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$1,499,000
4 Beds 3 Baths 73534421 MLS ACTIVE Status
Enjoy breathtaking, ever-changing ocean views stretching across Eastern Point and beyond. Set in one of Gloucester’s most picturesque locations, this charming property offers unobstructed water vistas and a truly memorable coastal lifestyle. Rich in character, the home is surrounded by lush, professionally landscaped gardens, a welcoming patio, beautiful flowering trees, and vibrant perennial beds. A private beach is just steps from your door, while stunning ocean views can be enjoyed from nearly every room and outdoor space. Wake each morning to spectacular sunrises over the water and spend your days taking advantage of endless opportunities for boating, swimming, and seaside relaxation. With sweeping views, exceptional natural beauty, and an unmatched setting, this is a rare opportunity to create a lifetime of cherished Gloucester memories.

69 Dolliver Neck Rd, Gloucester

Listing courtesy of Listing Agent: Kristin Francoeur from Listing Office: Gibson Sotheby's International Realty.

$2,590,000
73533334 MLS ACTIVE Status
10-unit downtown Gloucester, consisting of 7 residential units & 3 commercial units w/ strong in-place income and long-term upside. The property generates approximately $262,920 in gross annual income w/ operating expenses of ~$71,000, delivering an attractive 7.4% cap rate; increasingly difficult to find in today’s market. Lead compliant certificates for 7 residential units. This asset has been significantly improved, featuring a new roof, updated siding, newer windows, and a rebuilt rear deck, minimizing near-term capital expenditures. Highly walk-able downtown location, tenants benefit from proximity to shops, restaurants, the waterfront, and public transportation supporting strong rental demand across both residential and commercial units. Ideal for an investor seeking stable cash flow with upside, or a 1031 exchange buyer looking to trade into a larger, higher-performing asset in a prime coastal market.

222 Main St, Gloucester

Listing courtesy of Listing Agent: Stephen Martin from Listing Office: Aluxety.

$2,590,000
14 Beds 10 Baths 73533333 MLS ACTIVE Status
10-unit downtown Gloucester, consisting of 7 residential units & 3 commercial units w/ strong in-place income and long-term upside. The property generates approximately $262,920 in gross annual income w/ operating expenses of ~$71,000, delivering an attractive 7.4% cap rate; increasingly difficult to find in today’s market. Lead compliant certificates for 7 residential units. This asset has been significantly improved, featuring a new roof, updated siding, newer windows, and a rebuilt rear deck, minimizing near-term capital expenditures. Highly walk-able downtown location, tenants benefit from proximity to shops, restaurants, the waterfront, and public transportation supporting strong rental demand across both residential and commercial units. Ideal for an investor seeking stable cash flow with upside, or a 1031 exchange buyer looking to trade into a larger, higher-performing asset in a prime coastal market.

222 Main St, Gloucester

Listing courtesy of Listing Agent: Stephen Martin from Listing Office: Aluxety.

$2,395,000
2 Beds 2 Baths 73531602 MLS ACTIVE Status
This is more than a home—it’s a coastal lifestyle. Follow the steps to the water and dive into the cove at high tide, or wander the beautiful beach at low tide. The views are simply unparalleled. Spend your evenings on the upper deck as the sunset sets the seascape ablaze with color.The chef’s kitchen features nearly new Thermador appliances, reclaimed American heart pine floors, and an oversized island perfect for casual dining. A 10-foot picture window, installed last year, frames the ever-changing coastal scenery. The living room, with its inviting fireplace, opens to a charming covered porch—ideal for outdoor dining from morning coffee to evening meals.Upstairs, the primary bedroom offers breathtaking views stretching beyond Eastern Point. A second-floor family room with access to the upper deck is especially magical in the summer and could be converted into a third bedroom. Welcome to Rocky Neck—a destination people love to visit and a place you’ll be proud to call home.

