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28 Eastern Point Road, Gloucester
$1,500,000
10 Beds ⋅ 10 Baths ⋅ 73505698 MLS
Located in beautiful East Gloucester and nestled between Rocky Neck and Niles Beach is this iconic, circa 1880's Colonial home that has been owned by the same family for 50+ years! The property features stunning, sweeping ocean views from many of the rooms and the charming covered porch. This gracious home also has a formal foyer, large over sized rooms, hardwood floors, wainscotting and a pocket door into the owner's apartment. The property has been used as an Inn for many years and features 8 bedrooms with baths and a 3rd floor auxiliary apartment that consists of 2 bedrooms, small kitchen, dining area, living room and a full bath. The first floor also has an "owner's" apartment with a fireplaced living room, pantry, large kitchen, an ample sized bedroom and updated full bath. This wonderful property awaits your ideas and creativity for many possibilities!

28 Eastern Point Road, Gloucester

Listing courtesy of Listing Agent: Nancy Goodick from Listing Office: Gibson Sotheby's International Realty.

4 Graystone Road, Gloucester
$1,475,000
4 Beds ⋅ 3 Baths ⋅ 73516887 MLS
Perched above Bass Rocks Golf Club with ocean views beyond, this exceptional home offers a rare blend of privacy and coastal charm in one of Gloucester’s most sought-after neighborhoods. Tucked away on a quiet dead-end street, the welcoming four-bedroom residence sits on a beautifully landscaped half-acre lot featuring mature trees, perennial gardens, and striking natural rock outcroppings. Gracious living spaces – including an open kitchen and dining room, large living room with fireplace/wood stove, three-season sunroom, and sizable bedrooms. The walk-out lower level offers excellent potential for additional living space, with above-grade light, direct yard access, and plumbing in place for a future bathroom. An oversized garage accommodates two vehicles and provides ample space for storage. Located just moments from Good Harbor Beach, this meticulously maintained property has been cherished by its current owners for over 30 years and is ready for its next chapter.

4 Graystone Road, Gloucester

Listing courtesy of Listing Agent: Monahan Barker Team from Listing Office: LandVest, Inc., Ipswich.

5 Mount Pleasant Ave, Gloucester
$1,405,000
4 Beds ⋅ 3 Baths ⋅ 73515559 MLS
Perfectly located just a short walk from Good Harbor Beach, Bass Rocks Golf & Tennis Club, Rocky Neck, and the Scenic Back Shore. This bright and open home is fresh and move-in ready offering a very flexible floor plan. The home has been recently painted inside and out, professionally landscape and has a large fenced in yard that sits on a quiet corner lot with plenty of greenery to enjoy from your oversized deck. Offering the rare first floor main bedroom with fireplace, the first floor also features beautiful wide pine flooring, a large foyer, full bath, an oversized dining room also with a fireplace, modern kitchen with stainless appliances and a family room with bar and adjacent sunroom/game room. The second floor includes two guest rooms, a second full bath, large laundry room, and another main bedroom with a sitting area, private balcony, and an en-suite bathroom with an elegant standalone tub. Move in just in time to enjoy summer on beautiful Cape Ann.

5 Mount Pleasant Ave, Gloucester

Listing courtesy of Listing Agent: Laura Howard from Listing Office: J. Barrett & Company.

129 Thatcher Rd, Gloucester
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 73501697 MLS
OPEN HOUSES CANCELED. OFFER HAS BEEN ACCEPTED. Perfectly located between Good Harbor Beach and Long Beach, this well-maintained 3-bedroom, 3-bath home offers the coastal lifestyle so many buyers are searching for. Inside, the layout is both comfortable and flexible, with a full bath on every level—ideal for guests, extended living, or working from home. The finished lower level is built for entertaining, featuring a custom hardwood bar, wet sink, and lounge space. A heated driveway makes winter effortless, while the 2-car garage and additional parking provide convenience year-round. Whether you're looking for a primary home, beach retreat, or smart investment, this property delivers comfort, space, and an unbeatable location on Cape Ann.

129 Thatcher Rd, Gloucester

Listing courtesy of Listing Agent: Militello Team from Listing Office: eXp Realty LLC - Corporate Office.

