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Edgartown Real Estate Listings
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56 North Summer Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 56 North Summer Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.24 Acres / 10,260 sq.ft.
$21,500,000.00

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined...

Property Details

33 Boldwater Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 33 Boldwater Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 9.10 Acres / 396,396 sq.ft.
$19,900,000.00

Experience the timeless beauty of Martha's Vineyard from this luxurious waterfront retreat where the landscape feels so effortlessly connected to daily life. This property embodies understated luxury and timeless design, featuring a meticulously crafted stone residence and guest house. The setting ...

Property Details

12 Calebs Pond Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 12 Calebs Pond Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 2.10 Acres / 91,476 sq.ft.
$17,500,000.00

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoo...

Property Details

114 North Water Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 114 North Water Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.00 Acres / 0 sq.ft.
$16,900,000.00

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. A rare combination of scale, craftsmanship, and location. The offering includes eight bedro...

Property Details

14 Starbuck Neck Road & 23 Thayer Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 14 Starbuck Neck Road & 23 Thayer Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.00 Acres / 14,810 sq.ft.
$15,250,000.00

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, t...

Property Details

211 Upper Main Street & 26 Curtis Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 211 Upper Main Street & 26 Curtis Lane, Edgartown MA 02539
Type: Commercial
Lot Size: 0.26 Acres / 11,135 sq.ft.
$14,900,000.00

Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each...

Property Details

14 Cow Bay Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 14 Cow Bay Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.50 Acres / 65,340 sq.ft.
$14,000,000.00

Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of pri...

Property Details

2 Old Farms Trail, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 2 Old Farms Trail, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 38.00 Acres / 1,655,280 sq.ft.
$12,500,000.00

Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly pos...

Property Details

14 Thayer Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 14 Thayer Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.62 Acres / 27,007 sq.ft.
$10,995,000.00

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, galler...

Property Details

14 Trapps Pond Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 14 Trapps Pond Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.79 Acres / 77,972 sq.ft.
$10,850,000.00

Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered c...

Property Details

139 Chappaquiddick Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 139 Chappaquiddick Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 5.03 Acres / 219,106 sq.ft.
$10,750,000.00

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and t...

Property Details

25 Lelands Path, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 25 Lelands Path, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 16.40 Acres / 714,383 sq.ft.
$9,995,000.00

YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent resi...

Property Details

12 Boldwater Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 12 Boldwater Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 9.87 Acres / 429,937 sq.ft.
$9,500,000.00

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 ...

Property Details

4 Jacobs Neck Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Jacobs Neck Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 10.27 Acres / 447,361 sq.ft.
$8,900,000.00

Great Potential with Pond & Beach Access ~ Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering...

Property Details

4 Sand Plain Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Sand Plain Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 4.73 Acres / 206,038 sq.ft.
$8,750,000.00

This truly remarkable Chappaquiddick property offers a rare opportunity to step back in time and experience the quintessential character of Martha’s Vineyard. The original historic home, built in 1892, is distinguished by its signature four-story tower with 270-degree water views and gracious wrap...

Property Details

15 Tilton Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 15 Tilton Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.23 Acres / 10,018 sq.ft.
$8,250,000.00

This traditionally styled residence offers exceptional quality and craftsmanship in a coveted Edgartown location, situated on a corner lot just blocks from downtown and the harborfront. Thoughtfully designed for both elegant entertaining and relaxed island living, the home features beautifully propo...

Property Details

9 Suttons Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 Suttons Way, Edgartown MA 02539
Type: Multi Family
Lot Size: 1.01 Acres / 43,995 sq.ft.
$7,999,000.00

Nestled in an enviable Katama setting, this masterfully designed shingle-style 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 ent...

Property Details

2 Lexington Avenue, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 2 Lexington Avenue, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$7,695,000.00

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed new construction by Morgan Studio, a husband-and-wife–led boutique design firm. A turn-key offering for elevated indoor-outdoor living, the residence features soaring ceilings, a fluid floor plan with multiple gatherin...

Property Details

16 Witchwood Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 16 Witchwood Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.50 Acres / 152,460 sq.ft.
$7,495,000.00

Situated down a long private driveway, this renovated 3.5-acre Katama estate offers a rare opportunity to acquire a turnkey property with a deep-water dock slip on Katama Bay. Impeccably executed throughout, the estate showcases exceptional craftsmanship, distinctive materials, top-of-the-line appli...

