Homes for Sale near Ralph B O'maley Middle School

Iconic and storied East Gloucester location with three floors of amazing potential! First floor condo unit is formerly Duckworth's Bistrot. This space could be a restaurant, office or business or could be converted to residential with a special permit. First floor consists of a large great room with beautiful floor to ceiling windows, half bath, kitchen and washroom. Second/Third floor condo unit

Andree Gillian Group Engel & Volkers By the Sea

Nestled above the scenic beauty of Smith Cove in Rocky Neck, this enchanting two-bedroom condominium offers a truly unique living experience. The open-concept layout invites you to personalize the space to suit your lifestyle. Step out onto the spacious deck to enjoy vibrant boating activity and breathtaking sunsets. Upstairs, you'll find two bedrooms—each with its own private bath—including a

Barbara Dugan Engel & Volkers By the Sea

Iconic and storied East Gloucester location with amazing potential! First floor condo unit is formerly Duckworth's Bistrot. This space could be a restaurant, office or business or could be converted to residential with a special permit. Consists of a large great room with beautiful floor to ceiling windows, half bath, kitchen and washroom. Outdoor space currently holds a walk-in refrigerator but

Andree Gillian Group Engel & Volkers By the Sea

Investors, developers, and homesteading enthusiasts — take note! Rare opportunity to acquire a 3.7-acre parcel in highly desirable West Gloucester. Includes a spacious three-family home on 2.44 acres plus an additional 1.26-acre lot, sold together. The existing property offers immediate income potential with three units — ideal for multi-generational living or rental income. Beyond investment

Antonia Tullercash Churchill Properties

Step into classic New England charm with this beautifully maintained two-story Colonial, ideally situated just moments from Gloucester’s famous beaches, vibrant downtown, and scenic harbor. This spacious 9-room home offers a flexible layout perfect for entertaining, working from home, or simply relaxing in comfort. The first floor features a welcoming living room, formal dining area, and a

Nicholas Coppola Keller Williams Realty

Discover an excellent investment opportunity with this solid three-family property, featuring three spacious one-bedroom apartments. Each unit offers generously sized rooms and convenient in-unit washer/dryer hookups—highly desirable for today’s renters. The building is centrally located near downtown Gloucester, just a short walk to the MBTA, restaurants, shops, and everyday amenities.

Debra Lovelace Churchill Properties

Investors/Developers! This mixed use building offers an excellent potential return and a variety of potential uses. The property is located among the busiest shops and restaurants on Main street and includes two retail stores and three residential apartments all currently leased. The residential units include beautiful architectural details including exposed brick, over-sized windows, tall

Bethany Pratt Churchill Properties

Good Harbor Beach Neighborhood – Coastal Living Minutes from Downtown Gloucester. Nestled in one of Gloucester’s most sought-after neighborhoods near Good Harbor Beach and just minutes from the Gloucester's historic and vibrant downtown, this beautifully crafted 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, style, and flexibility. Built in 2013, this home features a main suite

Heather Dagle RE/MAX Beacon

Iconic and storied East Gloucester location with two floors of amazing potential! Second/Third floor condo unit is a two-story apartment, with high ceilings, great light and lovely views of Smith Cove and Gloucester harbor. Large roof deck overlooking the water. The apartment consists of three bedrooms, one bathroom, large living room, dining room and kitchen with views. Kitchen and bathroom are

Andree Gillian Group Engel & Volkers By the Sea

This prime location 2-bedroom condo with ocean views is perfectly situated in downtown Gloucester, blending historic character with modern convenience. Immortalized by the great artist Edward Hooper this once sea Captain’s house was built in 1920 and thoughtfully converted to condos 1991. This Georgian-style building highlights classic architectural charm with high ceilings and period details.

Brian Rothe Coldwell Banker Realty - Manchester

Welcome to this recently converted and exquisitely appointed two-story condo in the idyllic seaside setting of East Gloucester. Enhanced with new exterior paint and fresh landscaping, this home exudes tranquility and charm. Step inside to discover a spacious, light-filled living room adorned with high ceilings and beautifully restored wood floors, seamlessly flowing into the airy dining room

Felicia Trupiano J. Barrett & Company

Located at 44 Lexington Ave Magnolia offers an inviting home ready to move in. The kitchen featuring granite countertops that provide a durable and elegant surface for meal preparation, complemented by a stylish backsplash. With 700 square feet of living area, this one-bedroom condominium offers an opportunity to embrace comfortable living in the center of Magnolia Village. Within walking

KRISTINA BENGSTON Annisquam Village Realty

Iconic and storied East Gloucester location with three floors of amazing potential! First floor condo unit is formerly Duckworth's Bistrot. This space could be a restaurant, office or business or could be converted to residential with a special permit. First floor consists of a large great room with beautiful floor to ceiling windows, half bath, kitchen and washroom. Second/Third floor condo unit

