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Price Reduced Homes for Sale in Edgartown, MA

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  • /43

    $389,000

    $139K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
  • /27

    $389,000

    $139K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02568
  • /41

    $1,395,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    44 Prices Way, Edgartown, MA 02539

    Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient

    Agent Photo

    Wendy Harman

    Compass

    44 Prices Way, Edgartown, MA 02539
  • /21

    $849,000

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In-Town Oak Bluffs Condo with Panoramic Water ViewsExperience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space.The condo features one generously sized bedroom plus a separate sleep nook, offering flexibility for guests, a home office, or additional sleeping accommodations. The nook could

    Lisa Lucier Anchor Realty of Martha's Vineyard

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /2

    $399,000

    $26K PRICE DROP
    • Land
    • 7,840 Sq Ft
    • $2,216,667 per Acre

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568

    Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

    Jennifer DaSilva Compass | Point B

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568
  • /33

    $1,499,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • /32

    $1,495,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557

    Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

    Rose Ryley Wallace & Co. Sotheby's International Realty

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
  • /43

    $2,455,000

    $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,039 Sq Ft

    99 The Blvd, Edgartown, MA 02539

    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 main floor features a wood-burning fireplace, custom kitchen, and direct access to a private

    Jennifer DaSilva Compass | Point B

    99 The Blvd, Edgartown, MA 02539
  • /37

    $14,000,000

    $1M PRICE DROP
    • 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
  • /28

    $2,850,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,927 Sq Ft

    2 Bold Meadow Rd, Edgartown, MA 02539

    Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a

    Stacy Ickes Donnelly + Co.

    2 Bold Meadow Rd, Edgartown, MA 02539
  • /42

    $2,590,000

    $360K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 4,530 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three

    Jennifer O'hanlon Compass

    15 21st St N, Edgartown, MA 02539
  • /31

    $1,775,000

    $75K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    99 Old Purchase Rd, Edgartown, MA 02539

    Enjoy privacy at the end of a quiet Edgartown cul-de-sac on .71 acres with easy access to 25+ acres of Land Bank conservation land. Ideally located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, this light-filled post-and-beam home offers a thoughtful floor plan and inviting indoor-outdoor living. The spacious kitchen features a large center island, walk-in pantry,

    Stephanie Roache Donnelly + Co.

    99 Old Purchase Rd, Edgartown, MA 02539
  • /24

    $879,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Intown Oak Bluffs Condo with Panoramic Rooftop ViewsDiscover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location.Step inside to an inviting custom wood interior that gives the home a distinctive coastal-island feel.

    Lisa Lucier Anchor Realty of Martha's Vineyard

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /31

    $2,595,000

    $650K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,023 Sq Ft

    44 Tiffany Dr, Oak Bluffs, MA 02557

    Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, family room, game room, a screened porch, ensuite bedroom and powder room. An attached one-bedroom

    Perry Patterson MV Luxury Homes

    44 Tiffany Dr, Oak Bluffs, MA 02557
  • /28

    $1,495,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557

    Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

    Rose Ryley Wallace & Co. Sotheby's International Realty

    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
  • /2

    $399,000

    $26K PRICE DROP
    • Land
    • 7,840 Sq Ft
    • $2,216,667 per Acre

    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568

    Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

    Jennifer B. DaSilva Compass

    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
  • /41

    $2,595,000

    $55K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    59 Tuckernuck Ave, Oak Bluffs, MA 02557

    Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood

    Jennifer B. DaSilva Compass

    59 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /50

    $2,299,000

    $276K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,910 Sq Ft

    76 Washque Ave, Edgartown, MA 02539

    This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick’s most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird’s-eye views capture the natural beauty that surrounds you. Thoughtfully renovated throughout, the home

    Katherine Donahue Sandpiper Realty

    76 Washque Ave, Edgartown, MA 02539
  • /60

    $10,995,000

    $2M PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,466 Sq Ft

    14 Thayer St, Edgartown, MA 02539

    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, galleries, and restaurants of downtown Edgartown.Expansive lawns, mature landscaping, and a

    Paul Pertile The Agency

    14 Thayer St, Edgartown, MA 02539
  • /8

    $685,000

    $65K PRICE DROP
    • Land
    • 11,417 Sq Ft
    • $2,613,506 per Acre

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

    GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD9 homes already built.Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
  • /33

    $1,225,000

    $25K PRICE DROP
    • 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
  • /44

    $4,600,000

    $200K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,715 Sq Ft

    9 Martha's Way, Edgartown, MA 02539

    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 free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to

    Michele Casavant Vineyard Village Realty

    9 Martha's Way, Edgartown, MA 02539
  • /45

    $1,595,000

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,898 Sq Ft

    20 Hidden Cove Rd, Oak Bluffs, MA 02557

    Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded

    Jennifer DaSilva Compass | Point B

    20 Hidden Cove Rd, Oak Bluffs, MA 02557
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