Homes for Sale in 02539

• 

  

  

  /11

  $650,000

  • 1 Bed
  • 1 Bath
  • 478 Sq Ft

  20 Peases Point Way N Unit 4, Edgartown, MA 02539

  Perfectly situated in the heart of downtown Edgartown, this recently renovated first-floor 1-bedroom, 1-bathroom retreat offers effortless access to the village’s acclaimed shops, galleries, restaurants, Fuller Street Beach, and Edgartown Harbor. The bright, open-concept living space seamlessly connects the kitchen, dining, and living areas, creating an inviting setting for relaxing or

  Jarrett Hurwitz Keller Williams Realty

  20 Peases Point Way N Unit 4, Edgartown, MA 02539
• 

  

  

  /43

  $6,595,000

  • 4 Beds
  • 7 Baths
  • 3,717 Sq Ft

  17 Town Lot Rd, Edgartown, MA 02539

  COMING SOON: COASTAL CHIC LIVING WITH POOL NEAR KATAMA BAY. Perfectly positioned in the highly coveted Edgartown Bay Road area, just moments from the Town Landing on Katama Bay, this custom-built coastal residence offers the very best of the Vineyard lifestyle—effortless, elegant, and ready for immediate enjoyment. Designed and built as a builder’s own home, every detail reflects exceptional

  

  Wendy Harman

  Compass | Point B

  (508) 392-5603

  17 Town Lot Rd, Edgartown, MA 02539
• 

  

  

  /54

  $7,999,000

  • 7 Beds
  • 6.5 Baths
  • 7,133 Sq Ft

  9 Sutton's Way, Edgartown, MA 02539

  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 entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a

  Jennifer DaSilva Compass | Point B

  9 Sutton's Way, Edgartown, MA 02539
• 

  

  

  /33

  $1,249,900

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  37 Dodgers Hole Rd, Edgartown, MA 02539

  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 designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with

  Beth Welch Viewpoints

  37 Dodgers Hole Rd, Edgartown, MA 02539
• 

  

  

  /37

  $3,195,000

  • 5 Beds
  • 4.5 Baths
  • 3,881 Sq Ft

  10 N Bog Rd, Edgartown, MA 02539

  Set on 2.2 private acres in Edgartown, this exceptional five-bedroom home with a heated saltwater pool offers the ideal blend of privacy, comfort, and convenience. Perfectly located just moments from Morning Glory Farm, South Beach, the bike path, and downtown Edgartown Village, the property provides easy access to some of the island’s most sought-after destinations while maintaining a peaceful,

  Michele Casavant Vineyard Village Realty

  10 N Bog Rd, Edgartown, MA 02539
• 

  

  /21

  $1,225,000

  • 3 Beds
  • 2.5 Baths
  • 1,100 Sq Ft

  34 10th St S, Edgartown, MA 02539

  Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

  Chrissie Teague

  34 10th St S, Edgartown, MA 02539
• 

  

  /18

  $3,295,000

  • 4 Beds
  • 3 Baths
  • 1,696 Sq Ft

  10 Fowler Ave, Edgartown, MA 02539

  Edgartown Waterfront - Enjoy sweeping water views and direct access to Sengekontacket Pond from this beautiful coastal retreat. Built in 2024, this four-bedroom, three-bath home blends classic Vineyard charm with modern coastal design and offers 95 feet of pond frontage with a private mooring. The open-concept living space is filled with natural light and features Thermador appliances, vaulted

  Andrew McElhinney Compass LLC

  10 Fowler Ave, Edgartown, MA 02539
• 

  

  /23

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  44 Prices Way, Edgartown, MA 02539

  COMING SOON! 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 residence, seasonal getaway or potential vacation rental, the setting and layout make it easy

  

  Wendy Harman

  Compass | Point B

  (508) 484-8644

  44 Prices Way, Edgartown, MA 02539
• 

  

  /36

  $4,850,000

  • 4 Beds
  • 3.5 Baths
  • 4,168 Sq Ft

  27 Knoll Dr, Edgartown, MA 02539

  Set the tone the moment you arrive with a dramatic first-floor foyer showcasing post-and-beam construction and warm architectural character. The heart of the home is an expansive great room anchored by a gas fireplace, seamlessly flowing through French doors that open to a sun-drenched pool area—perfect for indoor-outdoor living and entertaining. A generous dining area connects effortlessly to a

  Stacy Ickes Donnelly + Co.

