| 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. 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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Adorable 2 bedroom Chilmark Cottage with South Shore views, easy distance to Lucy Vincent |
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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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Large, lovingly maintained Colonial Style home situated a shortdistance from North Road in Chilmark. |
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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 living room and a large grassy yard. Only a short distance to Chilmark Center. |
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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. Vies of the Atlantic Ocean and walk to Private south shore beach. Link to Property |