27 Tower Ln, Chilmark, MA 02535
OFF MARKET

27 Tower Ln
Chilmark, MA 02535

  • 2 Beds
  • 1 Bath
  • 1,188 sqft (on 1.30 acres)

$2,006,500

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $10,878/mo*

$2,006,500

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $10,878/mo*
2 Beds
1 Bath
1,188 sqft
(on 1.30 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Large estate in Chilmark. As you turn off of Middle Road you are met by a cobblestone driveway that leads you through 7+acres of conservation land and up to the towering Carriage House archway that is the entryway to this majestic property. Emerging through the archway you are greeted by a unique assemblage of structures including the contemporary main house, guest house, and studio. These are surrounded by old stonewalls and newer detailed stonework that creates a harmonious balance between old farmland and new modern design. The Main House contains 4-bedrooms, large open living space and a rooftop deck. The nearby Guest House with 2-bedrooms and full kitchen overlooks raised bed gardens and rolling hills. Also located on the property is another 2-bedroom cottage with a full kitchen and an unfinished pool with pool house. On the far side of the property is over 45 acres of conservation land including portions of the Tiasquam River, all creating the utmost in privacy. There is potential to build one more single-family home on a portion of the property, or simply update the existing structures and enjoy the pristine land that surrounds you.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Patio, Deck, Pool
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Tower Ln

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: WoodPatio
Pool
Pool
Parking & Garage
Parking Spaces: 10

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: conventional

Community

Units in Building: 1

Lot Information

Lot Area: 1.30 acres

Building

Fitness & Sports
Tennis Court

Price History for 27 Tower Ln

DatePriceEventSource
01/05/2021$3,600,000ListingRemovedAgent Provided
09/09/2020$3,600,000Listed For SaleAgent Provided
05/13/2020$2,950,000ListingRemovedAgent Provided
10/03/2019$2,950,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$2,821
Assessment$1,253,800
Home facts updated by county records

Comparable Sales for 27 Tower Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.36
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
0.83
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
0.87
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
1.32
Single-Family Home
$1,607,000
07/10/25
4
3
2,850
1.05
Single-Family Home
$3,710,000
03/12/26
3
5
3,171
1.16
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
0.80
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
1.33
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
1.60
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
1.74
Single-Family Home
$3,772,500
05/29/25
4
4.5
3,234

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Tower Ln.
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!!"

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 27 Tower Ln

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Off Market Homes Near 27 Tower Ln

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Homes for rent near 27 Tower Ln

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27 Tower Ln, Chilmark, MA 02535 is a 2 bedroom, 1 bathroom, 1,188 sqft single-family home built in 1987. This property is not currently available for sale. The current Trulia Estimate for 27 Tower Ln is $2,006,500.