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Set on over half an acre, this lovely home enjoys sweeping views across a golf course to the ocean. A circular driveway welcomes you to gracious living spaces, including a primary bedroom suite with a separate sitting area. On the first level a sunroom opens onto a patio while an elegant screened porch offers another inviting place to relax and take in the surroundings.The eat in kitchen features a pantry and a separate utility room adds everyday convenience. Central air conditioning and updated utilities provide modern comfort. Mature plantings and handsome stone walls give the property timeless charm.

5 Beds ⋅ 4 Baths ⋅ 73596597 MLS ⋅ NEW Status

Set on over half an acre, this lovely home enjoys sweeping views across a golf course to the ocean. A circular driveway welcomes you to gracious living spaces, including a primary bedroom suite with a separate sitting area. On the first level a sunroom opens onto a patio while an elegant screened porch offers another inviting place to relax and take in the surroundings.The eat in kitchen features a pantry and a separate utility room adds everyday convenience. Central air conditioning and updated utilities provide modern comfort. Mature plantings and handsome stone walls give the property timeless charm.

12 Graystone Road, Gloucester

Listing courtesy of Listing Agent: Jane Meterparel & Brian Marvelley from Listing Office: Churchill Properties.

$680,000

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.

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.

$499,000

Tucked away on a side street in the heart of Gloucester, this charming blue cape-styled home puts so much of what makes Cape Ann special right outside your door. Head downtown for dinner - try out Stone's Pub and Eatery for burgers in a neighborhood setting, or enjoy live jazz and tapas at Saluti! - browse the local shops, catch live music at Harbor Loop on a summer Thursday, or head to one of Gloucester's beautiful beaches. From your own front deck, you can hear the concerts and watch the sunset, and you can head to Harbor Loop to catch the fireworks during the city's summer celebrations. Inside, sunlight fills the open living and dining area, with hardwood floors, a built-in bookcase, and a kitchen that keeps everyone connected whether you're cooking dinner or catching up over coffee. There's a large island, quartz countertops, stainless steel appliances, and a pantry with tucked-away laundry. A bedroom and full bath on the first floor give you options for guests, a home office, or having everything you need on one level. Upstairs, you'll find two more bedrooms with beautiful hardwood flooring. Outside, the wraparound deck and fenced yard give you your own little retreat in the middle of it all. Grow flowers in the garden, enjoy dinner outside, or rinse off the salt and sand in the hot-water outdoor shower with its cedar enclosure after a day at the beach. There's also off-street parking for two cars and an unfinished basement for storage. With downtown restaurants, shops, museums, the harbor, commuter rail, and Route 128 nearby, you can spend less time getting places and more time enjoying them. And when Gloucester's festivals, parades, and summer celebrations come around, you're just a hop, skip and a jump away from the fun.

3 Beds ⋅ 1 Baths ⋅ 73596210 MLS ⋅ NEW Status

Tucked away on a side street in the heart of Gloucester, this charming blue cape-styled home puts so much of what makes Cape Ann special right outside your door. Head downtown for dinner - try out Stone's Pub and Eatery for burgers in a neighborhood setting, or enjoy live jazz and tapas at Saluti! - browse the local shops, catch live music at Harbor Loop on a summer Thursday, or head to one of Gloucester's beautiful beaches. From your own front deck, you can hear the concerts and watch the sunset, and you can head to Harbor Loop to catch the fireworks during the city's summer celebrations. Inside, sunlight fills the open living and dining area, with hardwood floors, a built-in bookcase, and a kitchen that keeps everyone connected whether you're cooking dinner or catching up over coffee. There's a large island, quartz countertops, stainless steel appliances, and a pantry with tucked-away laundry. A bedroom and full bath on the first floor give you options for guests, a home office, or having everything you need on one level. Upstairs, you'll find two more bedrooms with beautiful hardwood flooring. Outside, the wraparound deck and fenced yard give you your own little retreat in the middle of it all. Grow flowers in the garden, enjoy dinner outside, or rinse off the salt and sand in the hot-water outdoor shower with its cedar enclosure after a day at the beach. There's also off-street parking for two cars and an unfinished basement for storage. With downtown restaurants, shops, museums, the harbor, commuter rail, and Route 128 nearby, you can spend less time getting places and more time enjoying them. And when Gloucester's festivals, parades, and summer celebrations come around, you're just a hop, skip and a jump away from the fun.