Property Details

103 Edgartown Bay Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 103 Edgartown Bay Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.00 Acres / 43,560 sq.ft.
$6,995,000.00

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 propert...

Property Details

CONTINGENT OFFER
STILL SHOWING
Contingent
28th August 2026

8 Beach Plum Meadows, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 8 Beach Plum Meadows, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.65 Acres / 71,874 sq.ft.
$6,900,000.00

BEACH PLUM MEADOWS: ARCHITECTURAL KATAMA COMPOUND NEAR SOUTH BEACH. Set on more than 1.6 acres in the coveted Beach Plum Meadows enclave, this distinctive property combines classic coastal architecture, private compound living, and distant views across the Katama plains to the Atlantic Ocean—all l...

Property Details

5 Atlantic Drive, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 5 Atlantic Drive, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 2.11 Acres / 91,911 sq.ft.
$6,750,000.00

Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence...

Property Details

38 Simpsons Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 38 Simpsons Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.11 Acres / 4,791 sq.ft.
$6,650,000.00

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows s...

Property Details

78 Plantingfield Way, Edgartown MA 02568

Town: EDGARTOWN | All Edgartown listings
Address: 78 Plantingfield Way, Edgartown MA 02568
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$6,125,000.00

Set within one of historic Edgartown Village’s most coveted neighborhoods, this gracious 4-bedroom, 5.5-bath home with guest suite is a rare opportunity to acquire a true heirloom property. Inside, a grand foyer, soaring ceilings and generously proportioned rooms create an atmosphere of understate...

Property Details

4 Somerset Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Somerset Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.53 Acres / 23,086 sq.ft.
$5,950,000.00

Refined New Construction in Katama. Introducing the fourth custom built residence in the new Somerset development. This exceptional new construction represents a sophisticated interpretation of modern Martha’s Vineyard living. With nearly 3,500 sq ft, the beautifully appointed 4-bedroom, 4.5 b...

Property Details

26 Curtis Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 26 Curtis Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.34 Acres / 15,000 sq.ft.
$5,900,000.00

Exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes...

Property Details

29 Llewellyn Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 29 Llewellyn Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.04 Acres / 45,302 sq.ft.
$5,820,000.00

Set on over an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the pr...

Property Details

98 Edgartown Bay Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 98 Edgartown Bay Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.63 Acres / 27,442 sq.ft.
$4,995,000.00

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...

Property Details

31 Butlers Cove Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 31 Butlers Cove Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.04 Acres / 132,422 sq.ft.
$4,850,000.00

This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 191...

Property Details

9 Marthas Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 Marthas Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$4,600,000.00

ONE MILE FROM HISTORIC EDGARTOWN VILLAGE; Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with fre...

Property Details

170 Katama Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 170 Katama Road, Edgartown MA 02539
Type: Commercial
Lot Size: 0.67 Acres / 29,185 sq.ft.
$4,450,000.00

Ideally situated just one-half mile from historic downtown Edgartown on the main access road to South Beach, the Katama General Store presents a rare opportunity to acquire a premier commercial property in one of Martha's Vineyard's most desirable locations. Set on 0.67 acres, the property features ...

Property Details

32 Marthas Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 32 Marthas Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$4,195,000.00

Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophist...

Property Details

CONTINGENT OFFER
STILL SHOWING
Contingent
22nd October 2026

148 Katama Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 148 Katama Road, Edgartown MA 02539
Type: Commercial
Lot Size: 0.44 Acres / 19,166 sq.ft.
$4,100,000.00

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 ow...

Property Details

148 Katama Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 148 Katama Road, Edgartown MA 02539
Type: Multi Family
Lot Size: 0.44 Acres / 19,166 sq.ft.
$4,100,000.00

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 ow...

Property Details

33 Main Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 33 Main Street, Edgartown MA 02539
Type: Commercial
$3,995,000.00

Rare opportunity to own a prominent commercial property on Main Street in the heart of downtown Edgartown. The first floor offers approximately 1,300 square feet of open retail space with excellent visibility on one of Martha’s Vineyard’s premier shopping streets. The second floor includes a two...

Property Details

23 Beetle Swamp Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 23 Beetle Swamp Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 2.40 Acres / 104,544 sq.ft.
$3,995,000.00

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 b...

