$1,830,000
$157K PRICE DROP

12 & 14 Maple Ave Oak Bluffs, MA 02557

Oak Bluffs Neighborhood

Estimated payment $11,802/month

Total Views 5,246
4 Beds
4 Baths
1,600 Sq Ft
$1,144 Price per Sq Ft

About This Home

Two Historic Oak Bluffs Cottages - Prime Location – Deeded Separately
Perched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout.
Built at a time when automobiles were rare, these homes were sited with ease of access in mind. Though they have no driveways, convenient on-street parking is always available—local residents often find it easier to stroll, or bike, into town than drive.
Both homes are separately deeded, giving you the flexibility to own them jointly or individually, and the ability to create a compound with rental options. They are fully furnished and move-in ready, with a long history of use as rentals and community housing. Whether you're looking for a full-time residence, income-generating property, or a flexible retreat for extended family or friends, these cottages provide a unique and practical setup—ideal for dual living or multi-generational use.
Set against a backdrop of cool breezes and peaceful surroundings, these modest yet solidly built mirror image cottages feature warm, weatherproof interiors, ground-level entries, and ensuite bathrooms. While they may not compare in size to modern builds, their simplicity is part of their charm—and their history is unmatched.
The Hughes family, who once lived here, famously hand-dug full basements in both homes in the late 1920s—a remarkable feat in a neighborhood where most homes sit on crawl-spaces. This added space offers valuable storage, office, or expansion options rarely found in similar homes of the era.
With a strong local school system, a welcoming neighborhood, and the charm of yesteryear combined with present-day comfort, these homes are an ideal place to put down roots, invest in community, or create a home-away-from-home.
Keep them as they are, or add your own touches.

Listing Agent

Leslie C. Floyd

Portfolio Real Estate, Inc. Listed on: 05/19/2025

Map

Home Details

Home Type

Single Family

Year Built

1909

Lot Details

0

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Co List Office Mls Id: 1010
  • Special Features: None
  • Year Built: 1909

Interior Features

  • Appliances: Stove: Yes, Washer: Yes
  • Has Basement: Full basements in both cottages - VERY rare for antique cottages in this neighborhood. Fully ducted propane hot air system as well as the mini split.
  • Full Bathrooms: 4
  • Total Bedrooms: 4
  • Fireplace Features: 2
  • Interior Amenities: Ins,MiniSplit,OSh, Floor 1: 4 bedrooms with ensuite full baths. Open kitchen, living and dining area in each cottage. #12 has a small office as well. Each cottage also has a a stone fireplace, outdoor shower and private patio.
  • Main Level Bedrooms: 2
  • Total Bedrooms: 8

Exterior Features

  • Pool Private: No
  • Foundation Details: Concrete-Full

Garage/Parking

  • Parking Features: On-street

Utilities

  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town

Lot Info

  • Lot Size Sq Ft: 4356
  • Land Lease Expiration Date: 2026-05-02
  • Zoning: R2

Multi Family

  • Number Of Units Furnished: Furnished

Tax Info

  • Tax Annual Amount: 7835
  • Tax Lot: 51 & 52
  • Tax Map Number: 8
  • Tax Other Annual Assessment Amount: 1047000
  • Tax Year: 2025

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/23/2025 07/23/25 For Sale $1,830,000 -- $1,144 / Sq Ft
Source: LINK (Vineyard)

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Source: LINK (Vineyard)

MLS Number: 43290

Massachusetts Dukes County Oak Bluffs Oak Bluffs

12 & 14 Maple Ave, Oak Bluffs, MA

This home is located at 12 & 14 Maple Ave, Oak Bluffs, MA 02557 and is currently priced at $1,830,000, approximately $1,143 per square foot. This property was built in 1909. 12 & 14 Maple Ave is a home located in Dukes County with nearby schools including Oak Bluffs Elementary School, Martha's Vineyard Regional High School, and Vineyard Montessori School.

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Nearby Homes
Listing Agent
Leslie C. Floyd
Portfolio Real Estate, Inc.