8 Bickford Way, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.

$1,249,000
4 Beds 3 Baths 73531534 MLS ACTIVE Status
Breathtaking new construction SF home nestled in the serene Bay View area of Gloucester, offering the perfect blend of modern luxury and seaside charm. Masterfully designed with fine craftsmanship and a coastal lifestyle, this spacious 2,600 sq. ft. home features a seamless open-concept layout. The chef-inspired kitchen boasts a large center island flowing into a cozy family room anchored by a contemporary electric fireplace all just steps to the outside deck. A versatile den/dining room, half bth, and convenient mudroom off the attached 2-car garage complete the main level. Upstairs, retreat to your private primary suite oasis with a stylishly tiled custom shower. 3 additional generous bedrooms share a beautifully appointed full bath, alongside a dedicated home office and separate laundry room. Situated on a tranquil private road, enjoy views of Ipswich Bay. Take a leisurely stroll to the pristine sands of Plum Cove Beach. Don't miss this opportunity to live in this seaside community!

5 Ciaramitaro Ct, Gloucester

Listing courtesy of Listing Agent: Melissa Skomurski from Listing Office: Churchill Properties.

$1,699,000
3 Beds 3 Baths 73531398 MLS ACTIVE Status
Some homes simply hold furniture. Others hold generations of sandy feet, late-night swims, and the kind of summer memories that seem to stretch on forever. Welcome to 8 Schooner Ridge. Tucked into Gloucester’s coveted Castleview Estates with deeded access to Coffin’s Beach, this sun-filled Acorn contemporary was designed for gathering, unwinding, and living coastal life to the fullest. Vaulted ceilings, walls of glass, and back-to-back fireplaces create warm, dramatic living spaces, while distant views of Ipswich Bay remind you the ocean is never far away. The open floor plan flows easily from kitchen to entertaining spaces to expansive outdoor decking overlooking the pool and beautifully reimagined landscaping. A spacious primary suite, finished lower level for games, workouts or guests, whole-house generator, and oversized 3-car garage complete the retreat. Beach days, pool nights, sea breezes, and space for everyone — this is the rhythm of summer on Cape Ann.

8 Schooner Ridge, Gloucester

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.

$619,900
4 Beds 2 Baths 73531280 MLS ACTIVE Status
Next showing @ Open House on Sunday, June 14, 2026 12:30 PM - 2:00 PM Excellent opportunity for both investors and owner-occupants! This beautifully renovated two-family home is located just moments from downtown Gloucester. Recent updates include a new roof, replacement windows, and upgraded heating systems. Unit 1 has been completely renovated with brand-new kitchen & bathroom, while Unit 2 has also been tastefully updated. The property features separate heating systems, hot water, and updated electrical utilities for each unit. A recently installed fire alarm system provides added peace of mind. Conveniently located within walking distance of Gloucester's vibrant restaurants, shops, harbor, and train station.Both units are currently vacant, offering immediate rental income potential or flexibility for owner occupancy.Don't miss this turnkey investment opportunity in a prime Gloucester location!

15 Shepherd St, Gloucester

Listing courtesy of Listing Agent: Stephen Curcuru from Listing Office: MP Realty Group.

$858,000
2 Beds 2 Baths 73530937 MLS ACTIVE Status ['Pirates Lane Condominium'] BLDG.
Experience spectacular sunsets and panoramic harbor views from this sun-filled, west-facing townhome in the heart of historic East Gloucester. Ideally situated beside the North Shore Art Association and just a short stroll to Rocky Neck, this charming residence offers the perfect blend of coastal beauty and convenience The main level features an open-concept design with a spacious living area, a beautifully appointed kitchen with quartz countertops, a generous bedroom, full bath, and in-unit laundry. Upstairs, a bright and versatile retreat opens through sliding glass doors to a private deck where you can relax and take in the breathtaking water views. The upper level can serve as a luxurious primary suite with its own full bath or, by folding away the Murphy bed, transform into an expansive living or entertaining space. An unbeatable location in one of Cape Ann’s most authentic waterfront neighborhoods. Whether you're looking for a serene weekend escape or a year-round residence.

