101 Tradewinds Road, CentralOak Bluffs, MA 02557Price: $1,435,000

  • Price: $1,435,000
  • Est. Mortgage of $/month
  • 90 Days on Market
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Federal 30-year interest rate: 6.0% last updated on Mar 5, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $1,435,000List Price
  • 3Bedrooms
  • 1.5Bathrooms
  • 0.53Acreage
  • 1,456Square Feet
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Listed by Nya Clarke,508-572 -3636 call /text of Martha's Vineyard Island-Wide Realty
Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room highlighted by an impressive wall of windows that fills the space with sunlight and frames serene views of protected pastoral land. The open-concept kitchen, dining, and living areas are anchored by a striking fireplace, creating an inviting setting for gatherings. Just off the kitchen, a charming, screened porch offers a cozy three-season retreat, perfect for morning coffee or evening relaxation. The main level includes three generous bedrooms and a full bath. while the walk-out basement provides a workshop area with sink and storage room. Outside, the property is thoughtfully landscaped with irrigation with mature rows of Arborvitae trees, giving it a private, park-like feel. A back patio and a detached office offer additional spaces to work, unwind, or take in the peaceful surroundings. Conveniently located, this property is within walking distance of the Oak Bluffs School, the Tradewinds walking trail just across the street, bike paths, and public transit. Downtown Oak Bluffs and the beach are only minutes away- an ideal combination of privacy, convenience, and potential. This lot could provide potential options for future enhancements such as expanded living space, a garage, guest house/ADU… Building possibilities should be explored and reviewed in accordance with town bylaws. Note: The property is being sold as-is, and the buyer will be responsible for replacing the existing septic system.

Property Details of 101 Tradewinds Road, Central

Property Details

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Based on information submitted to LINKMV as of March 12, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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