OFF MARKET

Off market jan 2020 for $750K

$1,446,024

Est. refi paymentEst. refi $1,538/mo

•

1,806

sq ft

135 Pennywise Path, Edgartown, MA 02539

About this home

This classic Cape home, with easy access to Edgartown, is located on a country road just outside of Edgartown proper - a world away from the hustle and bustle. Whether you are searching for a vacation property or place to call your own on the Vineyard, this property is a must see. The warm and welcoming first floor offers an extra room that can serve as an office, den or overflow room. Enjoy the shade or sun on an expansive deck surrounded by beautiful, established, perennial gardens. Amble just a bit further down the road and you pop out right across from Morning Glory Farm. This is truly a down-island home in an up island-like setting. Friends and family will enjoy easy access to the bike path and public transportation.

Single-familyProperty Type

1987Year Built

0.55 acresLot Size

$801Est. Price/Sq.Ft.

4 spacesParking

Listed by Leslie Floyd • Point B Realty, LLC

Bought with Non Member • Non Member Office

Redfin checked: 2 minutes ago

•Source:MLS PIN #72544740

Redfin Estimate

$1,446,024

$696K since sold in January 2020$46K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.2% higher than the average sale price ($1.27M) 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 SEP 11, 2026
$1,050,000
B
4 beds2 baths1,513 sq ft
1 Dodgers Hole Rd, Edgartown, MA 02539
SOLD MAY 7, 2026
$1,125,000
C
3 beds2 baths1,410 sq ft
52 Windsor Dr, Edgartown, MA 02539
SOLD APR 17, 2026
$1,775,000
D
3 beds2 baths1,458 sq ft
90 Schoolhouse Rd, Edgartown, MA 02539
SOLD OCT 3, 2012
$775,000
E
3 beds2.5 baths1,352 sq ft
21 Kitts Field Cir, Edgartown, MA 02539
SOLD APR 22, 2026
$1,175,000
F
3 beds2 baths1,196 sq ft
112 Third Street North, Edgartown, MA 02539

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,808/mo

Redfin rental estimate

List your home for rent

Market trends in 02539, MA

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.0%

+1.3% MoM

Median sale price

$2.6M

$134K MoM

Avg. days on market

24d

2 days MoM

Recently sold homes

5 MoM

New listings for sale

NEW 3 HRS AGO
$7,250,000
4 beds4.5 baths2,961 sq ft
8 Beach Plum Mdws, Edgartown, MA 02539
$2,950,000
8 beds6 baths3,770 sq ft
72 Chappaquiddick, Edgartown, MA 02539
$1,875,000
4 beds3 baths2,068 sq ft
42 Bold Meadow Rd, Edgartown, MA 02539
$9,950,000
8 beds10 baths7,585 sq ft
12 Boldwater Rd, Edgartown, MA 02539
$2,995,000
4 beds4.5 baths2,348 sq ft
24 Myober Ln, Edgartown, MA 02539
$1,850,000
4 beds5 baths2,518 sq ft
32 Norton Orchard Rd, Edgartown, MA 02539
VIDEO TOUR
$4,995,000
4 beds4.5 baths3,348 sq ft
98 Edgartown Bay Rd, Edgartown, MA 02539
$1,399,000
Studio0.5 baths1,992 sq ft
1 Mariners Way Unit A, Edgartown, MA 02539
$1,825,000
7 beds4 baths2,597 sq ft
4 Farm Way, Edgartown, MA 02539
See all

Provided by Redfin

Sale history for 135 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$2,467 (+11.8%)

$304,000 + $675,000

$979,000

2022

$2,207 (−3.5%)

$303,600 + $424,700

$728,300

2021

$2,287 (+5.2%)

$303,800 + $393,400

$697,200

2020

$2,173 (−13.4%)

$276,200 + $372,500

$648,700

2019

$2,510 (+15.5%)

$276,200 + $372,500

$648,700

2018

$2,173 (+9.0%)

$276,200 + $285,200

$561,400

2017

$1,993 (+3.8%)

$276,200 + $285,200

$561,400

2016

$1,920 (+2.3%)

$276,200 + $254,300

$530,500

2015

$1,877

$276,200 + $264,600

$540,800

Tax history for 135 Pennywise Path

Year

Property tax

Land + Additions

Assessment*

2023

$2,467 (+11.8%)

$304,000 + $675,000

$979,000

2022

$2,207 (−3.5%)

$303,600 + $424,700

$728,300

2021

$2,287 (+5.2%)

$303,800 + $393,400

$697,200

2020

$2,173 (−13.4%)

$276,200 + $372,500

$648,700

2019

$2,510 (+15.5%)

$276,200 + $372,500

$648,700

2018

$2,173 (+9.0%)

$276,200 + $285,200

$561,400

2017

$1,993 (+3.8%)

$276,200 + $285,200

$561,400

2016

$1,920 (+2.3%)

$276,200 + $254,300

$530,500

2015

$1,877

$276,200 + $264,600

$540,800

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.55 Acres

Year renovated

—

Sq. Ft.

1,806

Year built

1987

Style

Single Family Residential

County

Dukes County

APN

3768929

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jan 30, 2023.

