Homes in ZIP Code 02539

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  /28

  $2,600,000 Open Fri 12PM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 2,638 Sq Ft

  24 Dark Woods Rd, Edgartown, MA 02539

  Welcome to 24 Dark Woods Road, a beautifully maintained 3-bedroom, 3.5-bath Contemporary Colonial nestled in an upscale, tranquil neighborhood. This spacious residence abuts acres of Sheriffs Meadow conservation land, offering miles of trails, serene pond views and peaceful privacy at the end of a quiet road, yet is just a mile from the beach and closer to Edgartown Village. This association

  Stephanie Burke Martha's Vineyard Seacoast Properties

  24 Dark Woods Rd, Edgartown, MA 02539
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  /40

  $16,400 per month

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  20 Katama Bay Rd Ed350, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

  Karen Overtoom Karen M. Overtoom R.E.

  20 Katama Bay Rd Ed350, Edgartown, MA 02539
• 

  

  

  /19

  $2,100,000 Sold Mar 14, 2025

  • 2,784 Sq Ft
  • $754/SF
  • 208 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  30 Deacon Vincent Way, Edgartown, MA 02539

  Explore this colonial style home in the ideal Edgartown Estates neighborhood. The upside-down layout maximizes lush tree views and privacy. The main living area awaits—a bright cathedral-ceilinged room that seamlessly blends kitchen, dining, and lounging spaces. Two separate decks with sliding doors off dining and living area perfect for summer gatherings with a fireplace to anchor the open

  30 Deacon Vincent Way, Edgartown, MA 02539
• 

  

  

  /36

  Est $1,632,301 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft

  62 Whalers Walk, Edgartown, MA 02539

  62 Whalers Walk, Edgartown, MA 02539
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  /39

  $3,600,000

  • 4 Beds
  • 3.5 Baths
  • 4,372 Sq Ft

  110 5th St N, Edgartown, MA 02539

  This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, is flooded with light, open to breezes, and marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with an expansive breakfast island,

  Stephanie Roache Donnelly + Co.

  110 5th St N, Edgartown, MA 02539
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  /10

  $11,000 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
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  /24

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 138 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539
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  /36

  Est $3,508,309 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,902 Sq Ft

  94 Marthas Rd, Edgartown, MA 02539

  94 Marthas Rd, Edgartown, MA 02539
• 

  

  /24

  $4,850,000

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  56 Robinson Rd, Edgartown, MA 02539

  NEWER CONSTRUCTION, with POOL, 1/2 mile from the heart of EDGARTOWN VILLAGE! LOCATION, LOCATION! Approx. 3,500 square feet of open living space. The Great Room has a dramatic Two Story wall of windows which surround a gas fireplace and overlooks a 14 x 30 foot in ground, heated, saltwater pool which is surrounded by bluestone hardscape. In addition to the dramatic Great Room there is a first

  Michele Casavant Vineyard Village Realty

  56 Robinson Rd, Edgartown, MA 02539
• 

  

  /30

  $20,000 per month

  • 4 Beds
  • 3 Baths
  • 2,226 Sq Ft
  • House for Rent

  54 Schoolhouse Road Ed330, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

  Karen Overtoom Karen M. Overtoom R.E.

  54 Schoolhouse Road Ed330, Edgartown, MA 02539
• 

  

  /25

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 139 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd, Edgartown, MA 02539
• 

  

  /20

  Est $1,456,991 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,532 Sq Ft

  39 Prices Way, Edgartown, MA 02539

  39 Prices Way, Edgartown, MA 02539
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  /32

  $2,999,000

  • 8 Beds
  • 7.5 Baths
  • 3,770 Sq Ft

  72 Chappaquiddick Ave, Edgartown, MA 02539

  WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

  Michele Casavant Vineyard Village Realty

  72 Chappaquiddick Ave, Edgartown, MA 02539
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  /21

  $14,000 per month

  • 4 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  175 Meetinghouse Way Ed321, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

  Karen Overtoom Karen M. Overtoom R.E.