Property Details

4 Garrett Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Garrett Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.37 Acres / 146,797 sq.ft.
$3,995,000.00

Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defin...

Property Details

6 Hollow Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 6 Hollow Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.93 Acres / 40,510 sq.ft.
$3,950,000.00

Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths bet...

Property Details

10 Pease Point Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 10 Pease Point Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 1.14 Acres / 49,658 sq.ft.
$3,850,000.00

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot can afford up to 4 bedrooms and has the potential to subdivide with proper permitting (see proposed plan in documents), offering versetility and an exceptional canvas for your estate planning vision. Positioned at the end of a private dr...

Property Details

10 Pease Point Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 10 Pease Point Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.14 Acres / 49,658 sq.ft.
$3,850,000.00

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot can afford up to 4 bedrooms and has the potential to subdivide with proper permitting (see proposed plan in documents), offering versetility and an exceptional canvas for your estate planning vision. Positioned at the end of a private dr...

Property Details

8 Turkeyland Cove Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 8 Turkeyland Cove Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 5.50 Acres / 239,580 sq.ft.
$3,650,000.00

Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providi...

Property Details

0 Pocha Road Extension, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 0 Pocha Road Extension, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 11.39 Acres / 496,148 sq.ft.
$3,495,000.00

CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to ½ mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres...

Property Details

2 & 6 Clements Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 2 & 6 Clements Way, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.74 Acres / 32,234 sq.ft.
$3,300,000.00

A compelling opportunity to acquire raw land in Edgartown with exceptional development potential. Lots 4B and 4C based on the plot plan provided, each offer the potential for a five-bedroom residence, ADU/guest house, pool, and pool cabana, providing the flexibility to create a substantial Martha’...

Property Details

26 Pulpit Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 26 Pulpit Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$3,295,000.00

COASTAL CONTEMPORARY IN KATAMA. An exceptional Katama retreat, this beautiful coastal contemporary offers a refined expression of island living, thoughtfully designed for both casually elegant entertaining and effortless summer relaxation. Set on beautifully landscaped grounds between Edgartown Vill...

Property Details

19 Llewellyn Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 19 Llewellyn Way, Edgartown MA 02539
Type: Multi Family
Lot Size: 0.92 Acres / 40,075 sq.ft.
$3,200,000.00

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 aro...

Property Details

40 Edgewood Drive, Edgartown MA 02539-6328

Town: EDGARTOWN | All Edgartown listings
Address: 40 Edgewood Drive, Edgartown MA 02539-6328
Type: Single Family Residence
Lot Size: 0.57 Acres / 24,829 sq.ft.
$3,150,000.00

This is an excellent opportunity to own a beautiful crafted custom home set on over half an acre in a peaceful neighborhood just minutes from downtown Edgartown. The property offers striking curb appeal with stone walls, granite steps, professional landscaping, and ample parking, and it borders prot...

Property Details

114 Meetinghouse Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 114 Meetinghouse Way, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 3.04 Acres / 132,422 sq.ft.
$3,100,000.00

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, su...

Property Details

114 Meetinghouse Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 114 Meetinghouse Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.04 Acres / 132,422 sq.ft.
$3,100,000.00

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, sub...

Property Details

21 Vickers Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 21 Vickers Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$3,075,000.00

Katama at its best ~ WITH A POOL! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach. With the bike path, Katama General Store, and Edgartown ...

Property Details

15 & 27 Pennywise Path, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 15 & 27 Pennywise Path, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 5.00 Acres / 217,800 sq.ft.
$3,000,000.00

Five Acres in the Heart of Edgartown: Rare and Full of Possibility Land like this almost never comes to market. Set along Edgartown/Vineyard Haven Road, this level 5-acre offering (currently two parcels) in the R20 zone gives you room to dream big: a private island retreat, or a potential subdivisi...

Property Details

BACK ON MARKET

20th October,
2026

24 Myober Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 24 Myober Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.80 Acres / 78,408 sq.ft.
$2,995,000.00

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 an...

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CONTINGENT OFFER
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Contingent
10th October 2026

13 Young Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 13 Young Street, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.70 Acres / 30,491 sq.ft.
$2,950,000.00

Tucked in the heart of Katama, 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 seamless blend of comfort and classic Vineyard charm. The main living level is bri...

