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$4,695,000
4 Beds ⋅ 4 Baths ⋅ 73542573 MLS ⋅ ACTIVE Status
Experience the best of Magnolia waterfront living at 16 Hesperus Circle. Situated at the center of a truly private landscape with unobstructed, breathtaking views of the Atlantic, this exceptional residence offers over 4,000 square feet of living space with 4 bedrooms and 3.5 baths. A flowing open layout is designed to maximize natural light and showcase the spectacular coastal setting, creating an ideal space for both everyday living and entertaining. Step outside to a stunning infinity pool overlooking the water, where endless ocean vistas provide the backdrop for unforgettable gatherings and quiet moments alike. Enjoy the rare combination of privacy and convenience, with Magnolia Beach, downtown Magnolia's shops and restaurants, and all that Cape Ann has to offer just a short walk away. A remarkable opportunity to own a premier waterfront home in one of Gloucester's most coveted seaside neighborhoods.

16 Hesperus Circle, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.
$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.
$2,395,000
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.
$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.
$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.
$2,200,000
73509397 MLS ⋅ ACTIVE Status
Rare opportunity to own a 3+ acre coastal parcel in Gloucester overlooking Essex Bay and Crane Beach. Set on a private road, this elevated, wooded lot offers exceptional privacy and the potential for a custom home in a premier Cape Ann location. Enjoy close proximity to Wingaersheek Beach, marinas, and downtown Gloucester while surrounded by natural beauty. Generous acreage and topography provide a unique setting to design a year-round residence or seasonal retreat. Buyer to perform all due diligence. Board of Health has denied septic approval; property being sold as-is.

19 Two Penny Ln, Gloucester

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.
$4,595,000
5 Beds ⋅ 3 Baths ⋅ 73503067 MLS ⋅ ACTIVE Status
Presenting a rare waterfront Eastern Pt compound spanning 3 contiguous parcels, ideally located between the yacht club and iconic lighthouse. This unique offering includes two single-family homes and a charming bunkhouse. 127 features a two-story, 2-BR home with a flexible first floor: 2 BRs, den, and screened porch which can comfortably host additional sleeping, and the stunning second-floor features an open-concept kitchen, dining, and living area with cathedral ceiling and a 30-foot wraparound deck. 129 is a single level, 3-BR bungalow with an updated kitchen, open living/dining, sunroom, and spacious wraparound deck. Completing the property, 131 has the delightful 11' x 15“ bunkhouse (has electricity, no plumbing), and is outfitted with 4 beds and a waterfront window that opens to an outdoor bar. A one-of-a-kind coastal retreat, with character and versatility - perfect for hosting family and guests. Attached is a feature sheet that provides detailed information about each parcel.

127-131 Eastern Point Blvd, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.
$3,295,000
4 Beds ⋅ 3 Baths ⋅ 73421894 MLS ⋅ ACTIVE Status
OPEN HOUSE SAT JULY 25th 11AM - 1PM. DEEP WATER DOCK approx. 290 feet along with a renovated 4-bedroom 2 1/2 bath harbor front home on Smith's Cove. Are you looking for your own private dock? The dock comes is fully licensed with a Chapter 91 permit, providing legal compliance for the owner. Sits across the harbor from Rocky Neck, renowned for its artist colonies, galleries, shops, and restaurants, this home offers a front-row seat to the bustling, picturesque harbor and easy access to the vibrant cultural life of Gloucester's waterfront. The home has all the modern conveniences with a state-of-the-art kitchen and high-end appliances. A spacious primary bedroom suite over the heated garage includes its own bath, while two additional bedrooms feature walkout decks and a skylight in the fourth bedroom. There is another room that could be an office and is close to the main bedroom. There are two baths on the second level and a half bath with a washer-dryer on the first floor.

263 East Main Street, Gloucester

Listing courtesy of Listing Agent: Jeanne Carpenter from Listing Office: J. Barrett & Company.
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73397445 MLS ⋅ ACTIVE Status
Waterfront living with historic charm. Once a working mill, the structure has been transformed into a warm and inviting home, preserving its architectural heritage while embracing contemporary updates. The open-concept layout offers sunlit living spaces that showcase panoramic vistas of Annisquam River, Wingaersheek Beach, and Ipswich Bay. Whether you’re unwinding on the expansive deck, paddling across the water for a beach day, or gathering clams right from your shoreline, this property delivers a true coastal lifestyle. Inside, the ambiance is both airy and intimate, perfect for hosting family or enjoying quiet evenings. The main house exudes a nautical elegance, with a layout that evokes the feeling of life aboard a luxury vessel. A separate apartment above the garage provides private accommodations for guests, and the partially finished upper level offers opportunities to tailor the home to your future needs.

672 Washington Street, Gloucester

Listing courtesy of Listing Agent: Joshua Mulvey from Listing Office: Mulvey Real Estate, LLC.

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