21-23 Marble Road, Gloucester
$1,015,000
2 Beds ⋅ 4 Baths ⋅ 73497318 MLS
East Gloucester Charm. Abutting conservation land this gorgeous, upscale home's tall palladium windows overlook Goose Pond & the surrounding conservation land, providing privacy for a large, wide deck & two additional patios.A total of 9 rooms with cozy radiant heat in the kitchen & primary bathroom.The 3.5 baths offer a generous one level living design, with a guest suite & familyroom with loads of sunshine and a separate walkout lower level. The separate, 1 car garage has loft storage & parking for more than one car &4 additional spaces next to the home.Bonus: 3 sheds for seasonal storage. This tucked away home is a few short minutes to Niles, Good Harbor Beach & Bass Rocks. After an afternoon dip in the ocean relish in the lively nights of Rocky Neck where art galleries meet 5 star restaurant fare. Stroll along the craggy streets to The infamous Ocean Alliance Center or capture a panoramic view of city skyline from The Marine Railways & Inner Harbor. Who says you can't have it all?

21-23 Marble Road, Gloucester

Listing courtesy of Listing Agent: Mary Matthews from Listing Office: Coldwell Banker Realty - Manchester.

16 Highland Street, Gloucester
$990,000
3 Beds ⋅ 2 Baths ⋅ 73503364 MLS
Prominently positioned in the East Gloucester Square Historic District, 16 Highland Street is an exciting opportunity for the discerning buyer. This shingle-style cottage is proudly sited on a comfortable lot, complete with charming gardens and privet privacy fence. The wide covered front porch sets the stage for warm-weather gatherings to celebrate daily sunsets. A welcoming foyer leads to the primary reception rooms. The large living room features wood floors and decorative fireplace. The dining room has original built-in cabinets. A well-equipped kitchen offers adjacent mudroom and half bath. A cozy home office with fireplace and garden room complete the main living level. Upstairs finds three large bedrooms, shared oversized bathroom and separate laundry room. The third floor presents as a great family room, with wood floors and harbor views. The home is located wonderfully close to multiple marinas, Rocky Neck, Gloucester Stage, Good Harbor Beach and Downtown Gloucester.

16 Highland Street, Gloucester

Listing courtesy of Listing Agent: Scott Smith from Listing Office: Coldwell Banker Realty - Manchester.

11 Ocean View Drive, Gloucester
$895,000
3 Beds ⋅ 2 Baths ⋅ 73470438 MLS
Tucked away along a quiet, scenic backroad, 11 Ocean View Drive offers a peaceful retreat in the heart of Gloucester, Massachusetts. Surrounded by natural beauty and classic Cape Ann character, the property provides privacy and a sense of calm while remaining just a short drive from the ocean, beaches, and harbor. This ideal location allows residents to enjoy the best of both worlds: a tranquil setting removed from traffic and crowds, with easy access to Gloucester’s vibrant waterfront, dining, shopping, and cultural attractions. Known for its maritime heritage, thriving arts scene, and breathtaking coastline, Gloucester offers a lifestyle rooted in history and outdoor living. Whether used as a year-round residence or a coastal escape, 11 Ocean View Drive presents an inviting opportunity to experience the charm, character, and timeless appeal of life on Cape Ann. The setting is well suited for those who value serenity, scenery, and a strong connection to the surrounding community.

11 Ocean View Drive, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.

140 Mt Pleasant Avenue, Gloucester
$790,000
4 Beds ⋅ 2 Baths ⋅ 73518262 MLS
Nestled in the heart of East Gloucester, this four bedroom 2 ½ bath home has peeks of Gloucester Harbor and is near the Gloucester Stage Company with the Bass Rocks Golf Club and Good Harbor Beach footbridge are within a mile. The spacious yard is perfect for gardening, outdoor play, or hosting impromptu basketball games by the hoop. The detached garage, once enjoyed as a rec room complete with lively pool games, is easily used to get a vehicle out of bad weather. The finished lower level, with its own separate entrance has a kitchen and full bath and works as a gathering space or guest suite with living room and bedroom. This home is ready for its next chapter—and for you to create your own memories. See video at You Tube. Floor Plan available.

140 Mt Pleasant Avenue, Gloucester

Listing courtesy of Listing Agent: Ruth Pino from Listing Office: RE/MAX Beacon.

