Edgartown, MA Homes between $2,000,000 and $3,000,000 for Sale

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Newest Edgartown, MA Homes between $2,000,000 and $3,000,000 for Sale

$2,875,000

4 Beds ⋅ 5 Baths ⋅ 73594795 MLS

Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry.The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-burning fireplace, providing additional living space in every season. A mahogany deck overlooks the surrounding property. Above the detached garage is an additional bedroom and full bath, offering flexibility for guests, a home office, or studio. A new Mitsubishi inverter-technology heating and cooling system, installed in 2026, features six independently controlled zones, with heating and cooling extending to the basement and enclosed porch. Owned solar panels provide a net $100.00 per month positive utility bill. There is an 8 bedroom septic system and so expansion opportunities are plenty. Approximately one acre of the property is located across Litchfield Road, offering potential for a future guest house or accessory dwelling unit (ADU), subject to applicable approvals. Located on Chappaquiddick, the property offers convenient access to beaches, conservation trails, and the natural surroundings that define Chappy, all just a short ferry ride from downtown Edgartown.

91 Litchfield Rd, Edgartown

Listing courtesy of Listing Agent: Casandra Hyland from Listing Office: Sandpiper Realty, Inc..

$2,950,000

8 Beds ⋅ 7 Baths ⋅ 73586117 MLS

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

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

$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

Listing courtesy of Listing Agent: Jeffrey Pierce from Listing Office: Compass.

$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

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

131 North Water St-Huxford Cottage Unit 96, 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

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.

131 North Water St-Collins Cottage Unit 22, 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

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.

131 North Water St -Rowley Cottage Unit 62, 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

Listing courtesy of Listing Agent: Michele Lawlor from Listing Office: Corcoran Property Advisors.

$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

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.

$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.

$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

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$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

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$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

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$2,125,000

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

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$2,299,000

4 Beds ⋅ 3 Baths ⋅ 73472929 MLS

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

76 Washque Ave, Edgartown

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

$2,700,000

4 Beds ⋅ 5 Baths ⋅ 73471802 MLS

Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for four. The first floor hosts a primary suite with a luxurious private bath. Upstairs, you’ll find a cozy second living room and two spacious guest suites, each with private baths. The property includes a 900 sq ft detached accessory dwelling, complete with full kitchen, bath, and bedroom. With one acre of land, this property is poised for a future pool. Ready for your 2026 occupancy! Note: This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: Single-family residence not to exceed 1,850 sq ft of heated living area, min. 3 bedrooms, no short-term rentals.

6 Laura's Way, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Edgartown, MA Homes between $2,000,000 and $3,000,000 for Sale

Newest Edgartown, MA Homes between $2,000,000 and $3,000,000 for Sale

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