Peyton Wallace

Vineyard Haven MA Residential Income for Sale

Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful renovation, the property offers an excellent foundation to create long-term value. An attic and basement offer generous storage and space for updated mechanical systems, while an interior staircase provides the opportunity to reconnect the two residences into a single-family home if desired. The seller will provide a $50,000 credit at closing toward the installation of a new septic system.

Chilmark MA Land for Sale

This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience -- just minutes from Lucy Vincent and Squibnocket beaches, and the historic fishing village of Menemsha. Engineering for wells and home sites is complete and utilities are on site. Architectural plans by Morgan Studio for a multi-home compound with a swimming pool and accessory structures are available for review upon request.

Edgartown MA Home for Sale

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with easy access to South Beach, bike paths, Katama, and downtown Edgartown. A refined interpretation of the Vineyard summer house, thoughtfully designed for relaxed coastal living.

Vineyard Haven MA Home for Sale

Set privately in one of Vineyard Haven's most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for gathering and quiet retreat, with an effortless indoor-outdoor flow. Bedrooms are thoughtfully arranged in separate wings, with a private primary suite overlooking neighboring lawns, gardens, and conservation land. The inviting living room is anchored by a massive wood-burning fireplace and beautiful hardwood floors, while the chef's kitchen connects seamlessly to indoor and outdoor entertaining spaces. An attached two-car garage adds convenience. Outside, wide lawns, mature plantings, a classic stone wall, and a fenced vegetable garden create a timeless Vineyard setting. A post-and-beam barn offers flexible space for storage, recreation, or a workshop. Ownership includes neighborhood tennis courts and a dock on Lake Tashmoo for boating, paddling, and swimming. A rare opportunity to enjoy an up-island setting with the convenience of nearby Vineyard Haven shops, restaurants, and the ferry.

Oak Bluffs MA Home for Sale

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

Chilmark MA Home for Sale

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

Cataumet MA Land for Sale

A rare waterfront building opportunity on the protected waters of Squeteague Harbor. Ideally situated on Scraggy Neck, this beautiful parcel offers an exceptional setting for a custom coastal residence with sweeping water views and direct harbor frontage. A feasibility study has been completed exploring a residence, accessory structures, and private dock, offering a compelling vision for the property's potential. Available separately or together with neighboring 219 Scraggy Neck Road, creating the opportunity for an extraordinary waterfront compound. Please inquire for additional details, plans, and feasibility information.

Cataumet MA Home for Sale

Exceptional waterfront retreat on the protected waters of Squeteague Harbor. This private Scraggy Neck property offers an extraordinary boating lifestyle with a private dock, boathouse, heated saltwater pool, spa and beautifully landscaped grounds. Completely renovated to the studs in 2019, the residence features bright, inviting interiors with vaulted ceilings, expansive windows, light wood floors and picturesque harbor views. The chef's kitchen features professional-grade appliances, center island, butler's pantry and double-sided fireplace, opening to gracious living and dining spaces overlooking the water. The thoughtfully designed floor plan includes a private primary suite with deck, family room with wet bar, elevator, and guest apartment above the three-car garage. Expansive stone terraces and extensive hardscaping create seamless indoor-outdoor living, while mature landscaping provides exceptional privacy. A pool house, outdoor showers and waterfront boathouse with changing rooms complete this turnkey coastal property, offering an uncommon combination of privacy, boating, entertaining and waterfront living on Scraggy Neck.

West Tisbury MA Home for Sale

THE COMPOUND AT INDIAN HILL Three dwellings. One price. One house decides how you live. Three let you change your mind. More than three private acres in West Tisbury. 4,464 square feet across three buildings, each with its own front door. The Main House holds the center. Glass doors & generous windows pull the meadow inside. A stone fireplace anchors the room. The kitchen was built for dinners that run long. The Studio Barn is the open question. Four sets of French doors swing wide to a wildflower meadow, & the room goes with them. Artist's studio. Wellness space. Whatever you have been missing. The Guest House earns its keep. Three bedrooms, a loft-inspired living space, & a long rental history. Seven bedrooms. Four & a half baths. A heated saltwater pool. A full compound, or a primary residence with income built in. Lambert's Cove & Long Point beaches, farm stands, & Cedar Tree Neck Sanctuary. Walk to the market, apothecary, & post office. Rural enough to disappear into. Close enough to never feel cut off. Most homes are bought for one season of life. This one was built to hold many. Septic capacity for up to 10 bedrooms. Buyer to verify with West Tisbury Board of Health. On the gentle slopes of Indian Hill, more than three private acres hold a main house, a studio barn, & a guest house. 4,464 square feet in all. Wildflower meadows run between them. Layered perennial gardens soften the edges. A heated saltwater pool sits at the center, looking borrowed from a private resort. This is not a house with outbuildings. It is a quiet, self-sufficient world of its own. THE MAIN HOUSE | 2,088 SF Glass doors & generous windows pull the landscape inside. Every room frames meadow or garden. A stone fireplace grounds the living room, which opens to a sweeping dining area & a gracious, well-appointed kitchen. It handles a holiday table for twenty as easily as a Tuesday night for two. THE STUDIO BARN | 1,152 SF The open question. Four sets of French doors swing wide to the wildflower meadow, & the room goes with them. Set apart & private by design. Artist's studio. Yoga & wellness space. A place to retreat & reset. Few Island properties come with this much possibility already built. THE GUEST HOUSE | 1,224 SF Two stories, three bedrooms, one & a half baths, & a loft-inspired living space, tucked quietly on its own. Its long history as a leased rental means the income is not a projection. It is a record. Long-term tenants, visiting guests, the people you want close: this house has already done the job. Seven bedrooms. Four & a half baths. One heated saltwater pool. Arrange it as you like. A full compound for everyone you love. A primary residence with income built in. Or something in between that only you will think of. West Tisbury at its best. Lambert's Cove & Long Point beaches. Cedar Tree Neck Sanctuary for the long walk. Farm stands, village eateries, trails, & bike paths. Market, apothecary, post office, & cafes are an easy stroll. Most homes are bought for one season of life. This one was built to hold many. Three dwellings, two septic systems, capacity for up to 10 bedrooms. Buyer to verify with West Tisbury Board of Health.

