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$3,200,000
4 Beds 6 Baths 73554803 MLS
Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita offers a comfortable and welcoming retreat for family and guests. Beautifully manicured grounds and gardens overlook the picturesque fields of Morning Glory Farm, creating a serene backdrop and a true sense of tranquility. With town sewer available, the property offers the potential for additional bedrooms, providing even greater flexibility for future expansion. A rare opportunity to own a distinctive island compound in one of Edgartown's most convenient and desirable locations!Built in 2018, the guest house features exposed beams and cathedral ceilings in the open-concept kitchen and living area. The first floor also includes a den with porch access, a half bath with laundry, and interior access to an approximately 4-foot cement crawl space. Upstairs, the bedroom offers an ensuite bath and a private deck. Thoughtfully separated from the main house, the guest house also includes its own outdoor shower and dedicated parking area.

19 Llewellyn Way, Edgartown

$2,875,000
3 Beds 3 Baths 73553681 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft., second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits,.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

131 North Water St-Huxford Cottage Unit 96, Edgartown

$2,595,000
2 Beds 2 Baths 73553678 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. A rare opportunity to own a luxury residence at one of Martha’s Vineyard’s most celebrated destinations.

131 North Water St-Collins Cottage Unit 22, Edgartown

$1,975,000
2 Beds 2 Baths 73553679 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

131 North Water St-Huxford Cottage Unit 94, Edgartown

$2,425,000
2 Beds 2 Baths 73553676 MLS
LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind.

131 North Water St -Rowley Cottage Unit 62, Edgartown

$14,500,000
11 Beds 13 Baths 73552898 MLS
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 residence—an 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 pickleball—offering 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.

10 & 12 Boldwater Road, Edgartown

$1,395,000
3 Beds 2 Baths 73549401 MLS
Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town.

44 Prices Way, Edgartown

$9,495,000
4 Beds 6 Baths 73548919 MLS
Timeless architect-designed Katama retreat made for summer living. Privately set at the end of a long drive on 1.53 acres near South Beach, this Patrick Ahearn-designed estate offers 4,605 square feet of refined Vineyard living. Built in 2022, the home blends award-winning coastal architecture with vaulted ceilings, custom shiplap, millwork, antique rough-hewn beams, Rubio Monocoat floors, high-end fixtures, and luxury finishes. The Great Room is anchored by a floor-to-ceiling gas stone fireplace, while the gourmet kitchen opens to the living, dining, and family rooms, with a Butler’s Pantry for entertaining. French doors lead to a screened porch and resort-style outdoor setting with PebbleTec gunite pool, built-in spa, bluestone patio, outdoor shower, and pergola-covered lounge with wood-burning fireplace. Four en suite bedrooms include a serene Primary Suite with pool access. An attached two-bay garage and full unfinished basement add ease and future potential.

29 Slough Cove Rd, Edgartown

$3,695,000
3 Beds 4 Baths 73547874 MLS
A contemporary Katama retreat, newly refreshed and ready for summer. Set in one of Edgartown’s most coveted coastal enclaves, moments from South Beach, this tri-level home offers sun-filled interiors, generous gathering spaces, strong rental appeal, and a private backyard oasis with an 18x40-foot saltwater pool. The dramatic open-concept living level features vaulted ceilings, a wood-burning fireplace, updated kitchen with quartz countertops and stainless appliances, and walls of sliding glass doors opening to newly completed decks and railings. Three finished levels provide comfortable bedrooms, flexible bonus areas, and room for guests to spread out. Recent improvements include fresh interior paint, new sliding glass doors, railroad ties, and completed exterior updates. Outside, enjoy a bluestone terrace, outdoor shower, lush plantings, expansive decks, and resort-style pool setting. An attached two-car garage with finished bonus space above adds versatility. Ideal as a year-round ho

9 Thaxter Ln, Edgartown

$2,495,000
1 Beds 2 Baths 73540958 MLS
Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find one bedroom with an ensuite full bathroom, currently being used as the office. There is also an additional room being used for restaurant storage. With the flexibility to convert the property back to residential use, if desired, this is a rare opportunity in a prime location that should not be overlooked! This offering is for the real estate and the business. Please inquire with listing agent for additional details and information.

218 Upper Main Street, Edgartown

$1,775,000
4 Beds 3 Baths 73531632 MLS
Enjoy privacy at the end of a quiet Edgartown cul-de-sac on .71 acres with easy access to 25+ acres of Land Bank conservation land. Ideally located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, this light-filled post-and-beam home offers a thoughtful floor plan and inviting indoor-outdoor living. The spacious kitchen features a large center island, walk-in pantry, and garden access. A dining area with an enamel pellet stove opens to the expansive deck, while the sunken living room boasts cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. The first floor includes a guest bedroom and full bath. Upstairs are a primary suite with den/office and half bath, plus two additional bedrooms and a full bath. Established gardens, an outdoor shower, basement storage, and town sewer capacity for up to seven bedrooms add exceptional appeal and future potential.

