Real Estate Confidential: Midsummer Dreaming


Real Estate Confidential is a bi-weekly chit-chat about new listings, sales, or other insider info on the Martha’s Vineyard Real Estate market, presented by Fred Roven, owner/broker of Martha’s Vineyard Buyer Agents. It appears every other Friday in The Minute.

I think we should all take a deep breath, step away from real estate and lie in the sun imagining our favorite Island home. Every week brings new offers and reduced prices for homes that are very desirable and may have been priced too high even for this pressure-fueled market. Also, many new properties on the market that are perfect for this market and those dreaming of that new home office in a property that doubles as the ultimate summer vacation.

Over the past year, what many homeowners used to think they wanted in a home has changed. A survey conducted by Statista and Upwork projects 37.5% of U.S. workers will work remotely in some capacity over the next  five years (up from 22%). If you fall in that category, working from home may provide you with opportunities you didn’t realize you had. The ongoing rise in remote work means a portion of the workforce no longer needs to be tied to a specific area for their job. Instead, it gives those workers more flexibility when it comes to where they can live. You could also move to an area you’ve always dreamed of vacationing in — somewhere near the beach or simply an area that features better weather and community amenities. Without your job tying you to a specific location, you’re bound to find your ideal spot.

If you’ve found that what you’re looking for in a home has changed due to remote work, it may be time to make a move. This week’s selection of new to market properties includes an Oak Bluffs building lot priced at $459,900, a casual summer “tree house” on Chappy for $650,000, and a 7-bedroom waterfront estate in Aquinnah for $9,995,000.

The magnificent waterfront home at 53 Wequobsque sits on 6.4 acres atop the dramatic Wequobsque Cliffs. On Chilmark’s coveted South Shore,  ownership includes over 350 feet of private beach with access from your staircase in the backyard. The home spreads out over 4,000 square feet facing thousands of miles of Atlantic Ocean. Many features make this perfect summer living for large families with multiple living areas. My favorite is the “party barn” with a half bath and a loft that can be used as an office or extra sleeping area. There is a wet bar, ping-pong table, large screen TV and sofa. Island oceanfront living at its best. 

Find comfortable Vineyard living coupled with a feeling of warmth and home at 237 Vineyard Meadow Farms Road. is a charming and lovingly maintained home, nestled in a quiet setting on 1.5 acres, with numerous unique features. Of particular note are the three-season room. The home could be perfect for work from home families as the master bedroom suite has its own private office. The home captures the charm and ambiance of Island living, with the easy access to Long Point Beach, the bike path, and West Tisbury center and of course access to everyone’s favorite beach, Lambert’s Cove.

The perfect Edgartown location at 11 Boldt Farms sits across from Morning Glory Farm, with easy access to the shops and restaurants of the village, as well as miles of paved bike paths and hiking trails through Sheriff’s Meadow and the State Forest. You will have just a quick bike or car ride to South Beach on a newly paved road and no traffic delays plus the ability to avoid the Triangle to drive to town. Every detail of both the house and a most interestingly designed barn were meticulously planned and completed using the highest quality construction and finish materials. The barn is large enough to house several boats and cars or could be transformed into a true party barn. This space is totally flexible but would certainly be ideal for a home business, fitness studio, or entertaining area. The owners have a pool permit and contract in hand with a scheduled installation time frame, should the new owners wish to add a pool. 

If there is one new development that generates the most requests for the “next available house,” it is The Preserve at the Woodlands. The “to be built” home at 22 Paddock Road by one of the Island’s premier builders and is still in early design stages, so bring every idea you have ever wanted in a new Island home. Current plans call for a sprawling contemporary barn style residence with clean classic lines, natural timber beams, fieldstone fireplace and soaring ceilings. The open floor plan provides many gathering spaces with lots of glass overlooking the 20 by 40-foot Gunite pool. A generous walk-out finished basement, containing over 2000 square feet, will include additional living areas along with a bar, gym/media room and/or wine cellar. The home abuts 5,300 acres of conservation land for hiking, walking and biking!

Click here for a list of other new to market homes

For more Real Estate Confidentials, click here.