West Tisbury MA Home for Sale

Exquisite home with swimming pool in the perfect location in West Tisbury! Set on one of the rarely offered field view properties in Deep Bottom Pond, this gracious residence in one of the Island's most sought after enclaves exudes quality at every turn. Constructed by noted contractor Joe Grillo and designed by Breese Architects, a rare degree of achievement is on display. Through the front entry, an open and voluminous main living area captivates, with sumptuous detail engaging the senses. The front foyer features dramatic 2-storey height with gorgeous paneling and woodwork, and opens onto the home's grand central living room. This gracious gathering place is filled with light from multiple directions and accented by a bold white coffered ceiling and stately wood-burning fireplace, complete with elegant mantel and surrounds. A massive chef's kitchen overlooks the living room, and features Wolf, Sub-Zero, and Miele appliances, an oversize center island, custom cabinetry, and more. Immediately off the kitchen there is a beautiful screened porch with views over the pool and yard to the +/- 32 acres of association fields, where horses are often in sight. Also connected to the kitchen are a relaxing den and an inviting dining room, ideal for large gatherings. Bedrooms in the home are thoughtfully dispersed. There are ensuites on the first floor and above the two-car garage, while the master is set on the 2nd floor with private balcony, 5-fixture spa-like bathroom, and walk-in closet. Also on the 2nd floor are two more bedrooms, which share a full bathroom, and a bright and open landing. Systems inside the house include forced air heating and air-conditioning controlled by a Nest learning thermostat, and Sonos sound with multiple zones. Outside, the grounds are immaculately kept, with most attention being drawn to the pool and field views beyond. Leading from the house to the pool is an artful bluestone patio and walkway, and an outdoor shower serves as the perfect end to time spent enjoying summer water, sand, and sun. Neighborhood amenities include association tennis courts and private dock on the Tisbury Great Pond, and ownership in West Tisbury allows for access during town residents' only times at Lambert's Cove Beach.

Edgartown MA Home for Sale

Welcome to a world away! This contemporary home, with its Wasque plain location and Southeastern face, offers sweeping views of Katama Bay and the Atlantic beyond. Those who know Chappaquiddick covet the departure from in-town living. Only a few minutes' drive to the Chappy ferry, you can access all Edgartown has to offer without being in the press of the season's crowds. As a relatively young home, only personal touches are necessary to make this home your own. The spacious, light-filled and expansive living, dining and kitchen areas are ideal for year round entertaining. Enjoy the privacy while taking in the panoramic views extending from the front of your home. The idyllic surroundings of Chappaquiddick add to the ambiance and luxury of this lifestyle unlike no other.

Vineyard Haven MA Home for Sale

Historic waterfront home, renovated in 1997, with spectacular views of extensive gardens and Vineyard Haven Harbor. This unique property offers the convenience and congeniality of an in-town location, as well as a private sanctuary, where almost an acre of land slopes gracefully to a private beach. A two bedroom home that ''lives'' like three, with more than 2500 sf of living space. A breezy open plan renovated to provide all modern amenities, features a large eat-in kitchen, dining room and living room, all with harbor views. Both second floor bedrooms, one with a deck also offers expansive views of the harbor, dotted in season with anchored sailboats. The substantial Master Bedroom Suite, with two gable ends permits ample space for a king size bed, spacious sitting/TV area, built-in desk ensuite bath and even a large ficus tree. Many windows, french doors and skylights provide beautiful light throughout the house. Relax on the large decks, upstairs and down, whileenjoying great views and harbor activities before strolling to dinner or theatre in town. All this and three private parking spaces. It's no wonder this property has enjoyed excellent vacation rental history. Note: This property has an approved 4-bedroom septic.