Property details

Parking

Parking Information
Parking Spaces: 4
Parking Features: Off Street, Stone/Gravel

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Flooring - Wall to Wall Carpet

Bedroom #2 Information
Level: Second
Features: Flooring - Wall to Wall Carpet

Bedroom #3 Information
Level: Second
Features: Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower

Living Room Information
Level: First
Features: Flooring - Wood

Family Room Information
Level: First
Features: Flooring - Wood

Dining Room Information
Level: First
Features: Flooring - Wood,Deck - Exterior,Exterior Access

Kitchen Information
Level: Main,First
Features: Flooring - Hardwood,Exterior Access

Basement Information
Basement: Full, Concrete, Unfinished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 7
Door Features: Storm Door(s)
Window Features: Insulated Windows
Flooring: Tile, Carpet, Hardwood
Interior Features: Internet Available - DSL

Exterior

Building Information
Building Area (Total): 1,806
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Brown

Exterior Features
Roof: Shingle
Patio And Porch Features: Porch, Deck, Deck - Wood
Exterior Features: Porch, Deck, Deck - Wood, Rain Gutters

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.55
Lot Features: Wooded, Level
Frontage Length: 116
Road Surface Type: Unimproved
Road Frontage Type: Private Road
Road Responsibility: Private Maintained Road

Financial

Tax Information
Tax Annual Amount: $2,510
Tax Year: 2019

Utilities

Utility Information
Sewer: Private Sewer
Water Source: Private

Heating & Cooling
Has Heating
Heating: Baseboard, Oil

Location

Location Information
Directions: Edg/VH Road to Pennywise Path. 6/10 mile on left.
UnparsedAddress: 135 Pennywise Path, Edgartown MA 02539

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, House of Worship, Public School

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 1,806
Stories: 2.0
Lot Size: 0.55 acres
Style: Single Family Residential
Year Built: 1987
Year Renovated: —
County: Dukes County
APN: 3768929

Home facts updated by county records on Jan 30, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Edgartown Elementary School

Public PreK-8 • Assigned • 1.1mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.2mi

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

$1.37M – $1.66M

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

Nearby similar homes

$2,595,000

4 beds2.5 baths1,858 sq ft

59 Tuckernuck Ave, Oak Bluffs, MA 02557

$2,850,000

4 beds3 baths2,927 sq ft

2 Bold Meadow Rd, Edgartown, MA 02539

$2,495,000

1 bed1.5 baths1,236 sq ft

218 Upper Main St, Edgartown, MA 02539

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

$1,500,000

3 beds2 baths1,717 sq ft

8 Pip'n Cir, Edgartown, MA 02539

VIDEO TOUR

$2,225,000

3 beds2.5 baths2,630 sq ft

81 Whalers Walk, Edgartown, MA 02539

New listings for sale in 02539

NEW 3 HRS AGOVIDEO TOUR

$7,250,000

4 beds4.5 baths2,961 sq ft

8 Beach Plum Mdws, Edgartown, MA 02539

$2,950,000

8 beds6 baths3,770 sq ft

72 Chappaquiddick, Edgartown, MA 02539

$1,875,000

4 beds3 baths2,068 sq ft

42 Bold Meadow Rd, Edgartown, MA 02539

$9,950,000

8 beds10 baths7,585 sq ft

12 Boldwater Rd, Edgartown, MA 02539

$2,995,000

4 beds4.5 baths2,348 sq ft

24 Myober Ln, Edgartown, MA 02539

$1,850,000

4 beds5 baths2,518 sq ft

32 Norton Orchard Rd, Edgartown, MA 02539

VIDEO TOUR

$4,995,000

4 beds4.5 baths3,348 sq ft

98 Edgartown Bay Rd, Edgartown, MA 02539

$1,399,000

Studio0.5 baths1,992 sq ft

1 Mariners Way Unit A, Edgartown, MA 02539

$1,825,000

7 beds4 baths2,597 sq ft

4 Farm Way, Edgartown, MA 02539

Home values near 135 Pennywise Path

Data from public records.

Address	Redfin Estimate
137 Pennywise Path, Edgartown, MA 3 Beds \| 4 Baths \| 2528 Sq. Ft.	$1,730,550
159 Pennywise Path, Edgartown, MA 4 Beds \| 3 Baths \| 3164 Sq. Ft.	$2,100,379

Address	Redfin Estimate
140 Pennywise Path, Edgartown, MA 4 Beds \| 3 Baths \| 2086 Sq. Ft.	$1,525,740
150 Pennywise Path, Edgartown, MA 2 Beds \| 2.5 Baths \| 1556 Sq. Ft.	$1,341,835

Address	Redfin Estimate
139 Pennywise Path, Edgartown, MA 4 Beds \| 2.5 Baths \| 3328 Sq. Ft.	$1,889,723
58 Prices Way, Edgartown, MA 3 Beds \| 2.5 Baths \| 4015 Sq. Ft.	$3,156,965

Property information provided by MLS PIN when last listed in 2019. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Dukes County	Agents near me	Quincy, MA homes for sale	Dukes County Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Dukes County Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Plymouth County homes for sale
Barnstable County homes for sale
Bristol County homes for sale

Edgartown homes for sale
Oak Bluffs homes for sale
Falmouth homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 02539, MA

Sale history for 135 Pennywise Path

Tax history for 135 Pennywise Path

Public record

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 135 Pennywise Path

More real estate resources