Flanders Up-Island Real Estate

04/06/2026

Back on the Market this Spring! Charming 2-bedroom 1 bath ranch house in Vineyard Haven in town—just minutes from shops, restaurants, and schools.

This well-maintained property offers a functional layout with a bright living area, a cozy kitchen overlooking the backyard, and two comfortable bedrooms and a full bathroom. The house has a full basement with ample room for storage and projects. This home is situated on two lots, giving you the possibility to expand.

Available for $1,050,000. If you are interested in a showing please contact 508-645-2632

04/02/2026

Back on the Market this Spring!
1.63 Acres in West Tisbury with Main house & Garage apartment available at a new price $1,299,000. A great rental investment or your next Vineyard home!

Check out our Listings: https://www.flandersrealestate.net/sales

04/01/2026

Unbelievable rental location! A well maintained cottage just steps from Menemsha Pond available 8/22-8/30 for $5310 per week.

Please reach out for more information 508-645-2632 or [email protected]

See listing for details: https://flandersrealestate.site/rentals/vrp2/rentals/1063.htm

03/20/2026

Aquinnah 3 Bedroom, 2.5 Bath rental with stunning finishes available July 24- August 8 for $11,000-$12,500 per week.

Please reach out for more information 508-645-2632 or [email protected]

See listing for details: https://flandersrealestate.site/rentals/vrp2/rentals/prop1468.htm

03/18/2026

Chilmark Rental available this July overlooking the iconic Keith Fields. Enjoy the property's natural beauty and closeness to the General store, Chilmark Tavern and Community Center.

Please reach out for more information 508-645-2632 or [email protected]

See listing for details: https://flandersrealestate.site/rentals/vrp2/rentals/1098.htm

03/16/2026

Flanders Lane 3 Bedroom rental overlooking Menemsha Pond. A rare rental available now 8/15-8/29 for $4770 per week.

Please reach out to us for more information 508-645-2632 or [email protected]

See Listing for more details: https://flandersrealestate.site/rentals/vrp2/rentals/1110.htm

03/13/2026

Stunning three bedroom home in Stonewall available 8/15 and on for $12150 per week.

Please reach out for more information 508-645-2632 or [email protected]

See listing for details: https://flandersrealestate.site/rentals/vrp2/rentals/1343.htm

03/11/2026

Chilmark 3 Bedroom, 2 Bath Cottage available for renting this summer! Enjoy hilltop views with access to Squibnocket and Lucy Vincent beaches

For more information please call 508-645-2632 or email flandersrealestate.net

See Listing for more details: https://flandersrealestate.site/rentals/vrp2/rentals/prop1486.htm

03/09/2026

Menemsha Rental available August 15 to September 5! 2 Bedroom 1 Bath close by Menemsha Beach with screen porch to enjoy summer nights.

Reach out for more information:
[email protected]
508-645-2632

See listing for more details: https://flandersrealestate.site/rentals/vrp2/rentals/prop1485.htm

09/22/2025

A price improvement on this lovely property!

09/08/2025