Gloucester MA Real Estate

Beautiful coastline, great restaurants and a bustling town center, Gloucester is the quintessential North Shore community. In the 1800's Gloucester gained prominence as a center of commerce for the fishing industry.

Established in 1623, this colonial city is one of the original members of the Massachusetts Bay Colony. Relics from is storied past can be seen all over town from monuments to the historic Stage Fort Park. Gloucester now has a population of just under 30,000. 

In the 1800's Gloucester gained prominence as a center of commerce for the fishing industry. Its rich cultural heritiage combined with its gorgeous beaches and coastline has turned Gloucester into a popular summer tourist destination.

Below, you'll find the latest listings for homes in Gloucester, MA. 

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View upcoming open houses in Gloucester.

59 Grapevine Road, Gloucester, MA
Open House

MLS Number 72284115

  • Single Family
  • Next Open House: Sun 25th 12:30 pm - 2:00 pm
  • Bathroom 4
  • Full Bath 3
  • Bedrooms 4

Enjoy living just steps away from the "Back Shore" in one of Gloucester's most desirable neighborhoods. Good Harbor Beach, Nile's Beach and Rocky Neck are nearby. This spacious home offers a formal front-to back living room and seasonal sun room. The large eat-in kitchen has pearl white cabinets accented with bead board and glass doors, center island, breakfast bar and granite counters. The family room would also make a great formal dining room or study. Retire each evening in the large master suite and relax in the master bath with attractive oval soaking tub and separate shower. Two more bedrooms have a "Jack & Jill" bathroom connecting each, and the laundry room is also on this second level. At the kitchen entrance, a 3 bay garage, and mud room with half bath, has a stairway leading up to a large heated/air conditioned open room offering a family room, cabinets plumbed for a kitchen, a bedroom area and full bath... Great space for extended family or vacationing guests.

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Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Dune Lane, Gloucester, MA

MLS Number 72284118

  • Single Family
  • Bathroom 2
  • Full Bath 2
  • Bedrooms 2
  • Year Built 1951

Spectacular Ocean views from almost every room of this home perched atop a hill in the exclusive private section of Wingaersheek Beach. Features include, vaulted beamed ceiling, stone front wood burning fireplace, 2nd floor family room with deck and sweeping ocean views. The property offers plenty of outdoor space and parking. This home can be enjoyed seasonally or year round. Steps from private Coffins Beach. A unique opportunity to own in this exclusive beachfront community. *** Rare Oversized lot with striking ocean views. Great opportunity to add on or build new construction.***

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Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Maplewood Avenue, Gloucester, MA 01930

MLS Number 72284238

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 1
  • Full Bath 1
  • Year Built 1988

Take all the advantages of urban life style in this professionally managed townhouse!! Conveniently located in downtown Gloucester with access to commuter rail, bus, convenient store, shopping, great restaurants, museums and more! Like swimming in a beach? You have it within a walking distance to the beach and park. This very well kept townhouse was just freshly painted and new carpets installed. Features open floor plan in the first floor and cathedral ceiling for both bedrooms. In-unit washer and dryer for the convenience and plenty of storage. Condo fee includes Heat and hot water.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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36 Bennett St No, Gloucester, MA

Price$225,000

Est. Mortgage: $/month

MLS Number 72283275

  • Land Residential
  • Acreage 2.11

This 2+ acre lot is set in a quiet and peaceful country setting close to Annisquam Village. This newly created lot has town approvals from zoning and planning and the seller will assist in the remaining permitting process as well. As an added bonus the building envelope has been cleared and water and sewer are on site.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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326 Main Street, Gloucester, MA 01930

MLS Number 72282411

  • Rental
  • Date Available 03/01/2018
  • Bedrooms 2

Sit on your porch and watch the fishing boats! Walk to all that Gloucester has to offer. The "T", restaurants, shops, beaches Wonderful 2 Bedroom 2 Bath garden style unit with a 1 car garage overlooking the Harbor and boats.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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145 Essex Avenue, Gloucester, MA 01930
Open House

MLS Number 72281969

  • Condo or Co-op
  • Next Open House: Sun 25th 12:00 pm - 2:00 pm
  • Bedrooms 2
  • Bathroom 1
  • Full Bath 1

Exciting two bedroom opportunity in West Gloucester. This handsome condominium was one of the first to go under contract at the condo conversion. Sited high up off the Annisquam River. This unit is located in building #6. Over looking river , bridge, marshland, city of Gloucester , wildlife and small woodland area. Positioned on the top floor.This end unit with balcony faces east for gorgeous sunrises. What sets this condo apart from others in this tight market is - amenities, parking , laundry , pet policy and condo fees that include heat, water and sewer. Owners will enjoy the new wifi clubhouse with fireplace and coffee station. Exterior grilling area & , fire pits lit by natural gas, 24 hour fitness center with wifi and television. Two deeded parking spots come with the unit. They can be seen from the second bedroom. This is a pet friendly community . Dogs are allowed with restrictions and must be approved by the board. Located about a little over a mile to commuter line,

