33 Middle St

Gloucester MA 01930

4600 sq. ft.

7512 sq. ft.

Single-Family

Last sold for $1,160,000

Debra Lovelace, last sold this property on 30 April 2026 after 230 days on market.

Overview

Built in 1853 and beautifully updated for today’s lifestyle, the Obadiah Woodbury Home offers a rare chance to own a piece of Gloucester’s history. Just steps to Stacey Boulevard, the Inner Harbor, restaurants, galleries, shops, beaches, and the MBTA, this stately in-town residence delivers coastal living with standout walkability. Inside are soaring ceilings, spacious rooms, classic moldings, and ornate fireplaces that honor its character, while a fully modernized kitchen adds everyday function. With a flexible layout and generous proportions, it’s ideal for multi-generation living. Recent upgrades include new roofing, full removal of knob-and-tube wiring, a state-of-the-art gas heating system with zones, and custom library shelving. The private yard is a rare in-town oasis—perfect for entertaining, gardening, or quiet relaxation. Whether as a primary residence or second home, this gracious historic gem captures the best of Gloucester.

Features

9 bedrooms

5 bathrooms

4 carspaces

3 open car spaces

1 garage space

4600 sq. ft. floor area

7512 sq. ft. lot size

Single-Family

Estimated Value

We need at least 3 similar 9 bedroom single-family properties sold in Gloucester over the last 12 months.

Property history for 33 Middle St

2026

Sold

$1,160,000

30 Apr 2026 by Debra Lovelace, of Churchill Properties

2022

Sold

$950,000

21 Dec 2022 by Amanda Armstrong, of Compass

2018

Sold

$649,000

26 Sep 2018 by Amanda Armstrong, of Engel & Volkers By the Sea

Happy sellers in Gloucester

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