Boston Luxury Condos and Apartments
355 Boylston St / (617) 233-5800

33 Middle St

Gloucester, MA ID #73429533

1/42
2/42
3/42
4/42
5/42
6/42
7/42
8/42
9/42
10/42
11/42
12/42
13/42
14/42
15/42
16/42
17/42
18/42
19/42
20/42
21/42
22/42
23/42
24/42
25/42
26/42
27/42
28/42
29/42
30/42
31/42
32/42
33/42
34/42
35/42
36/42
37/42
38/42
39/42
40/42
41/42
42/42

33 Middle St

- Gloucester, MA ID #73429533

Property Description

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.

Additional Details

  • Status: ACT
  • Type: Single Family, Single Family Residence
  • Zip Code: 01930
  • Taxes: 9,219
  • Acres: 0.17

Parking

  • Garage: 1
  • Garage Capacity: 3
  • Parking: Attached, Off Street
  • Parking Spaces: 3

Rooms/Dimensions

  • Total Rooms: 17

Location

Get Directions
Luxury Condo Buildings
Luxury Apartment Buildings
More buildings

Request more Information or schedule a tour of:
33 Middle St, Gloucester, MA

When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are purchasing a luxury home, condo or renting an apartment, we pledge to make your experience as stress free and enjoyable as possible.

For prompt, expert service and answers to all your questions, please send us a message or call anytime at
617-233-5800

* Required Fields.

By submitting your information you agree to our Terms and Conditions and Privacy Policy.

Request Info
Content © 2025 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Debra L. Lovelace of Churchill Properties. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.