# 27 Longwood Drive, Nantucket, MA 02554

> **TL;DR:** 5bd/5ba single family, $3,975,000 ($1145/sqft), built 1990, 3,472 sqft.
> Fireplace. Est. $17,625/mo.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $3,975,000 |
| Price/sqft | $1145 |
| Bedrooms | 5 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 3,472 |
| Year Built | 1990 |
| Lot Size | 119,790 sqft (2.75 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 0 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $17,225 |
| HOA | $400 |
| **Total** | **$17,625** |

## Key Amenities

- Fireplace

## Property Highlights

- Built in 1990
- 2.75 acre lot
- Fireplace

## Description

### Agent Description
27 Longwood Drive is nestled on a sprawling 2.75-acre lot offering the ultimate in privacy and refined living. The generous foyer features a dramatic curved staircase leading to the second floor. This light-filled, charming, upside-down home features five bedrooms, three full bathrooms, and one half bathroom. The 2nd-floor open living space features a custom fireplace, a cathedral ceiling, a large dining area, and a kitchen with a distant view of Sankaty Light. The 2nd-floor deck, located off the living room, offers an uncompromising blend of comfort and seclusion, perfect for enjoying morning coffee or stargazing. Downstairs, you'll find two additional covered porches for entertaining and enjoying all year round. The carriage house, featuring an oversized two-bay garage, one bedroom, and one bathroom, is ideal for a large family and provides privacy for both you and your guests.

## Location

- **Address:** 27 Longwood Drive, Nantucket, MA 02554
- **Coordinates:** 41.2565089, -70.0011015
- **Google Maps:** https://www.google.com/maps?q=41.2565089,-70.0011015

## Listing Agent

- **Name:** Debbie Willett
- **Brokerage:** Great Point Properties
- **Phone:** 5082282266
- **Email:** debbiew@sconsetrealestate.com

## Primary Photo

![27 Longwood Drive - Primary Photo](http://lh.rdcpix.com/4db3ba33d93460d10923a8e4bf441938l-f4207600306r.jpg)

*81 total photos available on [listing page](https://www.propertysimple.com/listing/27-longwood-drive-nantucket-ma-02554-ma92560)*

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**MLS#:** 92560 | **Updated:** 2026-06-18
**Source:** listhub

*Copyright © 2026 LINK Nantucket. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/27-longwood-drive-nantucket-ma-02554-ma92560)

---

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