Google street view image for 59 Pennywise Path, Edgartown, MA 02539

Off market jul 1998 for $51K

$939,485

Est. refi paymentEst. refi $334/mo

•

1 ba

•

1,120

sq ft

59 Pennywise Path, Edgartown, MA 02539

About this home

59 Pennywise Path is a 1,120 square foot house on a 0.52 acre lot with 2 bedrooms and 1 bathroom. - it last sold on July 13, 1998 for $51,000. Based on Redfin's Edgartown data, we estimate the home's value is $939,485.

Single-familyProperty Type

2003Year Built

0.52 acresLot Size

$839Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$939,485

$888K since sold in July 1998$22K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 34.4% lower than the average sale price ($1.43M) of 6 comparable homes.

SOLD AUG 19, 2026
$1,100,000
A
3 beds2 baths1,100 sq ft
34 Tenth St S, Edgartown, MA 02539
SOLD OCT 1, 2026
$1,500,000
B
3 beds2 baths1,560 sq ft
9 Martha's Rd, Edgartown, MA 02539
SOLD APR 17, 2026
$1,775,000
C
3 beds2 baths1,458 sq ft
90 Schoolhouse Rd, Edgartown, MA 02539
SOLD OCT 23, 2026
$1,600,000
D
4 beds2 baths1,342 sq ft
58 Road To The Plns, Edgartown, MA 02539
SOLD MAY 7, 2026
$1,125,000
E
3 beds2 baths1,410 sq ft
52 Windsor Dr, Edgartown, MA 02539
SOLD OCT 8, 2026
$1,495,000
F
3 beds2 baths1,116 sq ft
25 Harbor View Ave, Edgartown, MA 02539

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Earn from this home

Refinance

Est. cash available

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Rent

$2,049/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 59 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$1,745 (−2.6%)

$303,000 + $389,500

$692,500

2022

$1,792 (+4.2%)

$302,800 + $288,500

$591,300

2020

$1,720 (−15.8%)

$275,400 + $238,000

$513,400

2019

$2,043 (+13.1%)

$275,400 + $252,400

$527,800

2018

$1,807 (+14.7%)

$275,400 + $191,400

$466,800

2017

$1,575 (+1.1%)

$275,400 + $168,300

$443,700

2016

$1,558 (+10.2%)

$275,400 + $154,900

$430,300

2015

$1,414

$275,400 + $132,000

$407,400

Tax history for 59 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$1,745 (−2.6%)

$303,000 + $389,500

$692,500

2022

$1,792 (+4.2%)

$302,800 + $288,500

$591,300

2020

$1,720 (−15.8%)

$275,400 + $238,000

$513,400

2019

$2,043 (+13.1%)

$275,400 + $252,400

$527,800

2018

$1,807 (+14.7%)

$275,400 + $191,400

$466,800

2017

$1,575 (+1.1%)

$275,400 + $168,300

$443,700

2016

$1,558 (+10.2%)

$275,400 + $154,900

$430,300

2015

$1,414

$275,400 + $132,000

$407,400

*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: 1

Heating & Cooling
Heating Type: Forced Air

Room Information
# of Rooms: 4

Exterior

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

Property Information
Living Sq. Ft: 1,120
Gross Sq. Ft: 1,920
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 22,651
Municipality Name: EDGARTOWN
Acres: 0.52
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 2
Baths: 1.0
Sq. Ft.: 1,120
Stories: 2.0
Lot Size: 0.52 acres
Style: Single Family Residential
Year Built: 2003
Year Renovated: —
County: Dukes County
APN: 3769047

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 • 0.8mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.5mi

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

$893,000 – $1.08M

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

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$4,100,000

5 beds3 baths3,654 sq ft

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Home values near 59 Pennywise Path

Data from public records.

Address	Redfin Estimate
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
40 Dark Woods Road, Edgartown, MA 4 Beds \| 2.5 Baths \| 2985 Sq. Ft.	$2,631,128
43 Dark Woods Road #C, Edgartown, MA 3 Beds \| 2.5 Baths \| 2412 Sq. Ft.	$2,090,412
50 Dark Woods Road, Edgartown, MA 3 Beds \| 3 Baths \| 1768 Sq. Ft.	$1,760,095
2 Penny Lane, Edgartown, MA 3 Beds \| 2 Baths \| 1763 Sq. Ft.	$1,487,440
43 Dark Woods Road #B, Edgartown, MA 1 Beds \| 1 Baths \| 720 Sq. Ft.	$972,485

Address	Redfin Estimate
73 Pennywise Path, Edgartown, MA 4 Beds \| 3 Baths \| 2200 Sq. Ft.	$1,497,914
77 Pennywise Path, Edgartown, MA 2 Beds \| 1.5 Baths \| 1506 Sq. Ft.	$1,129,629
1 Nickel Lane, Edgartown, MA 3 Beds \| 2 Baths \| 960 Sq. Ft.	$1,028,401
44 Dark Woods Road, Edgartown, MA 3 Beds \| 4.5 Baths \| 2701 Sq. Ft.	$2,515,572
37 Dark Woods Road, Edgartown, MA 4 Beds \| 3.5 Baths \| 3399 Sq. Ft.	$2,698,771
33 Clay Pit Road, Edgartown, MA 2 Beds \| 1 Baths \| 720 Sq. Ft.	$912,384
45 Clay Pit Road, Edgartown, MA 1 Beds \| 2 Baths \| 1140 Sq. Ft.	$1,107,815

Address	Redfin Estimate
51 Pennywise Path, Edgartown, MA 3 Beds \| 2.5 Baths \| 1776 Sq. Ft.	$1,410,859
75 Pennywise Path, Edgartown, MA 2 Beds \| 2 Baths \| 1344 Sq. Ft.	$1,390,825
42 Dark Woods Road, Edgartown, MA 4 Beds \| 4 Baths \| 4204 Sq. Ft.	$3,049,142
45 Dark Woods Road, Edgartown, MA 5 Beds \| 2.5 Baths \| 3797 Sq. Ft.	$2,730,244
48 Dark Woods Road, Edgartown, MA 4 Beds \| 2 Baths \| 2397 Sq. Ft.	$2,159,294
346 Edgartown Vineyard Haven Road, Edgartown, MA 2 Beds \| 1 Baths \| 648 Sq. Ft.	$757,949
39 Clay Pit Road, Edgartown, MA 2 Beds \| 1 Baths \| 1008 Sq. Ft.	$1,015,080

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