Nathan Kaiser
J Pepper Frazier Co.
(720) 549-4751
6 Total Sales
6 in Nantucket
$1.8M - $9.2M Price Range
Estimated Value: $5,925,000 - $8,076,000
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.
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Nathan Kaiser
J Pepper Frazier Co.
(720) 549-4751
6 Total Sales
6 in Nantucket
$1.8M - $9.2M Price Range
Kenny Hilbig-Ross
Jameson Sotheby's International Realty
(508) 680-0447
20 Total Sales
13 in Nantucket
$1.1M - $4M Price Range
John F. Trudel III
Maury People Sotheby's International Realty
(508) 419-4062
33 Total Sales
33 in Nantucket
$500K - $7M Price Range
Jennifer Shalley Allen
Fisher Real Estate
(508) 901-2706
42 Total Sales
42 in Nantucket
$852K - $18M Price Range
Brian Sullivan
Fisher Real Estate
(774) 551-1184
52 Total Sales
52 in Nantucket
$1M - $28.9M Price Range
Chandra Miller
Maury People Sotheby's International Realty
(508) 639-1348
133 Total Sales
133 in Nantucket
$400K - $17M Price Range
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $7,400,000 | -- | ||
| $2,275,000 | None Available | ||
| $400,000 | -- |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $4,100,000 | ||
| Closed | $1,592,500 |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 12/16/2025 12/16/25 | Sold | $7,400,000 | -4.5% | $1,451 / Sq Ft | |
| 12/11/2025 12/11/25 | Pending | -- | -- | -- | |
| 10/14/2025 10/14/25 | Price Changed | $7,750,000 | -6.1% | $1,519 / Sq Ft | |
| 08/08/2025 08/08/25 | Price Changed | $8,250,000 | -5.7% | $1,617 / Sq Ft | |
| 04/18/2025 04/18/25 | Price Changed | $8,750,000 | -10.3% | $1,715 / Sq Ft | |
| 01/16/2025 01/16/25 | For Sale | $9,750,000 | +328.6% | $1,911 / Sq Ft | |
| 02/05/2021 02/05/21 | Sold | $2,275,000 | -24.0% | $517 / Sq Ft | View Prior Sale |
| 01/06/2021 01/06/21 | Pending | -- | -- | -- | |
| 07/25/2019 07/25/19 | For Sale | $2,995,000 | -- | $681 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $13,408 | $4,087,900 | $1,545,700 | $2,542,200 |
| 2024 | $12,586 | $4,021,100 | $1,545,700 | $2,475,400 |
| 2023 | $7,776 | $2,422,400 | $1,472,000 | $950,400 |
| 2022 | $99 | $2,657,600 | $1,226,600 | $1,431,000 |
| 2021 | $9,854 | $2,714,700 | $1,129,800 | $1,584,900 |
| 2020 | $10,215 | $2,960,900 | $1,129,800 | $1,831,100 |
| 2019 | $9,958 | $2,963,700 | $1,129,800 | $1,833,900 |
| 2018 | $8,845 | $2,505,700 | $1,129,800 | $1,375,900 |
| 2017 | $8,280 | $2,442,600 | $1,129,800 | $1,312,800 |
| 2016 | $8,001 | $2,381,200 | $1,097,500 | $1,283,700 |
| 2015 | $8,419 | $2,332,200 | $1,108,400 | $1,223,800 |
| 2014 | $8,269 | $2,199,200 | $975,400 | $1,223,800 |
R
Seller's Agent in 2025
Robert Young
William Raveis Nantucket
(508) 325-1571
58 Total Sales
N
Buyer's Agent in 2025
Nicole Tirapelli
Douglas Elliman Nantucket
(312) 296-8048
8 Total Sales
D
Seller's Agent in 2021
Dalton Frazier
J Pepper Frazier Co.
(508) 360-6517
74 Total Sales
P
Buyer's Agent in 2021
Penny Dey
Atlantic East Nantucket Real Estate
(508) 221-0801
34 Total Sales
Source: LINK
MLS Number: 91894
APN: NANT-004-243-000-000-0000-18-000-000
Ask me questions while you tour the home.