Gloucester Real Estate

Gloucester is a coastal city on Cape Ann that combines its maritime traditions with tourism and a thriving arts culture that have energized the city’s downtown. The book and film “The Perfect Storm” in 2000 helped revitalize interest in this North Shore destination. The city center is just steps from the harbor while the famed Rocky Neck Art Colony includes bars, restaurants and numerous art galleries. Gloucester occupies most of the eastern end of Cape Ann and is split in half by the Annisquam River. The city comprises 41.5 square miles with 37% of that area occupied by water. The north side of the harbor is the most densely populated by the city’s 29,000 residents. A popular summer destination, Gloucester houses a few secluded ocean view properties that give off an “end of the world” ambiance. Neighborhoods include Annisquam, Bay View, East and West Gloucester, among others.  Read more about Gloucester.

Gloucester Homes & Condos For Sale

Gloucester Homes & Condos For Sale May 22, 2022
29
Listed
35
Avg. DOM
$546.97
Avg. $ / Sq.Ft.
$659,000
Med. List Price
29 Properties
Page 1 of 3
3
Beds
4F21/2
Baths
10,400
Sq.Ft.
1927
Year Built
199
Days on Site
72655588
MLS
Killybracken, an enchanting estate with expansive lawns and lush, perennial gardens, ensures absolute and self-sufficient privacy while enjoying stunning panoramic ocean views. The compound features...
4
Beds
4F11/2
Baths
8,443
Sq.Ft.
1999
Year Built
342
Days on Site
72849739
MLS
This oceanfront estate looks out over the Atlantic to the Twin Lights and beyond. Situated on 1.09 acres between the Atlantic and the Bass Rocks Golf course the property is 1 mile from Eastern Point...
5
Beds
3F11/2
Baths
4,148
Sq.Ft.
1991
Year Built
18
Days on Site
72977311
MLS
With commanding 180º views of the rocky coastline between Good Harbor and Long Beach, this striking 5 BR/3.5 BA contemporary/colonial offers a blend of elegance and the simple pleasures of life by...
Open 5/22
19 Chester Square Gloucester, MA 01930
$2,695,000
Neighborhood: Annisquam
5
Beds
4F11/2
Baths
3,259
Sq.Ft.
1880
Year Built
6
Days on Site
72982678
MLS
No unaccompanied appts. Nestled in a desirable enclave of Annisquam village, this newly renovated contemporary home makes maximum use of its idyllic setting with an open floor plan framed by floor to...
Contingent
54 Adams Hill Road Gloucester, MA 01930
3
Beds
2F11/2
Baths
1,273
Sq.Ft.
1920
Year Built
14
Days on Site
72978337
MLS
Once in a lifetime opportunity, steps from the beach! 54 Adams Hill Road, affectionally named "Stonepatch Cottage" evokes the spirit of Annisquam. The property overlooks the sandy shores of Cambridge...
$1,595,000
Neighborhood: Castle View
4
Beds
3F11/2
Baths
5,103
Sq.Ft.
1998
Year Built
11
Days on Site
72981209
MLS
APPOINTMENT REQUIRED FOR OPEN HOUSE SUNDAY 12-2- This impressive Contemporary, surrounded by beautiful conservation land, is within steps to the neighborhood path leading to private COFFINS BEACH....
2
Beds
2
Baths
1,629
Sq.Ft.
1900
Year Built
33
Days on Site
72969334
MLS
Newly rebuilt in 2022, this home provides panoramic views of the Annisquam River and the Little River. Situated on high ground, large windows and sliding glass doors provide dramatic water views and...
Open 5/22
2 Lane Rd Gloucester, MA 01930
$1,400,000
Neighborhood: Annisquam
3
Beds
2F11/2
Baths
2,509
Sq.Ft.
1920
Year Built
4
Days on Site
72984841
MLS
Annisquam - Idyllic and Tranquil! This unique & charming waterfront home offers stunning views of Lobster Cove. Beautiful granite walkways and a wisteria covered pergola provide a lovely shaded...
Open 5/22
9 Mechanic Place Gloucester, MA 01930
2
Beds
1
Baths
1,190
Sq.Ft.
1920
Year Built
6
Days on Site
72983166
MLS
Sold as a package w/7 Mechanic Place MLS ID 72983167 and not separately for $2,200,000. Blissfully perched at the edge of a sheltered, private cove in Gloucester s coveted Bayview community, with...
3
Beds
2F11/2
Baths
2,368
Sq.Ft.
1920
Year Built
33
Days on Site
72969261
MLS
Set amongst trees bordering Ravenswood Park, this handsome and thoughtfully designed three bedroom home has additional space in the walk up third level for a studio, extra space for guests or an...
Contingent
37 Coggeshall Rd Gloucester, MA 01930
3
Beds
1F11/2
Baths
1,311
Sq.Ft.
1941
Year Built
14
Days on Site
72978354
MLS
*DEEDED ACCESS TO IPSWICH BAY* Once in a generation (or two!) a seaside cottage like this comes up for sale. This rustic, Cape-style home sits at the very end of Coggeshall Lane overlooking Ipswich...
Open 5/22
75 Rocky Neck Ave #3 Gloucester, MA 01930
2
Beds
2
Baths
1,030
Sq.Ft.
2016
Year Built
4
Days on Site
72984863
MLS
ROCKY NECK WATERFRONT! Artists from all over the country have made this area a destination specifically to experience the amazing light that illuminates all of picturesque Smith Cove. This 2...

More About Gloucester

Gloucester Location

Gloucester is tucked between Ipswich Bay to the north and Massachusetts Bay to the south. Rockport borders the city on the east while Ipswich, Essex, and Manchester-by-the-Sea border Gloucester to the west. Gloucester lies 31 miles northeast of Boston and is home to the Cape Ann Transportation Authority which serves the city and surrounding towns. There are two railway stops in Gloucester that provide access to the MBTA Commuter rail which extends from Rockport along the North shore to Boston’s North Station.

Gloucester Recreation

Gloucester is home to Good Harbor Beach and to the white sands and tide pools of Wingaersheek. Known as a family-friendly beach, Wingaersheek Beach extends forever at low tide with shallow waters, gentle waves and tide pool formations ideal for kids to discover varying forms of marine life. Both beaches are accessible to the public and with facilities that include restrooms, showers, and lifeguards. Whale-watching is also a popular activity with tours exploring the Stellwagen Bank National Marine Sanctuary where dozens of humpback whales make their home. Harborwalk, a 1.2 mile path through the town, provides the best views of Gloucester’s coastal landscape from all angles. The Fisherman’s Memorial, Gloucester’s best known landmark erected at harbor side, is inscribed with the names of those lost at sea.

Gloucester also boasts the Gloucester Stage Company, a renowned professional theater company whose works have gone to critical success on Broadway as well as internationally.

Gloucester History

Gloucester was one of the first English settlements that would later become the Massachusetts Bay Colony although it was only formally incorporated in 1642. Because of its poor soil and rocky hills, Cape Ann was not well suited for farming. Gloucester struggled as an outpost until it came to dominate the finishing industry in the mid-1800s. The area’s fishing roots and wind-swept beauty have attracted and inspired painters since the early 19th century. Many local and nationally recognized artists are showcased in the Cape Ann Museum. The Rocky Neck Art Colony lives on as America’s oldest working art colony.

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