20 Smugglers Way, Edgartown, MA 02539
OFF MARKET

20 Smugglers Way
Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 2,724 sqft (on 2.30 acres)

$5,482,800

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $29,452/mo*

$5,482,800

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $29,452/mo*
3 Beds
3 Baths
2,724 sqft
(on 2.30 acres)

Homes for sale near 20 Smugglers Way

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This single-family home is located at 20 Smugglers Way, Edgartown, MA. 20 Smugglers Way is in Edgartown, MA and in ZIP code 02539. This property has 3 bedrooms, 3 bathrooms and approximately 2,724 sqft of floor space. This property has a lot size of 2.30 acres and was built in 1980.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20 Smugglers Way

Interior Features

Heating & Cooling
Heating: Baseboard, GasAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.30 acres
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Property Tax and Assessment

Year2025
Tax$12,869
Assessment$4,856,400
Home facts updated by county records

Comparable Sales for 20 Smugglers Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.35
Single-Family Home
$5,250,000
07/02/25
3
4.5
2,869
0.48
Single-Family Home
$14,750,000
03/27/26
6
4.5
4,744
0.94
Single-Family Home
$1,850,000
05/19/25
3
2.5
1,428
0.91
Single-Family Home
$1,800,000
12/23/25
3
1.5
1,188
1.19
Single-Family Home
$2,375,000
07/01/25
4
3
2,448
1.02
Single-Family Home
$4,750,000
11/21/25
3
3.5
4,131
1.31
Single-Family Home
$3,075,000
11/21/25
4
3
3,159
1.12
Single-Family Home
$3,300,000
12/09/25
3
2
2,194
1.03
Single-Family Home
$3,300,000
09/18/25
4
5
3,793
1.42
Single-Family Home
$2,340,000
12/19/25
4
4.5
2,912

Assigned Schools

These are the assigned schools for 20 Smugglers Way.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Edgartown

At least 17 Trulia users voted on each feature.
  • 89 % Say they plan to stay for at least 5 years

  • 85 % Say people would walk alone at night

  • 81 % Say it's dog friendly

  • 76 % Say yards are well-kept

  • 75 % Say car is needed

  • 70 % Say it's quiet

  • 68 % Say there's wildlife

  • 67 % Say kids play outside

  • 60 % Say it's walkable to restaurants

  • 59 % Say neighbors are friendly

  • 56 % Say there's holiday spirit

  • 52 % Say it's walkable to grocery stores

  • 52 % Say parking is easy

  • 46 % Say there are sidewalks

  • 46 % Say streets are well-lit

  • 36 % Say there are community events

Learn more about our methodology.
  • Trulia User
    "Some restaurants are dog-friendly but many are not. During the summer months, many shops provide water bowls outside "
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
  • Adriannen1114
    "Beautiful place! Lovely neighborhoods and very safe. The kind of place you want to live and or visit. Absolutely lovely. Everywhere you go there is another amazing fun spot. "
  • Olivia G.
    "I live in Edgartown and I work in OB. I work 7 miles from my home and I drive down one of the most beautiful roads I’ve ever seen. "
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
  • Megan S.
    "I leave close to e everything summer time is a cool time to enjoy it bad Martha’s live music winter very quiet and private "
  • Megan S.
    "I live in good neighborhoods very close to donoramas peaceful location very close to everything I need I don’t know much about people round but This is my opinion about it "
  • Mvrock17
    "My neighborhood is really great and has bike path beautiful roads in trees laying it all the way down into town it seems like every year improvements are made to make it better right now so"
  • Unspecified
    "Business area but after five gets quiet. Very close to everything you need is walking distance. Busses are near to go to the other towns. Short walk to a beach. "
  • Frank M. M.
    "I live and work in Edgartown and know this to be one of the top areas vacationers like to rent in. Edgartown Estates is well managed, clean, and known to be a "go to" place for vacationers wanting the Beach and In-town experience with easy access."

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Homes for rent near 20 Smugglers Way

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Off Market Homes Near 20 Smugglers Way

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20 Smugglers Way, Edgartown, MA 02539 is a 3 bedroom, 3 bathroom, 2,724 sqft single-family home built in 1980. This property is not currently available for sale. The current Trulia Estimate for 20 Smugglers Way is $5,482,800.