  27 Knoll Dr, Edgartown, MA 02539
• 

  

  /25

  $1,895,000

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  21 Schoolhouse Rd, Edgartown, MA 02539

  Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on

  Jim Joyce Carroll & Vincent R.E.

  21 Schoolhouse Rd, Edgartown, MA 02539
• 

  

  /29

  $2,790,000

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  2 Cosmos Way, Edgartown, MA 02539

  Tucked away on a private 1.5-acre parcel in Katama, this thoughtfully designed home offers the layout, amenities, and lifestyle buyers consistently seek in this location. With four bedrooms, 2.5 baths, and an open main living area with high ceilings and a fireplace, the home can live comfortably year-round or seasonally. The first floor features a true primary suite, while the second floor offers

  Jennifer O'hanlon Compass LLC

  2 Cosmos Way, Edgartown, MA 02539
• 

  

  /66

  $2,950,000

  • 4 Beds
  • 8 Baths
  • 3,740 Sq Ft

  15 21st St N, Edgartown, MA 02539

  Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

  Jennifer O'hanlon Compass LLC

  15 21st St N, Edgartown, MA 02539
• 

  

  /52

  $2,195,000

  • 5 Beds
  • 3.5 Baths
  • 2,628 Sq Ft

  7 Pip'N Rd, Edgartown, MA 02539

  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 everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

  Dawn Bellante-Holand Sandpiper Realty

  7 Pip'N Rd, Edgartown, MA 02539
• 

  

  /29

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  13 Young St, Edgartown, MA 02539

  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

  Stacy Ickes Donnelly + Co.

  13 Young St, Edgartown, MA 02539
• 

  

  /41

  $7,200,000

  • 5 Beds
  • 4.5 Baths
  • 4,389 Sq Ft

  2 Noras Ln, Edgartown, MA 02539

  Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.7 beautifully landscaped acres, this custom home, built in 2014, features over 4,000 square feet of living space across three levels. The open main living area includes a

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  2 Noras Ln, Edgartown, MA 02539
• 

  

  /56

  $9,995,000

  • 6 Beds
  • 7.5 Baths
  • 7,205 Sq Ft

  25 Lelands Path, Edgartown, MA 02539

  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 residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200

  

  Wendy Harman

  Compass | Point B

  (508) 403-9546

  25 Lelands Path, Edgartown, MA 02539
• 

  

  /65

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 2,348 Sq Ft

  82 Oyster Pond Rd, Edgartown, MA 02539

  A truly rare offering on Oyster Pond Rd. This property offer rights to boating and swimming in the pond plus a rare easement to access “The Barrier Beach", on the south shore. Access to the south beach is by boating down Oyster Pond.This beach access is a spectacular addition to this property. The land is 4.4 acres, very quiet and bordered by exceptional homes. Privacy abounds. This contemporary

  Neal Stiller Cronigs Real Estate

  82 Oyster Pond Rd, Edgartown, MA 02539
• 

  

  /41

  $2,195,000

  • 5 Beds
  • 3.5 Baths
  • 2,628 Sq Ft

  7 Pipn Cir, Edgartown, MA 02539

  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

  Dawn Bellante Sandpiper Realty, Inc.