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23 Thaxter Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 23 Thaxter Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.71 Acres / 30,927 sq.ft.
$2,950,000.00

OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a...

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72 Chappaquiddick Avenue, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 72 Chappaquiddick Avenue, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.01 Acres / 131,115 sq.ft.
$2,950,000.00

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 e...

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131 North Water St, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 131 North Water St, Edgartown MA 02539
Type: Condominium
$2,875,000.00

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 96 at 131 N Water Street in Edgartown, a 1061-square-foot, three-bedroom, three-bath, second & third floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The l...

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49 The Boulevard, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 49 The Boulevard, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.66 Acres / 28,749 sq.ft.
$2,850,000.00

A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence...

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2 Bold Meadow Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 2 Bold Meadow Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.70 Acres / 74,052 sq.ft.
$2,850,000.00

Nestled on a private 1.7-acre parcel in the peaceful Bold Meadow neighborhood, this classic expanded Cape offers a perfect blend of comfort, space, and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from all tha...

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9 Winter Street # A, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 Winter Street # A, Edgartown MA 02539
Type: Commercial
$2,800,000.00

Just a block off Main St, Winter Street grew alongside Edgartown's 19th Century maritime and whaling boom. In the mid 2010's local business owners began transforming the corridor, and affectionally dubbed Winter Street the "Left Bank" of Edgartown in comparison to Paris's famous boutique shopping di...

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Lot 4B Browns Farm Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: Lot 4B Browns Farm Lane, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 3.05 Acres / 132,858 sq.ft.
$2,795,000.00

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing...

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Lot 4A Browns Farm Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: Lot 4A Browns Farm Lane, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 3.05 Acres / 132,858 sq.ft.
$2,795,000.00

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...

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6 Lauras Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 6 Lauras Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.00 Acres / 43,560 sq.ft.
$2,700,000.00

Coastal Luxury Meets Versatility in Edgartown Welcome to a rare opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a sprawling one-acre plot with a stunning detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an exp...

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131 North Water St, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 131 North Water St, Edgartown MA 02539
Type: Condominium
$2,595,000.00

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN COLLINS COTTAGE, Unit 22 at 131 N Water Street in Edgartown, a 960-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harb...

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20 Meshacket Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 20 Meshacket Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$2,550,000.00

Incredible opportunity just a mile from downtown Edgartown. There are multiple options. This 3-bedroom/3.5-bath home is a garden oasis but also offers owners the option of running a significant business from the property with existing professional offices (reception, two offices, conference room, ha...

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Contingent
30th September 2026

9 Codman Spring Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 Codman Spring Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.88 Acres / 38,332 sq.ft.
$2,500,000.00

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 li...

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77 Sixth Street North, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 77 Sixth Street North, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.28 Acres / 12,000 sq.ft.
$2,500,000.00

WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to t...

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10 Woodhaven Drive, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 10 Woodhaven Drive, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.01 Acres / 43,995 sq.ft.
$2,500,000.00

Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equ...

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218 Upper Main Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 218 Upper Main Street, Edgartown MA 02539
Type: Commercial
Lot Size: 0.20 Acres / 8,712 sq.ft.
$2,495,000.00

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 ...

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9 North Neck Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 North Neck Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.00 Acres / 43,560 sq.ft.
$2,495,000.00

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue ...

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21 Llewellyn Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 21 Llewellyn Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.71 Acres / 30,927 sq.ft.
$2,495,000.00

Offering exceptional flexibility and potential, this 7-bedroom property is situated on a generous 0.71-acre conforming lot in a charmng and convenient Edgartown neighborhood. Originally built in 1988, the home presents an opportunity to update or reconfigure the space while taking advantage of its s...

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99 The Boulevard, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 99 The Boulevard, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.28 Acres / 12,196 sq.ft.
$2,455,000.00

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept ma...

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CONTINGENT OFFER
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Contingent
24th October 2026

131 North Water St, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 131 North Water St, Edgartown MA 02539
Type: Condominium
$2,425,000.00

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN ROWLEY COTTAGE, Unit 62 at 131 N Water Street in Edgartown, a 895-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbo...

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3 Janes Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 3 Janes Way, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.53 Acres / 23,086 sq.ft.
$2,375,000.00

Introducing this rare opportunity to acquire one or two buildable parcels in a prime Katama neighborhood. Located within a newly created four-lot subdivision, now referred to as 1 & 3 Jane's Way, these two conforming half-acre lots offer an exceptional setting for new construction, just minutes fro...