Tisbury MA Home for Sale

Perfectly set on Hines Point, just -3/4 of a mile to the ferry and Vineyard Haven harbor, this inviting waterfront residence features gorgeous water views over private sloping lawn and +/-160' of private shoreline on the Lagoon. The well-maintained home, which offers one-level living and an inviting, comfortable layout, includes views of the Lagoon, the Sound, and boats from nearly every room. Three bedrooms are nicely proportioned, with a large master suite set most privately from the main living space. The large living room features a fireplace and gracefully connects the front entry and bedroom wing to the dining room, kitchen, breezeway, two-car garage, and outdoor space. The house has a recently updated forced hot water heating system, utilities and storage located in the basement. The grounds offer expansive lawns both on the street and waterside of the home, and mature plantings provide excellent privacy. Stairs lead from lawn to the waterfront, where a variety of waterfront recreational pursuits are available, such as boating, kayaking, paddle-boarding and fishing on the calm blue waters of the Lagoon, a peaceful +/-544-acre pond that opens to Nantucket Sound along Martha's Vineyard's northern shoreline. Note: Buyer responsible for upgrading the septic system on the property.

Oak Bluffs MA Home for Sale

In the heart of Oak Bluffs just a couple of blocks to the sandy beach this ideally located home is just a short distance to the shops and restaurants of downtown Oak Bluffs. The house features 4 bedrooms, a beach stone fireplace, a wrap around porch, garage, private outdoor garden patio just to name a few. Off street parking and a detached garage are a big plus in this area. There is a strong rental history making this property a great investment.

Chilmark MA Home for Sale

A diamond in the rough in Chilmark, ready for your polish and perfection, this elegant waterfront home on 3.5 acres is truly an outstanding offering, having been owned by the same family for over 60 years. With private waterfront on Quitsa Pond and incredible views to Menemsha Pond, the Sound, Elizabeth Islands and Menemsha Harbor, this is a dramatic retreat, ideally situated for sunsets and recreation on the water. Originally built in 1950, the existing 4 bed home is a beautiful design, thoughtfully laid out with all attention paid to the outstanding water views. The grounds are relaxing, with ample lawns surrouding the home and down toward the waterfront. An update or modernization of the house could create a refined Chilmark destination, while the opportunity to rebuild could allow for larger home, with guest house and pool as possibilities in the future. The location is just 0.5 miles from Squibnocket Beach and all of Chilmark's best amenities are readily within your grasp.

Tisbury MA Home for Sale

Immerse yourself in the beautiful, natural character of Martha's Vineyard at this quintessential waterfront cottage on the Lagoon. Set perfectly atop a commanding 45' bluff, with irresistible water views, this recently updated home is charming and bright - perfect for relaxation - with attractive, nicely proportioned bedrooms and inviting living spaces, featuring a stunning light-filled dining room with panoramic views. From the spacious back deck, a path and stairs lead down to idyllic waters and sandy beachfront on the Lagoon, complete with a mooring for boating enthusiasts. Enjoy swimming, kayaking, fishing and more from just over 100' of private waterfront. An outstanding option for personal use or as an investment property, this home comes with a superb rental history and several leases in place for summer 2017.

Edgartown MA Home for Sale

Simply charming! Well maintained New England style 3 bedroom cottage with separate bunkhouse and peaceful rear lawn area. Includes a garage/barn building with loft for extra storage. All within walking distance of downtown and the Fuller Street beach. Step back in time and turn down the volume of life. Enjoy as is OR create your own in-Town oasis on this pre-existing non-conforming parcel.

Edgartown MA Home for Sale

This charming 5-bedroom home is perfectly located on a quiet street just steps from Downtown Edgartown. With a large backyard, unfinished walk-out basement, and distant views of Edgartown Harbor from the second floor, this property has multiple intriguing features. Whether you are looking for a summer retreat, an investment property with a strong rental history, or a renovation project this property has a lot of options to consider.

Aquinnah MA Residential Income for Sale

Fresh and inviting, this expansive two house waterview compound in the heart of Aquinnah has so much to offer. Beautifully set on 4 acres amidst manicured grounds, a 5 bedroom main house and 1,450 square foot, 2 bedroom second house welcome with open arms. Within the main house, high-ceilings and grand scale are readily apparent throughout, along with high-quality detail and design. The thoughtful floorplan includes master suites on both the first and second level, with plenty of open living areas and guest sleeping quarters. Water views from the main house are breathtaking from the 2nd level and above, featuring clear views of the Sound and Elizabeth Islands. Decking on the first level provides an expansive space for outdoor dining or entertaining, while the top level deck is a jaw-dropping point of view for sunsets and more. The second house on the property was built in 2010 and sits perched above an elegant stonewall. The living space is all on one level, with a gorgeous full kitchen and well-proportioned living room set perfectly for enjoyment of more fabulous waterviews. The location, in the center of Aquinnah, is convenient to many of the best beaches on Martha's Vineyard, including Philbin and Lobsterville beaches, which are both town residents' only in summertime. An outstanding offering with rare size and quality, along with water views - a true gem!