5 Pirates Lane Unit 11, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.

$794,000
3 Beds 2 Baths 73529180 MLS ACTIVE Status
Location, location, location – says it all for this hidden gem near Niles Beach in East Gloucester – as a full-time residence or summer/weekend getaway less than a half mile to the beach. A meandering paver path leads to this light-filled 3-bedroom, 2 full bath charmer with cathedral ceilings, multiple sets of sliders, skylghts, and huge windows throughout while the wraparound deck is a great gathering spot after a day at the beach or a quiet haven when sipping beverages or stargazing. The easy flow main level, which has a full bathroom, offers hardwood flooring in the great room, kitchen and primary bedroom. Designed for flexibility as well as privacy, one side of the house has 2 bedrooms, a full bathroom and a separate entrance. An oasis of peace and serenity, this beachy property is fully fenced and surrounded by sprawling lawns dotted with colorful plantings. Don’t let this be the “one” that gets away.

7 Lighthouse Way, Gloucester

Listing courtesy of Listing Agent: Ann Rick Gloucester Group from Listing Office: J. Barrett & Company.

$1,450,500
2 Beds 4 Baths 73528259 MLS ACTIVE Status ['Magnolia Shores'] BLDG.
Imagine the scale of a single-family home, the maintenance freedom of a luxury condominium, and the draw of the New England coast--all 30 miles north of Boston. Set within the exclusive Village at Magnolia Shores nestled on 50 park-like acres, this exceptional 2+bedroom, 3.5-bath, 3000+ sq ft residence redefines condominium living. Step inside to soaring 10ft coffered ceilings and a sun-flooded great room anchored by a gas fireplace, where living, dining, and a beautifully appointed designer kitchen open naturally into one another. An adjacent sunroom captures light from sunrise to sunset making it a spa-like sanctuary year round. The primary suite with a luxurious bath and walk-in closet, a second ensuite bedroom, and an inviting library/office make for easy first floor living. The lower level is a third suite: bedroom, full bath, and a spacious family room with sliders opening to the outdoors--it's where kids can play, teens can hide, and houseguests can find a home within your home!

28 Kennedy Rd Unit B, Gloucester

Listing courtesy of Listing Agent: Meg McGowan from Listing Office: Gibson Sotheby's International Realty.

$489,000
2 Beds 1 Baths 73526608 MLS ACTIVE Status
Just moments from beloved Plum Cove Beach, where spectacular sunsets and coastal beauty become part of everyday life, this newly renovated ground level condominium offers a turnkey opportunity in one of Gloucester's most sought-after seaside settings. Fresh, clean, and thoughtfully updated, the home features stone countertops, a dedicated office nook, and a new washer/dryer combo for modern convenience. An efficient layout maximizes every square foot, while a detached workshop/studio provides endless possibilities for artists, hobbyists, fitness enthusiasts, or storage for kayaks, paddleboards and beach gear. A private outdoor area, located a short distance from the unit, offers valuable additional space for gardening, boat storage or outdoor recreation. Whether you’re seeking a year-round residence, weekend retreat, or summer getaway, this low-maintenance property delivers exceptional access to the beach and all that Cape Ann has to offer.

6 Mt Locust Place Unit 2, Gloucester

Listing courtesy of Listing Agent: Sara Seber from Listing Office: Engel & Volkers By the Sea.

