36 Strawberry Hill Is Now Available Off-Market Before Its MLS Debut

One of Dover's Most Versatile Luxury Estates Is Now Available Off-Market

By Evan Walsh | The Walsh Team | William Raveis Real Estate

Having grown up in Dover and spent nearly two decades selling real estate throughout the community, I've had the privilege of representing many of the town's most significant homes. More than eight years ago, as Dover's luxury market was beginning to rebound, I had the opportunity to represent the purchase of 34-36 Strawberry Hill for its current owner. During that same period, I also represented the sale of 18 Walpole Street, which remains the highest publicly recorded residential sale in Dover at more than $13 million.

Revisiting 34-36 Strawberry Hill today has been especially rewarding. The home has been thoughtfully enhanced over the years while preserving the qualities that first made it one of Dover's exceptional estates. Having represented both the purchase of this property and now its sale gives me a unique perspective on its evolution and why I believe it represents one of the most compelling luxury opportunities currently available in our market.

For a limited time, 34-36 Strawberry Hill is being offered exclusively off-market before its anticipated MLS debut. Qualified buyers have a rare opportunity to privately tour this remarkable estate before it becomes available to the broader market.

Set on more than five private acres in Dover's prestigious Strawberry Hill neighborhood, this is much more than a luxury home. It is an estate designed to adapt to the changing needs of its owners while offering the privacy, amenities, and lifestyle expected of one of the area's premier properties.

The main residence encompasses more than 10,000 square feet with six to seven bedrooms, nine full bathrooms, and expansive living and entertaining spaces that strike the perfect balance between elegance and everyday comfort. Every bedroom is thoughtfully designed as a private suite, while multiple gathering spaces create an inviting atmosphere for both intimate family living and large-scale entertaining.

What truly separates this estate from many luxury homes is its exceptional flexibility.

Complementing the main residence is a beautifully appointed 1,200-square-foot detached guest house featuring two bedrooms, a full bath, and its own attached three-car garage. Opportunities like this are incredibly rare in Dover. Whether accommodating aging parents, adult children, long-term guests, an au pair, household staff, or simply creating a private retreat for family and friends, the possibilities are extensive.

As today's buyers continue to prioritize homes that can evolve with their families, properties offering this level of versatility have become increasingly desirable. In my experience, it's one of the qualities that transforms a beautiful home into a true legacy estate.

The outdoor living spaces are equally impressive.

Designed as a private resort, the grounds feature a spectacular heated pool, expansive stone patio, outdoor kitchen, fire pit, hot tub, beautifully manicured landscaping, and a private sport court. Whether hosting summer gatherings, relaxing with family, or simply enjoying the peaceful surroundings, every aspect of the outdoor environment has been thoughtfully designed to maximize both comfort and privacy.

Having lived in Dover, I've always considered Strawberry Hill one of the town's most coveted neighborhoods. The winding roads, estate-sized properties, mature trees, and peaceful setting create a level of privacy that is becoming increasingly difficult to find. At the same time, residents enjoy convenient access to Wellesley, Needham, Westwood, Boston, and major commuter routes while benefiting from Dover's nationally recognized schools and exceptional quality of life.

One of the aspects I find most exciting about this property is its long-term potential.

While the estate already offers an extraordinary combination of architecture, amenities, and lifestyle, it also provides an opportunity for its next owner to make it uniquely their own. Every great estate evolves over time, reflecting the vision and personality of each owner. Whether through thoughtful interior design, curated finishes, or future enhancements, 34-36 Strawberry Hill offers the rare chance to build upon an already exceptional foundation.

In my opinion, this property belongs in the same conversation as Dover's finest estates. Its combination of location, acreage, architectural presence, multigenerational flexibility, detached guest house, resort-caliber outdoor amenities, and future potential is extraordinarily difficult to replicate in today's market. I believe it has all the ingredients to become one of the landmark luxury estates not only in Dover, but throughout the MetroWest region.

For qualified buyers seeking an exceptional property before it reaches the public market, this is an opportunity that deserves serious consideration.

34-36 Strawberry Hill is currently available exclusively through confidential private showings prior to its MLS launch.

If you've been waiting for a truly special Dover estate—or know someone who has—I encourage you to reach out while this exclusive off-market opportunity remains available.

For additional information or to schedule a confidential private tour, please contact:

Evan Walsh
The Walsh Team | William Raveis Real Estate
📞 508-341-4904

Dover residents often ask me when a truly exceptional property becomes available. This is one of those homes. If you know someone who has always dreamed of living in Strawberry Hill or relocating to Dover, I'd greatly appreciate you sharing this opportunity with them before it officially comes to market.