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Chester Square, Gloucester, MA
Active With Contract

MLS Number 72281478

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Full Bath 3
  • Parking Spaces 2

DIRECT WATERFRONT Tucked away on a private lane in the sleepy village of Annisquam sits this fully renovated year round cottage style home directly on Lobster Cove. Open the front door and be drawn immediately to the wall of windows overlooking the water.You truly get the feeling that you are on a boat! Perfect for entertaining. A beautiful high end kitchen with gas range, SS appliances & honed granite counters.Gleaming fir floor, dining area & comfy living room with sliding door open to the picturesque views of Lobster Cove.There are 3 bedrooms on the main level including a master suite with a private waterview deck and bathroom with enlarged doorways. Upstairs is another master suite with spectacular views, private balcony, office space, dressing room, special soaking tub overlooking the cove, and beautiful tiled shower.Tidal dock directly on Lobster Cove for all your boating needs.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9 Friend Street, Gloucester, MA 01930

MLS Number 72281554

  • Rental
  • Date Available 02/25/2017
  • Bedrooms 2

Long-Term Rental! Heat & Hot Water included with this sun-lit year-round two bedroom apartment rental. First-Floor Unit! Meticulously maintained unit featuring views of our working harbor from its open concept eat-in kitchen and living room. This apartment further boast many other wonderful appointments to include slider to a rear expansive 19 x 8 deck overlooking the harbor, hardwood floors and period coffered ceilings in most rooms and an interior access basement to a large storage area with washer and dryer included. Parking is available. Very near Gloucester's downtown shopping and business district with easy access to highway, beaches and train station to Boston and beyond.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 Laurel Street, Gloucester, MA

Price$179,000

Est. Mortgage: $/month

MLS Number 72281150

  • Land Residential
  • Acreage 0.17

West Gloucester woods create serene country setting replete with nature walks, hiking trails, and river and beach access. Away from it all, yet accessible to all amenities, including commuter rail line, highway, downtown and widely acclaimed West Parish Elementary School. Existing uninhabited structure a probable tear-down leaving a slightly sloping but level cleared lot for new construction. Deeded access over 75' wide right of way. City water and electricity to site; soil tests being scheduled for new private sewer design installation to be buyer's responsibility. Estate procuring license to sell.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

54 Summer Street, Gloucester, MA 01930
Active With Contract

MLS Number 72281178

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 1
  • Full Bath 1

Fabulous Opportunity to buy a spacious condo wonderfully located in the heart of Gloucester and within walking distance to downtown shopping, Pavilion beach, commuter rail, & famous Stacey Boulevard! This wonderful 2 bedroom, 1 bath unit is part of a gorgeous Victorian building that sits up high so you can enjoy distant harbor views from outside! The interior has just been fully painted and the floors have been refinished and are now gleaming! The open concept floor plan and high ceilings are fantastic and some great bonuses include a private patio with exclusive use, 2 car tandem parking, in-unit laundry, and storage in the basement! Low condo fee and a domestic pet is allowed! Move right in! This is a superb value!

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

13 Middle Street, Gloucester, MA 01930

MLS Number 72280324

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 2
  • Full Bath 2

What an Opportunity! Ocean view condo in prime location near " The Boulevard", Marina and Stage Fort Park. Reportedly a Sea Captains home, this three bedroom, two full bath condo affords an eat-in kitchen, formal dining room, with a built-in china closet, high ceilings, as well as a fabulous dressing room/walk-in closet or office. Other amenities include a gas fireplace and additional storage. Dramatic ocean and harbor views from the two exclusive use decks.Be a part of historical Middle street homes while enjoying Gloucester's chic waterfront, beaches, dining and specialty shops.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Cleveland Place, Gloucester, MA 01930

MLS Number 72279537

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 1
  • Full Bath 1

This two bedroom condominium near the train station has been freshly painted, hardwood floors redone and is in move in condition. Good kitchen storage, granite counters, stainless appliances. Open concept living area has a spacious living room that will accommodate a good size sectional and there's still room for a dining set. Ideal location for commuters plus the Library, grocery shopping and some of Gloucester's finest restaurants are nearby.

{$agent->Name}

Windhill Realty
16 Market Street
Ipswich MA, 01938
Office: 978.356.8922

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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