Google satellite image for 159 Pennywise Path, Edgartown, MA 02539

OFF MARKET

$2,138,555

•

3 ba

•

3,164

sq ft

159 Pennywise Path, Edgartown, MA 02539

About this home

159 Pennywise Path is a 3,164 square foot house on a 1.5 acre lot with 4 bedrooms and 3 bathrooms. Based on Redfin's Edgartown data, we estimate the home's value is $2,138,555.

Single-familyProperty Type

1977Year Built

1.5 acresLot Size

$676Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,138,555

$93K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.7% lower than the average sale price ($2.20M) of 5 comparable homes.

SOLD MAR 31, 2026
$1,850,000
A
4 beds3 baths3,142 sq ft
7 South Meadow Ln, Oak Bluffs, MA 02557
SOLD JUN 26, 2026
$2,600,000
B
4 beds2.5 baths2,428 sq ft
2 Cosmos Way, Edgartown, MA 02539
SOLD AUG 11, 2026
$1,695,000
C
3 beds3 baths2,296 sq ft
177 West Tisbury Rd, Edgartown, MA 02539
SOLD JUL 24, 2026
$2,595,000
D
4 beds3.5 baths2,317 sq ft
471 West Tisbury Rd, Edgartown, MA 02539
SOLD DEC 10, 2025
$2,250,000
E
4 beds3.5 baths3,014 sq ft
10 Wood Duck, Oak Bluffs, MA 02557

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Earn from this home

Rent

$4,302/mo

Redfin rental estimate

List your home for rent

Market trends in 02539, MA

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

94.7%

0.1% MoM

Median sale price

$1.9M

$50K MoM

Avg. days on market

24d

17 days MoM

Recently sold homes

2 MoM

New listings for sale

$3,075,000
3 beds2 baths1,962 sq ft
21 Vickers St, Edgartown, MA 02539
$2,395,000
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
$2,850,000
6 beds1 bath1,957 sq ft
49 The Blvd, Edgartown, MA 02539
$4,725,000
3 beds4 baths2,969 sq ft
149 Litchfield Rd, Edgartown, MA 02539
$2,500,000
4 beds2.5 baths1,786 sq ft
9 Codman Spring Rd, Edgartown, MA 02539
See all

Provided by Redfin

Sale history for 159 Pennywise Path

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$4,235 (+11.4%)

$407,100 + $1,273,400

$1,680,500

2022

$3,801 (−2.7%)

$407,100 + $847,400

$1,254,500

2021

$3,908 (+4.8%)

$406,800 + $784,800

$1,191,600

2020

$3,728 (−13.4%)

$369,800 + $743,100

$1,112,900

2019

$4,307 (+11.0%)

$369,800 + $743,100

$1,112,900

2018

$3,879 (+8.4%)

$369,800 + $632,600

$1,002,400

2017

$3,577 (+8.4%)

$369,800 + $637,900

$1,007,700

2016

$3,299 (+1.7%)

$343,000 + $568,400

$911,400

2015

$3,243

$343,000 + $591,600

$934,600

Tax history for 159 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$4,235 (+11.4%)

$407,100 + $1,273,400

$1,680,500

2022

$3,801 (−2.7%)

$407,100 + $847,400

$1,254,500

2021

$3,908 (+4.8%)

$406,800 + $784,800

$1,191,600

2020

$3,728 (−13.4%)

$369,800 + $743,100

$1,112,900

2019

$4,307 (+11.0%)

$369,800 + $743,100

$1,112,900

2018

$3,879 (+8.4%)

$369,800 + $632,600

$1,002,400

2017

$3,577 (+8.4%)

$369,800 + $637,900

$1,007,700

2016

$3,299 (+1.7%)

$343,000 + $568,400

$911,400

2015

$3,243

$343,000 + $591,600

$934,600

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

Property details

Interior

Bathroom Information
# of Full Baths: 3

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 6

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Cape Cod
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 3,164
Gross Sq. Ft: 6,022
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 65,340
Municipality Name: EDGARTOWN
Acres: 1.5
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,164
Stories: 2.0
Lot Size: 1.5 acres
Style: Single Family Residential
Year Built: 1977
Year Renovated: —
County: Dukes County
APN: 3769174

Home facts updated by county records on Jan 30, 2023

Around this home

Schools

Edgartown Elementary School

Public PreK-8 • Assigned • 1.3mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.1mi

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, 18 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

$2.03M – $2.46M

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

Nearby similar homes

$3,075,000

3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

$1,800,000

4 beds3 baths2,864 sq ft

18 Wood Duck Way, Edgartown, MA 02539

OPEN SAT, 10AM TO 11AMVIDEO TOUR

$1,875,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

$1,850,000

4 beds2 baths1,833 sq ft

22 Old Harbor Ln, Oak Bluffs, MA 02557

$3,495,000

2 beds1.5 baths1,388 sq ft

48 Plantingfield Way, Edgartown, MA 02539

$1,755,000

3 beds3 baths2,695 sq ft

68 Front St, Oak Bluffs, MA 02557

New listings for sale in 02539

$3,075,000

3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

$2,395,000

4 beds3 baths1,968 sq ft

105 Whalers Walk, Edgartown, MA 02539

$2,850,000

6 beds1 bath1,957 sq ft

49 The Blvd, Edgartown, MA 02539

$4,725,000

3 beds4 baths2,969 sq ft

149 Litchfield Rd, Edgartown, MA 02539

$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

Home values near 159 Pennywise Path

Data from public records.

Address	Redfin Estimate
137 Pennywise Path, Edgartown, MA 3 Beds \| 4 Baths \| 2528 Sq. Ft.	$1,754,179
140 Pennywise Path, Edgartown, MA 4 Beds \| 3 Baths \| 2086 Sq. Ft.	$1,628,947

Address	Redfin Estimate
167 Pennywise Path, Edgartown, MA 4 Beds \| 2 Baths \| 1934 Sq. Ft.	$1,642,966
139 Pennywise Path, Edgartown, MA 4 Beds \| 2.5 Baths \| 3328 Sq. Ft.	$1,914,926

Address	Redfin Estimate
135 Pennywise Path, Edgartown, MA 3 Beds \| 2.5 Baths \| 1806 Sq. Ft.	$1,492,293
150 Pennywise Path, Edgartown, MA 2 Beds \| 2.5 Baths \| 1556 Sq. Ft.	$1,339,653

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About this home

Redfin Estimate

Earn from this home

Market trends in 02539, MA

Sale history for 159 Pennywise Path

Tax history for 159 Pennywise Path

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02539

Home values near 159 Pennywise Path

More real estate resources