  175 Meetinghouse Way Ed321, Edgartown, MA 02539
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  /27

  $1,500,000 Sold Feb 13, 2025

  • 2,066 Sq Ft
  • $726/SF
  • 154 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  37 Weeks Ln, Edgartown, MA 02539

  Welcome to this FULLY RENOVATED Charming Cape style home. In 2020 the home was completely gutted down to the studs and a tasteful full renovation was begun which included new electric, plumbing, walls, flooring, cabinetry, new bathrooms, a new kitchen and new exterior decking. In 2021 an oversized detached two car garage with storage above was added to the property. The home offers an attractive

  37 Weeks Ln, Edgartown, MA 02539
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  /48

  Est $3,207,386 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
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  /38

  $2,595,000

  • 3 Beds
  • 4 Baths
  • 3,039 Sq Ft

  99 The Blvd, Edgartown, MA 02539

  Welcome to a stunning blend of contemporary elegance and charm nestled in the heart of Edgartown. This exquisite water view residence offers 3 spacious bedrooms and 4 luxurious bathrooms, encompassing a generous amount of meticulously designed living space. The luxurious and versatile interior boasts a modern, move-in ready design, with a gourmet kitchen and recently renovated spaces. Whether

  Jennifer B. DaSilva Compass

  99 The Blvd, Edgartown, MA 02539
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  /28

  $29,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • House for Rent

  76 Mattakesett Way Ed313, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

  Karen Overtoom Karen M. Overtoom R.E.

  76 Mattakesett Way Ed313, Edgartown, MA 02539
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  /34

  $5,500,000 Sold Jan 27, 2025

  • 1,728 Sq Ft
  • $3183/SF
  • 107 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  25 Down Harbor Rd, Edgartown, MA 02539

  Rare Opportunity: Water View Retreat In Down Harbor With Private Beach, Dock And Mooring Access – Seize the opportunity to own one of the few water view properties in the prestigious Down Harbor neighborhood -- a true gem for boaters and beach enthusiasts as residents enjoy exclusive deeded access to a sandy association beach, plus the opportunity to keep a boat or dinghy on the association dock

  Wendy Harman Compass

  25 Down Harbor Rd, Edgartown, MA 02539
• 

  

  /52

  Est $5,377,721 Not Listed For Sale

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

  12 Plantingfield Wood Cir, Edgartown, MA 02539

  12 Plantingfield Wood Cir, Edgartown, MA 02539
• 

  

  /19

  $2,550,000

  • 5 Beds
  • 3.5 Baths
  • 2,205 Sq Ft

  11 Bernard Way, Edgartown, MA 02539

  Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, is this 4-bedroom home with a separate studio guest apartment, office, and heated 2-car garage with 10-ft doors. There is also an unfinished full basement. The living space is in excellent condition with a combination of hardwood, carpet, and tile floors. This light and bright home could be a reliable income

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  11 Bernard Way, Edgartown, MA 02539
• 

  

  /31

  $50,000 per month

  • 5 Beds
  • 5 Baths
  • 2,975 Sq Ft
  • House for Rent

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

  Karen Overtoom Karen M. Overtoom R.E.

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
• 

  

  /15

  $2,200,000 Sold Jan 24, 2025

  • 1,852 Sq Ft
  • $1188/SF
  • 103 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  13 Holly Bear Ln, Edgartown, MA 02539

  13 HOLLY BEAR LANE offers NEW CONSTRUCTION, with an anticipated completion date NOVEMBER 2024. The plot and septic system supports FOUR BEDROOMS, three bedrooms are being built, allowing a fourth bedroom for future design. The first floor layout offers an inviting entry which opens to the living room featuring a gas fireplace and wall of slider doors. Open to the living room is the dining area

  Michele Casavant Vineyard Village Realty

  13 Holly Bear Ln, Edgartown, MA 02539
• 

  

  /14

  Est $1,738,004 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  5 Westminster Ct, Edgartown, MA 02539

  5 Westminster Ct, Edgartown, MA 02539
• 

  

  /23

  $3,100,000

  • 1 Bed
  • 1 Bath
  • 1,028 Sq Ft

  114 Meeting House Way, Edgartown, MA 02539

  Discover this private Katama retreat, perfectly situated on over 3 acres of forested and landscaped grounds. Located just a mile from Edgartown Great Pond and a little over 2 miles from both South Beach and Edgartown Village, this contemporary guesthouse offers the ultimate island escape. Built in 2018, it boasts a proven rental history and is outfitted with every modern amenity. With a 6-bedroom

  Rose Ryley Sandpiper Realty Inc

  114 Meeting House Way, Edgartown, MA 02539
• 

  

  /17

  $48,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,675 Sq Ft
  • House for Rent

  9 Thaxter Lane Ed310, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

  Karen Overtoom Karen M. Overtoom R.E.

