Edgartown, MA Houses for Sale

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  /39

  $2,650,000

  • 4 Beds
  • 6 Baths
  • 2,694 Sq Ft

  16 Mockingbird Dr, Edgartown, MA 02539

  Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious

  Emma Kennedy Sandpiper Realty Inc

  16 Mockingbird Dr, Edgartown, MA 02539
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  /37

  $2,995,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  31 The Blvd, Edgartown, MA 02539

  Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

  Wendy Harman Compass

  31 The Blvd, Edgartown, MA 02539
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  /32

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 2,001 Sq Ft

  2 Orchard Ln, Edgartown, MA 02539

  Welcome to this 4 bedroom home, with a pool, perched on the neighborhood hilltop. This tri-level cape offers an eat in kitchen featuring granite countertops, a Viking gas range, a double basin sink, a built in banquette and views of the front covered porch and hardscaped rear yard. The primary level presents with a living room, a separate bar area offering a wine refrigerator/dishwasher, a full

  Michele Casavant Vineyard Village Realty

  2 Orchard Ln, Edgartown, MA 02539
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  /36

  $2,275,000

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  43C Dark Woods Rd, Edgartown, MA 02539

  Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff's Meadow conservation land. Tucked in the woods of the pleasant Dark Woods community, this property has been meticulously maintained and is ready for your enjoyment. Sited on a pleasant .77-acre lot, the property offers expansive space with a floor plan

  Stephanie Roache Donnelly + Co.

  43C Dark Woods Rd, Edgartown, MA 02539
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  /35

  $2,275,000

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  43C Dark Woods Rd, Edgartown, MA 02539

  Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff’s Meadow conservation land. Tucked in the woods of the pleasant Dark Woods community, this property has been meticulously maintained and is ready for your enjoyment. The first floor features a fabulous living room with a gas fireplace and a formal dining

  Stephanie Roache Donnelly + Co.

  43C Dark Woods Rd, Edgartown, MA 02539
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  /29

  $3,690,000

  • 4 Beds
  • 6 Baths
  • 3,793 Sq Ft

  28 Crocker Dr, Edgartown, MA 02539

  This beautifully renovated Katama retreat blends refined design, luxury amenities, and flexible living. The main house offers three bedrooms, including a peaceful primary suite with private deck, a second en suite, and a cozy bunkroom. The octagonal living room, skylit dining room with gas fireplace, and chef’s kitchen with quartz counters and high-end appliances are perfect for entertaining.

  Jennifer O'hanlon Compass

  28 Crocker Dr, Edgartown, MA 02539
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  /28

  $2,700,000

  • 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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  /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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  /60

  $3,500,000

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Picture yourself in this beautifully designed custom home offering the ultimate in privacy. The first floor has an open floor plan which includes the dining room, kitchen, wet bar, and living space. Bypass siding doors separate the living space from the dining and kitchen. Experience the ultimate in culinary luxury with a gourmet kitchen featuring custom cabinets, high end appliances, and ample

  Casandra Hyland Landmarks at TODAY Real Estate

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  /42

  $2,495,000

  • 3 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  6 Martha's Park Rd, Oak Bluffs, MA 02557

  Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

  Jennifer B. DaSilva Compass

  6 Martha's Park Rd, Oak Bluffs, MA 02557
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  /26

  $2,895,000

  • 3 Beds
  • 3 Baths
  • 2,750 Sq Ft

  109 Herring Creek Rd, Edgartown, MA 02539

  Coastal Retreat In Katama - Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with

  Wendy Harman Compass

  109 Herring Creek 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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  /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
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  /24

  $2,375,000

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

  Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

  Cassie Bradley Wallace & Co. Sotheby's International Realty

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
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  /23

  $2,495,000

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

  Brian Smith Portfolio Real Estate Inc.

