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CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace-ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

More Info

Basic Information

  • Bedrooms4
  • Mls StatusActive
  • Bathroom5
  • Lot Features Wooded, Cleared, Gentle Sloping
  • Parcel Number 3566352

Tax Information

  • Tax Assessed Value $5,859
  • Tax Year 2025
  • Taxes$13,900

Parking

  • Parking Spaces11
  • Covered Spaces 3
  • Garage YN Yes
  • Parking Features Detached

Rooms

  • Bathrooms Total Decimal 4.5
  • Full Bath4
  • Half Baths1

Basic Information

  • List Price$5,350,000
  • MLS Number73495595
  • Modification Date05/18/2026
  • Property SubTypeSingle Family Residence

Location

  • NeighborhoodChilmark
  • SubdivisionChilmark
  • Address205 South Road
  • Building Number205
  • CountyDukes
  • StateMA
  • StreetSouth Road
  • TownChilmark
  • Zip02575

Building

  • BasementFull, Partially Finished
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 1
  • FoundationConcrete Perimeter
  • Garage Spaces3
  • Property StyleCape
  • Rooms9
  • Year Built1940
  • Year Built Details Approximate
  • Year Built Source Public Records

Property

  • Acreage5.99

Exterior

  • Fencing Fenced/Enclosed

Utilities

  • Cooling Heat Pump
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Radiant, Heat Pump
  • Sewer Inspection Required for Sale
  • Water Source Private

Property Information

  • Square Feet5,402
  • Building Area Source Public Records
  • Living Area 5,402
  • Lot Size Square Feet 260,924
  • Lot Size Units Acres

Amenities

  • Appliances IncludedWater Heater

Water Body

  • Miles to Beach0.5
  • Waterfront Features Ocean,3/10 to 1/2 Mile To Beach, Beach Ownership(Deeded Rights)

Legal

  • ZoningRES

Other

  • Date Listed04/03/2026
  • Farm Land Area Units Square Feet
  • View Count4

Map Location

Driving Directions

Listed by Tina Miller of Donnelly + Co.

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