25 Pennacook Avenue
$2,180,000
Downtown, Oak Bluffs, MA 02557
Recently Listed
1 / 55
4 beds
4 baths
10 rooms
2,516 SqFt
MLS #44285
A 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!
Property highlights
Unfurnished
Porch
Public Beach
Deck
Tennis Court
Town Sewer
Cable
Town Water
Property Details
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- current sewer betterment usage fee: $1458.00 yrly
- Access to the main house basement cellar is located off the kitchen. In the cellar is a Viessmann heating system (Gas-FHW) hot water heater and electric panel.
- One stone fireplace with wood stove insert in the main house dining area
- Hardwood floors throughout both properties
- Cellar in main house and basement in guest house
- None
- GFHW
- AC,Ins,Irr,MiniSplit,OSh,WdStoveFloor 1: The main house, dating back to 1850, features a classic wraparound front porch and an original stained glass front door. Inside, an open living and dining area is centered around a stone hearth fireplace with a cast-iron potbelly wood stove insert. The living room has custom bookshelves and original brass lighting fixtures throughout highlighting the era of this home.
The updated kitchen has an eight-burner gas stove and a spacious pantry, with a convenient half bath located just off the kitchen. The back door leads to the shared 300sq ft rear deck with outdoor shower, and two off-street parking spots to further enhance the property’s appeal. Notable preserved Victorian details such as period woodwork, pocket doors, stained glass, porcelain sinks, antique lighting and doors with original hardware (the house has been updated with recessed lighting too)Floor 2: The main staircase off the dining area leads to the primary suite, featuring a vaulted ceiling, chandelier, and multiple closets, along with an en suite bath complete with a soaking tub and separate water closet. Two additional spacious bedrooms and a shared full bath offer comfortable accommodations for family and guests. The second floor also includes a centrally located laundry area with a washer and dryer, an additional third shower, and a dedicated storage space.
- Property is connected to town sewer. For sale in "as is condition.
Directions: Headed south from Circuit Ave, after Massasoit Ave - take a left onto Pennacook Ave. Go pass stop sign staying straight. #25 Pennacook is on the left side (one way street).
- Blue hydrangeas lined perimeter of the property, maintained w/ irrigation
- 2 off street parking spots
- 1024300.00
- 842400.00
Price History
April 11, 2026
$2,180,000
Tax Information
This property was most recently assessed in 2026. It has been assessed at a value of $1,866,700. The annual tax responsibility for this property is $9,579.3.
Contact an Agent
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©2026 LINK, All Rights Reserved. Not responsible for misinformation or typographical errors. Prices are subject to change without notice. Listed by Martha's Vineyard Island-Wide Realty.
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