16-R Spring St, Gloucester

Listing courtesy of Listing Agent: Diantha Phothisan from Listing Office: At Home With Diantha.

$2,150,000

Exceptional Annisquam waterfront living! Beautifully reimagined with thoughtful updates and coastal-inspired finishes, this distinctive waterfront retreat is being offered fully furnished, creating a wonderful turnkey opportunity. Enjoy breathtaking river views, direct water frontage and a Chapter 91 licensed dock. Ideally situated along the Annisquam River, near the Annisquam Yacht Club and across the water from Wingaersheek Beach, the setting is truly special. Sun-filled interiors showcase gleaming wood floors, soaring ceilings, expansive windows and inviting living spaces designed to capture the ever-changing water views. Recent improvements include a new roof, all new windows, an expansive composite waterfront deck, fresh interior paint, updated lighting, decorative millwork and stylish architectural accents throughout. The refreshed kitchen features additional cabinetry and updated appliances, while a newly added picture window enhances the main living area. An impressive upper-level sitting room features custom built-ins and redesigned windows, while the primary suite offers a private balcony, walk-in closet and dedicated office nook. All furniture is included in the sale, making this an exceptional opportunity to move right in and begin enjoying the waterfront lifestyle. Enjoy spectacular waterfront views, boating and the beauty of coastal living right outside your door.

4 Beds ⋅ 3 Baths ⋅ 73593675 MLS ⋅ ACTIVE Status

Exceptional Annisquam waterfront living! Beautifully reimagined with thoughtful updates and coastal-inspired finishes, this distinctive waterfront retreat is being offered fully furnished, creating a wonderful turnkey opportunity. Enjoy breathtaking river views, direct water frontage and a Chapter 91 licensed dock. Ideally situated along the Annisquam River, near the Annisquam Yacht Club and across the water from Wingaersheek Beach, the setting is truly special. Sun-filled interiors showcase gleaming wood floors, soaring ceilings, expansive windows and inviting living spaces designed to capture the ever-changing water views. Recent improvements include a new roof, all new windows, an expansive composite waterfront deck, fresh interior paint, updated lighting, decorative millwork and stylish architectural accents throughout. The refreshed kitchen features additional cabinetry and updated appliances, while a newly added picture window enhances the main living area. An impressive upper-level sitting room features custom built-ins and redesigned windows, while the primary suite offers a private balcony, walk-in closet and dedicated office nook. All furniture is included in the sale, making this an exceptional opportunity to move right in and begin enjoying the waterfront lifestyle. Enjoy spectacular waterfront views, boating and the beauty of coastal living right outside your door.

698 Washington St, Gloucester

Listing courtesy of Listing Agent: The Lopes Group from Listing Office: J. Barrett & Company.

$1,149,000

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.

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.

$4,500,000

A landmark of Magnolia's storied coastline, this extraordinary oceanfront estate has graced Shore Road since 1889. Set above the Atlantic on one of Cape Ann's most coveted seaside addresses, the residence masterfully blends timeless architecture with thoughtfully curated updates, creating a home that feels both historically significant and effortlessly livable. Sunlight pours through expansive windows, illuminating gracious rooms designed for intimate gatherings and grand entertaining alike, while six fireplaces add warmth and character throughout. Outside, terraces and gardens frame panoramic ocean vistas where the rhythm of the tides, passing sailboats, and spectacular coastal sunsets become part of everyday life. Just moments from Magnolia Village, beaches and miles of scenic conservation trails, this is a rare opportunity to become the next steward of one of the North Shore's most distinguished waterfront homes.

