Gloucester Real Estate

Welcome to Gloucester, Massachusetts – a charming coastal city that beautifully blends rich history with breathtaking natural beauty. Nestled in Essex County along the scenic North Shore, Gloucester is renowned for its vibrant maritime heritage, making it a beloved destination for both residents and visitors alike.

Founded in 1623, Gloucester is one of the oldest seaports in America, and its storied past is reflected in the picturesque architecture that lines its streets. Stroll through the historic downtown area, where you’ll find an array of boutique shops, art galleries, and delightful eateries serving fresh seafood caught right from the Atlantic Ocean. Don’t miss the iconic Fishermen's Memorial, a tribute to the city’s fishing industry and its resilient community.

Nature lovers will find paradise in Gloucester, with its stunning beaches, rocky shorelines, and lush parks. Visit Good Harbor Beach or Wingaersheek Beach for sun-soaked days, or take a scenic hike at Cape Ann’s beautiful trails, offering panoramic views of the ocean. For those interested in marine life, the area is a hotspot for whale watching and offers various boat tours that let you experience the beauty of the Atlantic firsthand.

Gloucester also hosts vibrant festivals throughout the year, including the famous Gloucester Schooner Festival, celebrating its maritime culture. With a welcoming community, excellent schools, and a perfect blend of urban and rural living, Gloucester is an ideal place to call home. Whether you’re looking for a seaside retreat or a bustling community, Gloucester is waiting to welcome you with open arms!

Newest Listings in Gloucester

$1,350,000

4 Beds ⋅ 4 Baths ⋅ 73575871 MLS

This spectacular property was custom-designed and built over the years by the owner of renowned builders Mill River Carpentry. Set on a beautiful lot along a peaceful street in Gloucester's desirable Riverdale neighborhood, this exceptional home showcases remarkable craftsmanship, expansive living spaces, and seamless indoor-outdoor living. A stone driveway welcomes you to an enormous mudroom that opens into a recently renovated custom kitchen featuring concrete quartz countertops and an impressive 60-inch refrigerator. The spacious living room is anchored by a woodstove with a beautiful granite surround and opens to a generous deck and pool area. The main level also offers a full bath with laundry, a comfortable sitting area off the kitchen, and a large dining room with cathedral ceilings. Exceptional details are found throughout, including radiant heat, tongue-and-groove pine ceilings, five-inch red oak flooring, and oversized windows that fill the home with natural light. The open first-floor layout extends effortlessly to a deck, patio, and screened porch, creating an ideal setting for entertaining and relaxing. The second floor features two bedrooms, a full bath, and an impressive primary bedroom with a cathedral ceiling and an oversized walk-in closet. The walkout portion of the basement provides a dedicated home gym area. A spacious breezeway offers flexible den or office space and leads to an oversized garage equipped with a 12-by-10-foot overhead door, a half bath, and radiant floor heat. Completing this remarkable property is a bright one-bedroom apartment above the garage - ideal for extended family, guests, or potential rental income. The apartment also features a large private deck with beautiful views of the Annisquam River and Ipswich Bay.

18 Holly St, Gloucester

$1,575,000

3 Beds ⋅ 3 Baths ⋅ 73575311 MLS ⋅ ['Good Harbor Beach Condo'] BLDG.

Perched at the top of 78 Thatcher Rd in Gloucester, this exceptional 2+ bedroom, 3 bath penthouse condo offers single level living while being one block to Good Harbor Beach. Arriving by elevator to your front door, you will enjoy soaring vaulted ceilings, hardwood floors, oversized windows, and abundant natural light. The home feels open, airy, and effortlessly connected to its spectacular surroundings. The open-concept living space is designed for both relaxed living and entertaining, featuring a bright kitchen with custom cabinetry and stainless-steel appliances, a welcoming fireplace. Each of the bathrooms have beautiful en-suite baths. An office/den provides flexible space for working or unwinding, while the upper-level deck offers an extraordinary place to take in the changing light, ocean breezes, and unforgettable sunsets. Residents also enjoy a gym and guest parking along with the rare combination of privacy, convenience, and outdoor space. Downtown Gloucester is nearby, with outstanding seafood and restaurants, galleries, shops, and a vibrant culture deeply rooted in the city's maritime traditions.Gloucester is a destination for every sesaon- and this home is an ideal place to experience it. Whether you're entertaining friends, enjoying a quiet evening by the fire, or simply watching the sunset over the water, 78 Thatcher offers an opportunity to slow down, breathe deeply, and truly enjoy the view. Offering includes all furniture providing you with a turn-key home by the sea.

