8 Driveway, Chilmark, MA 02535
Property image
Property image
OFF MARKET

$3,136,500

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,548 sqft (on 4.70 acres)

8 Driveway, Chilmark, MA 02535

Est. Refi. Payment $17,341/mo*
Refinance Your Home
Currently Off Market - Sold Oct 12, 2021 for $2,419,145

Home Value

Trulia Estimate
$3.14M
Since last month
Decreased$38K (-1.2%)
Since last year
Increased$32K (+1%)
Since last sale
Increased$712K (+29.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +72% in the last 10 years
MonthEstimated value
2026
August 2026$3.13M
July 2026$3.17M
June 2026$3.22M
May 2026$3.18M
April 2026$3.15M
March 2026$3.13M
February 2026$3.08M
January 2026$3.06M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
31 N Slope Ln, Chilmark, MA
0.86
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
6 Tabor Hls, Chilmark, MA
0.96
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
3 Fulling Mill Rd, Chilmark, MA
0.50
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
300 North Road 18 Belhaven Way, Chilmark, MA
1.18
Single-Family Home
$2,800,000
08/27/26
4
3.5
2,515
25 Osprey Ln, Chilmark, MA
0.90
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
18 Homeward Way, Chilmark, MA
0.85
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
9 Beetlebung Grove Way, Chilmark, MA
1.90
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
49 Gosnolds Way, Chilmark, MA
1.41
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
94 Menemsha Inn Rd, Chilmark, MA
1.69
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
10 Mollys Way, Chilmark, MA
1.66
Single-Family Home
$2,550,000
10/02/25
3
2
1,524

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
18 Allen Farm Rd, Chilmark, MA 02535
0.37
$2,250,000
1
1
726
For Sale
High Mark, Chilmark, MA 02535
0.37
$1,900,000
-
-
-
For Sale
1 Pond Mark, Chilmark, MA 02535
0.46
$4,038,500
3
2.5
1,316
Off Market
25 Fulling Mill Rd, Chilmark, MA 02535
0.48
$2,250,000
4
3
1,918
For Sale
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.49
$2,250,000
4
3
1,918
For Sale
3 Fulling Mill Rd, Chilmark, MA 02535
0.50
$1,775,000
3
2
1,728
Recently Sold
493 South Rd, Chilmark, MA 02535
0.59
-
-
-
-
Off Market
44 Cencelle St, Chilmark, MA 02535
0.60
$4,975,000
4
3
3,432
For Sale
391 Middle Rd, Chilmark, MA 02535
0.67
$6,282,900
6
4.5
3,859
Off Market
27 Ocean View Farm Rd, Chilmark, MA 02535
0.70
$3,001,600
4
3
2,450
Off Market
22 Ocean View Farm Rd #B, Chilmark, MA 02535
0.71
$1,149,800
2
1.5
1,520
Off Market
Cencelle, Chilmark, MA 02535
0.73
$1,275,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 8 Driveway.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1990
Lot Size
4.7 acres
Living Area
2,548 sqft
Price/Sqft
$1,231

About this House

Middle Road Water View: This fabulous location, just off Middle Road, and not far from Beetlebung Corner, offers views of the lush countryside extending south to the blue waters of the south shore. The residence, designed by noted architect Milton Klein, has modern lines, a minimalist white interior with bleached bamboo floors, a wall of glass sliders with southern exposure and a high ceiling in the Great Room which encompasses living, dining and kitchen. The main level master suite has a separate office space and en suite bathroom. Off the Great Room is a large deck also leading to the screened porch which has access from the kitchen. The lower level floor plan has a family room with built in cabinets for storage and media, glass sliders out to deck and 2 outdoor showers, 3 guest bedrooms, a full bathroom plus powder room, closet laundry room, and utility room. The house is designed with plenty of built-in drawers and cabinets. The 4.7 acre site provides plenty of room for expansion. It is less than two miles to Lucy Vincent Beach and less than 1 mile to the Chilmark Store. Mini-Split A/C in Great Room and Master Bedroom. House heated by both Gas FHW and Electric, and also receives good solar gain from south side. See attached deed for covenants and view maintenance.
8 Driveway, Chilmark, MA 02535 is a 4 bedroom, 3 bathroom, 2,548 sqft single-family home built in 1990. It last sold for $2,419,145 on Oct 12, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,136,500, with a rent estimate of $7,693/month.

Home Details for 8 Driveway

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood

Property Information

Year Built
Year Built: 1990Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 4.70 acres

Price and Tax history

DateEventPrice
Oct 12, 2021
Source: LINK #38298
Sold
$2,419,145
Jun 24, 2021
Source: LINK Martha's Vineyard #38298
Listed For Sale
$2,650,000
Sep 17, 2008
Source: LINK #17859
Sold
$1,750,000

Market trends in Chilmark

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
8MoM

Around this home

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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Frequently asked questions about 8 Driveway

  • What is 8 Driveway estimated to be worth?
    Trulia's estimated value for 8 Driveway in Chilmark, MA is $3,136,500.
  • What is the price history for 8 Driveway?
    8 Driveway in Chilmark, MA last sold for $2,419,145 in October 2021.
  • Is Chilmark a buyer's or seller's market?
    Chilmark is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 8 Driveway?
    The closest schools to 8 Driveway in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
  • How big is the lot at 8 Driveway?
    The lot at 8 Driveway in Chilmark, MA is about 4.7 acres.

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