65 E Main St Unit 3, Gloucester
$700,000
3 Beds ⋅ 2 Baths ⋅ 73554033 MLS ⋅ ['Harbour Gateway Condominium'] BLDG.
Experience coastal living in this beautifully appointed townhouse-style condominium in desirable East Gloucester, just moments from Good Harbor and Niles Beaches, Rocky Neck, Bass Rocks Golf Club, marinas, restaurants, and downtown Gloucester. The open-concept living, dining, and kitchen area features rich walnut floors, marble countertops, glass tile backsplash, stainless steel appliances, and a gas fireplace. A private composite deck overlooks a Beacon Hill-style garden, creating a peaceful outdoor retreat. The main level offers a bedroom currently used as a home office and a full bath, providing the option for single-level living. Upstairs, the spacious primary suite features cathedral ceilings, a gas fireplace, walk-in closet, and renovated bath with dual vanities and a walk-in shower. A generous third bedroom and second-floor laundry complete the upper level. Additional features include a detached one-car garage, central air, abundant natural light, and California shutters throughout the main living area. Recent improvements include a new roof (2018), boiler (2021), insulation upgrades, central air-conditioning unit (2023), renovated primary bath (2023), exterior painting and trim replacement (2025), and dishwasher (2025). Enjoy Cripple Cove and Gloucester's waterfront, shopping, and dining just minutes away.

65 E Main St Unit 3, Gloucester

Listing courtesy of Listing Agent: Patricia McCormick from Listing Office: J. Barrett & Company.

8 Blake Ct, Gloucester
$680,000
2 Beds ⋅ 1 Baths ⋅ 73521316 MLS
OPEN HOUSE CANCELLED. ACCEPTED OFFER.. Nestled in a quiet East Gloucester cul-de-sac, this 2 bedroom home is full of character and charm! Enjoy a fabulous location minutes from downtown, Niles Beach, Rocky Neck and Good Harbor Beach. This home is showered with light throughout. A remodeled kitchen with eat in dining area, welcomes your family or guests to mingle while you prepare a meal. After entertaining, you can take your beverage of choice onto the private deck, or retire to the sun filled living room with a good book. Upstairs you will find the primary bedroom with a cozy reading nook, full bathroom and 2nd bedroom. As a bonus, and often rare amenity in this area, is an attached garage and workroom. This cozy home is move in ready but also has room to expand upwards and outwards, with possible water views over the garage. This coastal gem is ready for your touch!

8 Blake Ct, Gloucester

Listing courtesy of Listing Agent: Andree Gillian Group from Listing Office: Engel & Volkers By the Sea.

26 Marina Dr., Gloucester
$675,000
4 Beds ⋅ 3 Baths ⋅ 73452671 MLS
Price Reduction and $10,000. TOWARDS BUYER'S CLOSING COST! 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. Re-Built in 2013 from bare bones, this home features a main suite with a spacious walk-in closet and modern ensuite bath. Upstairs, you’ll find three generously sized bedrooms, while the first-floor bedroom offers versatile options for single-level living, a private office, or a cozy playroom. The home’s open and airy floor plan creates a welcoming flow from the bright living area to the bonus room at the rear of the home—perfect for entertaining or relaxing with family. Step outside to a flat, private, fully fenced backyard, offering a peaceful retreat for outdoor activities.

26 Marina Dr., Gloucester

Listing courtesy of Listing Agent: Heather Dagle from Listing Office: RE/MAX Beacon.

30 Chapel Street Unit B, Gloucester
$562,000
4 Beds ⋅ 2 Baths ⋅ 73541550 MLS ⋅ ["Crow's Nest Condominium"] BLDG.
Welcome to this wonderfully appointed two-story condo in the idyllic seaside setting of East Gloucester. This condominium 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 featuring the same lofty ceilings, wood floors, and a custom bar complete with a wine chiller. The sleek kitchen showcases white cabinets, stainless steel appliances, custom shelving, and quartz countertops. A modern full bath and a bedroom/office on this level cater to convenience. Upstairs, three more bedrooms await, including a primary bedroom with an ensuite half bath. Basement storage, a driveway with two-car parking, and inviting common areas for outdoor relaxation enhance the appeal of this residence. Perfectly situated, enjoy easy access to Good Harbor & Niles Beaches, Rocky Neck, and Cripple Cove.

30 Chapel Street Unit B, Gloucester

Listing courtesy of Listing Agent: Felicia Trupiano from Listing Office: J. Barrett & Company.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

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