Last Sold Price
3 beds1,700 sqft$497/sqft
26 Whippoorwill Rd, Chilmark, MA 02535

Description

A short country road leads to this tri-level , reverse living post and beam home situated on a hilltop which captures water views West to Squibnocket and East to Edgartown. The expansive living room with cathedral ceilings provides wonderful views and showcases the post and beam structure. End you day viewing the magnificent sunsets. Several renovations in 2014 include a new kitchen, Anderson windows and exceptional landscaping. This warm and inviting home is in move in condition and priced to sell.A short country road leads to this tri-level , reverse living post and beam home situated on a hilltop which captures water views West to Squibnocket and East to Edgartown. The expansive living room with cathedral ceilings provides wonderful views and showcases the post and beam structure. End you day viewing the magnificent sunsets. Several renovations in 2014 include a new kitchen, Anderson windows and exceptional landscaping. This warm and inviting home is in move in condition and priced to sell.
LISTING CLOSED: 11/10/2016 12:00 AM

  1. Listed by Natalie Conroy • Conroy & Company R.E., Inc.

Property Details for 26 Whippoorwill Road

Status
MLS #
29094
Days on Market
278
Taxes
$2,100 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
1 Family / Single Family Residence
Year Built
1987
Lot Size
3.60 AC / 156,816 SF
Zoning
RES
View
Trees/Woods

Recent comparable sales

Median sold price

$1,775,000

Avg days on market

75

Sale-to-list ratio

90.1%

[Chilmark, MA]

9 comparable properties found

a view of a back yard
1/49
1

$1,775,000

Sold 11/07/25

3
Bedrooms
1,728
Square Feet
0.70
Acres
a front view of a house with a garden
1/28
2

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Sold 12/05/24

3
Bedrooms
1,862
Square Feet
3.1
Acres
$2,550,000 | 10 Mollys Way, Chilmark, MA 02535
1/29
3

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Sold 10/02/25

3
Bedrooms
1,524
Square Feet
0.20
Acres
$1,050,000 | 10 Rumpus Ridge Road, Chilmark, MA 02535
1/33
4

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Sold 05/29/25

4
Bedrooms
1,701
Square Feet
0.5
Acres
a front view of house with yard and green space
1/31
5

$1,680,000

Sold 10/09/24

3
Bedrooms
1,200
Square Feet
0.4
Acres
a view of a house with backyard and sitting area
1/2
6

$2,099,400

Sold 10/31/24

2
Bedrooms
1,836
Square Feet
1.6
Acres
$1,550,000 | 2 Rockrose Path, Chilmark, MA 02535
1/38
7

$1,550,000

Sold 09/05/24

4
Bedrooms
1,900
Square Feet
1.6
Acres
a front view of a house with a yard
1/44
8

$2,100,000

Sold 11/25/25

4
Bedrooms
1,968
Square Feet
3
Acres
$1,000,000 | 31 N Road, Chilmark, MA 02535
1/23
9

$1,000,000

Sold 06/03/26

2
Bedrooms
576
Square Feet
0.1
Acres

Location

Add your commute

Building Information for 26 Whippoorwill Road

Stories-Year Built1987Building Size-Lot Size3.60 AC / 156,816 SF

Payment Calculator

$4,470 per month

30 year fixed, 6.55% Interest

Principal and Interest

$4,295

Property Taxes

$175

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 26 Whippoorwill Road

Summary
Location and General Information
  • Latitude: 41.364353
  • Longitude: -70.718724
  • Listing ods: WViews, Deck, Garden, PubBch
Taxes and HOA Information
  • Tax Assessed Value: $156,000.00
  • Tax Lot: 14
  • Tax Map Number: 19
  • Tax Other Annual Assessment Amount: $622,200.00
  • Tax Year: 2015
Parking
  • Parking Features: yes
Property
Lot Information
  • Lot Features: landscaped
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 20
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2014
Utilities
  • Sewer: Septic Tank
  • Utilities: Sat
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: WViews, Deck, Garden, PubBch
Interior Features
  • Main Level Bedrooms: 3
  • Rooms Total: 8
  • Appliances: Stove: Frigidaire, Washer: yes
  • Fireplace: No
  • Flooring: 2 plus loft
  • Foundation Details: partial
  • Furnished: Unfurnished
  • Heating: GFHW
  • Interior Features: Ins,OSh, Floor 1: Three bedrooms, Master suite with sitting room which opens onto the private deck. Two other bedrooms and two baths., Floor 2: Open plan living room, kitchen and dining with access to large deck and the loft with skylights., Floor 3: loft with skylights.

Property History for 26 Whippoorwill Road

DateEvent & SourcePriceAppreciation
Nov 14, 2016

Sold (Public Record)

Public Record #583648896

$845,000
Nov 14, 2016

Sold (Public Record)

Public Record #583648896

$845,000
Nov 14, 2016

Sold

Martha's Vineyard MLS #10003892

$845,000
DateEvent & SourcePrice
11/14/2016

Sold (Public Record)

Public Record #583648896

$845,000
11/14/2016

Sold (Public Record)

Public Record #583648896

$845,000
11/14/2016

Sold

Martha's Vineyard MLS #10003892

$845,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 26 Whippoorwill Road

Taxable ValueLand$948,900Additions$331,500Total$1,280,400
Tax Record2025$2,881 ($240 / month)
Home Facts
Beds4Baths1Total Finished SqFt1,344 SqFtAbove Grade Finished SqFt1,344 SqFtStories2Lot Size156,816 SqFtStyleSingle Family ResidenceYear Built1978Zoning1-3CountyDUKESAPNCHIL M:19 P:14

Schools near 26 Whippoorwill Road

This home is within Up-Island Regional School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - PK to 8
Public - 9 to 12
Rating
School
Distance
Chilmark Elementary School
PublicK to 5

West Tisbury Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 26 Whippoorwill Road, Chilmark, MA 02535
$845,000
3
1,700
156,816
$1,775,000
3
2,375
135,036
$1
6
2
3,118
65,340
$250,000
4
2,792
156,816
$319,800
6
4
4,522
319,730
$850,000
4
1,113
87,120

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Conroy & Company R.E., Inc., Natalie Conroy

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.