luxury houses with terrace for sale Chilmark, United States

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residencean architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleballoffering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today. Off Edgartown West Tisbury Road via Pohoganot Road.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a spacious kitchen with a center island that opens to a dining area. A sunken living room with floor-to-ceiling windows overlooks the surrounding tree canopy, filling the space with natural light. Just off the living room, a large screened porch offers a peaceful setting for relaxing outdoors. Two bedrooms, a full bath, and a laundry room complete this floor. Up the wood staircase, the second level includes a dramatic hallway that overlooks the living area below and leads to a generous primary suite with a spacious bathroom and additional laundry. The third level features a private guest bedroom with its own living area and full bath, ideal for visitors or extended stays. The finished lower level adds even more living space, offering a full bathroom, bedroom windows, and a walkout door to the side yard. A spacious garage provides added convenience and storage. Convenient to the public boat landing on Lake Tashmoo and the Lake Street tennis and pickleball courts, and just a short distance to Downtown, this is the ideal Vineyard Haven location.

Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the homeowner has poured into every detail. The grounds are equally impressive, featuring beautiful stonework, handcrafted bluestone patios, and professionally landscaped outdoor spaces designed for effortless entertaining. Enjoy summer evenings by the outdoor fireplace, unwind in the Jacuzzi, or rinse off after the beach in the private outdoor shower, all creating a true Vineyard lifestyle experience. Lovingly maintained and thoughtfully designed, this property offers both comfort and refinement just moments from Vineyard Haven Harbor, the ferry, shops, restaurants, and the island’s renowned beaches.

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests, or multi-generational living. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy - this is a rare combination in this price point.

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is.

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown.Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings.At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr., builder of Edgartown’s iconic Old Whaling Church, lending architectural significance to an already exceptional property.Yet it is the combination of land, location, and lifestyle that truly distinguishes 14 Thayer Street. Opportunities to own this level of acreage and privacy within Edgartown Village are exceedingly limited, making this a compelling chance to acquire a true in-town estate in one of Martha’s Vineyard’s most coveted settings.

Set within the historic fabric of Edgartown Village, 14 Thayer Street is a property of uncommon scale and quiet distinction. Occupying a 0.62-acre parcel, rare for this in-town setting, the grounds offer a sense of space and privacy just moments from the harbor and village center. The residence is attributed to Frederick Baylies Jr., the builder of the Whaling Church, and reflects the enduring architectural traditions that define Edgartown. With five bedrooms and five baths across more than 3,100 square feet, the home is both comfortable and unpretentious, suited to long summer stays and informal gatherings. Mature landscaping and open lawn frame the house, lending a sense of seclusion that is increasingly difficult to find within the village. Properties of this scale and provenance seldom come to market, offering a measured opportunity to steward a piece of Edgartown's architectural legacy. MLS® ID: 44225 Interior: Fireplace: 3 Appliances: Stove: Viking Stove, Washer: LG Washer Flooring: 2 Total Bedrooms: 5 Half Bathrooms: 1 Full Bathrooms: 4 Other Interior Features: A, AC, Ins, Irr, Media, OSh, Floor 1: half bath, queen size bedroom with ensuite bath kitchen and wet bar screened in porch sitting room with fire place formal dining room 2 living rooms with a wood burning fireplace, Floor 2: primary suite with ensuite bath, sitting room and fireplace 2 queen size bedrooms with a full bath Exterior: Heat type: OFHW Water Source: Town Sewer: Twn Other Exterior Features: Patio, Scr Porch, Pub Bch, Garden, Deck Parking: 2 car parking Lot Features: Beautifully landscaped Utilities: Cbl

The best architecture doesn't compete with nature... It embraces it. At 78 Gardiner Road, walls of glass, expansive decks, and clean modern lines place the ever-changing waters of Buzzards Bay at center stage. Presiding over a rugged shoreline in one of Cape Cod's most intellectually and culturally rich communities, this restored waterfront residence captures the spirit of a remarkable era in architecture while providing an extraordinary setting for life today. Walls of glass frame endless water views. Clean lines and soaring ceilings dissolve the boundaries between indoors and out. Sunlight dances across the bay from morning until evening when sunsets astound. The rhythms of tide, wind, and sea become part of everyday life. This is not a home that competes with its surroundings... It is at one with them. A broad sweep of lawn gives way to a seating area overlooking a dramatic natural shoreline where weathered boulders, native vegetation, and the waters of Buzzards Bay create a landscape that changes by the hour and by the season. Morning coffee on the deck. Afternoon swims. Sailboats crossing the horizon. Winter storms rolling in from the west. Every day offers a different perspective. Inside, this four bedroom 3,700+ square foot home has been carefully restored to its original coolness. There are huge ocean front family rooms on each level, multiple other gathering areas for both larger and intimate. Please verify all information contained herein.