$1,099,000
4 Beds 2 Baths 73523928 MLS ACTIVE Status
This beautifully maintained home has been extensively updated, offering true move-in-ready living. The 1st floor features a stunning chef’s kitchen with quartz countertops, custom cabinetry, and quality finishes throughout. Also on the main level are a spacious bedroom, dining area, front-to-back living room with a new gas fireplace, full bath, and an exceptional sunroom overlooking the expansive deck and backyard. Upstairs, you'll find a generously sized primary bedroom, two additional bedrooms, and a second full bath. A standout feature is the 12' x 20' shed with electricity and plumbing, offering exciting potential as a guest suite, in-law space, private office, studio, or workshop. Just steps from the property, enjoy deeded/shared access to the scenic Little River (which flows into the Annisquam), where you can swim, launch kayaks or paddleboards, go clamming, or simply take in the water views and coastal charm that make this location so desirable.

43 Woodward Ave, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.

$995,000
1 Beds 1 Baths 73522580 MLS ACTIVE Status ['Habror Haven At Rocky Neck'] BLDG.
Dock, Dine & Drift Away at Harbor Haven. This newly-created condominium offers a rare opportunity to embrace the quintessential Cape Ann waterfront lifestyle. Tucked away in a secluded harborfront setting, COMPLETE WITH an exclusive seasonal deep-water boat slip accommodating up to a 25-foot vessel—allowing easy access from your private deck to the open waters of Gloucester Harbor and beyond! Enjoy unobstructed water/cityscapes, gentle sea breezes, and a tranquil backdrop that feels worlds away, yet is convenient to vibrant galleries, restaurants, and the maritime charm of Rocky Neck. Thoughtfully refreshed, the residence features A/C, quartz countertops, stainless steel appliances, refinished hardwood floors and individually-metered municipal water service. Envisioning a weekend retreat, pied-à-terre by the sea, year-round waterfront residence, or an investment addition to your portfolio? Harbor Haven is an exceptional offering in one of Cape Ann's most iconic coastal locations.

64 Rocky Neck Ave Unit C, Gloucester

Listing courtesy of Listing Agent: Janet Breiter from Listing Office: Keller Williams Realty Evolution.

$995,000
1 Beds 1 Baths 73522248 MLS ACTIVE Status ['Habror Haven At Rocky Neck'] BLDG.
Dock, Dine & Drift Away at Harbor Haven. This newly-created condominium offers a rare opportunity to embrace the quintessential Cape Ann waterfront lifestyle. Tucked away in a secluded harborfront setting, COMPLETE WITH an exclusive seasonal deep-water boat slip accommodating up to a 25-foot vessel—allowing easy access from your private deck to the open waters of Gloucester Harbor and beyond! Enjoy unobstructed water/cityscapes, gentle sea breezes, and a tranquil backdrop that feels worlds away, yet is convenient to vibrant galleries, restaurants, and the maritime charm of Rocky Neck. Thoughtfully refreshed, the residence features A/C, quartz countertops, stainless steel appliances, refinished hardwood floors and individually-metered municipal water service. Envisioning a weekend retreat, pied-à-terre by the sea, year-round waterfront residence, or an investment addition to your portfolio? Harbor Haven is an exceptional offering in one of Cape Ann's most iconic coastal locations.

64 Rocky Neck Ave Unit B, Gloucester

Listing courtesy of Listing Agent: Janet Breiter from Listing Office: Keller Williams Realty Evolution.

$1,100,000
2 Beds 2 Baths 73521436 MLS ACTIVE Status
One of the oldest surviving homes in Annisquam, this historic First Period Colonial (circa 1717) is part of the property known as "The Old Castle." On Lobster Cove, this waterfront residence showcases a seasonal dock providing direct access. Located on the North Shore in Gloucester, the historic village of Annisquam offers a distinct coastal experience, distinguished by its narrow winding lanes, historic architecture, and a community atmosphere. Exceptional views are enjoyed both inside and out. Original craftsmanship has been preserved, including wide pine floors, woodwork, and two fireplaces. A sunroom along the water side was added and designed with three walls of full-length windows to watch the cove, with ample space for dining and multiple seating areas. The layout offers a bathroom on each floor, second-floor laundry, a back stairway, and third-floor bonus space. Practical updates include an updated heating system, replaced sunroom windows, basement work, and a repaired seawall.