99 Old Purchase Road, Edgartown

$7,999,000
7 Beds 7 Baths 73527262 MLS
Nestled in an enviable Katama setting, this majestic farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a dedicated sunroom that bathes the main level in natural light. At the heart of the home is a true culinary haven—a premier chef’s kitchen anchored by a massive center island, supported by a walk-in pantry and flanked by a quiet, professional study. Offering unparalleled versatility for multi-generational living, the main level also features a completely self-contained guest suite featuring its own private full bath and customized dual walk-in closets. The oversized mudroom offers access to the attached two-car garage and leads outside to the gunite pool, spa and al fresco entertainment area. Schedule your private tour today!

9 Suttons Way, Edgartown

$2,590,000
4 Beds 8 Baths 73523165 MLS
Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three bedrooms, plus a finished lower level for added living space. Outdoor highlights include a deck, heated pool, patio, pool house, and outdoor shower.The guest house was built in 2011 and provides additional living space, multiple baths, a garage, and its own private setting. Near conservation land and water access, and just 1.5 miles to town, this property offers strong rental potential and exceptional versatility.

15 Twenty First St N, Edgartown

$2,950,000
4 Beds 3 Baths 73522670 MLS
This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

13 Young Street, Edgartown

$6,995,000
4 Beds 3 Baths 73520913 MLS
Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay.

103 Edgartown Bay Road, Edgartown

$2,195,000
5 Beds 4 Baths 73520213 MLS
Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting — your own private park among Martha’s Vineyard most beautiful natural setting.

7 Pip'n Circle, Edgartown

$21,500,000
10 Beds 14 Baths 73517157 MLS
A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

56 North Summer Street, Edgartown

$439,500
73516268 MLS
Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows for a home of up to 1,850 sq. ft. of heated living space. Use as a seasonal residence or short-term rental is not permitted, ensuring a stable year-round neighborhood setting. Please note, the property may not be used as a seasonal residence or short-term rental. An excellent opportunity to design and build your future home on Martha’s Vineyard.

5 Candlemaker Circle, Edgartown

$4,600,000
4 Beds 4 Baths 73514104 MLS
ONE MILE FROM HISTORIC EDGARTOWN VILLAGE. NEW home with a POOL, and close to SOUTH BEACH. The facade offers a covered porch. The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room has a soaring cathedral ceiling and a rear wall of two story windows with a gas fireplace. The great room opens to the dining room with a wall of glass doors overlooking the pool area. The dining room flows into the gourmet kitchen with a seating island. Off the dining and kitchen area is access to the mudroom which has a half bath, pantry, and laundry area. Off the mudroom area is an outdoor shower. The first floor hosts the primary bedroom with a luxurious bathroom. The second floor has three guest rooms and two full bathrooms. The rear yard offers privacy in the 14 x 30 ft. salt water heated pool that is surrounded by bluestone and professional landscape.

9 Marthas Way, Edgartown

$2,795,000
73513600 MLS
Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore. Neighboring Wilson’s Landing provides water access to the Edgartown Great Pond for kayaking, paddleboarding, and other activities. With 8 bedrooms possible and the potential to build a guest house, the development options here are many. Whether you envision a family compound, a retreat with room for extended family and friends, or a legacy property designed to be enjoyed for generations, this land provides the canvas. This is one of two parcels for sale.

Lot 4A Browns Farm Lane, Edgartown

$2,895,000
3 Beds 2 Baths 73511131 MLS
Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove . Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor.

24 Beetle Swamp Rd, Edgartown

$7,850,000
4 Beds 6 Baths 73504170 MLS
This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

24 Katama Bay View Road, Edgartown

$2,850,000
4 Beds 3 Baths 73494371 MLS
Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space.

2 Bold Meadow Road, Edgartown

$2,225,000
3 Beds 3 Baths 73493917 MLS
Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom banquette seating 10. The home features a formal dining room, oak floors, a wood-burning stone fireplace featured in Architectural Digest, and a view-facing living room with balcony. The primary suite includes a walk-in closet and en-suite bath with soaking tub and double vanity, plus two additional bedrooms. A spiral staircase leads to a loft lounge with private balcony and two bonus rooms. The walk-out lower level adds flexible space for a gym, office, or lounge. Expansion potential allows up to seven bedrooms, plus guest house, pool, and pool house. $25,000 credit at closing for sewer tie-in.

81 Whalers Walk, Edgartown

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