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

61 Pennywise Path
Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 984 sqft (on 0.50 acres)

$1,310,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $7,329/mo*

$1,310,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $7,329/mo*
2 Beds
2 Baths
984 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 61 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
1987
Lot Size
0.5 acres
Living Area
984 sqft
Price/Sqft
$1,331

About this House

Simply magical is the only way to describe this compound nestled on the outskirts of downtown Edgartown. The two-bedroom main home, well equipped for all seasons, is a real charmer. A large barn, which serves as a fun and fabulous living space in the summer, is equipped with a half bath and large sleeping loft. Additionally, the detached studio, perfect for a quiet office or additional guests, rounds out the manicured landscape and storybook setting. Connected to town sewer, a rarity in this area, expansion is possible if desired. A true gem!
61 Pennywise Path, Edgartown, MA 02539 is a 2 bedroom, 3 bathroom, 984 sqft single-family home built in 1987. It last sold for $685,000 on Sep 4, 2009. It is currently off market. The Trulia Estimate is $1,310,100, with a rent estimate of $4,090/month.

Home Details for 61 Pennywise Path

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Other, Hardwood

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.50 acres

Price History for 61 Pennywise Path

DatePriceEventSource
06/20/2020$935,000ListingRemovedAgent Provided
06/15/2020$935,000Listed For SaleAgent Provided
09/04/2009$685,000Sold
LINK #18829
07/05/2009$750,000Listed For SaleAgent Provided
01/05/2006$715,500Sold
LINK #10819
01/02/1997$166,500Sold
N/A

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$2,480
Assessment$935,800
Home facts updated by county records

Comparable Sales for 61 Pennywise Path

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.35
Single-Family Home
$1,525,000
10/07/25
2
2
2,042
0.32
Single-Family Home
$950,000
03/19/26
3
2
1,728
0.34
Single-Family Home
$950,000
03/19/26
3
2
1,728
0.50
Single-Family Home
$915,000
04/17/26
2
2
1,352
0.05
Single-Family Home
$1,850,000
05/01/26
4
3.5
2,695
0.08
Single-Family Home
$1,850,000
05/01/26
4
3.5
2,695
0.27
Single-Family Home
$1,600,000
06/18/26
4
2.5
2,706
0.31
Single-Family Home
$2,075,000
09/29/25
3
3.5
2,638
0.79
Single-Family Home
$1,100,000
04/30/26
3
1.5
1,304
0.81
Single-Family Home
$1,450,000
02/19/26
3
2
1,324

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 61 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 61 Pennywise Path

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Off Market Homes Near 61 Pennywise Path

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Frequently asked questions about 61 Pennywise Path

  • What is 61 Pennywise Path estimated to be worth?
    Trulia's estimated value for 61 Pennywise Path in Edgartown, MA is $1,310,100.
  • What is the price history for 61 Pennywise Path?
    61 Pennywise Path in Edgartown, MA last sold for $685,000 in September 2009.
  • Is Edgartown a buyer's or seller's market?
    Edgartown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Edgartown?
    Residents describe Edgartown, MA as established, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Edgartown, MA.
  • Does 61 Pennywise Path have air conditioning?
    Yes, 61 Pennywise Path in Edgartown, MA has air conditioning.
  • How big is the lot at 61 Pennywise Path?
    The lot at 61 Pennywise Path in Edgartown, MA is about 0.50 acres (21,780 sq ft).