78 Thatcher Rd Unit 6, Gloucester

$620,000

4 Beds ⋅ 2 Baths ⋅ 73575107 MLS

Fantastic Two-Family Investment Opportunity! Ideally located in a desirable neighborhood walking distance to East Veterans Elementary school, this well-maintained two-family offers an excellent opportunity for investors or buyers looking to owner-occupy while generation rental income. Unit #1 entrance is the front door home with three bedrooms upstairs on the second floor, an open concept kitchen with center island stainless steel appliances, granite countertops, hardwood floor and a full bathroom. The spacious family with stackable laundry in closet. This unit has a parking spot in the driveway and off street parking. Unit # 2 is located in the back of the house, pull in the driveway and walk in your one bedroom, a kitchen, full bathroom, pantry/storage area, and in unit laundry. The property has a sharable yard to have grills and outside table and chairs. Whether you're looking to expand your investment portfolio or get into multifamily ownership with tenants already in place, this offers versatility, convenience, and excellent potential. Don't miss this opportunity to own a two-family in a great neighborhood close commuter rail, downtown Gloucester, parks and beaches.

19 Sadler Street, Gloucester

$4,500,000

7 Beds ⋅ 6 Baths ⋅ 73575037 MLS

A landmark of Magnolia's storied coastline, this extraordinary oceanfront estate has graced Shore Road since 1889. Set above the Atlantic on one of Cape Ann's most coveted seaside addresses, the residence masterfully blends timeless architecture with thoughtfully curated updates, creating a home that feels both historically significant and effortlessly livable. Sunlight pours through expansive windows, illuminating gracious rooms designed for intimate gatherings and grand entertaining alike, while six fireplaces add warmth and character throughout. Outside, terraces and gardens frame panoramic ocean vistas where the rhythm of the tides, passing sailboats, and spectacular coastal sunsets become part of everyday life. Just moments from Magnolia Village, beaches and miles of scenic conservation trails, this is a rare opportunity to become the next steward of one of the North Shore's most distinguished waterfront homes.

31 Shore Rd., Gloucester

$599,000

1 Beds ⋅ 1 Baths ⋅ 73575009 MLS ⋅ ['Peabody Estate Condominium'] BLDG.

Discover sophisticated living at 158 Hesperus Ave U:2L in Gloucester, MA. This water view renovated 5 room 2nd floor one level condo offers 1145 square feet of refined space in great condition. Located in a private Magnolia area estate setting on 1 acre of lovely grounds in an attractive grand Victorian style home that blends historical charm with contemporary comfort. The fully applianced kitchen is a culinary delight, featuring custom oversized white wood cabinets, gleaming stainless steel appliances and elegant granite counters. Its intelligent peninsula design w/ 3 person breakfast bar creates a natural flow into the family room, fostering an open-plan environment perfect for entertaining or daily living. Adjacent to the kitchen, the living room provides a welcoming atmosphere for sitting and reading while taking in the water views, defined by its rich fir flooring that extends throughout the space. The primary bedroom features the warmth and elegance of a fireplace with marble trim and fir flooring, creating a cohesive and inviting private retreat. Work remote from your home office with built in shelving and ample closet space. Enjoy the smell of salty ocean air and expand your living space on the inviting exclusive use private deck off kitchen ideal for drinks and Summer meals! Modern updated tile bath. A flexible floor plan allows for a variety of room uses. Perfect for those buyers looking to downsize to more manageable living space. Located close to Magnolia and Manchester downtown villages, shops, library, restaurants, and beautiful beaches! 2 car paved parking and ample secure exclusive basement storage area. Ready to move in and start enjoying maintenance free living! Experience the allure of this thoughtfully designed condominium; schedule your private viewing today.

158 Hesperus Ave Unit 2L, Gloucester

$789,000

7 Beds ⋅ 4 Baths ⋅ 73574965 MLS

Set on a quiet side street with convenient access to Route 128, the MBTA Commuter Rail, and Gloucester's many amenities, this spacious three-family property presents an excellent opportunity for investors and owner-occupants alike. Unit 1 is a generously sized three-bedroom, two-bath townhouse-style residence. The main level features a living room, dining room, and kitchen, while the second floor offers three bedrooms and a full bath. A large finished lower level includes a second bathroom and four additional rooms, providing flexible space for a home office, recreation room, storage, and more. Unit 2 is also townhouse-style and offers a versatile layout that can function as either a two- or three-bedroom unit. Unit 3, located on the top floor, is a two-bedroom garden-style residence. Additional highlights include a private backyard and ample off-street parking. With flexible living arrangements, generous space, and a central Gloucester location, this property offers outstanding potential.