7 Beds ⋅ 6 Baths ⋅ 73575037 MLS ⋅ ACTIVE Status

A landmark of Magnolia's storied coastline, this extraordinary oceanfront estate has graced Shore Road since 1889. Set above the Atlantic on one of Cape Ann's most coveted seaside addresses, the residence masterfully blends timeless architecture with thoughtfully curated updates, creating a home that feels both historically significant and effortlessly livable. Sunlight pours through expansive windows, illuminating gracious rooms designed for intimate gatherings and grand entertaining alike, while six fireplaces add warmth and character throughout. Outside, terraces and gardens frame panoramic ocean vistas where the rhythm of the tides, passing sailboats, and spectacular coastal sunsets become part of everyday life. Just moments from Magnolia Village, beaches and miles of scenic conservation trails, this is a rare opportunity to become the next steward of one of the North Shore's most distinguished waterfront homes.

31 Shore Rd., Gloucester

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

$2,495,000

Set on the coveted waterfront of Eastern Point, this iconic property offers a truly exceptional location overlooking the open Atlantic. During World War II, the home was owned by the U.S. government and served as a lookout station for enemy submarines.The first floor features an inviting open floor plan, with a kitchen flowing into the living and dining areas. A dramatic floor-to-ceiling fieldstone fireplace anchors the living room, while sliders open to a beautiful waterside patio—perfect for enjoying the spectacular setting.The expansive great room, once a garage, offers tremendous flexibility and could be converted back if desired. On the second floor, two generous decks flank the main structure, while a cozy second living room with fireplace provides an intimate retreat. The spacious primary bedroom features a full bath and access to the remarkable outdoor spaces.A spiral staircase leads to the third-floor loft, where the views are truly magnificent, stretching across the open Atlantic. Renovate to your taste or build anew—properties in a setting this rare and extraordinary seldom become available.

2 Beds ⋅ 2 Baths ⋅ 73564204 MLS ⋅ ACTIVE Status

Set on the coveted waterfront of Eastern Point, this iconic property offers a truly exceptional location overlooking the open Atlantic. During World War II, the home was owned by the U.S. government and served as a lookout station for enemy submarines.The first floor features an inviting open floor plan, with a kitchen flowing into the living and dining areas. A dramatic floor-to-ceiling fieldstone fireplace anchors the living room, while sliders open to a beautiful waterside patio—perfect for enjoying the spectacular setting.The expansive great room, once a garage, offers tremendous flexibility and could be converted back if desired. On the second floor, two generous decks flank the main structure, while a cozy second living room with fireplace provides an intimate retreat. The spacious primary bedroom features a full bath and access to the remarkable outdoor spaces.A spiral staircase leads to the third-floor loft, where the views are truly magnificent, stretching across the open Atlantic. Renovate to your taste or build anew—properties in a setting this rare and extraordinary seldom become available.

8 Rouse Rd., Gloucester

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

$2,200,000

Welcome to Coffins Beach, where private roads, rare deeded beach rights, pristine white sand and crystal-clear waters and tennis/pickleball courts all create an exceptional coastal setting. Set on a large lot, this well-maintained 1971 Contemporary offers 2,038 sq. ft. of comfortable living space with four bedrooms and two full baths—equally suited for seasonal escapes or year-round living. Elevated among the trees, the home enjoys expansive bird's-eye views toward the Annisquam River and the Ocean bringing together coastal scenery with the privacy and shade of its wooded surroundings. The open main level is oriented toward the view, with large picture windows and sliding glass doors connecting the living spaces to the deck. A remodeled kitchen with upgraded cabinetry, glass tile backsplash, countertop dining and stone countertops opens to the dining and living areas, while a fireplace adds warmth for cooler evenings and year-round enjoyment. Multiple decks and outdoor spaces extend the living area outside, with plenty of room to relax after a day at the beach or simply enjoy the surrounding landscape that also includes a private patio garden. Four well-proportioned bedrooms provide flexibility for family and guests, while two full baths complete the home. Master suite with vaulted ceilings opens to a private sunroom and deck for stunning view. Move-in ready and set within a highly sought-after coastal community, offering the rare combination of private beach access, water views, privacy and the flexibility to enjoy Gloucester in every season. Schedule a private viewing to experience the setting, views and distinctive lifestyle this property offers. Extensive renovations also include newer roof, windows, exterior, decking, sunroom, energy efficient Viessmann furnace, hot water heater and more. Furnishings and Household items negotiable making this a turn key option.

