Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network. The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch in this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, whole-house generator, integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.
For sale
$5,200,000
49 Gosnolds Way, Chilmark, MA 02535
5beds
4,044sqft
Single Family Residence
Built in 2003
9.8 Acres Lot
$4,863,600 Zestimate®
$1,286/sqft
$42/mo HOA
What's special
Air conditioningIntegrated sound systemScreened porchTennis courtDeeded private beach accessLarge open deckOutdoor lighting
- 122 days
- 180
- 8
Zillow last checked:
Listing updated:
Listed by:
Bonnie Pierce,
Wallace & Co. Sotheby's
Source: LINK,MLS#: 44546
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bedrooms: 4
Heating
- GFHA
Appliances
- Included: Stove: Yes, Washer: Yes
Features
- AC, Ins, OSh, Floor 1: Warm inviting entry, office area, study/reading area, four bedrooms, two full bathrooms and access to one-car garage, Floor 2: Open kitchen, living room, dining room, breakfast nook, sitting area, screened porch, powder room, primary bedroom suite with full bathroom and private deck, office space, laundry room and expansive outside deck
- Flooring: hardwood/tile
- Basement: Large full basement
- Fireplace features: Yes in living room (gas)
Interior area
- Total structure area: 4,044
- Total interior livable area: 4,044 sqft
Video & virtual tour
Property
Parking
- Parking features: Two parking areas
Features
- Exterior features: WViews, Deck, Garden, Tennis, PvtBch
- Has view: Yes
- View description: Sound, Pasture
- Has water view: Yes
- Water view: Sound
- Frontage type: None
Lot
- Size: 9.8 Acres
- Features: Beautifully landscaped with mature plantings, gardens & meadow
Details
- Additional structures: Private tennis court
- Parcel number: CHILM14P35
- Zoning: RU
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: poured
Condition
- Year built: 2003
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cbl
Community & HOA
HOA
- Has HOA: Yes
- Services included: Road maintenance
- HOA fee: $500 annually
Location
- Region: Chilmark
Financial & listing details
- Price per square foot: $1,286/sqft
- Tax assessed value: $3,636,900
- Annual tax amount: $8,293
- Date on market: 6/7/2026
- Listing agreement: E
Estimated market value
$4,863,600
$4.62M - $5.11M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/7/2026 | Listed for sale | $5,200,000+7.2%$1,286/sqft |
Source: LINK #44546 Report a problem | ||
| 12/5/2025 | Sold | $4,850,000-2%$1,199/sqft |
Source: LINK #43016 Report a problem | ||
| 9/18/2025 | Pending sale | $4,950,000$1,224/sqft |
Source: LINK #43016 Report a problem | ||
| 8/25/2025 | Contingent | $4,950,000$1,224/sqft |
Source: LINK #43016 Report a problem | ||
| 7/17/2025 | Price change | $4,950,000-6.5%$1,224/sqft |
Source: LINK #43016 Report a problem | ||
| 5/2/2025 | Listed for sale | $5,295,000-11%$1,309/sqft |
Source: LINK #43016 Report a problem | ||
| 12/3/2024 | Listing removed | $5,950,000$1,471/sqft |
Source: LINK #42197 Report a problem | ||
| 6/23/2024 | Listed for sale | $5,950,000$1,471/sqft |
Source: LINK #42197 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,795 +8.4% | $3,464,500 +2.1% |
| 2024 | $7,193 +6.5% | $3,393,000 +32.2% |
| 2023 | $6,751 +14.9% | $2,566,900 +23.2% |
| 2022 | $5,875 +5.4% | $2,083,500 +8.8% |
| 2021 | $5,574 +3.6% | $1,915,400 +1.8% |
| 2020 | $5,379 +3.1% | $1,880,900 +3.8% |
| 2019 | $5,218 +4.7% | $1,811,900 |
| 2018 | $4,983 +3.8% | $1,811,900 +1.1% |
| 2017 | $4,802 -0.2% | $1,791,900 +0.9% |
| 2016 | $4,811 | $1,775,300 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 02535
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