Andree Gillian Group Engel & Volkers By the Sea

Enjoy coastal living at its finest in this new construction Townhouse with ocean views in sought-after Lanesville! Almost 2400 sq ft of luxury living. Large open floor plan. Enjoy your top of the line eat in kitchen with a gorgeous island. Sun filled living room with sliders out to your private deck. Half bath on 1st floor. Upper level consists of 3 large bedrooms. Primary bedroom has his and her

Tyler Scaglione Cameron Real Estate Group

Located on iconic Rocky Neck, this charming seaside penthouse retreat offers water views of Smith Cove and Gloucester Harbor. Sun-drenched spaces, vaulted ceilings, and thoughtfully crafted custom design details create an inviting and truly one-of-a-kind home. Located just moments from beloved galleries, boutiques, and restaurants, allowing you to fully immerse yourself in the vibrant lifestyle

Ginger Attaya

Welcome to one of the most spectacular oceanfront retreats on the North Shore — 100 Eastern Point Blvd. This 1.78-acre coastal property offers panoramic views of the Atlantic Ocean, Lighthouse Cove, Raymond’s Beach, Gloucester Harbor, and even the Boston skyline. The renovated Cape Cod-style home features 4 bedrooms, 2.5 baths, and expansive ocean views from nearly every room. Enjoy a wide, flat

Lanse Robb LandVest, Inc., Manchester -by-the-Sea

Nestled at the end of a quiet side street, this home offers breathtaking views of Gloucester’s outer harbor.Just a short stroll from the beach, it’s the perfect retreat, whether vacation or year-round living. With 4 bedrooms (all ensuite) and multiple decks, this home comfortably accommodates several guests while maintaining a cozy, welcoming atmosphere.The main living area is on the 2nd fl to

Barbara Dugan Engel & Volkers By the Sea

Waterfront living with historic charm. Once a working mill, the structure has been transformed into a warm and inviting home, preserving its architectural heritage while embracing contemporary updates. The open-concept layout offers sunlit living spaces that showcase panoramic vistas of Annisquam River, Wingaersheek Beach, and Ipswich Bay. Whether you’re unwinding on the expansive deck, paddling

Joshua Mulvey Mulvey Real Estate, LLC

Welcome to Gloucester. Just in time for winter. A handsome three bedroom colonial located between Gloucester Harbor ,Stacy Boulevard, boat launch and the MBTA Commuter line to Beverly,Salem and Boston. Lovingly lived in and enjoyed for decades. Impeccably maintained with love and care . A great location to leave the car at home. Enjoy the easy access to all of downtown including- shopping,

Michele Allison-Elwell Coldwell Banker Realty - Beverly

The price on this magnificent ocean view suite has be reduced to $1,430,000 from $1,625,000! The Penthouse at The Residences at 191 Main Street is an unparalleled opportunity to own a most spectacular part of Gloucester history. The Penthouse Suite is one of three completely unique and rare luxury condominium units, available now in this 1880 Pigeon Cove granite and brick landmark property in the

Jason Saphire www.HomeZu.com

Make this "Home for the Holidays". A rare & remarkable opportunity to own a piece of Gloucester’s architectural history on Eastern Point. Built in 1916 & set on a little over an acre of land, this distinguished single-family home offers over 5600 sq. ft. of living space, blending timeless character w/ endless potential. Step inside & be captivated by the grand great room, an impressive space with

Charleen McCarthy Five Mark Realty Group LLC

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,

Debra Lovelace Churchill Properties

Just steps from Wingaersheek Beach, 226 Atlantic Street is an extraordinary new home that blends timeless design with coastal living. Crafted for year-round comfort, this residence offers a chef-inspired kitchen with custom cabinetry, Thermador appliances, and walk-in pantry. The great room soars with a cathedral ceiling and stone fireplace, leading to a four-season porch that brings the outside

Nest / Syndi Zaiger Group Compass

Price has been reduced to $599,000 from $660,000! The Street view suite at The Residences at 191 Main Street is an unparalleled opportunity to own a most spectacular part of Gloucester history. This historic suite is a unique luxury unit, in this spectacular 1880 Pigeon Cove granite and brick landmark property in the heart of downtown Gloucester. This iconic building has been lovingly restored to

Jason Saphire www.HomeZu.com

Sailor Stan’s has been an iconic landmark since 1977, offering the perfect blend of business opportunity and coastal living. The restaurant portion features seating for 34–36 guests, a welcoming outdoor deck, and a convenient half bath—ideal for continuing its long tradition as a beloved breakfast and lunch spot. The attached residential section offers 3 bedrooms, 2 baths, a full kitchen, and a

Ginger Attaya

97 & 99 East Main Street combine a classic 1900 Colonial (approx. 1,941 sq. ft., 5 bedrooms) with an adjoining lot in the Marine Industrial (MI) zone. Overlooking Cripple Cove and the harbor, the property has been home to Cripple Cove Studios and offers flexible space for residential, live/work, or creative use (subject to city approvals). The Colonial retains charm and scale with room for

McDermott Group Gibson Sotheby's International Realty