2 Youngs Way, Chilmark, MA 02535
Property image
Property image
OFF MARKET

2 Youngs Way
Chilmark, MA 02535

  • 4 Beds
  • 2 Baths
  • 2,116 sqft

$4,542,500

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $25,129/mo*

$4,542,500

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $25,129/mo*
4 Beds
2 Baths
2,116 sqft

Local Information

  • Map ViewExplore the area around 2 Youngs Way.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1986
Living Area
2,116 sqft
Price/Sqft
$2,147

About this House

Located in the heart of quintessential Chilmark, this property is nestled between the Allen Farm to the north and Lucy Vincent Beach to the south. Local architect, Ben Moore, designed a single level home for a life of ease beside Chilmark Upper Pond. Living room, dining and a large office form the central core of the house, all enjoying large windows with wide channel views to the Atlantic ocean. The kitchen is on the north side. The wing to the east includes 3-bedrooms, a full bath and laundry room. The west wing holds the en suite master bedroom. Across the entire south side of the house is a multi-level deck system including a large hot tub. A leg of the property extends south to 235' of frontage on Chilmark Pond and a perfect launch for kayaks, canoes, or a Sunfish.
2 Youngs Way, Chilmark, MA 02535 is a 4 bedroom, 2 bathroom, 2,116 sqft single-family home built in 1986. It last sold for $2,462,500 on Dec 17, 2015. It is currently off market. The Trulia Estimate is $4,542,500, with a rent estimate of $5,852/month.

Home Details for 2 Youngs Way

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Wood

Property Information

Year Built
Year Built: 1986Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 4 sqft

Building

Fitness & Sports
Tennis Court

Price History for 2 Youngs Way

DatePriceEventSource
12/17/2015$2,462,500Sold
LINK #28725
06/10/2015$2,750,000ListingRemovedAgent Provided
11/16/2014$2,750,000PriceChange
Agent Provided
11/24/2013$2,900,000PriceChange
Agent Provided
07/26/2013$3,200,000PriceChange
Agent Provided
06/28/2013$3,600,000Listed For SaleAgent Provided
06/18/2001$341,750Sold
N/A

Market trends in Chilmark

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
31
4
MoM
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Property Tax and Assessment

Year2025
Tax$8,237
Assessment$3,661,100
Home facts updated by county records

Comparable Sales for 2 Youngs Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.39
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
0.82
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
1.26
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
1.45
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
1.44
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
2.34
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
1.54
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
2.06
Single-Family Home
$2,550,000
10/02/25
3
2
1,524
2.00
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
2.25
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Youngs Way.
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 2 Youngs Way

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Off Market Homes Near 2 Youngs Way

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