Tucked into the coveted village of East Dennis, 58 Pleasant Street offers an extraordinary Cape Cod retreat where sophisticated coastal design, beautifully landscaped grounds, and exceptional resort-style amenities come together in a setting of understated luxury. Comprising a meticulously renovated main residence and a charming separate guest house, this distinctive six-bedroom, five-bathroom property accommodates up to 14 guests, providing an ideal setting for extended families and friends seeking an elevated summer experience. With a heated saltwater swimming pool, spa, and the sandy shores of Cape Cod Bay just 0.6 miles away, the property captures the very best of refined coastal living.
The estate's spectacular outdoor setting is among its most compelling features. Surrounded by mature landscaping and thoughtfully maintained grounds, the heated saltwater swimming pool and adjoining spa create the atmosphere of a private resort. Spend leisurely afternoons basking in the summer sunshine, enjoy refreshing swims after a morning at the beach, or settle into the spa as evening approaches. The surrounding outdoor spaces provide a beautiful backdrop for relaxation and gathering, while the separate guest house adds an exceptional degree of flexibility and privacy for larger groups.
Inside the main residence, an extensive renovation has created interiors that balance timeless New England character with sophisticated contemporary finishes. The expansive main level is centered around a beautifully appointed gourmet kitchen featuring premium appliances, generous preparation space, and an inviting breakfast nook. An adjoining sitting area encourages conversation while meals are prepared, while the elegant dining room, comfortably seating 14 guests, offers an exceptional setting for gathering everyone around the table for memorable summer dinners.
Beyond the principal entertaining spaces, the home offers a thoughtful collection of additional rooms designed for both relaxation and privacy. A welcoming den provides an intimate setting for conversation, games, or quiet evenings, while a separate library and office offers a peaceful retreat for reading or attending to work during an extended stay. A convenient side entrance opens to a mudroom and full bathroom, providing a practical transition between the home's interior and its outdoor amenities.
The main residence features five beautifully furnished bedrooms arranged across the upper and lower levels. On the second floor, the spacious primary suite features a king bed, private en-suite bathroom, and access to a generous deck overlooking the swimming pool and guest house. This inviting outdoor space offers a wonderful vantage point for enjoying morning coffee or the peaceful atmosphere of the property. Three additional second-floor bedrooms include a queen bedroom with its own en-suite bathroom, a second queen bedroom, and a flexible guest room furnished with two double beds, one of which includes a pullout double trundle. The finished lower level features a fifth bedroom with four twin beds arranged as two sets of trundle daybeds, along with a recreation room that provides another welcoming space for guests to gather and unwind.
Complementing the main residence is a delightful detached guest house, providing a private retreat within the estate. Complete with a king bedroom on the upper level, a full bathroom, a well-equipped kitchenette, and its own comfortable living area, this separate accommodation is particularly appealing for grandparents, extended family, or guests who appreciate additional independence. Together, the two residences offer an exceptional balance of shared gathering spaces and private accommodations, making the property especially well suited for multigenerational vacations.
The setting places guests in one of Cape Cod's most desirable Northside communities, celebrated for its historic charm, beautiful beaches, and relaxed coastal sophistication. Cold Storage Beach is just 0.6 miles away, offering convenient access to the sandy shoreline and inviting waters of Cape Cod Bay. Spend the day enjoying the beach, explore nearby Sesuit Harbor, or discover the natural beauty and maritime character that distinguish this exceptional stretch of coastline.
Historic Dennis Village, approximately 3 miles away along scenic Route 6A, offers an appealing collection of boutiques, restaurants, galleries, and local attractions. From leisurely lunches and evenings dining out to discovering nearby beaches and picturesque coastal roads, East Dennis provides an ideal setting for experiencing the quieter, more refined side of Cape Cod summer living.
Whether spending sun-filled afternoons beside the heated saltwater pool, gathering for dinner in the elegant dining room, or enjoying quiet moments surrounded by the property's beautifully maintained grounds, 58 Pleasant Street offers a vacation experience defined by exceptional comfort, thoughtful design, and an enviable coastal location. With its remarkable combination of beautifully renovated interiors, separate guest accommodations, resort-style amenities, and proximity to Cape Cod Bay, this extraordinary estate provides a memorable setting for generations of family and friends to come together.
The property is available year-round, with accommodations and amenities varying by season. The heated pool and spa are open from May 22 through October 2, 2027. During this period, guests enjoy access to the full six-bedroom property, including the separate guest house, with accommodations for up to 14 guests. Peak-season reservations require a seven-night minimum with Saturday arrivals and departures, while four-night stays are available during the shoulder seasons.
Outside of the pool season, the property is available with a three-night minimum stay and includes the five-bedroom main residence only, accommodating up to 12 guests. The guest house, pool, and spa are closed during this period, and the cleaning fee is reduced accordingly. Bed linens and bath towels are provided for all reservations. Pets are not permitted.
Booking is subject to all applicable taxes and fees. All Robert Paul Vacation Rental bookings include a nonrefundable fee of $150 to $250, which covers administrative services and damage-waiver protection for up to $1,000 in self-reported incidental damage. Upon receipt of a booking request, an agent will contact you to explain the process for signing the required rental agreement. Additional damage protection is also required for this home. The preferred option is the purchase of damage insurance providing $5,000 in coverage. In lieu of purchasing this coverage, a refundable security deposit of $5,000 will be added to the reservation. Please inquire before booking with any questions.
BEDROOM CONFIGURATION:
Main House 2nd Floor:
Bedroom 1 (Primary Suite)- 1 king bed w/ ensuite bathroom
Bedroom 2- 1 queen bed w/ ensuite bathroom
Bedroom 3- 1 queen bed
Bedroom 4- 2 double beds (1 double w/ double trundle bed underneath)
Main House Lower Level:
Bedroom 5- 4 single beds (2 sets of trundle day beds)
Guest House 2nd Floor:
Bedroom 6- 1 king bed