9 Knowlton Sq, Gloucester

$698,000

3 Beds ⋅ 2 Baths ⋅ 73574637 MLS ⋅ ['3 Babson Street Condominium'] BLDG.

Looking for something that is really special? This three bedroom, 1.5 bath, two level condominium unit has views out to Gloucester Harbor and winter views from west facing windows of the Annisquam River. Everything about Gloucester's best features are nearby. The unit lives like a single family. Updated by the prior owner with windows, boiler and electric plus many updates and renovations by the current owner makes this a move in home. With Thanksgiving around the corner, you can be the owner in time to have guests and family see your new home. The attractive living room with built ins has room for your dining furniture plus the bright, efficient kitchen has an island with seating and plenty of work space, The kitchen includes quartz counters, cabinets galore, a pantry cabinet, gas cooking and a newer thermal slider door leading to a East facing deck - where it is perfect to enjoy the views over Gloucester and the harbor. Watch the sun rise with your morning coffee from the deck or use it to just hang to relax after a long day. The primary bedroom has a great view and an alcove perfect for use as an office or reading nook. The updated full bath has a stack washer & dryer, a double sink and soaking tub with a rain shower head and there's a linen closet for storage. The unit also has a convenient half bath on the bedroom level. The walk in 5'x5' closet off the living room is actually big enough to use as a comfortable office. The unit has use of a parking space in the garage plus two additional tandem parking spaces in the driveway. There is shared storage in the basement and the garage has enough room for skis, bikes and kayaks and fits most vehicles which will be a relief during snow season. If you commute by Train, the station is a half mile away. Gloucester Boulevard and Pavilion Beach are less than a half mile and some of the best restaurants on the North Shore are also a short half mile away. Walk into this freshly updated and sunny home, fall in love and call it your own.

3 Babson Street Unit 2, Gloucester

$499,900

2 Beds ⋅ 1 Baths ⋅ 73573696 MLS

Charming European cottage in Gloucester’s Riverdale neighborhood, tucked beneath Pole’s Hill and across from the Mill Pond and nearby sports fields. This home has been in the same ownership for nearly 50 years and is ready for its next chapter. The property offers a wonderful opportunity to update, restore and make it your own while building equity over time. Outside, a large private patio creates an inviting extension of the living space, perfect for relaxing and entertaining. Update to your taste and create something truly special in one of Gloucester’s sought after neighborhoods! SHOWINGS BEGIN AT THE OPEN HOUSES, THIS SATURDAY 9/12 AND SUNDAY 9/13 from 11:00am to 12:30pm.

350 Washington Street, Gloucester

$849,900

3 Beds ⋅ 2 Baths ⋅ 73573899 MLS

Welcome to 26 Acacia St, Gloucester — a beautifully maintained single-family residence where timeless character meets refined modern living. Originally built in 1900, this distinctive home offers 1,568 square feet of above-grade living space, complemented by an additional approximately 150-square-foot finished basement room that is not included in the stated living area.At the heart of the home is a thoughtfully designed kitchen created for both everyday living and effortless entertaining. Stainless steel appliances, a generous center island with an integrated sink, and abundant preparation space create a sophisticated yet inviting setting for everything from casual mornings to memorable gatherings.The inviting living room provides a warm and elegant gathering space, highlighted by a fireplace that adds character and ambiance. The home features **two full bathrooms**, including a beautifully appointed bath with a walk-in shower and multiple showerheads, creating a spa-inspired retreat.The true showstopper continues outdoors. A private, thoughtfully designed yard offers an exceptional extension of the living space, complete with an outdoor kitchen and expansive entertaining areas. Enjoy al fresco dining on the patio, relax beneath the covered deck, or unwind in the covered outdoor living area — all designed for effortless entertaining and year-round enjoyment.The finished basement room provides approximately 150 additional square feet of flexible space, ideal for a home office, fitness area, media room, creative studio, or additional recreational space.Blending the charm and character of a historic Gloucester home with modern comforts and exceptional indoor-outdoor living, 26 Acacia St offers a rare opportunity to experience a home designed not simply for living, but for enjoying life to its fullest.

