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$5,795,000
5 Beds ⋅ 6 Baths ⋅ 73569858 MLS
Sophisticated Katama Retreat with Pool and Custom Finishes - Tucked at the end of a lightly traveled road, this modern farmhouse blends sophisticated design, generous living spaces, and exceptional backyard privacy. Thoughtfully customized by the owners in collaboration with the builder, the home features distinctive design details and elevated finishes throughout. A dramatic wall of glass fills the open-concept great room with natural light and connects seamlessly to the outdoor entertaining areas. Spacious living and dining spaces are anchored by a gas fireplace and custom built-ins. The chef’s kitchen features marble countertops, commercial-style stainless and integrated appliances, an oversized center island, beverage refrigerator, and sliding glass panels opening to a poolside bar. A luxurious first-floor primary suite, private office, laundry area, and powder room complete the main level. The home offers five bedrooms and four-and-one-half baths, including a second en suite primary bedroom upstairs. Two additional upper-level bedrooms share a well-designed Jack-and-Jill bath. The finished lower level includes a fifth bedroom, full bath, and expansive game/media room with pool and ping-pong tables, providing flexible space for guests and recreation. Outside, the property becomes a private resort-style retreat with a heated 16-by-38-foot gunite saltwater pool and generous sun shelf. An expansive bluestone patio offers multiple lounge and dining areas, a fire table, and a separate wood-burning fire pit. Manicured grounds, thoughtful landscaping, broad lawn areas, and an enclosed outdoor shower complete the setting. With a strong rental income history, the property offers compelling potential for personal enjoyment and investment. Offered turnkey with indoor and outdoor furnishings for immediate enjoyment or continued rental use.

37 Plain Field Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$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

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.
$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

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$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

Listing courtesy of Listing Agent: Thomas Wallace from Listing Office: Wallace & Co. Sotheby's International Realty.
$16,900,000
8 Beds ⋅ 8 Baths ⋅ 73485121 MLS
Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana—an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location.

114 North Water Street, Edgartown

Listing courtesy of Listing Agent: Erin Hegarty from Listing Office: Donnelly + Co..
$3,995,000
8 Beds ⋅ 6 Baths ⋅ 73483686 MLS
Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses. Private guest quarters above the detached oversized garage offer additional comfortable accommodations. Sweetened Water Farm combines the tranquility of an up-island location with the convenience of being just moments from the boutiques, restaurants, and harbor of downtown Edgartown. A home for all generations in a setting like no other.

23 Beetle Swamp Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$9,000,000
4 Beds ⋅ 7 Baths ⋅ 73476388 MLS
Behind its classic Village façade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and thoughtfully curated finishes define every level of the home. The backyard is a true extension of the home, anchored by a fully equipped cabana, heated saltwater pool, sunken fire pit, and striking custom glass wall. A strong rental history further enhances the property's appeal, offering exceptional flexibility as a private family retreat or a compelling investment opportunity. A home where exceptional quality meets effortless living, offering a fresh and relaxed interpretation of luxury in the heart of Edgartown Village.

43 Peases Point Way S, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

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