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /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
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  /34

  $1,895,000

  • 5 Beds
  • 2 Baths
  • 1,918 Sq Ft

  35 Tuckernuck Ave, Oak Bluffs, MA 02557

  Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience.As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a generous

  Jennifer B. DaSilva Compass

  35 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /9

  $975,000

  • 1 Bed
  • 2 Baths
  • 1,000 Sq Ft

  128 Manchester Ave, Oak Bluffs, MA 02568

  This delightful, modern cape-style home features thoughtful and impressive finish details. It is almost ready for move in day! The covered porch welcomes you into the home where you will find a well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, a French-door refrigerator, dishwasher, and back splash finished with subway tiles. There is an

  Michele Moore Island Real Estate

  128 Manchester Ave, Oak Bluffs, MA 02568
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  /23

  $1,825,000

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft

  16 Majors Cove Ln, Edgartown, MA 02539

  Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting

  Stephanie Roache Donnelly + Co.

  16 Majors Cove Ln, Edgartown, MA 02539
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  /18

  $1,050,000

  • 1 Bed
  • 2 Baths
  • 1,401 Sq Ft

  249 County Rd, Oak Bluffs, MA 02557

  This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy

  Katherine Donahue Sandpiper Realty Inc

  249 County Rd, Oak Bluffs, MA 02557
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  /21

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  99 Old Purchase Rd, Edgartown, MA 02539

  Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was

  Stephanie Roache Donnelly + Co.

  99 Old Purchase Rd, Edgartown, MA 02539
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  /26

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  5 Pip'N Rd, Edgartown, MA 02539

  Tucked away in a quiet, wooded setting on picturesque Chappaquiddick, this charming three-bedroom Cape offers a peaceful island retreat. Designed for laid-back living, the home features a cheerful and versatile floor plan with generous indoor and outdoor spaces. The star of the show? A sprawling screened-in porch with a cozy wood-burning fireplace--perfect for summer nights or crisp fall

  Katherine Donahue Sandpiper Realty Inc

  5 Pip'N Rd, Edgartown, MA 02539
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  /26

  $2,100,000

  • 3 Beds
  • 3.5 Baths
  • 960 Sq Ft

  23 13th St N, Edgartown, MA 02539

  Coming Soon April 1st! New Construction! This newly built clean three-bedroom three-and-a-half-bathroom home in Edgartown offers a modern open concept design ideal for entertaining. The updated fresh kitchen features stainless steel appliances functional island with new induction oven ideal for the cooks in the family. Beautiful flawless hardwood flooring throughout the home. Upstairs are two

  Janna O'Loughlin Martha's Vineyard Seacoast Properties

  23 13th St N, Edgartown, MA 02539
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  /40

  $4,500,000

  • 3 Beds
  • 5.5 Baths
  • 4,046 Sq Ft

  267 Barnes Rd, Oak Bluffs, MA 02557

  Enjoy waterfront living at its best with 163’ of Lagoon frontage including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the water…boating, swimming, kayaking, clamming, and more. Perfect for entertaining and comfortable living,

  Stephanie Roache Donnelly + Co.

  267 Barnes Rd, Oak Bluffs, MA 02557
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  /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
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  /37

  $1,800,000

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

  8 Massasoit Rd, Edgartown, MA 02539

  This incredibly charming Katama Cape Cod-style home that has been completely refreshed top to bottom! An updated kitchen with high-end appliances, including a wine fridge, two brand new bathrooms, central AC and a new second floor deck are just some of the improvements. There are two bedrooms, one on each floor. The second floor has a comfortable lounge area, and a cozy loft is accessed with a

  Cheri Mason LandVest MV

  8 Massasoit Rd, Edgartown, MA 02539
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  /23

  $1,650,000

  • 4 Beds
  • 2 Baths
  • 1,666 Sq Ft

  60 Windsor Dr, Edgartown, MA 02539

  Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  60 Windsor Dr, Edgartown, MA 02539
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  /26

  $9,995,000

  • 8 Beds
  • 11 Baths
  • 7,585 Sq Ft

  12 Boldwater Rd, Edgartown, MA 02539

  Uncover unparalleled Martha’s Vineyard opulence within a sprawling 9.8-acre estate. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom | 10-bathroom main home, designed by the renowned architect, Robert A.M. Stern. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience

