Wendy Harman
Point B Realty
(774) 252-9876
89 Total Sales
12 in Oak Bluffs
$850K - $5.8M Price Range
25 Pennacook Ave Oak Bluffs, MA 02557
Oak Bluffs Neighborhood
4
Beds
5
Baths
2,516
Sq Ft
3,485
Acre Lot
Highlights
- 3,485 Acre Lot
- Vaulted Ceiling
- Fireplace
- Deck
- Furnished
- 1-minute walk to Waban Park
About This Home
As of August 2026A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invites you to experience the essence of Oak Bluffs! The main house, dating back to the 1850s, has been well maintained, preserving its period architectural details while incorporating modern updates, including an updated kitchen with a walk-in pantry. At the heart of the home, a classic stone fireplace anchors the living and dining areas, creating an inviting gathering space. On the second floor, the primary suite gives a sense of grandeur and charm, with a vaulted ceiling, chandelier and multiple closets. The bathroom includes a soaking tub and separate water closet. Two more bedrooms and a shared full bath provide comfortable accommodations for family and visitors. The second floor is thoughtfully centered around a laundry area, complete with an additional third shower for added convenience. The guest cottage is a sweet retreat~ built in 1999. The first floor features a full kitchen, living room, and half bath, along with a convenient stackable washer and dryer. Upstairs, the second floor offers a one-bedroom layout with an adjoining dressing room or office area that leads to a full bath. Hardwood floors run throughout and forced hot water heating allows for comfortable year-round use. The guest house and the main house share the rear deck, and an outdoor shower that's perfect for island living. The properties are connected to town sewer and equipped for year-round use with a heating and A/C Viessmann system for efficiency. When in bloom, blue hydrangeas frame the properties, enhancing their classic Vineyard charm.
Both homes feature quintessential front porches, ideal for greeting neighbors and enjoying the island community.
This an opportunity to become a part of this enduring legacy and create lasting memories for generations to come.
With a strong rental history, this property presents a great investment opportunity too!
Last Agent to Sell the Property
Nya Clarke
Martha's Vineyard Island-Wide Realty Listed on: 04/11/2026
Last Buyer's Agent
Nya Clarke
Martha's Vineyard Island-Wide Realty Listed on: 04/11/2026
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $9,579
Year Built
- Built in 1999 | Remodeled in 2008
Lot Details
- 3,485 Acre Lot
- Property is zoned R1
Interior Spaces
- 2,516 Sq Ft Home
- Furnished
- Vaulted Ceiling
- Fireplace
Bedrooms and Bathrooms
- 4 Bedrooms
- Soaking Tub
Outdoor Features
- Deck
- Porch
Utilities
- Cable TV Available
Community Details
- Association fees include current sewer betterment usage fee: $1458.00 yrly
Listing and Financial Details
- Tax Lot 96
- $842,400 per year additional tax assessments
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Closed on
Oct 9, 1997
Sold by
Bought by
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Oak Bluffs, MA
-
Wendy Harman
-
Stephen Medeiros
Stephen Medeiros
Keller Williams Realty
(774) 713-9210
55 Total Sales
1 in Oak Bluffs
$875,000 Price
-
Stephanie Burke
Stephanie Burke
Portfolio Properties
(208) 738-9835
10 Total Sales
3 in Oak Bluffs
$685K - $1.1M Price Range
-
Rene Ben David
Rene Ben David
Ocean Park Realty, Inc.
(508) 372-8913
23 Total Sales
29 in Oak Bluffs
$450K - $2.5M Price Range
-
Allison Cameron Parry
Allison Cameron Parry
Douglas Elliman of MA, LLC
(508) 960-7540
7 Total Sales
2 in Oak Bluffs
$1,375,000 Price Range
-
Jennifer O'hanlon
Jennifer O'hanlon
Compass Massachusetts, LLC
(774) 469-2653
44 Total Sales
13 in Oak Bluffs
$465K - $3.5M Price Range
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $171,500 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $938,250 | Reverse Mortgage Home Equity Conversion Mortgage |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/11/2026 08/11/26 | Sold | $2,100,000 | -3.7% | $835 / Sq Ft |
| 05/26/2026 05/26/26 | Pending | -- | -- | -- |
| 04/11/2026 04/11/26 | For Sale | $2,180,000 | -- | $866 / Sq Ft |
Source: LINK (Vineyard)
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $9,136 | $1,809,200 | $810,000 | $999,200 |
| 2024 | $8,693 | $1,662,200 | $695,200 | $967,000 |
| 2023 | $8,422 | $1,595,000 | $635,700 | $959,300 |
| 2022 | $7,947 | $1,170,400 | $425,000 | $745,400 |
| 2021 | $4,860 | $997,300 | $357,400 | $639,900 |
| 2020 | $2,162 | $933,000 | $340,400 | $592,600 |
| 2019 | $2,498 | $892,600 | $311,500 | $581,100 |
| 2018 | $6,724 | $858,800 | $273,800 | $585,000 |
| 2017 | $2,003 | $792,500 | $268,500 | $524,000 |
| 2016 | $5,954 | $734,200 | $276,800 | $457,400 |
| 2015 | $5,529 | $694,600 | $276,800 | $417,800 |
| 2014 | -- | $736,200 | $282,100 | $454,100 |
Source: Public Records
Agents Affiliated with this Home
-
NC
Seller's Agent in 2026
Nya Clarke
Martha's Vineyard Island-Wide Realty
Map
Source: LINK (Vineyard)
MLS Number: 44285
Nearby Homes
- 8 Pequot Ave
- 12 Samoset Ave
- 99 Ocean Ave
- 59 Tuckernuck Ave
- 61 Ocean Ave Unit 4
- 4 Canonicus Ave
- 50 Canonicus Ave
- 46 Kennebec Ave
- 53 Circuit Ave
- 37 Circuit Ave Unit 5
- 37 Circuit Ave Unit 4
- 66 Canonicus Ave
- 10 Forest Cir
- 10 Siloam Ave
- 3 Dukes County Ave
- 112 Dukes County Ave Unit 209
- 112 Dukes County Ave
- 0 Heather Ln Unit 56
- 0 Heather Ln Unit 73560451
- 26 Winthrop Ave
Your Personal Tour Guide
Ask me questions while you tour the home.