OFF MARKET

Off market apr 2005 for $965K

$2,515,572

Est. refi paymentEst. refi $5,970/mo

•

2,701

sq ft

44 Dark Woods Rd, Edgartown, MA 02539

About this home

Walk to Edgartown Village-Tucked far into Dark Woods, abutting 27 acres of conservation land...home and grounds have been remodeled over the years with a new kitchen and bathrooms completed in 02. Home has a wonderful floor plan. Front of the house formal living room and dining room. A country kitchen and fireplace open to a spectacular three season room and master bedroom. Upstairs is a den with second fireplace and two bedrooms, private baths. There are many other fine features to be seen.

Single-familyProperty Type

1987Year Built

0.52 acresLot Size

$931Est. Price/Sq.Ft.

2 car garageParking

Listed by Elaine Miller • Sandpiper Realty Inc

Bought with Elaine Miller • Sandpiper Realty Inc

Redfin checked: a minute ago

•Source:CCIMLS #2042082

Redfin Estimate

$2,515,572

$1.6M since sold in April 2005$113K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17.5% higher than the average sale price ($2.14M) of 6 comparable homes.

SOLD AUG 11, 2026
$1,695,000
A
3 beds3 baths2,296 sq ft
177 West Tisbury Rd, Edgartown, MA 02539
SOLD FEB 20, 2026
$2,475,000
B
4 beds3.5 baths2,566 sq ft
28 Martha's Rd, Edgartown, MA 02539
SOLD MAY 1, 2026
$2,325,000
C
3 beds3 baths2,830 sq ft
42 Deacon Vincent Way, Edgartown, MA 02539
SOLD SEP 24, 2026
$2,150,000
D
4 beds3.5 baths3,016 sq ft
3 Hidden Cove Rd, Oak Bluffs, MA 02557
SOLD OCT 23, 2026
$2,350,000
E
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
SOLD MAY 1, 2026
$1,850,000
F
4 beds3.5 baths2,695 sq ft
43 C Dark Woods Rd, Edgartown, MA 02539

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Earn from this home

Refinance

Est. cash available

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Rent

$4,152/mo

Redfin rental estimate

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Market trends in 02539, MA

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

95.2%

0.7% MoM

Median sale price

$3.1M

$499K MoM

Avg. days on market

58d

32 days MoM

Recently sold homes

2 MoM

Provided by Redfin

Sale history for 44 Dark Woods Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,977 (+11.9%)

$590,800 + $1,384,200

$1,975,000

2022

$4,448 (+7.1%)

$590,500 + $877,400

$1,467,900

2020

$4,155 (−8.8%)

$468,200 + $772,200

$1,240,400

2019

$4,557 (+18.5%)

$454,300 + $723,300

$1,177,600

2018

$3,847 (+7.0%)

$413,100 + $580,900

$994,000

2017

$3,596 (+9.1%)

$440,600 + $572,400

$1,013,000

2016

$3,297 (+2.0%)

$399,300 + $511,600

$910,900

2015

$3,231

$399,300 + $531,800

$931,100

Tax history for 44 Dark Woods Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,977 (+11.9%)

$590,800 + $1,384,200

$1,975,000

2022

$4,448 (+7.1%)

$590,500 + $877,400

$1,467,900

2020

$4,155 (−8.8%)

$468,200 + $772,200

$1,240,400

2019

$4,557 (+18.5%)

$454,300 + $723,300

$1,177,600

2018

$3,847 (+7.0%)

$413,100 + $580,900

$994,000

2017

$3,596 (+9.1%)

$440,600 + $572,400

$1,013,000

2016

$3,297 (+2.0%)

$399,300 + $511,600

$910,900

2015

$3,231

$399,300 + $531,800

$931,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.52 Acres

Year renovated

—

Sq. Ft.

2,569

Year built

1987

Style

Single Family Residential

County

Dukes County

APN

3769052

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jan 30, 2023.