4 Beds ⋅ 2 Baths ⋅ 73563828 MLS ⋅ ACTIVE Status

Welcome to Coffins Beach, where private roads, rare deeded beach rights, pristine white sand and crystal-clear waters and tennis/pickleball courts all create an exceptional coastal setting. Set on a large lot, this well-maintained 1971 Contemporary offers 2,038 sq. ft. of comfortable living space with four bedrooms and two full baths—equally suited for seasonal escapes or year-round living. Elevated among the trees, the home enjoys expansive bird's-eye views toward the Annisquam River and the Ocean bringing together coastal scenery with the privacy and shade of its wooded surroundings. The open main level is oriented toward the view, with large picture windows and sliding glass doors connecting the living spaces to the deck. A remodeled kitchen with upgraded cabinetry, glass tile backsplash, countertop dining and stone countertops opens to the dining and living areas, while a fireplace adds warmth for cooler evenings and year-round enjoyment. Multiple decks and outdoor spaces extend the living area outside, with plenty of room to relax after a day at the beach or simply enjoy the surrounding landscape that also includes a private patio garden. Four well-proportioned bedrooms provide flexibility for family and guests, while two full baths complete the home. Master suite with vaulted ceilings opens to a private sunroom and deck for stunning view. Move-in ready and set within a highly sought-after coastal community, offering the rare combination of private beach access, water views, privacy and the flexibility to enjoy Gloucester in every season. Schedule a private viewing to experience the setting, views and distinctive lifestyle this property offers. Extensive renovations also include newer roof, windows, exterior, decking, sunroom, energy efficient Viessmann furnace, hot water heater and more. Furnishings and Household items negotiable making this a turn key option.

2 Dune Circle, Gloucester

Listing courtesy of Listing Agent: Suzanne Manley from Listing Office: Charlesgate Realty Group, llc.

$1,250,000

Enchanting Waterfront Cottage w/private dock on peaceful Goose Cove. Enjoy gorgeous water views and looking over the Cove at the most spectacular nightly sunsets. Very serene and much like living on your very own nature preserve. The cottage is warm and welcoming, with a wood paneled, multi-windowed mudroom with storage benches at the entryway, front to back living/dining room, kitchen, first floor bedroom (currently used as a den with pull-out couch) and full bath, a family room/sunroom across the back of the home. The kitchen is older style with a fabulous classic double porcelain sink and tons of storage. You will find four more bedrooms upstairs and a second full bath w/tub and shower. Windows abound throughout the home, offering stellar views from every room, and letting in abundant light and heavenly breezes. The property is beautifully landscaped, providing a continuous rolling display of colorful perennials. Close to Plum Cove Beach, the coveted Lighthouse Beach, the Annisquam River, and multiple trailheads into protected woodlands a short walk from your door.

5 Beds ⋅ 2 Baths ⋅ 73563023 MLS ⋅ ACTIVE Status

Enchanting Waterfront Cottage w/private dock on peaceful Goose Cove. Enjoy gorgeous water views and looking over the Cove at the most spectacular nightly sunsets. Very serene and much like living on your very own nature preserve. The cottage is warm and welcoming, with a wood paneled, multi-windowed mudroom with storage benches at the entryway, front to back living/dining room, kitchen, first floor bedroom (currently used as a den with pull-out couch) and full bath, a family room/sunroom across the back of the home. The kitchen is older style with a fabulous classic double porcelain sink and tons of storage. You will find four more bedrooms upstairs and a second full bath w/tub and shower. Windows abound throughout the home, offering stellar views from every room, and letting in abundant light and heavenly breezes. The property is beautifully landscaped, providing a continuous rolling display of colorful perennials. Close to Plum Cove Beach, the coveted Lighthouse Beach, the Annisquam River, and multiple trailheads into protected woodlands a short walk from your door.

79 Dennison Street, Gloucester

Listing courtesy of Listing Agent: Nina Quinlan from Listing Office: Melcher Real Estate Group.