26 Acacia St, Gloucester

$4,295,000

4 Beds ⋅ 4 Baths ⋅ 73573613 MLS

OCEANFRONT LIVING AT ITS BEST! Welcome to 41B Wingaersheek Road, an exceptional 2023 modular coastal residence offering a rare combination of modern comfort, energy efficiency, investment potential, and direct access to one of Gloucester’s most coveted stretches of shoreline. Thoughtfully engineered and factory-built in precision-fabricated modules before being assembled on site, the home offers a sophisticated alternative to conventional construction. A combination of structural steel and wood framing creates a durable, highly engineered building envelope while maintaining a clean, modern aesthetic. Designed for year-round comfort and efficiency, this home features extensive closed-cell spray-foam insulation throughout the walls, floors, and roof. The property consists of two beautifully appointed residences, each offering 2 bedrooms and 2 full baths, creating a versatile 4-bedroom, 4-bath configuration. Both units feature bright, open-concept living spaces, sleek kitchens with quartz countertops, center islands, and stainless steel appliances, as well as in-unit washers and dryers. A convenient lockout door provides the option for the two residences to function independently as a multi-family property or be incorporated into one expansive single-family home, offering an ideal setup for extended family, guests, or those seeking additional private space. Steel structural components are integrated throughout the modular system, including engineered connections between modules, resulting in exceptional structural integrity and energy performance. Mechanical systems were carefully incorporated into the design, including heat-pump HVAC and air-conditioning, along with a heat-recovery ventilation system providing continuous whole-house ventilation. Plumbing and electrical systems were substantially installed within the factory-built modules and seamlessly connected during on-site assembly, allowing for an efficient and highly coordinated construction process.Designed for effortless coastal living, this home is equipped for year-round enjoyment. Step outside and follow the private path directly to the beach, where you can spend your days swimming or strolling the shoreline. This home offers the opportunity to create a private family compound, a sought-after vacation retreat, or an income-producing investment. Rarely available, this is a remarkable opportunity to own a piece of the Gloucester coastline.

41-B Wingaersheek Rd, Gloucester

$409,000

1 Beds ⋅ 2 Baths ⋅ 73573446 MLS

Absolutely adorable and newly renovated 1 bedroom 1.5 bath adobe style bungalow with an extra bonus room which could serve as a home office, studio, or guest room. This one level home located downtown Gloucester, is perfect as a condo alternative convenient to many restaurants, music venues, the train station, churches and Gloucester harbor and beaches... all just a short distance away! Many improvements include kitchen, dining area, new remodeled interior walls, ceiling, and new floors. The washer dryer has been moved upstairs to the living level. In addition, the full basement offers plenty of storage. This cozy home is in move in condition and just waiting for you!

139A Prospect St., Gloucester

$718,000

3 Beds ⋅ 2 Baths ⋅ 73565358 MLS

Set on nearly an acre surrounded by nature, this home offers a sense of serenity that's increasingly hard to find, yet you're still close to all of the best of Gloucester. Offering 1722 square feet of comfortable single-level living, this 3-bedroom, 2-bath home combines privacy and flexibility. Step inside to freshly painted interiors and beautifully refinished hardwood floors that bring warmth and character throughout the home. Both full bathrooms are refreshed with a modern touch, while versatile bonus rooms offer the perfect space for a home office, nursery, den or personal gym space. The generously sized primary bedroom is it's own private retreat, featuring large closets, new luxury vinyl plank flooring and a slider leading directly to a covered porch—a peaceful spot to enjoy your morning coffee, unwind with a book or simply take in the natural surroundings. The large eat-in kitchen offers plenty of potential for a future owner to make it their own. The home's comfortable layout and improvements already completed make it easy to settle in and update over time. The garage and connecting walk-out basement provide convenient parking and valuable additional storage. Enjoy nearby Plum Cove Beach, sunsets and the waterfront charm of Lane's Cove. Close to Goosecove Reservoir and Dogtown or decide to forge your own nature trails in your very own backyard. Whether you're looking for the ease of one-level living, room to work from home or simply a home you can personalize over time, this home offers a wonderful opportunity to put down roots in one of Gloucester's most beloved neighborhoods. Come discover the quieter side of town and why this is such a special place to live.

59 Holly St, Gloucester

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