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86 East Main Street, Gloucester
$1,620,000
4 Beds ⋅ 3 Baths ⋅ 73596765 MLS ⋅ NEW Status
Are you looking for a rare opportunity to embrace the coastal lifestyle Cape Ann is known for? Imagine waking up to picturesque views of Cripple Cove, watching the boats come and go as you sip your morning coffee, and enjoying the peaceful rhythm of life by the sea. Beautifully renovated with thoughtfully designed living spaces, modern finishes, and energy-efficient features, this property offers two distinct condominiums, available for purchase individually or together as a two-family. Unit #1: 3 BR, 2BA Embraces a relaxed coastal feel, this beautifully appointed residence features an inviting open-concept kitchen and living area that makes the most of its spectacular water views. The modern kitchen offers granite countertops, stainless steel appliances, an induction range, and a breakfast bar. The thoughtfully designed primary suite features a walk-in shower, powder room, and separate toilet room. Radiant heat in the bedrooms, a second bedroom and bathroom, and electric dryer and washer hookups complete the space. With Cripple Cove as your backdrop, everyday living feels like a getaway. Unit #2: 1BR, 1BA A striking contrast in style, this residence brings modern industrial loft-inspired living to the Gloucester waterfront. Featuring an open layout, contemporary finishes, granite countertops, stainless steel appliances, a breakfast bar, and a bathroom with a walk-in shower, every space is thoughtfully designed. The bedroom opens to a private rooftop deck with breathtaking water views, creating the perfect place to relax and enjoy the ocean air. Both units feature energy-efficient design elements, ENERGY STAR appliances, insulated windows, solar features, 200-amp electrical service, and an EV charging station, along with two parking spaces and rear shed. With easy access to Route 128 and a prime location minutes from Gloucester's beaches, downtown, restaurants, and working waterfront, convenience meets charm. Just steps from a public landing where you can launch a kayak or catch the water shuttle, this location makes it easy to embrace life on the water. Whether you're seeking a year-round residence, summer escape, or investment opportunity, 86 East Main Street offers the flexibility to purchase one condominium or both as a multi-family, inviting you to experience the best of Cape Ann living, where the ocean is always part of the view.

86 East Main Street, Gloucester

Listing courtesy of Listing Agent: Ron Goulart & Jennifer Anderson from Listing Office: RE/MAX Beacon.
320 Main St, Gloucester
$680,000
3 Beds ⋅ 2 Baths ⋅ 73596254 MLS ⋅ NEW Status
Enjoy the beauty and activity of Gloucester Harbor from this recently converted and renovated 2 story, commercial/office building into 2,208 square foot, Two Family residence. The property is facing and has stunning views of Gloucester Harbor across the street from Cruiseport and the very popular Seaport Grille Restaurant. Unit #1: 881 sf features bright, contemporary, open concept floor plan with 3 rooms: 1 bedroom, 1 full bath and kitchen / living room seamlessly connected and new appliances. Unit #2, larger second-floor unit, has stunning views of Gloucester Harbor: 1,327 sf, 4 rooms; 2 bedrooms, kitchen, living room / dining room open floor plan, new appliances, laundry, storage and fireplace in the Main Bedroom. Second floor unit walks out to a terraced backyard. All utilities including electric, heat, central AC and hot water are common. There is an attached one car garage at street level plus on-street parking and a single story, concrete structure to rear of the home that is electrified and housed a generator and could work well as an owner's work shop or storage unit. The 3,600 sf lot includes a terraced backyard. Location is central to coastal dining, maritime culture, shopping and downtown convenience. Whether you are looking for a savvy investment, year-round or vacation residence for extended family, this turn-key property is an excellent choice. Showings begin Saturday & Sunday 10/31 & 11/1 (daylight savings time!) 1-2:30PM.

320 Main St, Gloucester

Listing courtesy of Listing Agent: Kathleen Sullivan from Listing Office: RE/MAX Beacon.
35-37 Sargent St, Gloucester
$995,000
16 Beds ⋅ 10 Baths ⋅ 73595656 MLS ⋅ NEW 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..
19 Sadler Street, Gloucester
$620,000
4 Beds ⋅ 2 Baths ⋅ 73575107 MLS ⋅ ACTIVE Status
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. Both units are currently occupied by tenants at will and they each pay for own Utilities.

19 Sadler Street, Gloucester

Listing courtesy of Listing Agent: Jill Michaud 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.
141 Prospect St, Gloucester
$574,000
2 Beds ⋅ 2 Baths ⋅ 73517492 MLS ⋅ ACTIVE Status
Additional improvements just completed on this beautifully renovated 2 family home in the heart of Downtown Gloucester! In addition to new kitchens with updated cabinetry, countertops, and appliances, beautifully renovated baths and energy-efficient mini-split systems for year-round comfort, the owners have just added a new water heater, additional insulation, vapor barrier and new dehumidifier. Perfectly located just moments from restaurants, shopping, entertainment, beaches, the waterfront, and train station. This unique property offers the ultimate blend of coastal charm, modern updates, and investment potential, with no car needed. Each thoughtfully updated unit features 1 bedroom, 1 bath, and a spacious open-concept living/dining & kitchen area designed for comfortable daily living and effortless entertaining.The 2nd floor unit includes a small private deck, the perfect spot to unwind. Whether a smart investment, summer retreat, owner-occupied rental opportunity, or multi-generational living this property checks every box. Also offered for sale as 2 separate condos.

141 Prospect St, Gloucester

Listing courtesy of Listing Agent: Kathleen McHugh 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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