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1 Janes Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 1 Janes Way, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.50 Acres / 21,780 sq.ft.
$2,375,000.00

Introducing this rare opportunity to acquire one or two buildable parcels in a prime Katama neighborhood. Located within a newly created four-lot subdivision, now referred to as 1 & 3 Jane's Way, these two conforming half-acre lots offer an exceptional setting for new construction, just minutes fro...

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60 Crocker Drive, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 60 Crocker Drive, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.96 Acres / 41,817 sq.ft.
$2,300,000.00

Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing struc...

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76 Washque Avenue, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 76 Washque Avenue, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.23 Acres / 10,018 sq.ft.
$2,299,000.00

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...

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2 Old Poucha Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 2 Old Poucha Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.30 Acres / 56,628 sq.ft.
$2,295,000.00

Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were...

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7 Pip'n Circle, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 7 Pip'n Circle, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.05 Acres / 132,858 sq.ft.
$2,195,000.00

A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everyth...

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81 Whalers Walk, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 81 Whalers Walk, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.92 Acres / 40,075 sq.ft.
$2,125,000.00

Imagine owning your own beach house on Martha’s Vineyard, ready for summer fun. Perched atop a rise that captures sweeping views over the property, floods interiors with natural light, and opens to a spectacular night sky, this furnished move-in-ready home delivers the Vineyard lifestyle you've be...

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9 Sparrow Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 9 Sparrow Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.54 Acres / 23,522 sq.ft.
$1,995,000.00

Set on a quiet cud-de-sac near the State Forest, in Dodger's Hole, amidst lovely landscaping with stonework defining a circular driveway & parking. This spacious, well maintained home offers very comfortable living with significant upgrades. Large living room with vaulted ceilings, abundant natura...

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131 North Water St, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 131 North Water St, Edgartown MA 02539
Type: Condominium
$1,975,000.00

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 94 at 131 N Water Street in Edgartown, a 730-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harb...

Property Details

42 Bold Meadow Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 42 Bold Meadow Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.75 Acres / 32,670 sq.ft.
$1,875,000.00

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 additi...

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STILL SHOWING
Contingent
11th October 2026

4 Cormorant Circle, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Cormorant Circle, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.54 Acres / 23,522 sq.ft.
$1,875,000.00

Tucked at the end of a quiet cul-de-sac in the desirable Island Grove neighborhood of Edgartown, this charming three-bedroom, (plus bonus space and 6 bedroom sewer capacity), two-bathroom residence offers a private setting, association amenities and excellent proximity to Edgartown Village and Katam...

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32 Norton Orchard Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 32 Norton Orchard Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.29 Acres / 12,797 sq.ft.
$1,850,000.00

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 ...

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4 Farm Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 4 Farm Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 1.10 Acres / 47,916 sq.ft.
$1,825,000.00

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 w...

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99 Old Purchase Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 99 Old Purchase Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.71 Acres / 30,927 sq.ft.
$1,775,000.00

Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike ...

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14 Donaldbin Close, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 14 Donaldbin Close, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.84 Acres / 36,590 sq.ft.
$1,750,000.00

Tucked into a quiet neighborhood and surrounded by mature trees, this home sits elevated on a 0.84-acre lot. With an open floorplan, the kitchen, dining, and living areas flow comfortably together, enhanced by vaulted ceilings, a stone gas fireplace, and French doors that bring in abundant natural ...

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63 Division Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 63 Division Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 1.57 Acres / 68,389 sq.ft.
$1,650,000.00

LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new resid...

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31 Dodgers Hole Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 31 Dodgers Hole Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.51 Acres / 22,215 sq.ft.
$1,625,000.00

Dodgers Hole - Delightful contemporary cape style home, centrally located, suitable for seasonal or year-round use. The privately sited half acre lot features a first floor primary bedroom with en-suite bath, a light filled eat-in kitchen, central A/C, full unfinished basement, a detached 18'x24' s...

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501 West Tisbury Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 501 West Tisbury Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 2.00 Acres / 87,120 sq.ft.
$1,595,000.00

Prime 2-acre parcel situated close to the bike path, state forest, Morning Glory Farm and Edgartown village. Per Edgartown BOH, this lot is approved to support a 5-bedroom home with a standard septic system. Additionally, with an advanced treatment system and a variance, the potential exists to expa...