65 Leonard Street, Gloucester

Listing courtesy of Listing Agent: John Farrell from Listing Office: Coldwell Banker Realty - Beverly.

$635,000
2 Beds 2 Baths 73520543 MLS ACTIVE Status ['Ravenswood Condominiums'] BLDG.
Built in 2022 and thoughtfully designed with quality craftsmanship throughout, this stunning 2-bedroom townhome offers the perfect blend of modern coastal style and easy beachside living. Featuring high-end appliances, upscale finishes, and an open, light-filled layout, every detail was carefully curated for comfort and style. Enjoy the convenience of garage parking, in-unit laundry, radiant floor heating in the bathrooms and a fenced-in yard ideal for relaxing or entertaining after a day at the beach. Located just moments from the shoreline in beautiful Gloucester, this home is the perfect year-round retreat or summer escape with low-maintenance living and a true coastal vibe. Showing to begin immediately.

302 Western Ave Unit A, Gloucester

Listing courtesy of Listing Agent: Katelyn Ciaramitaro from Listing Office: Engel & Volkers By the Sea.

$607,900
2 Beds 2 Baths 73517492 MLS ACTIVE Status
Rare opportunity to own 2 beautifully renovated condominiums in the heart of Downtown Gloucester! 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. New kitchens with updated cabinetry, countertops, and appliances pair perfectly with beautifully renovated baths and energy-efficient mini-split systems for year-round comfort. 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.

$295,000
1 Beds 1 Baths 73517482 MLS ACTIVE Status
Experience the best of coastal living in the heart of Downtown Gloucester! Ideally located just moments from restaurants, cafés, shopping, entertainment, the waterfront, beaches, and the train, this charming top-floor 1-bedroom condo offers the perfect blend of convenience, comfort, and style. Filled with natural light, this sunny home features an open-concept living, dining & kitchen area that feels spacious and inviting. The beautifully updated kitchen showcases new cabinetry, countertops, and appliances, hardwood flooring throughout adds warmth and character. Upgrades include an updated bath and a new energy-efficient mini-split system for year-round comfort. Enjoy relaxing on your private, cozy back deck. Part of a newly converted 2 unit condominium property, this home is also available as part of a multi-family offering. Whether looking for the perfect weekend getaway, investment opportunity, or year-round residence, this unbeatable location means you can leave the car behind!

141 Prospect St Unit B, Gloucester

Listing courtesy of Listing Agent: Kathleen McHugh from Listing Office: Churchill Properties.

$279,000
1 Beds 1 Baths 73517477 MLS ACTIVE Status
Live the ultimate coastal lifestyle in the heart of Downtown Gloucester! Perfectly located just moments from vibrant restaurants, waterfront dining, beaches, shopping, entertainment, and the train station, this beautifully renovated one-bedroom condo offers convenience, charm, and modern comfort all in one. Step inside to discover a bright and inviting open-concept living, dining, and kitchen space designed for easy everyday living. The stunning new kitchen features stylish cabinetry, updated countertops, and brand-new appliances, while the bathroom boasts a gorgeous shower, storage, and beautiful finishes. A perfect get-away or primary residence, no car needed in this convenient location! Part of a newly converted 2 unit condominium property, this home is also available as part of a multi-family offering.

141 Prospect St Unit A, Gloucester

Listing courtesy of Listing Agent: Kathleen McHugh from Listing Office: Churchill Properties.