  7 Pipn Cir, Edgartown, MA 02539
• 

  

  /30

  $6,995,000

  • 4 Beds
  • 3 Baths
  • 2,624 Sq Ft

  103 Edgartown Bay Rd, Edgartown, MA 02539

  Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an

  Bonnie Pierce Wallace & Co. Sotheby's

  103 Edgartown Bay Rd, Edgartown, MA 02539
• 

  

  /4

  $945,000

  $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  51 Chase Rd, Edgartown, MA 02539

  Edgartown opportunity! Bring your vision to this two-bedroom, one-bath ranch situated close to the heart of downtown Edgartown. This property presents a rare chance to create value in a highly sought-after location. Just minutes to downtown, with off-street parking for three vehicles, the home features functional single-level living, including a living area, kitchen, two bedrooms, and a

  Lisa Gilberto C McManus Realty Group

  51 Chase Rd, Edgartown, MA 02539
• 

  

  /21

  $3,850,000

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  10 Pease Point Rd, Edgartown, MA 02539

  NEWLY LISTED l PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Ideally situated just minutes from Edgartown Village, with

  Emma Bryant Studio Realty

  10 Pease Point Rd, Edgartown, MA 02539
• 

  

  /42

  $21,500,000

  • 10 Beds
  • 14 Baths
  • 7,598 Sq Ft

  56 N Summer St, Edgartown, MA 02539

  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

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  56 N Summer St, Edgartown, MA 02539
• 

  

  /34

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 2,912 Sq Ft

  40 Edgewood Dr, Edgartown, MA 02539

  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 protected association land that will remain undeveloped. Inside, the home features three spacious

  Carol McManus C McManus Realty Group

  40 Edgewood Dr, Edgartown, MA 02539
• 

  

  /20

  $1,225,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,110 Sq Ft

  34 10th St S, Edgartown, MA 02539

  Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

  Michael McGuire Insight Realty Group, Inc

  34 10th St S, Edgartown, MA 02539
• 

  

  /5

  $439,500

  • Land
  • 24,393 Sq Ft
  • $784,821 per Acre

  5 Candle Maker Cir, Edgartown, MA 02539

  Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  5 Candle Maker Cir, Edgartown, MA 02539
• 

  

  /4

  $445,000

  • Land
  • 23,958 Sq Ft
  • $809,091 per Acre

  11 Boylston Dr, Edgartown, MA 02539

  A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  11 Boylston Dr, Edgartown, MA 02539
• 

  

  /33

  $3,150,000

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  8 Atwood Cir, Edgartown, MA 02539

  This charming and historic home is ideally situated at the head of Atwood Circle, a private neighborhood just off Dunham Road, and only a short stroll to town. Recently renovated, the residence blends classic character with modern comfort. The main level features a spacious living room, a cozy den with fireplace, a dining area, and an updated kitchen—perfect for both everyday living and

  Gerrett Conover Landvest MV

  8 Atwood Cir, Edgartown, MA 02539
• 

  

  /22

  $1,100,000

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft

  4 5th St N, Edgartown, MA 02539

  An exciting rare find off the Edgartown / Tisbury road directly across from the bike path. The first floor open plan includes a fire place, family room and kitchen with a walk out to the wrap around porch. Two pleasant bedrooms and a full bath are on the first floor. The upper level loft opens to the living room visually expanding the living space. The house has the benefit of a full basement

  Doug Burke Signal House Group at Compass

  4 5th St N, Edgartown, MA 02539
• 

  

  /6

  $2,795,000

  • Land
  • 3.05 Acres
  • $916,393 per Acre

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539

  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. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

  Courtney Marek Sandpiper Realty

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539
• 

  

  /20

  $8,900,000

  • 4 Beds
  • 8 Baths
  • 7,767 Sq Ft

  4 Jacobs Neck Rd, Edgartown, MA 02539

  Extraordinary Privacy in Boldwater, Edgartown. Over 10 acres of pristine acreage abutting extensive conservation land. Dwellings built by master craftsmen with a variety of potential options to combine with your vision of the perfect Vineyard compound for your family and friends to enjoy for generations. Deeded pond and beach access along with association tennis courts and common land are

