Redfin
View 49 Gosnolds Way on Redfin Full photos, price history & neighborhood details
$ 5,200,000
49 Gosnolds Way Chilmark, MA 02535
Schedule a Tour
49 Gosnolds Way, Chilmark, MA 02535
See all 32 photos
49 Gosnolds Way, Chilmark, MA 02535
49 Gosnolds Way, Chilmark, MA 02535
49 Gosnolds Way, Chilmark, MA 02535
49 Gosnolds Way, Chilmark, MA 02535
REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.
In-PersonVirtual Tour
Brian OKeefe

Brian OKeefe

brian.okeefe@redfin.com +1(781) 591-9611
$ 5,200,000
Est. payment /mo
Save Virtual Tour
Active

49 Gosnolds Way Chilmark, MA 02535

5 Beds

3.5 Baths

4,044 SqFt


UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,044 sqft

Price per Sqft $1,285

MLS Listing ID 73534187

Style Contemporary

Bedrooms 5

Full Baths 3

Half Baths 1

HOA Fees $500/ann

HOA Y/N true

Year Built 2003

Annual Tax Amount $8,293

Tax Year 2026

Lot Size 9.800 Acres

Acres 9.8

Property Sub-Type Single Family Residence

Property Description

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

Location

State MA

County Dukes

Zoning RU

Direction North Rd to Prospect Hill entrance, follow main road as it becomes Gosnolds Way and curves to the ri

Rooms

Family Room Flooring - Hardwood

Basement Full

Primary Bedroom Level Second

Dining Room Vaulted Ceiling(s), Flooring - Hardwood, French Doors, Exterior Access

Kitchen Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Recessed Lighting

Interior

Interior Features Internet Available - DSL

Heating Forced Air, Propane

Cooling Central Air

Flooring Wood, Tile

Fireplaces Number 1

Fireplaces Type Living Room

Appliance Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer

Laundry Electric Dryer Hookup, Recessed Lighting, Walk-in Storage, Washer Hookup, Sink, Second Floor

Exterior

Exterior Feature Porch - Screened, Deck, Tennis Court(s), Professional Landscaping

Garage Spaces 1.0

Utilities Available for Gas Range

Waterfront Description Ocean,1/2 to 1 Mile To Beach,Beach Ownership(Deeded Rights)

View Y/N Yes

View Scenic View(s)

Roof Type Shingle

Total Parking Spaces 10

Garage Yes

Building

Lot Description Wooded, Sloped

Foundation Concrete Perimeter

Sewer Private Sewer

Water Private

Architectural Style Contemporary

Others

Senior Community false

Virtual Tour https://mls.ricoh360.com/2244d417-4a26-4e31-90e6-831596a263af


MLSPIN
Listed by Wallace & Co. Sotheby's International Realty
Redfin
View 49 Gosnolds Way on Redfin Full photos, price history & neighborhood details
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
download (1)

Redfin

Redfin Corporation

+1(844) 759-7732 outreach@redfin.com

Brian OKeefe

+1(781) 591-9611 brian.okeefe@redfin.com

  • Home
  • Listings
  • About
  • Blog

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures. 

Get My App

Name: Mark Bennett 

CA DRE #: 01723159

contact: 1 (949) 294-6186

email: mark.bennett@redfin.com

Designation: Licensed Broker of Redfin for MLSListings Inc., California Regional MLS, Conejo Semi Moorpark Association of Realtors, MetroList Services, Inc and Bay Area Real Estate Info Services (BAREIS)

 

Name: Courtney King

contact: 1 (832) 336-1071

email: courtney.king@redfin.com

Designation: Licensed Broker of Redfin for Greater Tyler Association of Realtors


Name: Kristi Penrod

contact: 1 (520) 744-691

email: kristi.penrod@redfin.com

Designation: Licensed Broker of Redfin for Pikes Peak Association of Realtors

 

Name: Matthew Brennan

contact: 1 (206) 369-6332

email: matthew.brennan@redfin.com

Designation: Licensed Broker of Redfin for Willamette Valley Multiple Listing Service

 

Name: John Webb

contact: 1 (808) 230-7475

email: john.webb@redfin.com

Designation: Licensed Broker of Redfin for Hawaii Information Service

Name: Douglas Gartley

contact: 1 (206) 406-5745

email: doug.gartley@redfin.com

Designation: Licensed Broker of Redfin for Maine Real Estate Information System, Prime MLS, MichRic, MiRealSource, Global MLS, New York State Alliance of MLS.

 

Name: Sandy Fay-Wotherspoon

contact: 1 (864) 999 0410

email: sandy.faywotherspoon@redfin.com

Designation: Licensed Broker of Redfin for Charleston Trident MLS, Consolidated MLS and Western Upstate MLS

Name: Michelle Leader

contact: 1 (405) 693-7317

email: michelle.leader@redfin.com

Designation: Licensed Broker of Redfin for MLSOK/ OKC Metropolitan Association of REALTORS®

Powered by Lofty Inc. Copyright 2026. All Rights Reserved. Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility