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$1,850,000
4 Beds ⋅ 4 Baths ⋅ 73557136 MLS ⋅ NEW Status
Set on one of Castleview's highest points, this beautifully crafted Contemporary Shingle-Style residence captures distant views of the Annisquam River and Ipswich Bay while offering the privacy and tranquility that define Cape Ann's coastal lifestyle. Filled with natural light and thoughtfully designed to maximize its surroundings, the home blends relaxed elegance with everyday comfort. The open-concept floor plan creates an easy flow between the main living spaces, making it equally suited for entertaining and quiet evenings at home by the fire. The well-appointed chef's kitchen features granite countertops, stainless steel appliances, custom cabinetry, a generous walk-in pantry with dumbwaiter, and built-in wine storage. The primary suite serves as a private retreat, with water views, a gas fireplace, vaulted ceilings, and its own deck overlooking the surrounding landscape. The spa-like bath includes a Jacuzzi tub, steam shower, and adjoining walk-in closet. Additional living spaces offer flexibility for guests, remote work, or extended family while maintaining a comfortable and welcoming feel throughout. Outside, the backyard provides a peaceful setting with a hot tub, outdoor shower, and fantastic grounds, with irrigation and sublime lighting. A standout feature of the property is deeded access to private Wingaersheek/Coffin Beach, offering a rare opportunity to enjoy one of Cape Ann's most sought-after stretches of shoreline. Located in one of Gloucester's most desirable seaside neighborhoods, this exceptional home combines quality craftsmanship, privacy, and an enviable coastal setting, just minutes from downtown Gloucester's dining, shops, galleries, marinas and waterfront.

7 Sea Fox Lane, Gloucester

Listing courtesy of Listing Agent: Scott Smith from Listing Office: Coldwell Banker Realty - Manchester.
$898,000
4 Beds ⋅ 2 Baths ⋅ 73556343 MLS ⋅ NEW Status
Character, charm and potential define this 1873 Italianate Colonial with a sensational water view beyond Gloucester Harbor and the breakwater. Owned by the same family for almost 100 years, this versatile property with a separate apartment – for guests, generational living or rental - is in a multi-family zone. Additional highlights include 2,203+ sf of living space, 4 bedrooms, 2 full baths, eat-in kitchen, enclosed front porch, and captivating period details like the built-in china cabinet in the generous dining room with a sweet bay window bump out, striking etched glass window and original woodwork and rosewood newel post. One-of-a-kind, the 3-story home also offers new owners the opportunity to create personalized living spaces from the lower level to the top floor with all 4 bedrooms or add more living space by expanding into the large backyard. Hardwood flooring and oversized windows accent many rooms in this classic property near the New Balance Stadium and picturesque harbor. Minutes to shops, dining, parks, and schools. Don’t miss this rare opportunity to be the new stewards of this versatile property!

32 Blynman Avenue, Gloucester

Listing courtesy of Listing Agent: Ann Rick Gloucester Group from Listing Office: J. Barrett & Company.
$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.
$565,000
2 Beds ⋅ 2 Baths ⋅ 73540674 MLS ⋅ ACTIVE Status
Welcome to the heart of East Gloucester's highly desirable neighborhood, where coastal charm meets everyday convenience. Just a short stroll to Good Harbor Beach, this delightful 2-bedroom, 1.5-bath home offers the perfect opportunity for year-round living, a weekend retreat, or a summer getaway by the sea.Nestled on a private, secluded lot, the property features an absolutely charming backyard—ideal for relaxing, entertaining, or enjoying the peaceful surroundings. A beautiful sunroom overlooks the backyard, creating a bright and inviting space to enjoy your morning coffee or unwind after a day at the beach.Ocean lovers will appreciate the unbeatable location, while commuters will love the easy access to Route 128. Additional features include off-street parking and the rare combination of privacy and proximity to Gloucester's beaches, restaurants, shops, and coastal attractions. THIS IS A MUST SEE!

38R Bass Ave, Gloucester

Listing courtesy of Listing Agent: Lisa Gaglione from Listing Office: Churchill Properties.
$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.
$1,800,000
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.
$1,800,000
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.
$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.
$429,000
73519210 MLS ⋅ ACTIVE Status
Looking for a woodland wonderland to build your dream home? This consists of 2.05 acres of improved land with driveway, upgraded private well, cleared building envelope, stone walls and privacy borders. The Soil Test results are for a four bedroom system, buyer is responsible for septic design. The Zoning is R-80, requiring 100 feet of frontage and 80,000.00 square feet of land for a single family, with 40,000 square feet of land required for additional units. Acreage will allow a two possibly three family residence. Nice private location in woodland setting to build dream home or two family residence.

79 Woodman St, Gloucester

Listing courtesy of Listing Agent: Holly Chiancola from Listing Office: Holly C & Co. Fine Homes.
$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.
$799,900
2 Beds ⋅ 2 Baths ⋅ 73510157 MLS ⋅ ACTIVE Status
Just steps from Lane’s Cove, this home is a testament to enduring architectural charm, offering beautiful wood floors throughout, spacious living room, dining room and kitchen, wood pellet stove, two bedrooms with vaulted ceilings, deck, yard, outdoor shower and garden shed.

