| Flanders Up-Island Real Estate offers a variety of rental choices located within the Up-Island area and beyond. Our inventory is not limited to the rentals seen here. Click on the Advanced rental search tab above or Please feel free to call us and we will individualize your search. |
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Classic Chilmark cape. Situated in a meadow surrounded by ancient stonewalls. Link to Property |
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Spacious Chilmark Home, only a short distance from Chilmark Center. Menemsha pond views and more. |
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Quitsa Pond frontage. It doesn't get better than this! A home filled with character, great for entertaining and the views are endless...not to mention Dock Space and Private beach access!
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Amazingly situated 4 bedroom modern Aquinnah Home. Perched on a hill with far reaching waterviews, pond access, inground pool and more. |
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Quansoo Home, newly built and beautifully furnished. A main house and Guest House situated next to the Great Pond. Link to Property |
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Located on Stonewall Pond. Excellent views, comfortable home all within walking distance to Stonewall beach. |
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Just steps to your own private Dogfish bar. this newly finished home has full views overVineyard Sound. |
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This large home, Guest house and Bunk House overlook stunning views of the Atlantic shore from Highmark Hill in Chilmark. |
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Charming Chilmark home situated off a quiet Lane off of Middle Road. Views toward South Shore. |
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Large Home just off of Moshup Trail. Complete with private south shore beach access only steps from your front door. Link to Property |
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Views from Menemsha Pond to the Elizabeth islands. This quality constructed four bedroom home in Aquinnah sits atop a secluded hill. Link to Property |
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Aquinnah Main and Guest House, wonderfully appointed and set in peaceful surroundings with views. |
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Unsurpassed views from this rambling five bedroom home located only a short distance from menemsha. |
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Striking four bedroom home. Nicely furnished, large open living room and well manicured grounds.. |
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Located down Stonewall Road, complete with access to the beach, this large 5 bedroom house has all the necessary amenities. Link to Property |
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Recently renovated quality four bedroom, three bathroom home located down a quiet Chilmark Lane. Distant North and South views. Link to Property |
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Aquinnah cottage...2 Bedroom home situated only steps from Menemsha Pond |
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Chilmark Cottage, only a short distance to Menemsha and walk to conservation beach. Link to Property |
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Stonewall pond at your yard's edge. Three spacious bedrooms and a home with every needed amenity. Link to Property |
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Large rambling Chilmark Farmhouse nestled in a hill overlooking Squibnocket. Link to Property |
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Open and sun filled with unmatched views over Squibnocket and Noman's Land. Link to Property |
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With the Tiasquam river streaming through your backyard, this 3 bedroom is an ideal getaway. Link to Property |
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A 4 bedroom contemporary gem situated at Quitsa Pond's edge. Complete with deep water dock. Link to Property |
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Immaculate 4 bedroom home, overlooking chilmark meadows and south shore. Link to Property |
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Situated on its own private peninsula, this Chilmark home offers astounding views and seclusion. Link to Property |
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Remarkable Views from this 3 bedroom cottage, comes with dock access. Link to Property |
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Custom Architectual home with 4 bedrooms, Open airy feel. Views of the Atlantic Ocean and walk to Private south shore beach. Link to Property |