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Oak Bluffs, MA Multifamily Properties for Sale

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Charming Oak Bluffs Compound
$5,325,000
2,890 SF

Charming Oak Bluffs Compound

4 Canonicus Ave, Oak Bluffs, MA 02557

Unique compound near downtown with ocean views and rental history.

  • Nantucket Sound views and proximity to downtown Oak Bluffs.
  • Main house with four bedrooms, updated with contemporary comforts.
  • Includes a private guest house ('The Nest') with private deck, outdoor shower, and water views.
  • Bunk house ('Lilac House') with waterviews, outdoor shower and deck.
  • Established rental history.
Updated: Jan 21
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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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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 8 Potential Opportunities for your consideration. Besides 3 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
Contact for pricing

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
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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 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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Edgartown Multifamily Residence For Sale
Contact for pricing

Edgartown Multifamily Residence For Sale

Rare multifamily residence in desirable location near shops and harbor.

48 West 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
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Oak Bluffs, MA Multifamily Properties Investment Opportunities Market Analysis

Explore 4 multifamily properties for sale in Oak Bluffs, MA, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 13,068 square feet of properties for sale, with an estimated market value of $7,155,000.

Sale prices for multifamily properties in Oak Bluffs, MA start at $1,830,000, averaging $3,577,500, and reaching up to $5,325,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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