Chilmark, MA 02535 205 South Road

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Presented By: Tina Miller with Donnelly + Co -
  • MLS# 44028
  • 04/03/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 4 / 1
  • SQFT • 6,162

Home Details

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room. A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews. Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land. Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.
Presented By: Tina Miller with Donnelly + Co -

Interior Features for 205 South Road

Bedrooms

Main Level Bedrooms3
Total Bedrooms4

Bathrooms

Half Baths1

Other Interior Features

BasementFull, High ceilings, partially finished.
Fireplace Features1
Fireplace Y/NNo
Flooring1.5
Furnished Y/NUnfurnished
Interior AmenitiesIns, OSh, Floor 1: Open kitchen, living room, sprawling primary bedroom wing. Three-season living area, two en suite bedrooms, Floor 2: Art studio, office or media space. Also, a loft area off the living room.

General for 205 South Road

AppliancesStove: Bertazzoni, Washer: Yes
Building Area UnitsSquare Feet
CityChilmark
Full Baths4
HeatingGFHA
Lot Size Square Feet260924
MLS Area5
Other StructuresGuest house, Horse Barn or Party Barn, Three Bay Garage, Boat House, Grid Tied Solar Panels System and Fenced Pasture land.
Property SubtypeSingle Family Residence
Property Type1 Family
SewerSeptic Tank
Standard StatusActive
StatusA
Tax Annual Amount13900
Tax Assessed Value4351000
Tax Lot18
Tax Year2026
TaxOtherAnnualAssessmentAmount1508000
Total Rooms9
UtilitiesCbl
ViewNone, Pasture
Year Built1940
Year Built Effective2014
ZoningRES

Exterior for 205 South Road

Building Area Total6162
Exterior AmenitiesDeck, Patio, DdBch, Garden
Foundation DetailsPoured concrete
Frontage TypeNone
Lot Featuresample
Lot Size Acres5.99
Lot Size Area5.99
Parking Featuresample
Water SourceWell

Additional Details

Price History

Brian Skidmore

Price $4,995,000
MLS#44028
List Date 04/03/2026
Property Type Single Family
Phone 617.834.3227
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