33 Middle St Gloucester, MA ^$ 1,199,000

33 Middle St

^$ 1,199,000

Back to search

33 Middle St

Gloucester, MA, 01930

^$ 1,199,000

Bedrooms9 Baths5.0 Sq 4,600

Monthly Estimate*

^$ 7,382

33 Middle St, Gloucester, MA 01930 - Image 1

33 Middle St, Gloucester, MA 01930 - Image 2

33 Middle St, Gloucester, MA 01930 - Image 3

33 Middle St, Gloucester, MA 01930 - Image 4

33 Middle St, Gloucester, MA 01930 - Image 5

33 Middle St, Gloucester, MA 01930 - Image 6

33 Middle St, Gloucester, MA 01930 - Image 7

33 Middle St, Gloucester, MA 01930 - Image 8

33 Middle St, Gloucester, MA 01930 - Image 9

33 Middle St, Gloucester, MA 01930 - Image 10

33 Middle St, Gloucester, MA 01930 - Image 11

33 Middle St, Gloucester, MA 01930 - Image 12

33 Middle St, Gloucester, MA 01930 - Image 13

33 Middle St, Gloucester, MA 01930 - Image 14

33 Middle St, Gloucester, MA 01930 - Image 15

33 Middle St, Gloucester, MA 01930 - Image 16

33 Middle St, Gloucester, MA 01930 - Image 17

33 Middle St, Gloucester, MA 01930 - Image 18

33 Middle St, Gloucester, MA 01930 - Image 19

33 Middle St, Gloucester, MA 01930 - Image 20

33 Middle St, Gloucester, MA 01930 - Image 21

33 Middle St, Gloucester, MA 01930 - Image 22

33 Middle St, Gloucester, MA 01930 - Image 23

33 Middle St, Gloucester, MA 01930 - Image 24

33 Middle St, Gloucester, MA 01930 - Image 25

33 Middle St, Gloucester, MA 01930 - Image 26

33 Middle St, Gloucester, MA 01930 - Image 27

33 Middle St, Gloucester, MA 01930 - Image 28

33 Middle St, Gloucester, MA 01930 - Image 29

33 Middle St, Gloucester, MA 01930 - Image 30

33 Middle St, Gloucester, MA 01930 - Image 31

33 Middle St, Gloucester, MA 01930 - Image 32

33 Middle St, Gloucester, MA 01930 - Image 33

33 Middle St, Gloucester, MA 01930 - Image 34

33 Middle St, Gloucester, MA 01930 - Image 35

33 Middle St, Gloucester, MA 01930 - Image 36

33 Middle St, Gloucester, MA 01930 - Image 37

33 Middle St, Gloucester, MA 01930 - Image 38

33 Middle St, Gloucester, MA 01930 - Image 39

33 Middle St, Gloucester, MA 01930 - Image 40

33 Middle St, Gloucester, MA 01930 - Image 41

33 Middle St, Gloucester, MA 01930 - Image 42

Single Family Home for sale in Gloucester, MA

for $1,199,000 with 9 bedrooms and 5 full baths. This 4,600 square foot home was built in 1853 on a lot size of 0.17.

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.

Single Family Active

Price

^$ 1,199,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 9,219

Style

Colonial

Lot Size

0.17

Year Built

1853

Town/City

Gloucester

County/Region

Essex

MLS | Web ID

73429533

List By

Debra L. Lovelace

Listing Agent

Churchill Properties

Broker

Affordability Calculator

$8,151

Per Month

Monthly Principal & Interest: $7,382
Monthly Property Taxes: $768
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends

Single family listings in Gloucester, MA

Average List Price ^$1,681,580

Percent of Sale Price 40%

About Gloucester, MA

29,325 Population

-3% Since 2002

^$65,220 Median Income

48.77 Median Age

20% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

MLS Property Information Network, Inc rules require that you sign in here to see more detail on this property.

Pricing History

Date	Price	Price Change	Description
9/11/2025	$1,199,000		Listed Price

Map

More homes like this one

homes for you

See all

33 Middle St, Gloucester, MA, 01930 is a Single Family Home for sale at $1,199,000 with 4,600 sqft and a lot size of 0.17. 33 Middle St has 9 bedrooms, 5.0 baths, and was built in 1853. The property's zip code is 01930 which is in Gloucester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 1/20/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

*Full Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

33 Middle St

Single Family Home for sale in Gloucester, MA

Affordability Calculator

Neighborhood & Schools

Map

More homes like this one

Get more info about this home