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Michael Breshears
REALTOR®
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49 Gosnolds Way, Chilmark, MA 02535

$5,200,000
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New to the Market Active
BEDS5 BATHS3 full 1 partial SQUARE FEET4,044 MLS#73534187
STATUSActive PROPERTY TYPEResidential - Single Family

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.

49 Gosnolds Way | MLS# 73534187

This single family home located at 49 Gosnolds Way, Chilmark, MA 02535 is currently listed for sale with an asking price of $5,200,000. This property was built in 2003 and has 5 bedrooms and 3 full and 1 partial baths with 4044 sq. ft. Search Chilmark real estate on michaelbreshears.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Full
Basement: Yes
Cooling: Central Air
Fireplaces: 1
Garage: 1 car attached
Heating: Forced Air, Propane
Home Style: Contemporary
Lot Size: 9.80 Acres
Roof Type: Shingle
Taxes: $8,293
Year Built: 2003

Amenities

Internet Available - DSL
Porch - Screened
Deck
Tennis Court(s)
Professional Landscaping

Feature Descriptions

Appliances: Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Association Fee: $500/Annually
Building Area Total: 4044
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 1
Dining Room: Vaulted Ceiling(s), Flooring - Hardwood, French Doors, Exterior Access
Door Features: Insulated Doors, French Doors
Electric: Generator,220 Volts
Exterior: Frame
Family Room: Flooring - Hardwood
Fireplace Features: Living Room
Fireplace Y/N: Yes
Flooring: Wood, Tile
GarageY/N: Yes
HeatingY/N: 1
HOA Y/N: Yes
Kitchen: Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Recessed Lighting
Laundry: Electric Dryer Hookup, Recessed Lighting, Walk-in Storage, Washer Hookup, Sink, Second Floor
Living Room: Beamed Ceilings, Vaulted Ceiling(s), Flooring - Wood, Balcony / Deck, Lighting - Overhead
Lot Features: Wooded, Sloped
Master Bathroom: Yes
Master Bedroom: Bathroom - Double Vanity/Sink, Vaulted Ceiling(s), Walk-In Closet(s), Flooring - Hardwood, Balcony / Deck, French Doors, Exterior Access, Recessed Lighting, Lighting - Overhead
Open Parking Y/N: Yes
Parcel Number: 3566150
Parking Features: Attached, Driveway
Parking Total: 9
Patio And Porch: Screened, Deck
Rooms Total: 13
Security: yes
Security Features: Security System
Sewer: Private Sewer
Special View Info: Scenic View(s)
Utilities: for Gas Range
Water: Private
Waterfront Features: Ocean,1/2 to 1 Mile To Beach, Beach Ownership(Deeded Rights)
Window Features: Insulated Windows
Wooded: Yes

Listed By / Shown By

Listed By

Agency Name: Wallace & Co. Sotheby's International Realty
Agent Name: Bonnie Pierce
Agency Phone: 508-627-3313

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Estimated Payment

$ 13,780.70 per month $11,572.95 Principal & Interest $691.08 Property Tax $1,516.67 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/12/2026. The listing information on this page last changed on 06/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 06/12/2026 12:03:05 AM EST) or MLSPIN MLS (last updated Thu 06/11/2026 11:38:53 PM EST) or Prime MLS (last updated Thu 06/11/2026 11:33:22 PM EST) or MREIS (last updated Thu 06/11/2026 11:55:26 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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