4 Langsford St, Gloucester

Listing courtesy of Listing Agent: Michael Beaton from Listing Office: Churchill Properties.
$1,300,000
73504591 MLS ⋅ ACTIVE Status
Outstanding land opportunity on coveted Eastern Point. This prime parcel is beautifully positioned on Elm Avenue and has views of Gloucester Harbor, Dog Bar Breakwater and the distant Boston skyline. There is an appoved 5-bedroom septic system in hand, with water and electricity at the street. A short stroll will take you to multiple beaches, private clubs and conservation land with endless trails to explore. Downtown Gloucester is moments away with fine dining, galleries, boutiques and cultural attractions that make the city the hub of the North Shore.

5 Elm Avenue, Gloucester

Listing courtesy of Listing Agent: Scott Smith from Listing Office: Coldwell Banker Realty - Manchester.
$1,425,000
5 Beds ⋅ 5 Baths ⋅ 73503932 MLS ⋅ EXTENDED Status
Treasure at Lane's Cove. A rare opportunity to live in the heart of Lanesville with water views & access to Lanes Cove a protective inlet leading out to Ipswich Bay & beyond. Launch your kayak, paddle board or small boat away from the busy summer crowds. This modern & updated home offers 5 bedrooms, 5 bathrooms and a profitable Air BNB in the lower level with a separate entrance. The main kitchen boasts an oversized granite chef's island, Viking Stove, a refinished maple floor & oversized Anderson windows overlooking the water & sunsets that will make your heart skip a beat. Entertain guests in the formal living room featuring a handsome Brazilian wood floor, wet bar, refrigerator & granite counters. The outdoors come alive inside with easy access to wrap around decks and balconies. The heft and quality of the new Anderson sliders and windows is noticed upon each turn or pull of the door handle. Many unique features unlike any other; port hole windows, tiled entry foyer, paid in full solar panels with a profitable return, an oversized garden shed to store your lawn mower, boating equipment, snow blowers. Lovely & established perennial beds offering sequential blooming & flowering shrubs, just mulch and enjoy. Entertain guests on the 15'X30' deck just sanded and stained bringing out the deep rich tones of mahogany wood. Enjoy morning coffee or a weekend BBQ overlooking the water while watching boats, swimmers and the occasional herd of whales coasting through. Stunning ocean views from most rooms! Discover Plum Cove Beach around the corner with crystal clear & calm waters many family's enjoy. Explore miles of woodland trails, bike paths and quintessential Dog town steeped in history and lore. Downtown Lanesville offers all the goods you need in case you forgot something from in town, Grab a yummy lunch to go from The Cove Cafe or pick out a fine wine and a steak at Lanesville Liquor and mail out that package at the Post Office next door. Lanesville: So unique you will never want to leave.

12 Andrews Street, Gloucester

Listing courtesy of Listing Agent: Mary Matthews from Listing Office: Coldwell Banker Realty - Manchester.
$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.
$1,198,000
73499819 MLS ⋅ ACTIVE Status
An unparalleled opportunity for development comes to light on these private lots near Good Harbor Beach. Ideally situated well with stunning water views, the property is zoned R-10, allowing both single family and multifamily development. Build your private escape and experience the best of the Good Harbor Beach life with birds-eye view of the Atlantic from the comfort of your gorgeous home, or, have your feet in the sand in minutes. The property has a great potential. Please do not walk on site without listing agent.

6-8 Joppa Way, Gloucester

Listing courtesy of Listing Agent: Nest | Syndi Zaiger Group from Listing Office: Compass.
$1,225,000
3 Beds ⋅ 3 Baths ⋅ 73482119 MLS ⋅ ACTIVE Status
Moments from the pristine shores of Wingaersheek Beach, this beautifully maintained three bedroom, two and a half bath home offers the perfect weekend retreat, seasonal escape, or year round coastal residence. Set in a picturesque setting with views of the Jones River, the property is filled with natural light and features hardwood floors with comfortable living spaces throughout including a kitchen open to the dining area and a family room with fireplace. The second level features three bedrooms and two full baths, including the primary suite. Outside, established perennial gardens and inviting outdoor spaces create a wonderful setting for relaxing or entertaining. Unfinished basement houses utilities & storage space. Two car garage beneath the home provides convenient parking and additional storage. Thoughtfully updated throughout, the home offers a low maintenance coastal lifestyle just moments from one of Cape Ann’s most beloved beaches.

178 Atlantic Street, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.
$2,999,000
4 Beds ⋅ 5 Baths ⋅ 73433660 MLS ⋅ ACTIVE Status
Just steps from Wingaersheek Beach, 226 Atlantic Street is an extraordinary new home that blends timeless design with coastal living. Crafted for year-round comfort, this residence offers a chef-inspired kitchen with custom cabinetry, Thermador appliances, and walk-in pantry. The great room soars with a cathedral ceiling and stone fireplace, leading to a four-season porch that brings the outside in. Two serene primary suites—including one on the first floor for the ease of single-level living—feature spa-like baths with heated floors and soaking tubs. Expansive decks and a patio with gas hookups create ideal spaces for entertaining. With energy-efficient systems, EV and solar-ready infrastructure, and Wingaersheek’s crystal-clear waters and soft sand just steps away, this home is both a retreat and a destination.

226 Atlantic Street, Gloucester

Listing courtesy of Listing Agent: Nest | Syndi Zaiger Group from Listing Office: Compass.
$3,295,000
4 Beds ⋅ 3 Baths ⋅ 73421894 MLS ⋅ ACTIVE Status
OPEN HOUSE SAT AUG 1st 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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