Section Image Section Image

Explore Similar Condos Within 10 Miles of Chilmark, MA

  • /32

    $985,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /24

    $935,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 422-4131

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /30

    $1,495,000

    • 2 Beds
    • 2 Baths
    • 2,354 Sq Ft

    48 N Shore Dr Unit 3&7, South Dartmouth, MA 02748

    Located in Round Hill —one of South Dartmouth’s most iconic waterfront communities—this stunning two-level Mansion condominium offers the unique opportunity to embrace elevated coastal living. With 2 bedrooms, 2 full baths and a 2300+/- sq ft footprint, this residence showcases lofty ceilings, a bright open floor plan on both levels, and a sleek, move-in-ready interior with coastal contemporary

    Team MCM Gibson Sotheby's International Realty

    48 N Shore Dr Unit 3&7, South Dartmouth, MA 02748
  • /9

    $1,445,000

    • 1 Bed
    • 1.5 Baths
    • 1,551 Sq Ft

    286 Grand Ave Unit 4, Falmouth, MA 02540

    Unit 4 is an oversized one bedroom with an ideal layout for living with an ocean breeze at all times! Amongst the most cherished properties in Falmouth Heights, The Casino Wharf Residences offer timeless connection to Vineyard Sound and the best of Cape Cod living. The beachfront jewel offers residents with a private beach oasis, surrounded by open grassy fields, shimmering water views, and

    William Senne Senne

    286 Grand Ave Unit 4, Falmouth, MA 02540
  • /42

    $1,350,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

    Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

    Emily Flake Viewpoints

    145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
  • /11

    $1,675,000

    • 2 Beds
    • 2.5 Baths
    • 1,547 Sq Ft

    533 Woods Hole Rd Unit E301, Falmouth, MA 2543

    Walk to Woods Hole Village - New Construction Luxury Townhome with Stunning Views of Vineyard Sound & Martha's Vineyard. Welcome home to Lighthouse Station at Woods Hole, a 55+ community perched on 5.3 acres overlooking Little Harbor & Vineyard Sound. Enjoy this spacious, 3rd floor 1500+ SF 2 bedroom/2.5 bathroom one-level unit with an open concept great room & professionally designed kitchen.

    Mark Bogosian Waterside Real Estate LLC

    533 Woods Hole Rd Unit E301, Falmouth, MA 2543
  • /16

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

    East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

    Perry Patterson MV Luxury Homes, LLC

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
  • /12

    $1,995,000

    • 2 Beds
    • 1 Bath
    • 879 Sq Ft

    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568

    East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
  • /17

    $1,995,000

    • 2 Beds
    • 1 Bath
    • 802 Sq Ft

    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
  • /13

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 736 Sq Ft

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
  • /12

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 731 Sq Ft

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
  • /34

    $1,675,000

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

    26 Union St Unit 7, Tisbury, MA 02568

    Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower. Also on

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    26 Union St Unit 7, Tisbury, MA 02568
  • /43

    $1,795,000

    • 2 Beds
    • 3 Baths
    • 1,737 Sq Ft

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568

    The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area

    Michele Moore Island Real Estate

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568
  • /17

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568

    East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new

    Perry Patterson MV Luxury Homes

    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
  • /49

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 1,682 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    ASSOCIATION POOL, TENNIS, LAKE TASHMOO BEACH, PLUS GOLF NEARBY! Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in the prestigious Tashmoo Woods Association.The updated kitchen, with granite countertops and high-end appliances, opens to a dining room with access to a private deck overlooking lush woods. The living room, featuring a wood-burning fireplace, flows into

    Jen O'Hanlon Compass | The O'Hanlon Group

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • /13

    $1,325,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,466 Sq Ft

    533 Woods Hole Rd Unit E202, Falmouth, MA 2543

    Walk to Woods Hole Village - Construction Pricing! Luxury Townhome within walking distance to Woods Hole Village - Ready Late 2025. Welcome home to Lighthouse Station at Woods Hole, a 55+ community perched on 5.3 acres overlooking Little Harbor & Vineyard Sound. Enjoy this lovely, 1466+ SF 2 bedroom/2.5 bath one-level unit on the 2nd story overlooking a quiet, wooded neighborhood. This unit

    Mark Bogosian Waterside Real Estate LLC

    533 Woods Hole Rd Unit E202, Falmouth, MA 2543
  • /8

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

    Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway Harborview association. Easy access to downtown shops, restaurants, harbor, ferry, and beaches. Building amenities include a shared pool, convenient storage, and on-site laundry facilities. The perfect blend of convenience and comfort for year-round living or as your ideal summer retreat.

    Emma Kennedy Sandpiper Realty Inc

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
  • /30

    $1,175,000 Open Wed 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 1,323 Sq Ft

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    FULLY FURNISHED Ready to live in or rent~ COASTAL CHIC CONDO in a TERRIFIC LOCATION with WATERFRONT ACCESS ~Meticulously crafted and exceptionally appointed, this end unit condo/townhouse has been architecturally designed with style. Featuring 2 bedrooms, a flexible third-floor loft flex room, and 1.5 bathrooms, this stylish 1,323 sq. ft. residence blends designer touches with top-tier appliances

    Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
  • /21

    $650,000

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

    Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • /9

    $2,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,459 Sq Ft

    286 Grand Ave Unit 8, Falmouth, MA 02540

    Amongst the most cherished properties in Falmouth Heights, The Casino Wharf Residences offer timeless connection to Vineyard Sound and the best of Cape Cod living. The beachfront jewel offers residents with a private beach oasis, surrounded by open grassy fields, shimmering water views, and nearby dining and nightlife. Unit 8 is an oversized three bedroom duplex with a loft for additional

    William Senne Senne

    286 Grand Ave Unit 8, Falmouth, MA 02540
  • /32

    $941,000

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft

    4 Quail Run Rd, Oak Bluffs, MA 02568

    Amazing Turnkey End Unit with Kayak & EV Charger! Not to be missed!Island living made easy in this private 3-story Year Round end-unit townhouse with carport parking for 3, saltwater access, dock, and mooring potential. Features 2 bedrooms plus a versatile loft, open-concept living area with gas fireplace, modern kitchen with granite countertops, and a large private deck overlooking park-like

    Janna O'Loughlin Portfolio Properties

    4 Quail Run Rd, Oak Bluffs, MA 02568
  • /31

    $941,000

    • 2 Beds
    • 2 Baths
    • 1,323 Sq Ft

    4 Quail Run Unit 7, Oak Bluffs, MA 02557

    Turnkey End Unit with Kayak & EV Charger! Private End Unit being Sold Turnkey including a kayak, paddles and lifejacket!Island living made easy in this private 3-story end-unit townhouse with saltwater access, dock, and mooring potential. Features 2 bedrooms plus a versatile loft, open-concept living area with gas fireplace, modern kitchen with granite countertops, and a large private deck

    Janna O'Loughlin Portfolio Real Estate, Inc.

    4 Quail Run Unit 7, Oak Bluffs, MA 02557
  • /43

    $955,000 Open Sat 11:30AM - 1:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    480 Main St Unit 1, Falmouth, MA 02540

    Steps from the charm and culture of Main Street, yet offering the privacy and presence of a standalone home, 480 Main Street Unit 1 is a masterfully restored residence immersed in the heart of Falmouth Village. Designed for those who appreciate architectural integrity and effortless living, this three-level home lives like a private retreat--paired with the low-maintenance benefits of condominium

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    480 Main St Unit 1, Falmouth, MA 02540
  • /15

    $1,065,000

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

    A wonderful home on the outskirts of town. This property is being offered as part of a 2 unit condo. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice shared 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed on the 2nd condo unit that will serve an additional 5

    Jim Feiner Feiner Real Estate

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
  • /22

    $2,285,000 New Construction

    • 3 Beds
    • 3 Baths
    • 2,519 Sq Ft

    533 Woods Hole Rd Unit D101, Falmouth, MA 2543

    Walk to Woods Hole Village - New Construction Luxury Townhome with Stunning Views of Vineyard Sound & Martha's Vineyard. Welcome home to Lighthouse Station at Woods Hole, a 55+ community perched on 5.3 acres overlooking Little Harbor & Vineyard Sound. Enjoy this spacious, 2400+ SF 3 bedroom/3 bathroom 2-story townhome with an open concept great room & professionally designed kitchen. Watch the

    Mark Bogosian Waterside Real Estate LLC

    533 Woods Hole Rd Unit D101, Falmouth, MA 2543
  • /9

    $2,675,000 Pre-Foreclosure

    • 3 Beds
    • 3.5 Baths
    • 3,175 Sq Ft

    286 Grand Ave Unit 6, Falmouth, MA 02540

    Spacious and amazing, unit 6 at Casino Wharf has an open first floor ideal for taking in beach life in Falmouth Heights! Expansive water views and double height ceilings with great windows. Amongst the most cherished properties in Falmouth Heights, The Casino Wharf Residences offer timeless connection to Vineyard Sound and the best of Cape Cod living. The beachfront jewel offers residents with a

    William Senne Senne

    286 Grand Ave Unit 6, Falmouth, MA 02540

Why Live in Chilmark

Chilmark, located in the up-island region of Martha’s Vineyard, is characterized by its serene, rural landscape and expansive rolling hills reminiscent of Ireland. This quiet town is known for its privacy, with homes set on large lots of at least three acres, often at the end of private dirt roads. The area lacks a downtown district and gastropubs, offering instead the tranquility of mighty-waved beaches like Lucy Vincent Beach, exclusive to town residents. The neighborhood is home to gray-shingled Cape Cod-style houses and vast family compounds, reflecting its reputation for high property values, though it maintains one of the lowest property tax rates on the island. Menemsha, a quaint fishing village within Chilmark, features markets selling fresh seafood and offers scenic hikes along Menemsha Hills. Residents enjoy local amenities such as the Chilmark General Store, known for its pizza and locally sourced goods, and the Yard, a performing arts venue. Chilmark School serves younger children with a unique multi-age classroom approach, while older students attend Martha’s Vineyard Regional High School, which provides a range of educational programs. The town is about a 30-minute drive from Edgartown and Oak Bluffs, with Martha’s Vineyard Airport just 15 minutes away, offering both year-round and seasonal flights.

Home Trends in Chilmark, MA

Housing Trends

Median Sale Price
$419,485
Median Single Family Sale Price
$421,000
Median Townhouse Sale Price
$372,390
Median 2 Bedroom Sale Price
$353,000
Average Price Per Sq Ft
$252
Number of Homes for Sale
6
Last 12 months Home Sales
74
Months of Supply
1.00
Median List Price
$435,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
30%
How to Buy a Home How to Finance a Home How to Sell a Home