  9 Thaxter Lane Ed310, Edgartown, MA 02539
• 

  

  /46

  $3,305,000 Sold Jan 22, 2025

  • 2,548 Sq Ft
  • $1297/SF
  • 48 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1820

  34 School St, Edgartown, MA 02539

  *Total selling price was $3343,700, which included the cost to tie into Town Sewer*Welcome to 34 School Street, a distinguished residence nestled in Edgartown's much sought-after Historic District. This stately home, built in 1820, is located steps from the shops and restaurants on Main Street. Sited on a 0.13-acre lot, the property has four bedrooms and three bathrooms. Updates include new

  34 School St, Edgartown, MA 02539
• 

  

  /27

  Est $1,831,019 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1 Gray Gull Cir, Edgartown, MA 02539

  1 Gray Gull Cir, Edgartown, MA 02539
• 

  

  /56

  $4,950,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  4 Down Harbor Rd, Edgartown, MA 02539

  Coveted Down Harbor! This 3-bedroom 2-bath home sits in the Down Harbor association in a prime Katama location. This charming home is an entertainer's delight with a spacious yard, a large deck, an outdoor kitchen, pool, and recently built pool house with 2 outdoor showers, 1/2 bath and a storage shed. This home features vaulted ceilings, exposed beams, and a bright kitchen with a breakfast bar

  Cheri Mason LandVest MV

  4 Down Harbor Rd, Edgartown, MA 02539
• 

  

  /29

  $18,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,027 Sq Ft
  • House for Rent

  12 Cottle Lane Ed341, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

  Karen Overtoom Karen M. Overtoom R.E.

  12 Cottle Lane Ed341, Edgartown, MA 02539
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  /7

  $1,350,000 Sold Jan 22, 2025

  • Land
  • 0.82 Acre
  • $1,646,341 per Acre

  • 54 Days On Market

  1 Wilsons Ln, Edgartown, MA 02539

  Vacant land in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of the Village. This wooded parcel is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool is allowed "by right" and so is a guesthouse after 5 years. The property, shown as Lot 4 in a "Plan of Land in Edgartown Mass" dated November 5, 2013 and

  1 Wilsons Ln, Edgartown, MA 02539
• 

  

  /23

  Est $2,526,500 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,252 Sq Ft

  5 Bold Meadow Cir, Edgartown, MA 02539

  5 Bold Meadow Cir, Edgartown, MA 02539
• 

  

  /42

  $4,150,000

  • 4 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  4 Boldwater Rd, Edgartown, MA 02539

  A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and

  Thomas Wallace Wallace & Co. Sotheby's International Realty

  4 Boldwater Rd, Edgartown, MA 02539
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  /9

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 1,645 Sq Ft
  • House for Rent

  23 Ocean Ave Unit OB539, Edgartown, MA 02539

  THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away

  Karen Overtoom Karen M. Overtoom R.E.

  23 Ocean Ave Unit OB539, Edgartown, MA 02539
• 

  

  /22

  $1,025,000 Sold Jan 22, 2025

  • 1,296 Sq Ft
  • $791/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  5 12th St S, Edgartown, MA 02539

  Here is your opportunity to own a charming Cape close to beaches, the bike path and plenty of dining and shopping options. This home features wide plank wood floors on the first level and a full unfinished basement for storage and potential additional living space. Second level has two spacious bedrooms with cathedral ceilings and ample natural light. Rooftop widow's walk provides panoramic

  Jared Bicknell Compass

  5 12th St S, Edgartown, MA 02539
• 

  

  /22

  Est $2,609,785 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,050 Sq Ft

  23 Majors Cove Ln, Edgartown, MA 02539

  23 Majors Cove Ln, Edgartown, MA 02539
• 

  

  /19

  $2,495,000

  • 4 Beds
  • 6 Baths
  • 2,518 Sq Ft

  32 Norton Orchard Rd, Edgartown, MA 02539

  32 Norton Orchard Rd, Edgartown, MA 02539
• 

  

  /15

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 2,888 Sq Ft
  • House for Rent

  101 Peasepoint Way Ed324, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

  Karen Overtoom Karen M. Overtoom R.E.

  101 Peasepoint Way Ed324, Edgartown, MA 02539
• 

  

  /29

  $3,336,000 Sold Jan 07, 2025

  • 2,100 Sq Ft
  • $1589/SF
  • 213 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1999

  99 Cooke St, Edgartown, MA 02539

  Welcome to this beautiful in-town oasis! With a brand new gunite pool with integrated spa, this charming four bedroom home shines in downtown Edgartown. Perfect for a variety of buyers with an established rental history (summertime rate consistently at $20,000/week), this home is a fabulous gathering place and a true gem. The first floor is exceptionally sunny and open, with a high-ceilinged

  99 Cooke St, Edgartown, MA 02539
• 

  

  /32

  Est $2,376,379 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,101 Sq Ft

  10 Codman Spring Rd, Edgartown, MA 02539

  10 Codman Spring Rd, Edgartown, MA 02539

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