$5,750,000

Chelmsford

  • 6 Beds
  • 8 Baths
  • 7,000 Sqft
  • 18,121 Sqft lot
  • 43
    Views for last 30 days
  • 13

About the Property

This iconic Bermuda residence on Pitt’s Bay Road invites you through a grand foyer that immediately sets the tone for a home rich in history, character, and refined charm. Designed for entertaining, Chelmsford offers a formal sitting room for intimate gatherings and a spacious dining room with an adjoining bar room that has hosted countless memorable dinner parties. A dedicated office provides

This iconic Bermuda residence on Pitt’s Bay Road invites you through a grand foyer that immediately sets the tone for a home rich in history, character, and refined charm. Designed for entertaining, Chelmsford offers a formal sitting room for intimate gatherings and a spacious dining room with an adjoining bar room that has hosted countless memorable dinner parties. A dedicated office provides the ideal setting for working from home, while the gourmet kitchen (featuring indoor-outdoor flow to the pool patio) caters beautifully to both chefs and entertainers alike. For outdoor dining, plenty of space is available for gatherings of any size, as well as a fire pit lounge and a large flat yard, ideal for kids or pets at play. Upstairs, five generous bedrooms each include their own en-suite bathrooms, offering privacy, comfort, and understated luxury for family and guests. Additional amenities include a full bathroom on the lower level and two powder rooms. Tucked away on the property is a separate one-bedroom apartment, ideal for guests, staff, or extended family. An oversized garage, gym, and even a wellness retreat within the lower level of the estate create a private sanctuary designed for both convenience and rejuvenation. This is more than just a home. It’s a piece of Bermuda’s heritage, thoughtfully reimagined for contemporary living. Please contact co-listing agents Ben Rego and Christina Georgopoulos for a tour at your earliest convenience.

  • Property type

    House

  • Price/sqft

    $821

Features

  • Pool
  • Water View
  • Garden
  • Terrace
  • Game Room
  • Fire Pit
  • Fitness Center / Gym
  • Garage
  • Modern
Features

Lot

  • Water View
  • Privacy
  • Modern

Indoor

  • Office
  • Fireplace
  • Air Conditioning
  • Kitchen island
  • Washer Dryer
  • Bar
  • Game Room
  • Stone Countertops
  • Fitness Center / Gym

Outdoor

  • Terrace
  • Balcony
  • Fire Pit
  • Pool
  • Garage
  • Outdoor Living Space
  • Garden

Explore the Area

Chelmsford 55 Pitts Bay Road, Pembroke, PEM HM06, Hamilton, Pembroke Parish, Bermuda View on Google Maps
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Ben Rego

Joined 11 years ago
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Ben Rego
Bermuda
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5
Listings
2016
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Rego Sotheby's International Realty
Rego Sotheby's International Realty
85 Front Street, HM AX, Hamilton, Bermuda
View agency profile
Rego Sotheby’s International Realty is Bermuda’s oldest full service real estate
firm and leaders in luxury, co
Rego Sotheby’s International Realty is Bermuda’s oldest full service real estate
firm and leaders in luxury, commercial and hotel-tourism real estate. Founded in
1949 by Benjamin Rego, the company in 1983 became one of the first companies
invited to join the Sotheby’s International Realty network under the second
generation leadership of Buddy Rego. In 2014, Penny MacIntyre became Partner and
continues to head up the Commercial practice. Today, Rego Sotheby’s
International Realty is called upon by Bermudians, Government, Fortune 100
companies and international clients to service their residential and commercial
real estate needs. Rego Sotheby’s International Realty is a licensed auctioneer
and provides services from property management, valuations, professional
services and hotel-tourism sales and leasing throughout the island and around
the world through the Sotheby’s International Realty brand’s 850 offices in 65
countries and territories worldwide. Rego Sotheby’s International Realty and its
team members have been recognized year-over-year with Best of Bermuda Awards for
Best Residential Agent, Best Commercial Agent and Best Commercial Real Estate
Team. Visit us at [hidden information], [hidden information] and
[hidden information]
Last updated
July 7
First listed
Oct 14, 2025
Listing reference
MFDHZS
Contract status
Contract Pending
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