  Michael Carucci Gibson Sotheby's International Realty

  12 Boldwater Rd, Edgartown, MA 02539
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  /28

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  11 Flamingo Dr, Edgartown, MA 02539

  Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

  Skip Dostal, Jr Martha's Vineyard Real Estate

  11 Flamingo Dr, Edgartown, MA 02539
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  /39

  $1,895,000

  • 5 Beds
  • 3 Baths
  • 2,432 Sq Ft

  32 Flamingo Dr, Edgartown, MA 02539

  This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

  Skip Dostal, Jr Martha's Vineyard Real Estate

  32 Flamingo Dr, Edgartown, MA 02539
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  /21

  $1,195,000

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft

  31 9th St N, Edgartown, MA 02539

  Nestled among the trees near the Sengekontacket Pond, this distinctive contemporary home offers privacy while being conveniently close to Downtown Edgartown and the picturesque trails at Felix Neck Sanctuary. Designed by architect Robert Orr, this multi-level residence showcases unique architectural details and striking angled ceilings. The main living area is bathed in natural light, surrounded

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  31 9th St N, Edgartown, MA 02539
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  /26

  $1,775,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  37 Knoll Dr, Edgartown, MA 02539

  TURN KEY ready for personal use or renting. 37 Knoll Drive in the heart of Katama 3-bdrm, 2 full bth home offers 1,232 SF of living space on a16,552 SF lot. An open living/dining area, complete with wood-burning fireplace & a bow window that fills the space w/ natural light. Oak floors throughout. The kitchen boasts stainless steel appliances & stone counters & opens onto a deck that leads to

  Josseph Barkett Compass

  37 Knoll Dr, Edgartown, MA 02539
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  /17

  $1,169,999

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  96 Manchester Ave, Oak Bluffs, MA 02557

  Nestled in the sought-after Lagoon Heights in Oak Bluffs, 96 Manchester Ave is a charming Cape-style home offering a perfect blend of comfort and coastal charm. This well-maintained residence features three spacious bedrooms and two bathrooms. Recent updates enhance both style and functionality, including a new roof, numerous Andersen windows, an outdoor shower, and fresh interior paint. The

  Jordan Pavao Keller Williams South Watuppa

  96 Manchester Ave, Oak Bluffs, MA 02557
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  /31

  $1,975,000

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft

  15 Jernegan Pond Rd, Edgartown, MA 02539

  Simply enchanting! The setting is picturesque with a pond, towering trees and flowering shrubbery, privately tucked away yet less than 11/4 mile to the Edgartown Village. The existing home is set at the edge of the pond and is awaiting reimagination and renovation. Parcel will support 5 bedrooms once connected to municipal sewer. Structures are being sold 'as is'.

  Lesley Heidt Sandpiper Realty Inc

  15 Jernegan Pond Rd, Edgartown, MA 02539
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  /16

  $1,249,000

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  108 Charles Neck Way, Vineyard Haven, MA 02568

  This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  108 Charles Neck Way, Vineyard Haven, MA 02568
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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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  /42

  $19,900,000

  • 8 Beds
  • 7.5 Baths
  • 6,041 Sq Ft

  114 N Water St, Edgartown, MA 02539

  Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living quarters.Designed for relaxation and entertainment, the private backyard oasis

  114 N Water St, Edgartown, MA 02539
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  /28

  $3,500,000

  • 6 Beds
  • 2.5 Baths
  • 1,666 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

  Lisa Lucier Anchor Realty of MV

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /59

  $4,950,000

  • 5 Beds
  • 5.5 Baths
  • 2,651 Sq Ft

  31 Old Harbor Ln, Oak Bluffs, MA 02557

  Enjoy spectacular views of Sengekontacket Pond and State Beach all the way to Chappaquiddick from this newly constructed home that has been only lightly used in the 3 years since it was built. There are also beautiful views of the third, fourth and fifth holes at Farm Neck Golf Club. The fresh and bright home was built by top-notch Stedman Construction and is set on the largest lot in Waterview

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  31 Old Harbor Ln, Oak Bluffs, MA 02557
• 

  

  /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

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