34 Windy Gates Rd, Chilmark, MA 02535
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Property image
OFF MARKET

34 Windy Gates Rd
Chilmark, MA 02535

  • 4 Beds
  • 5 Baths
  • 5,456 sqft (on 4 acres)

$5,341,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $28,528/mo*

$5,341,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $28,528/mo*
4 Beds
5 Baths
5,456 sqft
(on 4 acres)

Local Information

  • Map ViewExplore the area around 34 Windy Gates Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

No explanation is needed when referring to this historic uniquely secluded community. Perfect design and function are obvious in this nine room rambling country house . Supreme uninterrupted living spaces connected by charming covered porches, all majestically set on 4.3 acres of rolling lawns, with specimen trees and perennial gardens. There is an additional carriage house with one bath and numerous out buildings plus access to one of the finest and most private ocean beaches in the country.
34 Windy Gates Rd, Chilmark, MA 02535 is a 4 bedroom, 5 bathroom, 5,456 sqft single-family home built in 1994. It last sold for $485,000 on Apr 13, 1993. It is currently off market. The Trulia Estimate is $5,341,300, with a rent estimate of $6,913/month.

Home Highlights

Parking
No Info
Outdoor
Porch, Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 34 Windy Gates Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Solarium Atrium
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPatioPorch

Property Information

Year Built
Year Built: 1994Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 4.00 acres

Price History for 34 Windy Gates Rd

DatePriceEventSource
07/27/2014$5,750,000ListingRemovedAgent Provided
02/11/2014$5,750,000Listed For SaleAgent Provided
12/03/2013$5,750,000ListingRemovedAgent Provided
09/30/2013$5,750,000Listed For SaleAgent Provided
04/13/1993$485,000Sold
N/A

Market trends in Chilmark

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
27
11
MoM
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Property Tax and Assessment

Year2025
Tax$12,174
Assessment$5,410,800
Home facts updated by county records

Comparable Sales for 34 Windy Gates Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1.16
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
1.50
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
1.40
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
1.78
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
1.66
Single-Family Home
$1,607,000
07/10/25
4
3
2,850
1.48
Single-Family Home
$6,550,000
11/14/25
4
3.5
3,355
1.31
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
1.95
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
1.93
Single-Family Home
$5,900,000
10/31/25
6
4.5
3,143
1.94
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044

Nearby homes

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Assigned Schools

These are the assigned schools for 34 Windy Gates Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.
  • 100 % Say there's wildlife

  • 100 % Say there are community events

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 78 % Say neighbors are friendly

  • 75 % Say it's dog friendly

  • 75 % Say people would walk alone at night

  • 67 % Say parking is easy

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 43 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Elaine V.
    "I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"

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Apartments for Rent

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Homes for sale near 34 Windy Gates Rd

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Off Market Homes Near 34 Windy Gates Rd

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