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1 Chester Street • $7,750,000 Pending

Town, Nantucket, MA 02554

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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.

Floor 1: 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.

Floor 2: 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.

Floor 3: 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.

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.

Parking:> 4 Car Off Street

Listed by William Raveis Nantucket

Virtual Tour
1 Chester Street Location
Property Code: #91894
Bedrooms:
6 beds
Bathrooms:
5 and 1 half
Lot:
5,227 sq ft
Year Built:
1777
Heating Type:
GFHA
Listed:
328 ago
Assessed Value:
$4,087,900

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Property Information for 1 Chester Street
Property Summary

Type: 1 Family

Rooms: 15

Year Built: 1777

Remodeled: 2023

Water View:

Other View: Hbr, D/Hrb

Zoning: ROH

Lot Size(SF): 5101

Furnished: Furnished

2nd Dwelling: None

Water: Town

Sewer: Twn

Lot Size(A): 0.12

Beds/Baths: 6/5

Wtr Frontage:

Total SqFt(GLA): 5227

Amenities

First Floor Bedrooms: 1

Heating: GFHA

Fireplaces: 6

Floors: Antique wide pine

Yard: Yes

Parking: 4 Car Off Street

Foundation: Stone

Lead Paint:

Recreation and Outdoor Spaces: Deck, Patio, Garden

Amenities:

Taxes and Fees

Building Assessment: 2542200

Land Assessment: 1545699.99

Total Assessment: 4087899.99

Tax Year: 2025

Property History for 1 Chester Street
Dec 11, 2025
Pending
1 Chester Street :: Town
$7,750,000
1 Family
328 Days on Market
Listed by: William Raveis Nantucket
Nov 16, 2022
Closed
23A West Chester Street # 1 - Town
Listed Price
$895,000
Sold Price
$850,000
Condo
40 Days on Market
Listed by: Great Point Properties
Feb 5, 2021
Closed
1 Chester Street - Town
Listed Price
$2,595,000
Sold Price
$2,275,000
1 Family
271 Days on Market
Listed by: J Pepper Frazier Co.
Dec 7, 2020
Closed
23A West Chester Street # 1 - Town
Listed Price
$695,000
Sold Price
$642,900
Condo
174 Days on Market
Listed by: BHHS Island Properties Nantucket
Oct 7, 2020
Withdrawn
1 West Chester Street Extension - Cliff
$9,875,000
1 Family
1421 Days on Market
Listed by: Maury People Sotheby's International Realty
Oct 28, 2019
Closed
19 1/2 West Chester Street # 2 - Town
Listed Price
$1,475,000
Sold Price
$1,440,000
1 Family
123 Days on Market
Listed by: Great Point Properties
Jul 30, 2019
Off Market
1 Chester Street - Town
$0
1 Family
0 Days on Market
Listed by: J Pepper Frazier Co.
Feb 11, 2018
Withdrawn
23 West Chester Street # 1 - Town
$699,000
Condo
211 Days on Market
Listed by: William Raveis Nantucket
Dec 17, 2016
Withdrawn
23A West Chester Street # 1 - Town
$750,000
Condo
180 Days on Market
Listed by: Fisher Real Estate
Sep 12, 2016
Closed
1 West Chester Street - Town
Listed Price
$1,995,000
Sold Price
$1,795,000
1 Family
439 Days on Market
Listed by: William Raveis Nantucket
Jul 8, 2014
Closed
19 West Chester Street #1 - Town
Listed Price
$1,299,000
Sold Price
$1,290,000
Condo
431 Days on Market
Listed by: Great Point Properties
May 24, 2012
Withdrawn
19 West Chester Street #1 - Town
$1,495,000
Condo
233 Days on Market
Listed by: Great Point Properties
Oct 6, 2010
Closed
1 West Chester Street Extension - Cliff
Listed Price
$6,905,000
Sold Price
$6,905,000
1 Family
0 Days on Market
Listed by: LINK Listing Information Network
Jan 17, 2008
Off Market
19 West Chester Street # 1 - Town
$1,695,000
Condo
0 Days on Market
Listed by: Country Village
Jul 25, 2007
Withdrawn
19 1/2 West Chester Street # 2 - Town
$1,450,000
Condo
1 Days on Market
Listed by: Lee Real Estate
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