OFF MARKET

Off market apr 2015 for $650K

$1,497,914

Est. refi paymentEst. refi $4,925/mo

•

2,200

sq ft

73 Pennywise Path, Edgartown, MA 02539

About this home

Down a quite lane on the out skirts of town sits a bright and sunny farmhouse. Enjoy walking to Main Street and Village amenities or bike to Bend in the Road Beach just over a mile away. The home boasts a large wrap around porch from which to take in the natural yet landscaped grounds and the oversized windows allow a similar experience from within. A wood burning fireplace with hand carved mantle anchors the living room with soaring ceilings. Beyond is the well-appointed kitchen with center-island and intimate dining area. Sleeping accommodations include a first floor bedroom, a lofty second floor master suite with fireplace and an additional room for guest overflow or den. The custom details including antique doors and leaded windows make for a truly unique and visually pleasing home. Enjoy abundant privacy with nearly an acre of land f

Single-familyProperty Type

1995Year Built

0.94 acresLot Size

$681Est. Price/Sq.Ft.

3 spacesParking

Listed by Lesley Heidt • Sandpiper Realty Inc

Bought with Unknown Member • cci.unknownoffice

Redfin checked: a minute ago

•Source:CCIMLS #21406987

Redfin Estimate

$1,497,914

$848K since sold in April 2015$0 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8% lower than the average sale price ($1.63M) of 5 comparable homes.

SOLD OCT 1, 2026
$1,500,000
A
3 beds2 baths1,560 sq ft
9 Martha's Rd, Edgartown, MA 02539
SOLD OCT 23, 2026
$2,350,000
B
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
SOLD OCT 8, 2026
$1,075,000
C
3 beds2 baths1,800 sq ft
52 Oak Knl, West Tisbury, MA 02575
SOLD NOV 6, 2025
$2,240,000
D
3 beds2 baths1,764 sq ft
29 Pradas Way, Edgartown, MA 02539
SOLD MAR 30, 2026
$975,000
E
3 beds2 baths1,469 sq ft
12 Park Ave, Vineyard Haven, MA 02568

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Earn from this home

Refinance

Est. cash available

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Rent

$3,325/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 73 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$2,728 (−1.6%)

$317,300 + $765,200

$1,082,500

2022

$2,771 (+14.5%)

$313,300 + $601,200

$914,500

2020

$2,421 (−16.4%)

$285,900 + $436,700

$722,600

2019

$2,896 (+9.8%)

$285,900 + $462,500

$748,400

2018

$2,638 (+20.7%)

$285,900 + $395,700

$681,600

2017

$2,186 (+2.2%)

$285,900 + $330,000

$615,900

2016

$2,138 (+12.6%)

$285,900 + $304,600

$590,500

2015

$1,898

$285,900 + $261,100

$547,000

Tax history for 73 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$2,728 (−1.6%)

$317,300 + $765,200

$1,082,500

2022

$2,771 (+14.5%)

$313,300 + $601,200

$914,500

2020

$2,421 (−16.4%)

$285,900 + $436,700

$722,600

2019

$2,896 (+9.8%)

$285,900 + $462,500

$748,400

2018

$2,638 (+20.7%)

$285,900 + $395,700

$681,600

2017

$2,186 (+2.2%)

$285,900 + $330,000

$615,900

2016

$2,138 (+12.6%)

$285,900 + $304,600

$590,500

2015

$1,898

$285,900 + $261,100

$547,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

40,946

Year renovated

2022

Sq. Ft.

2,200

Year built

1995

Style

Single Family Residential

County

Dukes County

APN

3769010

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Features

—

Last updated by owner on Jan 25, 2023.