Property details

Parking

Garage Infromation
Has Garage
Has Attached Garage
Garage Spaces: 2

Interior

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (1/2): 1

Basement Information
Basement: Full

Other Room Information
Total Rooms : 7

Interior Features
Flooring: Wood, Carpet
Appliances: Oil
Patio And Porch Features: Deck

Exterior

Exterior Features
Construction Materials: Shingle Siding
Roof: Wood, Shingle

Property Information
Property Sub Type: Single Family Residence

Lot Information
Water Source: Public

Building Information
Year Built: 1987

Utilities

Heating & Cooling
Has Cooling
Cooling: Central Air

Location

HOA Information
Has Association

Public facts

Beds: 3
Baths: 4.5
Sq. Ft.: 2,569
Stories: 2.0
Lot Size: 0.52 acres
Style: Single Family Residential
Year Built: 1987
Year Renovated: —
County: Dukes County
APN: 3769052

Home facts updated by county records on Jan 30, 2023

Around this home

Schools

K - 12
Preschool & daycare

Edgartown Elementary School

Public PreK-8 • Assigned • 0.7mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.6mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

6 days above 88° expected this year, 17 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Edgartown, MA • 02539

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.5 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.39M – $2.89M

Sell confidently with a local market expert in Edgartown. 3 minutes to get started.

Nearby similar homes

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Finished lower level • 3.37 acre lot • Listed 29 days

Home values near 44 Dark Woods Rd

Data from public records.

Address	Redfin Estimate
40 Dark Woods Rd, Edgartown, MA 4 Beds \| 2.5 Baths \| 2985 Sq. Ft.	$2,631,128
43 Dark Woods Rd Apt C, Edgartown, MA 3 Beds \| 2.5 Baths \| 2412 Sq. Ft.	$2,090,412
35 Dark Woods Rd, Edgartown, MA 4 Beds \| 3.5 Baths \| 2972 Sq. Ft.	$2,792,218
48 Dark Woods Rd, Edgartown, MA 4 Beds \| 2 Baths \| 2397 Sq. Ft.	$2,159,294
61 Pennywise Path, Edgartown, MA 2 Beds \| 1.5 Baths \| 984 Sq. Ft.	$1,472,201
47 Pennywise Path, Edgartown, MA 3 Beds \| 1.5 Baths \| 2055 Sq. Ft.	$1,479,602
346 Edgartown Vineyard Haven Rd, Edgartown, MA 2 Beds \| 1 Baths \| 648 Sq. Ft.	$757,949

Address	Redfin Estimate
33 Dark Woods Rd, Edgartown, MA 3 Beds \| 2.5 Baths \| 2379 Sq. Ft.	$2,375,981
38 Dark Woods Rd, Edgartown, MA 3 Beds \| 3.5 Baths \| 2647 Sq. Ft.	$2,476,327
50 Dark Woods Rd, Edgartown, MA 3 Beds \| 3 Baths \| 1768 Sq. Ft.	$1,760,095
43 Dark Woods Rd Apt B, Edgartown, MA 1 Beds \| 1 Baths \| 720 Sq. Ft.	$972,485
73 Pennywise Path, Edgartown, MA 4 Beds \| 3 Baths \| 2200 Sq. Ft.	$1,497,914
59 Pennywise Path, Edgartown, MA 2 Beds \| 1 Baths \| 1120 Sq. Ft.	$939,485
75 Pennywise Path, Edgartown, MA 2 Beds \| 2 Baths \| 1344 Sq. Ft.	$1,390,825

Address	Redfin Estimate
42 Dark Woods Rd, Edgartown, MA 4 Beds \| 4 Baths \| 4204 Sq. Ft.	$3,049,142
45 Dark Woods Rd, Edgartown, MA 5 Beds \| 2.5 Baths \| 3797 Sq. Ft.	$2,730,244
37 Dark Woods Rd, Edgartown, MA 4 Beds \| 3.5 Baths \| 3399 Sq. Ft.	$2,698,771
43c Dark Woods Rd, Edgartown, MA 4 Beds \| 3.5 Baths \| 2695 Sq. Ft.	$2,311,552
51 Pennywise Path, Edgartown, MA 3 Beds \| 2.5 Baths \| 1776 Sq. Ft.	$1,410,859
66 Jernegan Pond Rd, Edgartown, MA 3 Beds \| 2 Baths \| 1680 Sq. Ft.	$1,403,520

Property information provided by CCIMLS when last listed in 2004. This data may not match . Learn more.

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