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35-37 Sargent St, Gloucester
$995,000
16 Beds ⋅ 10 Baths ⋅ 73595656 MLS ⋅ ACTIVE Status
Great investment opportunity in downtown Gloucester. This existing two-family property is currently occupied by two long-term tenants, providing immediate rental income while you move forward with an approved expansion project. All city approvals are in place for approximately 4,200 square feet of additional building area, comprising four townhouse-style units, each with three bedrooms and 1.5 baths. As an added benefit, the seller has already obtained a quote from a modular construction company for the four proposed units. The level and mostly cleared lot is ready for the next stage of development. Continue collecting rent from the existing units while completing the construction process. Centrally located near downtown amenities and the MBTA Commuter Rail, this property offers a compelling combination of current income and future growth potential.

35-37 Sargent St, Gloucester

Listing courtesy of Listing Agent: Mark Ventimiglia from Listing Office: Vadala Real Estate.
368 Essex Avenue, Gloucester
$1,149,000
8 Beds ⋅ 4 Baths ⋅ 73583315 MLS ⋅ ACTIVE Status
A rare opportunity in West Gloucester! This 4,000+ sq. ft. three-family property is being offered with TWO parcels totaling approximately 3.7 acres—an exceptional combination of multi-family living, acreage, income potential, and possible future development. The offering includes 368 Essex Ave., featuring a spacious three-family home situated on approximately 2.44 acres with substantial frontage along Essex Ave., plus 368R Essex Ave., an additional approximately 1.26-acre R-30 zoned parcel located behind the main property and described as an “orchard” on the deed. Investors, contractors, developers, flippers, and cash buyers—bring your vision! The multi-family home is in need of updating and improvement, but offers tremendous space and potential for renovation, rental income, or repositioning. With two parcels and nearly 4 acres combined, the possibilities are intriguing. Property is being sold as-is. Buyers and buyers’ agents to perform their own due diligence regarding zoning, subdivision potential, permitted uses, approvals, and development possibilities.

368 Essex Avenue, Gloucester

Listing courtesy of Listing Agent: Lillian LoGrasso from Listing Office: J. Barrett & Company.
6 Mystic Ave, Gloucester
$799,000
6 Beds ⋅ 2 Baths ⋅ 73581926 MLS ⋅ PRICE CHANGED Status
Discover Coastal Living at Its Best! A wonderful opportunity to own a charming six-bedroom, two-family home on the beautiful North Shore! Rich in classic character, this inviting property features spacious rooms, gleaming hardwood floors, abundant natural light, and high ceilings throughout the home, including the basement! Large closets and plenty of storage add to the home's appeal. Enjoy the welcoming porches and generous decks, perfect for relaxing, entertaining, and taking in the refreshing sea breeze! The garage offers valuable parking and additional storage. Recent updates include a new roof in 2025 and a newer heating system and hot water tanks installed in 2020. Whether you're looking to owner-occupy while generating rental income, accommodate extended family, or expand your investment portfolio, this versatile property offers exceptional possibilities. Conveniently located near public transportation, commuter rail, major highways, downtown shops and restaurants, and the beautiful beaches of Gloucester and Rockport, this home combines everyday convenience with the charm of coastal living. Don't miss this opportunity to own a spacious two-family property with character, and incredible potential in a desirable location. Come explore the possibilities!

6 Mystic Ave, Gloucester

Listing courtesy of Listing Agent: Rosa Rescigno from Listing Office: Mango Realty, Inc..
31 Shore Rd., Gloucester
$4,500,000
7 Beds ⋅ 6 Baths ⋅ 73575037 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.
186 Washington Street, Gloucester
$789,900
6 Beds ⋅ 2 Baths ⋅ 73564843 MLS ⋅ ACTIVE Status
Opportunity awaits at 186 Washington Street! This spacious Gloucester two-family offers a flexible layout, generous room sizes and excellent potential for an owner-occupant, investor or multi-generational buyer. Each unit features its own kitchen, full bath and comfortable living spaces, with the second-floor unit also offering a bright sunroom. Off-street parking, basement storage and convenient access to downtown Gloucester, the harbor, shops, restaurants and area beaches add to the appeal. A substantial third floor attic with multiple existing rooms provides an exciting value-add opportunity for future expansion or additional living space. The third floor requires renovation; buyers to perform their own due diligence regarding permitted uses, zoning and approvals. A unique opportunity to bring your vision to a classic Gloucester multifamily and unlock its full potential.

186 Washington Street, Gloucester

Listing courtesy of Listing Agent: Garett Webb from Listing Office: Churchill Properties.
366 Main St, Gloucester
$1,139,999
9 Beds ⋅ 4 Baths ⋅ 73564309 MLS ⋅ ACTIVE Status
Rare opportunity to acquire a fully renovated 3-family property in a highly desirable Gloucester location, just minutes from Good Harbor Beach and offering beautiful ocean views. The property combines strong rental fundamentals with the lifestyle appeal of one of the North Shore’s most sought-after coastal markets. The property has been thoughtfully renovated throughout, featuring updated kitchens and bathrooms, modern finishes, in-unit laundry, and two dedicated parking spaces. The flexible three-family configuration provides multiple income streams and makes the property attractive for both long-term rental and seasonal/vacation rental strategies. With its proximity to Good Harbor Beach, Gloucester’s restaurants, harbor, and downtown amenities, the property is well positioned to benefit from strong demand from both year-round tenants and summer visitors. The property also offers excellent potential for an Airbnb/short-term rental strategy, subject to applicable City of Gloucester regulations and permitting requirements. A major component of the investment opportunity is the separate 368R Main Street lot, located directly behind the property. This additional parcel provides meaningful future upside and could potentially support an ADU, additional residential unit, or other development concept, subject to zoning, permitting, utilities, and site requirements. Please reach out for private showings.

366 Main St, Gloucester

Listing courtesy of Listing Agent: Kristi Gjikondi from Listing Office: Gjikondi Realty.
53-55 Western Ave, Gloucester
$1,500,000
9 Beds ⋅ 6 Baths ⋅ 73523157 MLS ⋅ ACTIVE Status
The Inn at Babson Court is a 1741 post & beam Colonial overlooking historic Gloucester Harbor and the Fisherman's Memorial. The property is currently used as an inn/multi family. Currently there are 3 "apartments" and 2 suites (no kitchen). Public record states 4 family. Exposed beams and historic charm throughout. Many possibilities exist for its future uses. Plenty of parking behind house including a 2 car garage (ADU?). 4-100amp electric service panels plus house meter. Common decks and patio, covered outside sitting area. Beach and harbor across the street!

53-55 Western Ave, Gloucester

Listing courtesy of Listing Agent: Michael Beaton from Listing Office: Churchill Properties.
53 Western Ave, Gloucester
$1,500,000
9 Beds ⋅ 6 Baths ⋅ 73523156 MLS ⋅ ACTIVE Status
Step into a piece of history overlooking Gloucester Harbor. Built in 1741 as a single family home, the property is currently used as an inn/multi unit property offering an expansive 4610 square feet of living space. Large exposed beams and unique features throughout. Conversion back to a single family would create a very stately captains house. Discover the enduring charm and potential of this historic Gloucester residence in the heart of America’s oldest seaport.

53 Western Ave, Gloucester

Listing courtesy of Listing Agent: Michael Beaton from Listing Office: Churchill Properties.

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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