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Agent Name: Jeffrey Lee
Agent Email: jefflee@leerealestate.com
Agent Phone: 508-325-5800
Town - 1 Chester Street
Primary Photo
Asking Price: $7,750,000
Original Price: $9,750,000 Type: Single Family
Lot Size (Acres): 0.12 Sq. Ft. (GLA): 5101
Total Rooms: 15 LINK ID: 91894
Beds/Baths: 6/5.5 Status: Available
Furnished: Furnished Owner: ONE CHESTER SMILEY LLC
One Chester Street is an exceptional residence that perfectly blends historic charm with modern luxury. Situated at the edge of Nantucket's historic district where the Cliff area meets Brant Point, this home offers a prime location that provides easy access to the best of island living. This 18th-century ship captain’s home has been meticulously restored, preserving its original details, including five working fireplaces, while integrating contemporary amenities for today's lifestyle. Sold fully furnished with interior design by The Nantucket Looms, the home boasts four levels of living space, with six bedrooms and five and a half baths, it comfortably accommodates large groups, offering ample room for relaxation and privacy. The spacious open kitchen features the original 6' walk-in fireplace, breakfast area, adjoining a bright family/TV room that opens directly onto the rear deck, patio, and garden. The formal dining room features a beautiful lacquered finish. The outdoor space is equally impressive, with a unique artist-built gazebo and fire pit—a perfect spot for evening gatherings. The home’s renovations are top of the line, including all new plumbing, electrical, and HVAC systems, with high-end finishes throughout. The lower level is dedicated to entertainment, with a fully equipped game room including a combination ping pong/pool table, three TVs, a separate seating area, and a kitchenette. For quieter moments, the third-floor guest suite provides access to the roof walk with panoramic views of Nantucket Sound and Harbor, making it a wonderful spot to unwind. One Chester Street is the perfect combination of historic elegance and modern comfort. Approximately 350+/-sf remaining ground cover for an addition or a garage.
Property / Parcel Info
Map: 4243
Parcel: 18
Zoning: ROH
Plan: 0
Deed Ref.: Book 1801 Page 049
Lot #: 1
Water: Town
Sewer: Town
Easements: None known
Water Frontage: None
Water Views: Harbor
Other Views: Distant Harbor
Lead Paint: Unknown
Second Dwelling: None
Taxes and Fees
Assessment Year: 2025
Land Assessment: $1,545,700
Building Assessment: $2,542,200
Total Assessment: $4,087,900
Estimated Taxes: $0.00
Building Information
Year Built: 1777
Year Renovated: 2023
# of Rooms: 15
Total # of Bedrooms 6
First Floor Bedrooms: 1
# of Full Bathrooms 5
Half Baths 1
Fireplaces: 6
Floors: Antique wide pine
Heat: Gas\FHA
Yard: Yes
Parking: 4 Car Off Street
Foundation: Stone
Other Buildings:
Outdoor Spaces/Recreation: Deck, Patio, Garden
Appliances & Other Amenities
Stove: Wolf
Refrigerator: 48" Sub Zero PRO Legacy
Dishwasher: 2 Bosch
Washer: Yes 2
Dryer: Yes 2
TV Service Type: Cable
Amenities: Alarm, Central A/C, Disposal, Insulation, Irrigation, Outdoor Shower
Descriptions / Comments
Basement: The lower level has large windows for natural light and is finished with an epoxy floor. The game room is equipped with a kitchenette, storage cupboards, banquette seating, a combination ping pong/pool table, a poker table, with 2 TVs. There is an additional sitting room with a 3rd TV, as well as a 2nd laundry and a utility/storage room. A bulkhead leads to the side yard, where there is an attached storage shed.
1st Floor: The house is elevated above the street and is accessed via a set of “friendship stairs". On entering the front hallway, the first room to your left is the original front parlor. With a rebuilt fireplace, antique raised paneling, wide pine floors, corner posts, and original trim detail. To the right of the front door is an en-suite queen bedroom. The private tiled bath features a quartz vanity and brushed nickel hardware. The powder room and front hall closet are on the right as you walk toward the heart of the home. Here you’ll find the sun-filled family room which is open to the modern kitchen and breakfast area featuring the original 6’ walk-in kitchen fireplace. Two sets of French doors open onto the deck, patio and backyard. To the left is the formal dining room, finished in a dramatic blue lacquer, with antique paneling, a working fireplace, and built-in casework. There is a small bar that leads back to the front parlor. The kitchen is equipped with a Wolf stove, a 48” Subzero Pro Legacy refrigerator/freezer, 2 Bosch dishwashers, and 2 XO drink coolers for wine and soft drinks. The countertops are quartz, except for the island which is wood.
2nd Floor: The primary bedroom connects to a spacious, fully built-out dressing room, providing ample storage and organization. The en-suite primary bathroom offers a luxurious double quartz vanity and an oversized, tiled shower. Every bathroom throughout the home are equipped with heated tile floors for added comfort. Two additional queen-sized bedrooms, each with en-suite bath, offer privacy. A convenient laundry closet is located in the 2nd floor central hallway. At the back of the house, a small office with built-in bookcases creates a cozy workspace, while a rear staircase leads directly down to the kitchen, making it easy to move between floors.
3rd Floor: The third floor is set up as a separate guest suite/apartment. It features two bedrooms, 1 has two twin-size built-in bunks and a double bed, the other has a built-in queen bed. There is a kitchenette that has everything required for your guests and a full bath. Open seating area with TV and stairs to the expansive roof walk where you can sit and enjoy the quiet privacy and views of Nantucket harbor and sound.
Other Structures: Fire pit, Artist built cedar gazebo and arbor, storage shed, raised bed vegetable garden, and apple, peach, and pear trees.
Second Dwelling:
Map
Listing has been viewed 1933 times.
 DocumentDate Added
Plot Plan1/10/2025
Plot Plan1/10/2025
Floor Plan7/25/2025
Plot Plan7/25/2025
View In Full Screen 
Price Changes
Original Asking: 9,750,000
  1. 4/18/2025-$8,750,000- -10.26%
  2. 8/7/2025-$8,250,000- -5.72%
  3. 10/14/2025-$7,750,000- -6.07%
Discount From Original: 20.51%
Listing Updates
1/16/2025-New Listing
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