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    Oak Bluffs, MA Residential Income Properties for Sale

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    Historic Oak Bluffs Twin Cottages
    $1,830,000
    1,600 SF

    Historic Oak Bluffs Twin Cottages

    12 Maple Ave, Oak Bluffs, MA 02557

    Two charming, furnished cottages in a prime Oak Bluffs location.

    • Two separately deeded cottages offer flexibility: own jointly or individually.
    • Prime Oak Bluffs location: short distance to harbor, downtown, and Winston's takeout.
    • Historic 1909 twin cottages with established gardens in a desirable neighborhood.
    • Fully furnished and move‑in ready, with a history of rental income.
    • Ideal for dual living or multi‑generational use.
    Updated: Aug 10, 2025
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    Victorian Multifamily Near Oak Bluffs
    $3,500,000
    3,880 SF

    Victorian Multifamily Near Oak Bluffs

    35 New York Ave, Oak Bluffs, MA 02557

    Five-unit apartment building near Oak Bluffs center, harbor, and beaches.

    • Rare opportunity to own a five‑unit apartment building on Martha's Vineyard.
    • Ideally located within walking distance to Oak Bluffs Center, Harbor, ferry, and beaches.
    • Strong income potential from year‑round and seasonal tenants.
    • Five well‑maintained apartments with a total of 7 bedrooms (2 two‑bedroom and 3 one‑bedroom units).
    • Thoughtfully renovated and consistently cared for.
    Updated: Jan 28
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    Charming Oak Bluffs Compound
    $5,325,000
    2,890 SF

    Charming Oak Bluffs Compound

    Unique compound near downtown with ocean views and rental history.

    4 Canonicus Ave, Oak Bluffs, MA 02557
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    Two Cottages Near the Ocean
    $1,199,000
    0.11 Acres

    Two Cottages Near the Ocean

    Two cottages on one lot, close to the beach.

    47 Winemack Ave, Oak Bluffs, MA 02557
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    Oak Bluffs Condotel Investment
    $235,000
    329 SF

    Oak Bluffs Condotel Investment

    51-Unit Island Inn Condo

    27 Island Inn Rd, Oak Bluffs, MA 02557
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    Based on your search, we've compiled 10 Potential Opportunities for your consideration. Besides 5 Active listings in Oak Bluffs, MA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 1 Off-Market properties to explore as potential leads

    Explore Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Mixed-Use Building in Vineyard Haven
    $2,900,000

    Mixed-Use Building in Vineyard Haven

    Mixed-use property with retail and residential units in prime location.

    15 Main St, Vineyard Haven, MA 02568
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    Four-Unit Multifamily Home
    $1,495,000

    Four-Unit Multifamily Home

    Centrally located four-unit multifamily property with recent upgrades.

    140 Midland Ave, Vineyard Haven, MA 02568
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    Edgartown Multi-Family Saltbox Compound
    $1,985,000
    2,836 SF

    Edgartown Multi-Family Saltbox Compound

    Private compound with main house, guest house, and detached garage.

    36 Smith Hollow Dr, Edgartown, MA 02539
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    Edgartown Compound: Main and Guest House
    $2,650,000
    4,115 SF

    Edgartown Compound: Main and Guest House

    Edgartown property with main house, guest house, and pool.

    357 W Tisbury Rd, Edgartown, MA 02539
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    Explore Off-Market Properties in Oak Bluffs, MA

    Consider similar Off-Market properties in Oak Bluffs, MA. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    27 Is Inn Rd

    27 Is Inn Rd

    Multifamily properties • 329 SF
    Value Estimation by Request
    27 Is Inn Rd, Oak Bluffs, MA 02557
    View details

    Oak Bluffs, MA Residential Income Properties Investment Opportunities Market Analysis

    Explore 6 residential income properties for sale in Oak Bluffs, MA, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 28,519 square feet of properties for sale, with an estimated market value of $11,854,000.

    Prices for residential income properties in Oak Bluffs, MA start at $1,199,000, averaging $2,963,500, and reaching up to $5,325,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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