$750,000
1 Beds 1 Baths 73515187 MLS ACTIVE Status
Artist's Cottage — Annisquam/Back Bay, Gloucester. Originally built as an artist's barn, this magical one bedroom cottage sits on nearly an acre of land in one of Cape Anns most beautiful neighborhoods. Enjoy sunrises near the ocean, watch the stars appear at night, and step outside to gardens lovingly cultivated with organic care for over 25 years. A haven for sailors, kayakers, gardeners, writers, and dreamers. Make this your year round or perfect weekend get away spot. Perched atop a hill and safely above coastal storms, yet minutes from Gloucester's finest beaches, quarries, and so many hiking trails. The privacy, beauty and convenience is unmatched. Zoned R-40 with town water and sewer and two potential driveways — build your dream home and use the cottage for guests, studio space, or explore ADU or subdivision potential. Minutes to Annisquam Village and Plum Cove Beach. Come live by the ocean.This diamond is a rare find and won't be on the market long!

38 Revere Street, Gloucester

Listing courtesy of Listing Agent: Krista Julian from Listing Office: Coldwell Banker Realty - Manchester.

$534,000
2 Beds 2 Baths 73514328 MLS ACTIVE Status
Turnkey Victorian Cottage in downtown Gloucester offering the perfect blend of character and convenience. Ideally located near the train, beaches, shopping, and highway access, the home enjoys ample street parking and added privacy with undeveloped land across the street. The first floor features a spacious living room with coffered ceilings, hardwood floors, and a large picture window, a petite but efficient kitchen along with an adjoining light infused dining room with sliding glass doors leading to a sunny, enclosed backyard, perfect for relaxation. Upstairs includes two generously sized bedrooms, a large bath with stackable washer/dryer, and a versatile third room ideal for office space, nursery, or oversized dressing room. The finished lower level houses a half bath, open living space, separate entrance, and abundant storage.

8 1/2 Myrtle Square, Gloucester

Listing courtesy of Listing Agent: Julia Virden from Listing Office: J. Barrett & Company.

$1,899,000
3 Beds 4 Baths 73510260 MLS ACTIVE Status
Perched above the Atlantic, this brand-new luxury condo at The Overlook offers breathtaking views of the crashing waves and surfers at Good Harbor Beach. This is the last remaining opportunity to own in Gloucester’s most sought-after new development, The Overlook. Designed to maximize its dramatic elevation, the home features panoramic ocean vistas from every level. The interior is a study in light and volume, boasting soaring cathedral ceilings and a sophisticated 3-BR, 3.5-BA layout. The crowning jewel is the top-floor roof deck and flex suite with a wet bar—the ultimate setting for a high-end home office, art studio, or sunset lounge. Outside, expansive decks and a private rear patio offer seamless indoor-outdoor entertaining and provides places to relax and enjoy the views. With premium finishes and a track record of high demand, the peak of coastal living has arrived. Grab your surfboard and head to Good Harbor Beach or enjoy the view from your own home.

18R Starknaught Heights Unit A, Gloucester

Listing courtesy of Listing Agent: Nest | Syndi Zaiger Group from Listing Office: Compass.

$2,699,000
4 Beds 5 Baths 73510015 MLS ACTIVE Status
Exceptional waterfront living on the Mill River, this 2021-built contemporary home offers beautiful unobstructed riverfront views with glimpses extending toward Wingaersheek Beach and Ipswich Bay. Thoughtfully designed with 4 bedrooms and 4.5 baths, the home features an expansive open-concept layout centered around a dramatic great room that flows seamlessly onto a spacious deck, perfect for enjoying the ever-changing waterfront scenery. A chef’s kitchen with walk-in pantry anchors the main living space, complemented by high-end finishes and effortless indoor-outdoor living ideal for entertaining. Step outside to your private dock - an exceptional bonus - offering direct access to the Mill River for boating, kayaking, or paddleboarding right from your backyard. Additional highlights include a dedicated home office, oversized 2-car garage, and energy-efficient systems for modern comfort. A rare opportunity to own a nearly new waterfront home in a prime Gloucester location.

498 Washington St, Gloucester

Listing courtesy of Listing Agent: Atlee Alman from Listing Office: Vadala Real Estate.

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