61 Pennywise Path
Edgartown, MA 02539
- 2 Beds
- 2 Baths
- 984 sqft (on 0.50 acres)
2 Beds
2 Baths
984 sqft
(on 0.50 acres)
Local Information
-- mins to
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
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Heating & Cooling Heating: Baseboard, ElectricAir ConditioningCooling System: WallHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Other, Hardwood |
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Year Built Year Built: 1987 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 0.50 acres |
Price History for 61 Pennywise Path
| Date | Price | Event | Source |
|---|---|---|---|
| 06/20/2020 | $935,000 | ListingRemoved | Agent Provided |
| 06/15/2020 | $935,000 | Listed For Sale | Agent Provided |
| 09/04/2009 | $685,000 | Sold | LINK #18829 |
| 07/05/2009 | $750,000 | Listed For Sale | Agent Provided |
| 01/05/2006 | $715,500 | Sold | LINK #10819 |
| 01/02/1997 | $166,500 | Sold | N/A |
Market trends in Edgartown
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
64
1MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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.Assigned Schools
These are the assigned schools for 61 Pennywise Path.
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.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 61 Pennywise Path
Off Market Homes Near 61 Pennywise Path
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).