Property details

Parking

Parking Information
Parking Features: Driveway, Unpaved

Interior

Bathroom Information
# of Bathrooms (Full): 2

Basement Information
Basement: Full

Fireplace Information
FireplacesTotal: 2

Other Room Information
Total Rooms : 6

Interior Features
Flooring: Wood
Appliances: Propane Gas
Patio And Porch Features: Deck, Porch

Exterior

Exterior Features
Exterior Features: Outdoor Shower, Garden
Construction Materials: Shingle Siding
Roof: Asphalt

Property Information
Property Sub Type: Single Family Residence
Other Structures: Outbuilding

Lot Information
Lot Features: Gentle Sloping, Wooded, Level
Waterfront Features: Salt, Other - See Remarks

Building Information
Year Built: 1995

Utilities

Heating & Cooling
Has Heating
Heating: Propane, Other
Has Cooling
Cooling: Central Air

Utility Information
Sewer: Other

Location

Location Information
Directions: As you head out of Edgartown on the VH/EDG Road, take a left onto Pennywise Path. 1/2 mile down on the left is #73, marked on the gate post.

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,200
Stories: 2.0
Parking Spaces: 3
Basement: Yes
Accessible: No
Lot Size: 0.94 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: 2022
County: Dukes County
APN: 3769010
HOA Dues: —
Garage: No
Features: —

Home facts updated by owner on Jan 25, 2023

Around this home

Schools

K - 12
Preschool & daycare

Edgartown Elementary School

Public PreK-8 • Assigned • 0.9mi

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

$1.53M – $1.86M

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Nearby similar homes

$2,495,000

1 bed1.5 baths1,236 sq ft

218 Upper Main St, Edgartown, MA 02539

Bii zoning district • 8,712 sq ft lot • 10 parking spots

$3,995,000

4 beds5 baths4,904 sq ft

4 Garrett Way, Edgartown, MA 02539

Finished lower level • 3.37 acre lot • Listed 29 days

$4,100,000

5 beds3 baths3,654 sq ft

148 Katama Rd, Edgartown, MA 02539

Walk-up deck • In-unit laundry • Dedicated parking

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

First floor den • Spacious deck • Outdoor shower

$2,950,000

8 beds6 baths3,770 sq ft

72 Chappaquiddick, Edgartown, MA 02539

Private compound • Sports courts • Expansive porches

$1,500,000

3 beds2 baths1,717 sq ft

8 Pip'n Cir, Edgartown, MA 02539

3 acre parcel • Guest house • Direct access

Home values near 73 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
75 Pennywise Path, Edgartown, MA 2 Beds \| 2 Baths \| 1344 Sq. Ft.	$1,390,825
44 Dark Woods Road, Edgartown, MA 3 Beds \| 4.5 Baths \| 2701 Sq. Ft.	$2,515,572
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
49 Jernegan Pond Road, Edgartown, MA 3 Beds \| 2 Baths \| 1764 Sq. Ft.	$1,364,597

Address	Redfin Estimate
59 Pennywise Path, Edgartown, MA 2 Beds \| 1 Baths \| 1120 Sq. Ft.	$939,485
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
64 Jernegan Pond Road, Edgartown, MA 1 Beds \| 2.5 Baths \| 1637 Sq. Ft.	$1,560,773
43 Dark Woods Road Unit B, Edgartown, MA 1 Beds \| 1 Baths \| 720 Sq. Ft.	$972,485
45 Clay Pit Road, Edgartown, MA 1 Beds \| 2 Baths \| 1140 Sq. Ft.	$1,107,815

Address	Redfin Estimate
77 Pennywise Path, Edgartown, MA 2 Beds \| 1.5 Baths \| 1506 Sq. Ft.	$1,129,629
43 Dark Woods Road Unit 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
66 Jernegan Pond Road, Edgartown, MA 3 Beds \| 2 Baths \| 1680 Sq. Ft.	$1,403,520
2 N Bog Road, Edgartown, MA 4 Beds \| 3.5 Baths \| 2532 Sq. Ft.	$2,473,325
43c Dark Woods Road, Edgartown, MA 4 Beds \| 3.5 Baths \| 2695 Sq. Ft.	$2,311,552

Property information provided by CCIMLS when last listed in 2014. This data may not show owner updates. Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02539, MA

Sale history for 73 Pennywise Path

Tax history for 73 Pennywise Path

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 73 Pennywise Path

More real estate resources