# 34 Windemere Road, Oak Bluffs, MA 02557 > **TL;DR:** 4bd/2ba single family, $2,579,000 ($1843/sqft), built 1910, 1,399 sqft. > Fireplace, Hardwood. Est. $13,793/mo. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $2,579,000 | | Price/sqft | $1843 | | Bedrooms | 4 | | Bathrooms | 2 full | | Square Feet | 1,399 | | Year Built | 1910 | | Lot Size | 46,004 sqft (1.06 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 0 | ## Why This Home Stands Out - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $13,041 | | Estimated Insurance | $752 | | **Total** | **$13,793** | ## Key Amenities - Fireplace - Hardwood ## Property Highlights - Built in 1910 - 1.06 acre lot - Fireplace ## Description ### Agent Description Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together a combined total of just over an acre of land. Included is Deeded Access, via a boardwalk to Brush Pond, with more wonderful views. Directly in front of the property lies a sandy beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf & a host of activities. This property offers both tranquility and convenience in one of Martha's Vineyard's most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for purchase separately. Excellent Rental History. ## Location - **Address:** 34 Windemere Road, Oak Bluffs, MA 02557 - **Coordinates:** 41.4598791, -70.5813219 - **Google Maps:** https://www.google.com/maps?q=41.4598791,-70.5813219 ## Listing Agent - **Name:** Alisan Lohan-Conway - **Brokerage:** Alisan Lohan-Conway Properties - **Phone:** 5086271858 - **Broker Phone:** (508) 627-1858 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/34-Windemere-Rd_Oak-Bluffs_MA_02557_M48084-58720?f=listhub&s=LNKMVMA&m=44300&c=propsimple) ## Photos ![34 Windemere Road - Photo 1](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f98328444r.jpg) ![34 Windemere Road - Photo 2](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f197666109r.jpg) ![34 Windemere Road - Photo 3](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1959066453r.jpg) ![34 Windemere Road - Photo 4](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f894387778r.jpg) ![34 Windemere Road - Photo 5](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1943780512r.jpg) ![34 Windemere Road - Photo 6](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3983971851r.jpg) ![34 Windemere Road - Photo 7](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2818731951r.jpg) ![34 Windemere Road - Photo 8](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3625105521r.jpg) ![34 Windemere Road - Photo 9](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f955163477r.jpg) ![34 Windemere Road - Photo 10](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3406899648r.jpg) ![34 Windemere Road - Photo 11](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1665038288r.jpg) ![34 Windemere Road - Photo 12](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1039962512r.jpg) ![34 Windemere Road - Photo 13](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3029280177r.jpg) ![34 Windemere Road - Photo 14](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1572739481r.jpg) ![34 Windemere Road - Photo 15](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3675952426r.jpg) ![34 Windemere Road - 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Photo 36](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1431421442r.jpg) ![34 Windemere Road - Photo 37](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2999502754r.jpg) ![34 Windemere Road - Photo 38](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f85601194r.jpg) ![34 Windemere Road - Photo 39](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3174179557r.jpg) ![34 Windemere Road - Photo 40](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1564012449r.jpg) ![34 Windemere Road - Photo 41](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3572268966r.jpg) ![34 Windemere Road - Photo 42](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f308621049r.jpg) ![34 Windemere Road - Photo 43](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2032791665r.jpg) ![34 Windemere Road - Photo 44](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1338439042r.jpg) ![34 Windemere Road - Photo 45](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3863912392r.jpg) ![34 Windemere Road - Photo 46](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2796513616r.jpg) ![34 Windemere Road - Photo 47](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3367115826r.jpg) ![34 Windemere Road - Photo 48](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1214868595r.jpg) ![34 Windemere Road - Photo 49](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2082258432r.jpg) ![34 Windemere Road - Photo 50](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2245075721r.jpg) ![34 Windemere Road - Photo 51](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2758489957r.jpg) ![34 Windemere Road - Photo 52](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f868848048r.jpg) ![34 Windemere Road - Photo 53](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1140910458r.jpg) ![34 Windemere Road - Photo 54](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2902237529r.jpg) ![34 Windemere Road - Photo 55](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3496238204r.jpg) ![34 Windemere Road - Photo 56](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3485709378r.jpg) ![34 Windemere Road - Photo 57](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1288262542r.jpg) ![34 Windemere Road - Photo 58](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f3918139965r.jpg) ![34 Windemere Road - Photo 59](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f40244342r.jpg) ![34 Windemere Road - Photo 60](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2854931325r.jpg) ![34 Windemere Road - Photo 61](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f2376016756r.jpg) ![34 Windemere Road - Photo 62](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1546209519r.jpg) ![34 Windemere Road - Photo 63](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f383296874r.jpg) ![34 Windemere Road - Photo 64](http://lh.rdcpix.com/21cd88c96ec4efe99f2371ce042df3e0l-f1071265795r.jpg) --- **MLS#:** 44300 | **Updated:** 2026-08-25 **Source:** listhub *Copyright © 2026 LINK Martha’s Vineyard. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/34-windemere-road-oak-bluffs-ma-02557-ma44300) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/34-windemere-road-oak-bluffs-ma-02557-ma44300#listing", "url": "https://www.propertysimple.ai/listing/34-windemere-road-oak-bluffs-ma-02557-ma44300", "name": "34 Windemere Road, Oak Bluffs, MA 02557", "description": "Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the street, bordered by the Land Bank property of Dougs Preserve. Together a combined total of just over an acre of land. Included is Deeded Access, via a boardwalk to Brush Pond, with more wonderful views. Directly in front of the property lies a sandy beach where a sandy shoreline meet calm, inviting, Lagoon waters. After a day at the beach, rinse off in the beautifully constructed mahogany outdoor shower, an elegant Vineyard touch. The home is equipped with central air conditioning, a full basement, wood and tile floors throughout, updated insulation, and irrigation. Located just minutes from the vibrant centers of Oak Bluffs and Vineyard Haven, as well as their respective Ferry terminals, minutes to Eastville Beach, easy access to stores, restaurants, Farm Neck Golf, Mink Meadows Golf & a host of activities. This property offers both tranquility and convenience in one of Martha's Vineyard's most desirable water view settings. An 'Up Island' feeling with a 'Down Island' location. Contents available for purchase separately. 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