond compound abounds with rare features. Set in a coveted, private location on Turkeyland Cove, the 4.8 acre parcel includes two full sized homes, custom pool with pool house, +/- 400 feet of waterfront, outstanding views, and a private beach lot on the Atlantic. The main residence sits right on the shoreline, with four bedrooms and beautiful quality throughout. The second home, built in 2010, is set back from the waterfront - still with water views - with 2556 sf, two bedrooms, three car attached garage, and full basement. The property is tied together gracefully with extensive plantings, landscaping and custom fence/gateways. The pool area is an oasis unto itself, with two outbuildings supporting the L shaped gunite swimming pool. Open lawns lead easily to the waterfront, where you have access by boat to the Atlantic beach or other recreation on these pristine waters. Held by the same owner for over 30 years, this property is an opportunity not to be missed.

Listed by Peyton Wallace of Compass | MV Team

MLS Number 42478

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 5.5
• Acreage 0.56

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and custom cabinetry. The five spacious bedrooms are thoughtfully positioned throughout the home, providing unparalleled privacy and comfort. The main house features four private bedrooms with three full bathrooms and private balconies. The fifth bedroom is housed over the detached two-car garage. The detached two-car garage not only provides ample storage for vehicles but also features a private one-bedroom suite above, perfect for accommodating guests or serving as a tranquil home office space. The meticulously landscaped grounds are a true masterpiece, featuring a sparkling pool surrounded by a flagstone patio complete with an outdoor dining area and fire pit, making indoor and outdoor living seamless. This property offers both tranquility and convenience. Just moments away from the charming shops and restaurants of downtown Edgartown, and a short distance from the island's pristine beaches. A well rounded offering that should not be overlooked!

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

MLS Number 41291

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 5
• Acreage 1.03

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The french doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a three-car garage, providing ample space for your vehicles and storage needs including a large one bedroom and bath upstairs. Katama Bay View Road is located adjacent to Sheriffs Meadow Conservation land and public access to Katama Bay. Conveniently located near South Beach, one of Martha's Vineyard's most beautiful and sought-after beaches.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's