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$1,199,000

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 5 Full Baths
  • 4,600 Sq. Ft.
  • 0.17 Acres
  • 1 Car Garage
  • Updated 4 days ago
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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.

Full Property Details for 33 Middle St

General

  • Price: $1,199,000
  • Taxes: $9,219 (2024)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73429533
  • Updated: 1/12/2026
  • Added to Site: 127 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5
  • Bathroom 1: First
  • Bathroom 2: Second
  • Bathroom 3: Second

Bedrooms

  • Total Bedrooms: 9
  • Primary Bedroom: Second
  • Bedroom 2: Second
  • Bedroom 3: Second
  • Bedroom 4: Third

Other Rooms

  • Living Room: First
  • Family Room: First
  • Kitchen: Main, First
  • Dining Room: First

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Parking Features: Attached, Off Street

Location

  • County: Essex

Structural Information

  • Architectural Style: Colonial
  • Basement: Yes
  • Square Feet: 4,600
  • Year Built: 1853

Lot Features

  • Lot Size (Acres): 0.17

Financial Considerations

  • Tax Amount: $9,219
  • Tax Year: 2024

Disclosures and Reports

  • Disclosures/Rstr.: First showings at Open House on Saturday 13, 2025 1:00pm to 2:00pm
  • Property ID: M:0007 B:0085 L:0000, 1893752

Listed by Churchill Properties, Debra L. Lovelace

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Listing agent

— 33 Middle St —

  • Debra L. Lovelace

    Churchill Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 33 Middle St

School District:Gloucester School District
NameGradesDistance
Beeman Memorial
138 Cherry Street, Gloucester, MA 01930
K-51.7 mi
Ralph B O'maley Middle School
32 Cherry Street, Gloucester, MA 01930
6-81.3 mi
Gloucester High School
32 L O Johnson Rd, Gloucester, MA 01930
9-120.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 33 Middle St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/11/2025
Listed
$1,199,000
26.21%
MLS
12/20/2022
Sold
$950,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 33 Middle St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,281
1%
$954,800
1%
2024
$9,219
15%
$947,500
25%
2023
$8,026
3%
$757,900
14%
2022
$7,792
3%
$664,300
10%
2021
$7,535
-1%
$605,700
-2%
2020
$7,625
31%
$618,400
35%
2019
$5,809
3%
$457,800
5%
2018
$5,644
4%
$436,500
6%
2017
$5,411
21%
$410,200
24%
2016
$4,487
6%
$329,700
6%
2015
$4,248
8%
$311,200
2%
2014
$3,951
—
$304,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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Listed by Churchill Properties, Debra L. Lovelace

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Price Reduced near 33 Middle St

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Recent Sales near 33 Middle St

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5 Washington Square  Gloucester, MA 01930

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33 Middle St, Gloucester, MA 01930 (MLS# 73429533) is a Single Family property with 9 bedrooms and 5 full bathrooms. 33 Middle St is currently listed for $1,199,000 and was received on September 11, 2025. Want to learn more about 33 Middle St? Do you have questions about finding other Single Family real estate for sale in Gloucester? You can browse all Gloucester real estate or contact a Coldwell Banker agent to request more information.

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