Set within the coveted Racing Beach community, this exceptional Shingle Style residence offers a quintessential Cape Cod lifestyle just a short stroll from the private beach. With 4,665 square feet of beautifully appointed living space, 5 bedrooms, 3 full baths, and 2 half baths, the home is designed for both relaxed coastal living and effortless entertaining. Spend summer days at the beach, gather with family and friends, or simply watch the sun set over Buzzards Bay. Lovely marsh views provide a constantly changing backdrop, reflecting the beauty of the seasons. The heart of the home is its beautifully renovated kitchen, completed in 2024 and thoughtfully designed for both everyday living and entertaining. A generous quartzite island anchors the space, complemented by a Viking cooktop, Wolf double ovens and microwave, and a full-size Sub-Zero refrigerator and freezer. A pantry with wine and beverage refrigerators adds exceptional convenience and storage. The home has also been enhanced with solar panels purchased in 2024 and a whole house generator installed in 2022, providing added efficiency and peace of mind. A rare opportunity to own a substantial coastal home in one of Falmouth's most sought-after beach communities, where privacy, natural beauty and the pleasures of seaside living come together.

Rarely does a property offer the privacy of 2.88 acres while being just a short stroll to downtown Falmouth and the beautiful surf drive beaches. This spacious 4-bedroom Cape is designed for comfortable year-round living and memorable gatherings. The inviting living room is centered around a wood-burning fireplace, while the eat-in kitchen features a convenient walk-in pantry for exceptional storage. Two bright sunrooms provide the perfect spaces to relax with a morning coffee, entertain guests, or simply enjoy views of the surrounding gardens and natural landscape. Step outside to the expansive wraparound elevated deck, where you'll overlook a peaceful yard that feels like your own private bird sanctuary. Mature gardens, two storage sheds, and abundant privacy create a truly tranquil setting. Additional features include a walk-out basement, one-car garage, whole-house generator, oil heat, and mini-split air conditioning for year-round comfort. Whether you're looking for a year-round residence or a Cape Cod getaway, this exceptional property offers the best of both worlds--peaceful seclusion with the convenience of being so close to Main Street and Surf drive beach.

Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft., providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand.

Nestled in sought-after Sippewissett Highlands, this extraordinary custom home offers seasonal water views across Buzzards Bay to Marion, Mattapoisett, and Cleveland Ledge Lighthouse. Thoughtfully renovated from 2022-2026, the 6,331 sq ft residence blends timeless architecture with modern luxury and exceptional craftsmanship. Designed for multigenerational living, the home features 4 bedrooms including two ensuite bedrooms, one on the main level and a luxurious second-floor primary retreat with spa bath, sitting room, private balcony, and loft office. Elevator access services all floors. The custom kitchen showcases a 5' x 10' walnut island, Thermador refrigerator, Bosch induction cooktop and dishwasher, double American Range ovens, and walk-in pantry with additional dishwasher. Elegant entertaining spaces include a sunken living room with fireplace, paneled library, formal dining room, and enclosed sunroom with mini-split. Outdoor living features 60+ feet of decks, stone terrace with custom made authentic Forno Bravo pizza oven, private pond, native landscaping, tennis/pickleball court and deeded beach rights. Exceptional coastal living in one of Falmouth's premier neighborhoods.

Some properties offer water views. This one invites you to live on the water. Tucked away at the end of a quiet cul-de-sac in Lower Davisville, this is a rare opportunity to purchase a single-owner property that enjoys spectacular views of Israels Cove and Bournes Pond from nearly every room. Across the water, protected conservation land preserves the natural setting and safeguards the view. Designed for easy first-floor living, the home features 4 bedrooms, 2½ baths, hardwood floors, and a newer deck overlooking the pond. The backyard becomes your gateway to summer, with direct water access for swimming, kayaking, canoeing, paddleboarding, and small sailboat adventures. For additional boating, the Green Pond Marina is nearby. Additional highlights include a passing Title V septic system installed in 2022, whole-house generator, outdoor shower, and two storage sheds. Just one mile from Menauhant Beach and available for the first time, this special waterfront property offers a setting that is increasingly rare to find and impossible to replicate.

Located in a sought-after Davisville neighborhood, this beautiful 3-bedroom, 2.5-bath contemporary home is just over a mile from Menauhant Beach. The main level features newer laminate flooring throughout most of the first floor, an oversized primary suite, second bedroom, full bath, and a bright living room with cathedral ceilings. The french doors in the kitchen and dining room open to the newer composite deck--perfect for summer gatherings, outdoor dining, or relaxing after a day at the beach. Upstairs, you'll find a third bedroom and a spacious loft area overlooking the living room below. The finished walkout lower level provides plenty of additional living space with potential for a future ADU. There is a wet bar, half bath with laundry, access to the two-car garage, and a door that leads to the partially fenced backyard. For those who enjoy spending time on the water, access to Green Pond is just a few houses away, making it easy to launch a kayak or canoe. Enjoy all that this Davisville location has to offer at 108 Pheasant Lane.

A sweet Cape Cod ranch with room to make it your own! Set on a half-acre lot in East Falmouth, this three-bedroom, two-bath home features an eat-in kitchen and a wood-burning fireplace for cozy evenings. Recently painted and featuring a new roof, it offers a welcoming starting point for your personal touches and updates. Enjoy morning coffee or summer gatherings on the backyard deck, with a garden shed for tools and outdoor essentials. The generous, agriculturally zoned lot offers space for gardening, keeping chickens, and potential expansion, subject to town requirements. Just 0.3 miles from the popular Cape Cod Winery and approximately two miles from town or the beach, 39 Kerrywood Drive combines convenience with room to grow. Bring your ideas—and your chickens—and create your own Cape Cod retreat! buyer to verify all information herein.