Google satellite image for 22 Smugglers Way, Edgartown, MA 02539

Off Market Nov 2008 for $2.9M

$4,476,115

Est. refi paymentEst. refi $16,906/mo

•

5.5 ba

•

3,211

sq ft

22 Smugglers Way, Edgartown, MA 02539

About this home

22 Smugglers Way is a 3,211 square foot house on a 2.3 acre lot with 5 bedrooms and 5.5 bathrooms. - it last sold on November 05, 2008 for $2,900,000. Based on Redfin's Edgartown data, we estimate the home's value is $4,476,115.

Single-familyProperty Type

1980Year Built

2.3 acresLot Size

$1,394Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$4,476,115

$1.6M since sold in November 2008$406K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 98% higher than the average sale price ($2.26M) of 6 comparable homes.

SOLD JUN 26, 2026
$2,600,000
A
4 beds2.5 baths2,428 sq ft
2 Cosmos Way, Edgartown, MA 02539
SOLD AUG 5, 2026
$2,013,500
B
4 beds3.5 baths2,428 sq ft
35 Nats Farm Ln, West Tisbury, MA 02575
SOLD DEC 19, 2025
$2,340,000
C
4 beds4.5 baths2,912 sq ft
8 Old Dunhams Corner Way, Edgartown, MA 02539
SOLD DEC 10, 2025
$2,250,000
D
4 beds3.5 baths3,014 sq ft
10 Wood Duck, Oak Bluffs, MA 02557
SOLD JUL 29, 2026
$1,885,000
E
5 beds3.5 baths2,527 sq ft
18 Puritan Dr, Oak Bluffs, MA 02557
SOLD FEB 20, 2026
$2,475,000
F
4 beds3.5 baths2,566 sq ft
28 Martha's Rd, Edgartown, MA 02539

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Refinance

Est. cash available

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Rent

$4,657/mo

Redfin rental estimate

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Market trends in 02539, MA

Last updated August 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 17 HRS AGO
$3,400,000
5 beds4 baths3,095 sq ft
62 Schoolhouse Rd, Edgartown, MA 02539
$1,595,000
4 beds3 baths1,898 sq ft
20 Hidden Cv, Oak Bluffs, MA 02557
$2,455,000
4 beds4.5 baths3,039 sq ft
99 The Blvd, Edgartown, MA 02539
$7,250,000
4 beds5.5 baths3,282 sq ft
96 South Summer St, Edgartown, MA 02539
$4,100,000
5 beds3 baths3,654 sq ft
148 Katama Rd, Edgartown, MA 02539
$2,650,000
3 beds2.5 baths2,876 sq ft
10 Woodhaven Dr, Edgartown, MA 02539
See all

Provided by Redfin

Sale history for 22 Smugglers Way

Year

Property tax

Land + Additions

Assessment*

2023

$12,297 (−7.4%)

$2,986,500 + $1,893,400

$4,879,900

2022

$13,280 (−2.8%)

$2,936,992 + $1,445,900

$4,382,892

2020

$13,661 (+1.3%)

$2,923,683 + $1,154,300

$4,077,983

2019

$13,486 (+3.5%)

$2,436,400 + $1,048,300

$3,484,700

2018

$13,032 (+18.0%)

$2,436,400 + $931,000

$3,367,400

2017

$11,042 (+6.2%)

$2,368,200 + $742,300

$3,110,500

2016

$10,401 (+16.9%)

$2,088,200 + $785,100

$2,873,300

2015

$8,900

$1,997,400 + $567,400

$2,564,800

Tax history for 22 Smugglers Way

Year

Property tax

Land + Additions

Assessment*

2023

$12,297 (−7.4%)

$2,986,500 + $1,893,400

$4,879,900

2022

$13,280 (−2.8%)

$2,936,992 + $1,445,900

$4,382,892

2020

$13,661 (+1.3%)

$2,923,683 + $1,154,300

$4,077,983

2019

$13,486 (+3.5%)

$2,436,400 + $1,048,300

$3,484,700

2018

$13,032 (+18.0%)

$2,436,400 + $931,000

$3,367,400

2017

$11,042 (+6.2%)

$2,368,200 + $742,300

$3,110,500

2016

$10,401 (+16.9%)

$2,088,200 + $785,100

$2,873,300

2015

$8,900

$1,997,400 + $567,400

$2,564,800

*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: 5
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Exterior

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

Property Information
Living Sq. Ft: 3,211
Gross Sq. Ft: 5,820
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 100,188
Municipality Name: EDGARTOWN
Acres: 2.3
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 3,211
Stories: 2.0
Lot Size: 2.3 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: —
County: Dukes County
APN: 3772209

Home facts updated by county records on Jan 30, 2023

Around this home

Schools

Edgartown Elementary School

Public PreK-8 • Assigned • 2.7mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 6.4mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

6/10 Flood Factor

Estimated 68-76% chance 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

8 days above 88° expected this year, 24 days in 30 years

8/10 Wind Factor

95% 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

$4.25M – $5.15M

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Nearby similar homes

NEW 17 HRS AGO3D WALKTHROUGH

$3,400,000

5 beds4 baths3,095 sq ft

62 Schoolhouse Rd, Edgartown, MA 02539

VIDEO TOUR

$1,875,000

3 beds2.5 baths1,431 sq ft

33 Vineyard Ave, Oak Bluffs, MA 02557

$1,800,000

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18 Wood Duck Way, Edgartown, MA 02539

VIDEO TOUR

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81 Whalers Walk, Edgartown, MA 02539

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4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, Edgartown, MA 02539

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4 beds2.5 baths1,858 sq ft

59 Tuckernuck Ave, Oak Bluffs, MA 02557

New listings for sale in 02539

NEW 17 HRS AGO

$3,400,000

5 beds4 baths3,095 sq ft

62 Schoolhouse Rd, Edgartown, MA 02539

$1,595,000

4 beds3 baths1,898 sq ft

20 Hidden Cv, Oak Bluffs, MA 02557

$2,455,000

4 beds4.5 baths3,039 sq ft

99 The Blvd, Edgartown, MA 02539

$7,250,000

4 beds5.5 baths3,282 sq ft

96 South Summer St, Edgartown, MA 02539

$4,100,000

5 beds3 baths3,654 sq ft

148 Katama Rd, Edgartown, MA 02539

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3 beds2.5 baths2,876 sq ft

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Home values near 22 Smugglers Way

Data from public records.

Address	Redfin Estimate
18 Smugglers Way, Edgartown, MA 3 Beds \| 3 Baths \| 2633 Sq. Ft.	$3,242,751
491 Katama Rd Apartment A, Edgartown, MA 3 Beds \| 2.5 Baths \| 1921 Sq. Ft.	$989,876

Address	Redfin Estimate
20 Smugglers Way, Edgartown, MA 3 Beds \| 3 Baths \| 2724 Sq. Ft.	$3,461,247
475 Katama Rd Apartment B, Edgartown, MA 3 Beds \| 2.5 Baths \| 1411 Sq. Ft.	$806,708

Address	Redfin Estimate
491 Katama Rd Apartment D-6, Edgartown, MA 3 Beds \| 2.5 Baths \| 1411 Sq. Ft.	$723,150
491 Katama Rd Apartment F, Edgartown, MA 3 Beds \| 2.5 Baths \| 1411 Sq. Ft.	$1,069,942

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