John F. Trudel III
Maury People Sotheby's International Realty
(508) 419-4062
32 Total Sales
32 in Nantucket
$779K - $7M Price Range
"Winds Aloft" 5 Bedrooms | 4 Baths | Private Pool | Two-Car Garage with Guest Suite.
Tucked away on a peaceful and generously sized 20,000 sq ft lot, "Winds Aloft" is an exceptional Nantucket residence that blends timeless design with effortless coastal living.
The sun-drenched, open-concept main house features three bedrooms plus a flexible den space, and gracious layout designed for both comfort and entertaining. Expansive windows frame picturesque views of the beautifully landscaped yard, lush gardens, and a private swimming pool, creating a seamless connection between indoor and outdoor living.
Perfect for hosting guests or working remotely, the detached two-car garage includes a fully equipped one-bedroom guest suite above—offering flexible space for extended family, visitors, or a private office retreat.
Located in R-1 zoning, this oversized parcel allows for 30% ground cover, leaving generous square footage for future expansion or a potential subdivision (with appropriate approvals). Just 0.8 miles from the center of downtown Nantucket and with easy access to bike paths and Nantucket’s pristine beaches, "Winds Aloft" offers exceptional lifestyle and investment potential.
Whether as a personal retreat or a high-performing rental, this distinctive property presents a rare opportunity to enjoy—and grow into—one of the island’s most desirable locations.
John F. Trudel III
Maury People Sotheby's International Realty
(508) 419-4062
32 Total Sales
32 in Nantucket
$779K - $7M Price Range
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
Chandra Miller
Maury People Sotheby's International Realty
(508) 639-1348
134 Total Sales
134 in Nantucket
$400K - $17M Price Range
Brian Sullivan
Fisher Real Estate
(774) 551-1184
56 Total Sales
57 in Nantucket
$1M - $28.9M Price Range
Cameron Gammill
Fisher Real Estate
(774) 768-5045
66 Total Sales
69 in Nantucket
$250K - $21M 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 |
|---|---|---|---|
| $5,300,000 | -- | ||
| S K Gargano 2018 | -- | None Available | |
| Gargano Paul | $115,000 | -- | |
| Barrett Roy K | $150,000 | -- |
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 |
|---|---|---|---|
| Open | $2,500,000 |
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 | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 09/23/2025 09/23/25 | Sold | $5,300,000 | +1.9% | $2,024 / Sq Ft |
| 08/20/2025 08/20/25 | Pending | -- | -- | -- |
| 06/18/2025 06/18/25 | For Sale | $5,200,000 | -- | $1,986 / 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 | $8,635 | $2,632,600 | $967,800 | $1,664,800 |
| 2024 | $8,476 | $2,708,000 | $1,051,900 | $1,656,100 |
| 2023 | $6,978 | $2,173,900 | $923,500 | $1,250,400 |
| 2022 | $61 | $1,628,800 | $607,500 | $1,021,300 |
| 2021 | $6,200 | $1,708,100 | $675,000 | $1,033,100 |
| 2020 | $6,038 | $1,750,200 | $675,000 | $1,075,200 |
| 2019 | $5,822 | $1,732,700 | $657,500 | $1,075,200 |
| 2018 | $6,211 | $1,740,800 | $749,600 | $991,200 |
| 2017 | $5,830 | $1,719,800 | $749,600 | $970,200 |
| 2016 | $5,620 | $1,672,600 | $723,300 | $949,300 |
| 2015 | $5,619 | $1,556,400 | $740,400 | $816,000 |
| 2014 | $5,809 | $1,545,000 | $729,000 | $816,000 |
CC
Seller's Agent in 2025
Christine Carpenter
William Raveis Nantucket
(508) 332-9955
7 Total Sales
RS
Buyer's Agent in 2025
Robin Slick
William Raveis Nantucket
(917) 991-4816
7 Total Sales
Source: LINK
MLS Number: 92318
APN: NANT-000-056-000-000-0000-57-000-000
Ask me questions while you tour the home.