Homes for Sale in Gloucester

Killybracken, an enchanting estate with expansive lawns and lush, perennial gardens, ensures absolute and self-sufficient privacy while enjoying stunning panoramic ocean views. The compound features an historic main residence, pool house, guest cottage, detached two car garage all built with the finest attention to detail. This estate is rooted in beauty and strength. Behind the high-quality craftsmanship of gorgeous granite, antique woods, and other natural stone finishes. First built in 1927 in the Arts and Crafts Style, the entire compound has undergone a painstaking and thorough renovation, making it ideal for modern entertaining. The pool house with its all-season, indoor-outdoor pool is a true gem, offering additional living and entertaining space as well as an 8-person spa and steam room.This magnificent manor is secluded on one of the most eastern points of land in the continental United States yet has convenient links to Boston and can be easily reached by land, air and sea.

Commanding an ideal anchorage on Gloucester’s coveted Eastern Point, “Stoneacre” sits at tide’s edge and floats above the water like a yacht in the harbor, the waves seemingly at arm’s reach from every room, a cruise or sail just a moment away at the end of a deep-water dock with double moorings. Constructed of hand-cut granite block and set deep in granite ledge, the home is aptly named and built for the ages. An iconic presence for over a century, Stoneacre today offers a seaside estate without peer. Drive through the hand-carved wooden gates and enter a world where all is “luxury, peace and pleasure.” The home’s lavish scale—9+ bedrooms, 6 full baths, 4 half baths, 8 fireplaces, 10,000 sf of living space (plus 6,000+ sf of partially finished space on the 3rd floor)—is balanced by interior spaces of understated elegance and ease. With its immaculate grounds and fortress-like construction, Stoneacre offers the ultimate refuge and family compound at a time when it is needed most.

Inspired by the glorious estates of Europe, Terra Firma is a sophisticated and luxurious retreat that reflects that magical merging of inspiration and architecture. Created with elegant materials that were masterfully hand-crafted, the estate is a masterpiece of design and craftsmanship featuring granite flooring with radiant heating, cherry doors and cabinetry, intricately created moldings and ceiling features, imported fireplace mantels from Italy, exquisite crystal chandeliers, and more. Sprawling entertaining spaces flow from one room to the next with grace and flexibility. Multiple outdoor living spaces are surrounded by professionally-landscaped grounds make way to a vast and expansive ocean views. Positioned between the Atlantic Ocean and Bass Rocks Golf Course, this European-inspired is the crème de la crème in prestigious Gloucester estates.

Beautifully designed Post and Beam water view home features views of Vineyard Sound, Elizabeth and amazing sunsets Bordered by stone walls and sited on 2.2 acres, this exceptional property offers a private and peaceful setting, Main house includes 3 levels of living space. Upper level offers a Great Room that includes living, dining and kitchen. Nice features include cathedral ceilings, stone fireplace and a row of french doors that lead to a spacious deck. The master bedroom has many built-ins, a private deck and en-suite bath that includes a soaking tub and tiled shower. The second level offers a cozy family room that opens to another spacious deck, guest bedroom with full bath and a second master with private deck and en-suite bath. Lower level includes a game room with bunks, a full bath and laundry room. Super efficient Geothermal heating and cooling, wind turbine for electric savings. The 2-car garage offers second floor 1 bedroom apartment. Separate 1.56 acre parcel included.

Panoramic ocean views, Japanese inspired gardens with stone outcroppings welcome you to this unique 1937 stone Arts & Crafts style private estate overlooking the Atlantic ocean.The hand painted Frieze adorns the expansive living room which is anchored by a granite fireplace. Moravian tile floor and french doors expand the living area to a stone patio that commands dramatic ocean views. This one of kind 5 bedroom, 5.5 bath estate abounds with custom amenities to include stained glass windows, Teak Balcony and chestnut wall panelling. This estate has a new heating system, renovated bathrooms, new interior painting, new windows and doors, custom front entry, extensive landscaping and meandering gardens that lead you to a newly renovated stone cottage with wood burning stove.This estate encompasses 4 lots on 1.5 acres including the main house, cottage, greenhouse and 2 car garage.Close to Good Harbor Beach, I invite you to tour this spellbinding Sea Birch Estate where art and nature unite.

Located in one of the most desirable communities in Gloucester, this estate with unique architectural elements, beach and ocean views, and impeccable landscaping presents a rare blend of timeless luxury and 21st century convenience. Steps to Cambridge and Lighthouse beach and Annisquam Yacht Club, this spectacular home has been meticulously cared for and incorporates the modern amenities and systems that allow for unfettered enjoyment of life in one of New England’s finest seaside communities. Features include airy passageways, ornate mantels & fireplaces, hardwood floors, custom built-ins and closets. Its luxurious interiors offer constant views of sea and sky while its tiered design and versatile floor plan facilitate a variety of living options.

Enchanting East Gloucester estate set on 28 private acres. Iconic Cranberry Hill offers a grand residence, elegant gardens, a large granite rimmed pond, charming playhouse with granite fireplace, rolling lawns, barn with fenced paddock and a three car garage with separate one bedroom apartment. Enjoy tree top ocean views from the terrace and pastoral vistas across the property to the cranberry bog. Panoramic ocean views from floors two and three. Convenient to Bass Rocks Golf (and Tennis) Club, Bass Rocks Beach Club, Good Harbor Beach, and the best dog walking along the Atlantic on Gloucester's famed back shore. The entire property has been meticulously cared for and thoughtfully updated. Cranberry Hill is a very special property where life long memories will be made. Few properties on the North Shore compare.

A landmark Victorian located in the heart of Annisquam Village! The best of the old and the new tastefully display the original 3 story late 1800's home; formal living room and dining room, 3 bedrooms and 2 full baths are unique to the original home. A 2005 addition offers an open concept chef's kitchen and family room with fireplace, a spacious master bedroom with 2 walk-in closets and bath; additional large 2nd floor area allows imagination for office, playroom, yoga or art studio. Two oversize heated garages complete this home made for easy living. Conveniently located close to the Annisquam Yacht Club, private beaches, Lobster Cove marina and restaurant.

“Craig Haven” is a magical cottage retreat in the Eastern Point section of Gloucester –comprised of 5 parcels totaling 6.99+ acres and at its highest elevation offers excellent views to Brace Rock, Bemo Ledge and the Atlantic. At the entrance is a two-bay garage,parking area and guest cottage with 2 beds & 1.5 baths, a winding footpath meanders through ledge outcroppings and lush vegetation towards the main house – part of the incredible charm of this special place is the calm that begins to take over during the approach by foot. The ranch-style cottage is nestled into the enormous boulders and blends into the landscape while taking advantage of the views, the home has a 3 beds and 1.5 baths, an eat-in kitchen, garden room, dining room and a great room with a vaulted beamed ceiling, a prominent fieldstone fireplace and picture window facing the ocean.The property features a ruggedly beautiful natural landscape with woodland trails, lawn areas, wetlands & an old footpath to the beach.

Perched on a granite outcropping high above the harbor, the views will make you say O.M.G.!!! Designed for maximum privacy, the only shared wall of this brand-new duplex is a staircase. Impressive great room blends kitchen, dining and living against a wall of glass and full-length deck. All three bedrooms have ensuite baths including one on the first floor. The master features a private deck, large walk-in closet & luxurious bath. Bonus room on the second floor works well as home office or perhaps bunk room for visiting grandkids. Additional 665 s.f. unfinished area over the garage for storage or your specific needs. Exclusive use outdoor space has a lawn, future fire-pit area, and large driveway with guest parking. All of this in desirable East Gloucester with excellent proximity to Good Harbor Beach, the Back Shore, Rocky Neck, marinas, shopping & all that Cape Ann has to offer! Did I mention the sunsets are spectacular? This is the only unit that will be offered. Come take a look.

Perched on a granite outcropping high above the harbor, the views both night and day will make you say “O.M.G.”!!! Designed for maximum privacy, with only a small shared wall at the staircases, this home is deeded as a condo but lives like a single family. Impressive great room blends kitchen, dining & living against a wall of glass w/full length deck. First floor bedroom w/full bath allows for 1-level living. Second floor has guest room/with full bath. Master bedroom features a private deck, large walk-in closet + luxurious bath. Bonus rm on 2nd floor works as home office, exercise or bunk room. Additional 665 sf unfinished room over garage for storage or your specific needs. Want to garden? Exclusive use outdoor space has a lawn, future fire-pit or BBQ area; & large driveway for guest parking. All of this in desirable East Gloucester. No condo fee-owners to share the few common expenses. Did I mention the sunsets are spectacular? This brand-new home is truly special.

Contemporary commanding a prime 2+ acre lot in the heart of Eastern Point, with walking trail to ocean and moments from Brace Cove, Niles Pond and Eastern Point Yacht Club. Owned continuously by one family, the home has served as primary residence, summer retreat and artist studio. The open and airy design offers living on multiple levels: the second level has four spacious bedrooms, master suite with master bath and bidet, and wrap-around deck opening to landscaped gardens and gunite pool with flagstone deck. The stunning third floor, accessed by a Douglas fir staircase, offers a bookshelf-lined study, loft storage, full bath, living room with wood-burning fireplace with granite hearth, and full kitchen with dumbwaiter from first floor, opening to dining room and expansive deck. A large attic allows for expansion, and detached 2-car garage with workshop and artist’s studio. A rare and versatile property in a highly sought-after community, ready for its second chapter.