73 Pennywise Path, Edgartown, MA 02539
Property image
Property image
OFF MARKET

73 Pennywise Path
Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,400 sqft (on 0.94 acres)

$1,557,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $8,712/mo*

$1,557,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $8,712/mo*
4 Beds
3 Baths
2,400 sqft
(on 0.94 acres)

Local Information

  • Map ViewExplore the area around 73 Pennywise Path.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Lot Size
0.94 acres
Living Area
2,400 sqft
Price/Sqft
$649

About this House

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
73 Pennywise Path, Edgartown, MA 02539 is a 4 bedroom, 3 bathroom, 2,400 sqft single-family home built in 1995. It last sold for $650,000 on Apr 13, 2015. It is currently off market. The Trulia Estimate is $1,557,000, with a rent estimate of $6,460/month.

Home Details for 73 Pennywise Path

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6Types of Rooms: Breakfast Nook, Laundry Room, Master Bath, Office, Sun RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenLawnPorchSprinkler System
Parking & Garage
Parking Spaces: 4Parking: Off Street

Property Information

Year Built
Year Built: 1995Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.94 acres

Price History for 73 Pennywise Path

DatePriceEventSource
04/13/2015$650,000Sold
LINK #27161
09/10/2014$695,000PriceChange
Agent Provided
08/15/2014$720,000PriceChange
Agent Provided
07/26/2014$780,000Listed For SaleAgent Provided
08/30/2005$755,000Sold
LINK #8954

Market trends in Edgartown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
64
1
MoM
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Property Tax and Assessment

Year2025
Tax$3,337
Assessment$1,259,400
Home facts updated by county records

Comparable Sales for 73 Pennywise Path

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.09
Single-Family Home
$1,850,000
05/01/26
4
3.5
2,695
0.12
Single-Family Home
$1,850,000
05/01/26
4
3.5
2,695
0.29
Single-Family Home
$950,000
03/19/26
3
2
1,728
0.30
Single-Family Home
$950,000
03/19/26
3
2
1,728
0.32
Single-Family Home
$1,600,000
06/18/26
4
2.5
2,706
0.34
Single-Family Home
$1,525,000
10/07/25
2
2
2,042
0.61
Single-Family Home
$1,675,000
12/08/25
3
2.5
1,914
0.36
Single-Family Home
$2,075,000
09/29/25
3
3.5
2,638
0.66
Single-Family Home
$2,275,000
05/14/26
4
2.5
2,760
0.61
Single-Family Home
$2,210,000
07/23/26
3
3
2,126

Nearby homes

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Assigned Schools

These are the assigned schools for 73 Pennywise Path.
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

Sourced by Trulia users. 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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Apartments for Rent

Homes for sale near 73 Pennywise Path

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Off Market Homes Near 73 Pennywise Path

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