Edgartown

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

72 Chappaquiddick, Edgartown

$1,875,000

4 Beds ⋅ 3 Baths ⋅ 22605017 MLS

A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

42 Bold Meadow Road, Edgartown

$1,875,000

4 Beds ⋅ 3 Baths ⋅ 73585957 MLS

A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

42 Bold Meadow Road, Edgartown

$9,950,000

8 Beds ⋅ 11 Baths ⋅ 73584420 MLS

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

12 Boldwater Road, Edgartown

$2,995,000

4 Beds ⋅ 5 Baths ⋅ 73583186 MLS

In a beautiful coastal setting, this 4-bedroom, 4.5-bath wood-sided contemporary is perched on 1.8 private waterfront acres in Major’s Cove, with frontage on Sengekontacket Pond, and offers a functional floor plan with exceptional views. Expanded over time, the home now includes a primary suite and laundry on the main living level, with comfortable living spaces opening to expansive wraparound decks. The home offers approximately 3,148 square feet of finished space, including approximately 800 square feet on the finished lower level, with substantial above-grade exposure at the rear. An upper-level ensuite bedroom and two additional bedrooms with two full baths on the lower level provide flexibility for family and guests. Improvements include newer windows and doors, new mini-split systems, new hot water heaters, and work to several bathrooms. The September 2026 Title V inspection passed and supports a five-bedroom septic capacity. With town water, only one existing structure on the 1.8-acre parcel, and substantial acreage, the property may offer long-term potential for expansion or future improvements, subject to applicable approvals. Life at Major’s Cove includes access to tennis and pickleball courts, a community boat launch, and kayak storage. HOA services include private-road maintenance, snow removal, and common-area landscaping. Whether enjoyed as a peaceful waterfront retreat or a home with room to evolve over time, this property offers exceptional privacy, versatility, and a distinctive island setting.

24 Myober Ln, Edgartown

$1,850,000

4 Beds ⋅ 6 Baths ⋅ 73582365 MLS

Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ceiling. All bedrooms have private en suite full baths, with two bedrooms on each floor. A sunroom opens to the deck and spacious backyard, offering room to relax or entertain. The home has town water and sewer and is being sold turnkey, excluding books and select personal items. Easy to show. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner occupants are those buyers that will occupy the property as their principal residence within 60 days of closing and will maintain their occupancy for at least 1 year. These buyers are required to sign an Owner Occupant Certification as part of the contract. An investor, trust, vacation or part-time residence, or purchasing for another person will be considered an Investor and are not eligible for First Look. Investors are welcomed to make offers the initial 30 DOM, but will not be countered until day 31. Some images in this listing have been virtually staged

32 Norton Orchard Rd, Edgartown

$4,995,000

4 Beds ⋅ 5 Baths ⋅ 73581090 MLS

COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows fill the interiors with sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing offer convenient access to Katama Bay and Edgartown Harbor.The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. A bright first-floor bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath.Future accessibility was incorporated into the original design through a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption.Offered turnkey with indoor and outdoor furnishings and an established rental history, 98 Edgartown Bay Road is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

98 Edgartown Bay Rd, Edgartown

$1,399,000

1 Baths ⋅ 73580947 MLS ⋅ ["Mariner's Landing"] BLDG.

A standout commercial offering in Edgartown, combining striking contemporary design with exceptional flexibility. Located just outside the historic district and just shy of 2,000 square feet, this commercial condominium offers a beautifully finished, thoughtfully designed interior that feels anything but ordinary. Soaring ceilings, polished concrete floors, dramatic black architectural details and walls of glass create a sophisticated, light-filled space with a modern industrial aesthetic. The versatile layout features an open reception or showroom area, multiple private rooms, a glass-enclosed conference room, additional work areas, and a half bath, allowing the space to adapt easily to a variety of business needs. A full 1,520± square foot basement provides substantial expansion, storage and utility space. Central heat and air conditioning, fire sprinkler system, town water and sewer, on-site parking and a dedicated loading area add everyday convenience and functionality. Renovated in 2021 with an uncommon level of style and attention to detail, this is a compelling opportunity for an owner-user or investor. The Master Deed allows for a broad range of commercial uses, subject to Edgartown zoning and other applicable regulations and restrictions.

1 Mariners Way Unit A, Edgartown

$1,825,000

7 Beds ⋅ 4 Baths ⋅ 73580261 MLS

Two complete homes on one acre in Edgartown's Smith Hollow neighborhood — a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy.The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full basement, and laundry. With a solid rental history already in place, this is a chance to get two houses for the price of one.

4 Farm Way, Edgartown

$4,100,000

4 Baths ⋅ 73575543 MLS

A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-to-month under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq. ft. of office with high efficiency heat pump heat & A/C, plus 1,148 sq. ft. of garage and storage. Ample on-site parking with 25 designated spaces and a loading dock for your business needs. Owned solar installed in 2018 conveys with the property, and the current owners have put significant capital improvements into the building since 2017 — electrical, roof, windows, integrated fire & security systems, mechanical systems, and irrigation system. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit in 2016 for the operation of a small-scale business in a residential neighborhood, and that permit predates the current owners' purchase. A buyer will need approval from the Zoning Board to continue commercial operations.

148 Katama Rd, Edgartown

$3,400,000

5 Beds ⋅ 5 Baths ⋅ 73577862 MLS

Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks—perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage’s main level is ideal for an office. A custom-built cedar shed provides convenient storage for bicycles and beach gear. Set on a half-acre lot with easy access to the nearby bike path leading to Edgartown Village and South Beach, this turnkey property combines an outstanding location with a strong rental history. With multiple living spaces and excellent income-producing potential, this versatile Katama compound is a must-see. Photo's have been enhanced

62 Schoolhouse Rd, Edgartown

$2,455,000

4 Beds ⋅ 5 Baths ⋅ 73577541 MLS

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with a strong rental history!

99 The Boulevard, Edgartown