  Deb Hancock Hancock Real Estate

  4 Jacobs Neck Rd, Edgartown, MA 02539
• 

  

  /7

  $2,795,000

  • Land
  • 3.05 Acres
  • $916,393 per Acre

  Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539

  Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

  Courtney Marek Sandpiper Realty

  Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539
• 

  

  /20

  $19,900,000

  • 5 Beds
  • 7 Baths
  • 6,577 Sq Ft

  33 Boldwater Rd, Edgartown, MA 02539

  Exceptional Waterfront Retreat on Edgartown Great Pond. A very special offering with lovely sandy pond beach and deeded ocean beach access. Located in a private but convenient area - only 12 minutes to the airport or Edgartown village. This is a rare opportunity to purchase a meticulously crafted stone house and guest house with pool in a naturalized setting that redefines the conventions of

  Deb Hancock Hancock Real Estate

  33 Boldwater Rd, Edgartown, MA 02539
• 

  

  /6

  $2,795,000

  • Land
  • 0 Sq Ft

  Lot 4B Browns Farm Ln, Edgartown, MA 02539

  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. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

  Courtney Marek

  Lot 4B Browns Farm Ln, Edgartown, MA 02539
• 

  

  /3

  $1,650,000

  • Land
  • 1.57 Acres
  • $1,050,955 per Acre

  63 Division Rd Unit 46, Edgartown, MA 02539

  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 residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own

  Cheri Mason Landvest MV

  63 Division Rd Unit 46, Edgartown, MA 02539
• 

  

  /34

  $11,250,000

  • 7 Beds
  • 8 Baths
  • 10,142 Sq Ft

  14 Trapps Pond Rd, Edgartown, MA 02539

  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 ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

  Gerrett Conover Landvest MV

  14 Trapps Pond Rd, Edgartown, MA 02539
• 

  

  /6

  $2,795,000

  • Land
  • 0 Sq Ft

  Lot 4A Browns Farm Ln, Edgartown, MA 02539

  Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

  Courtney Marek

  Lot 4A Browns Farm Ln, Edgartown, MA 02539
• 

  

  /30

  $1,245,000

  • 2 Beds
  • 2 Baths
  • 1,752 Sq Ft

  66 Barnes Rd, Vineyard Haven, MA 02568

  Oak Bluffs~ Classic Cape charm meets modern efficiency in this move-in-ready 2 bedroom plus finished bonus space in basement. Thoughtfully maintained and beautifully presented, the home features sun-filled living spaces, an updated kitchen, and comfortable bedrooms designed for easy everyday living. Enjoy year-round comfort with energy-efficient mini-split systems providing both heating and air

  Marilyn Moses Ocean Park Realty Inc

  66 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /41

  $4,800,000

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft

  9 Martha's Way, Edgartown, MA 02539

  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 free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to architectural detail presents at moment one.

  Michele Casavant Vineyard Village Realty

  9 Martha's Way, Edgartown, MA 02539
• 

  

  /37

  $15,000,000

  • 7 Beds
  • 9 Baths
  • 6,462 Sq Ft

  14 Cow Bay Rd, Edgartown, MA 02539

  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 private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion,

  Gerrett Conover Landvest MV

  14 Cow Bay Rd, Edgartown, MA 02539
• 

  

  /33

  $3,200,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  24 Beetle Swamp Rd, Edgartown, MA 02539

  Bucolic Sweetened Water Farm has the agrarian feel of up island yet it's close to the heart and vibe of Edgartown. 24 Beetle Swamp Rd is a custom built home, a Vineyard gem constructed by local craftsmen over time with pastoral views. The current main house has 3 bedrooms and two bathrooms, however the lot can support up to 6 bedrooms according to the Edgartown board of health and building

  Kathleen Dawson Donnelly + Co.

  24 Beetle Swamp Rd, Edgartown, MA 02539

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