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Contingent
22nd October 2025

8 Pip'n Circle, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 8 Pip'n Circle, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 3.04 Acres / 132,422 sq.ft.
$1,500,000.00

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Ch...

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36 Pine Street, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 36 Pine Street, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.48 Acres / 21,056 sq.ft.
$1,500,000.00

Imagine creating your own Vineyard retreat on this almost half-acre parcel, ideally located within walking distance to downtown Edgartown. This property offers the opportunity to build a custom home within a designated building envelope, while a protected no-build area provides an added sense of pri...

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7 Boylston Drive, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 7 Boylston Drive, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.53 Acres / 23,087 sq.ft.
$1,475,000.00

Well-maintained three-bedroom, two-bath home set on a quiet road in a convenient Edgartown location. The property is bordered by more than 100 acres of conservation land, offering a peaceful setting and added privacy while remaining close to Edgartown Village, beaches, bike paths, and everyday ameni...

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17 Chapman Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 17 Chapman Lane, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.25 Acres / 11,104 sq.ft.
$1,395,000.00

OPPORTUNITY KNOCKS: Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create...

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44 Prices Way, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 44 Prices Way, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.76 Acres / 33,105 sq.ft.
$1,395,000.00

CONTEMPORARY ISLAND RETREAT. As a smart opportunity for Vineyard buyers seeking a low-maintenance Island home close to Edgartown Village, this contemporary home offers easy access to shopping, services, and the bicycle path connecting the three down-Island towns. Whether used as a year-round residen...

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37 Dodgers Hole Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 37 Dodgers Hole Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$1,175,000.00

This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designe...

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15 Chapman Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 15 Chapman Lane, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.23 Acres / 10,100 sq.ft.
$1,125,000.00

OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just m...

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21 Flamingo Drive, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 21 Flamingo Drive, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.50 Acres / 21,780 sq.ft.
$1,075,000.00

Tucked away on a tranquil circle in the desirable Dodgers Hole neighborhood, 21 Flamingo Drive offers the perfect blend of island serenity, comfort, and investment potential. Cherished by its original owners for years as both a summer getaway and an income-producing rental, this inviting property is...

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NEW LISTING

25 Coffins Field Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 25 Coffins Field Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 1.00 Acres / 43,475 sq.ft.
$995,000.00

Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently located near town amenities, beaches, bike paths, a pub...

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21 Clay Pit Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 21 Clay Pit Road, Edgartown MA 02539
Type: Single Family Residence
Lot Size: 0.56 Acres / 24,393 sq.ft.
$896,000.00

This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry...

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87 Whalers Walk, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 87 Whalers Walk, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.90 Acres / 39,204 sq.ft.
Affordable Housing Restriction: Yes
$585,000.00

Beautiful .9 acre lot in a tranquil residential neighborhood, ideally located near Morning Glory Farm, Vineyard Golf Club, the bike paths to Edgartown Village, South Beach, and up-island. A unique chance to build your Martha’s Vineyard home in a private yet convenient Edgartown location. This prop...

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CONTINGENT OFFER
STILL SHOWING
Contingent
22nd May 2026

23 Calebs Common Lane, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 23 Calebs Common Lane, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 1.02 Acres / 44,487 sq.ft.
$550,000.00

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create...

Property Details

240 Chappaquiddick Road, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 240 Chappaquiddick Road, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 7.70 Acres / 335,412 sq.ft.
$525,000.00

A rare opportunity to own 7.7 acres on the beautiful and sought-after island of Chappaquiddick. This wooded parcel offers exceptional privacy, natural contours, and the quiet, untouched landscape that defines Chappy living. Preliminary information suggests there is potential upland area to support ...

Property Details

5 Candlemaker Circle, Edgartown MA 02539

Town: EDGARTOWN | All Edgartown listings
Address: 5 Candlemaker Circle, Edgartown MA 02539
Type: Unimproved Land
Lot Size: 0.56 Acres / 24,394 sq.ft.
Affordable Housing Restriction: Yes
$439,500.00

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 A...

Property Details

CONTINGENT OFFER
STILL SHOWING
Contingent
24th August 2026

 

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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals

PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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