$4,295,000

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.

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.

$2,495,000

Exceptional 3-bed, 4.5-bath Colonial on 1.2 acres in East Gloucester, moments from Eastern Point Yacht Club and Niles Beach. A study in understated elegance, the home features geothermal heating/cooling and over 4,200 sq ft of luxurious living space. The main level opens into a foyer with 18' ceiling, dark hardwood floors, and staircase rising to second floor landing. Pass through the wet bar-pantry to a formal dining room, with sliding doors to sunroom and large deck. A spacious living room has walls of windows and granite gas fireplace; the chef’s kitchen has custom cabinets and dining island; and a private office offers first floor living option. On the upper level are an expansive main suite with his-n-hers walk-in closets, private balcony, and spa bath; and two more bedrooms and two full baths. The finished walk-out lower level has family room, accessory apartment, and laundry, with access to insulated 3-car garage. Sense and sensibility in Gloucester’s most distinctive community!

3 Beds ⋅ 5 Baths ⋅ 73526366 MLS ⋅ ACTIVE Status

Exceptional 3-bed, 4.5-bath Colonial on 1.2 acres in East Gloucester, moments from Eastern Point Yacht Club and Niles Beach. A study in understated elegance, the home features geothermal heating/cooling and over 4,200 sq ft of luxurious living space. The main level opens into a foyer with 18' ceiling, dark hardwood floors, and staircase rising to second floor landing. Pass through the wet bar-pantry to a formal dining room, with sliding doors to sunroom and large deck. A spacious living room has walls of windows and granite gas fireplace; the chef’s kitchen has custom cabinets and dining island; and a private office offers first floor living option. On the upper level are an expansive main suite with his-n-hers walk-in closets, private balcony, and spa bath; and two more bedrooms and two full baths. The finished walk-out lower level has family room, accessory apartment, and laundry, with access to insulated 3-car garage. Sense and sensibility in Gloucester’s most distinctive community!

3 Toronto Ave, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.

$1,500,000

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!

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.

$1,500,000

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.

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.

$399,000

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.

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.

$685,000

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!

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.

$715,000

NEWLY PRICED!.... OPEN HOUSE: Saturday Oct. 31 12:00-1:30....Tucked away just steps from Lane’s Cove, this enchanting coastal retreat offers the perfect blend of charm, comfort, and adventure. Whether you're seeking a year-round home or a weekend escape, you'll love the easy access to kayaking, paddleboarding, waterfront walks, and the natural beauty that makes this corner of the coast so special. Inside, beautiful wood floors flow throughout the home, complemented by a spacious living room, dining room, and kitchen designed for relaxed everyday living. A wood pellet stove creates a warm and inviting atmosphere during the cooler months, making this a home to enjoy in every season. Upstairs, two large bedrooms with vaulted ceilings feel like a peaceful sanctuary perched among the trees, with seasonal ocean peaks that serve as a reminder of how close you are to the water's edge. Outside, a spacious second floor deck, private yard, enclosed outdoor shower, and sweet garden shed complete the coastal lifestyle experience. Offering quintessential Lanesville character, privacy, and an unbeatable location at an exceptionally attractive price point, this hidden gem is impossible to forget! A rare find that captures the essence of coastal living without compromise! Please DO NOT park in driveway.

2 Beds ⋅ 2 Baths ⋅ 73510157 MLS ⋅ PRICE CHANGED Status

NEWLY PRICED!.... OPEN HOUSE: Saturday Oct. 31 12:00-1:30....Tucked away just steps from Lane’s Cove, this enchanting coastal retreat offers the perfect blend of charm, comfort, and adventure. Whether you're seeking a year-round home or a weekend escape, you'll love the easy access to kayaking, paddleboarding, waterfront walks, and the natural beauty that makes this corner of the coast so special. Inside, beautiful wood floors flow throughout the home, complemented by a spacious living room, dining room, and kitchen designed for relaxed everyday living. A wood pellet stove creates a warm and inviting atmosphere during the cooler months, making this a home to enjoy in every season. Upstairs, two large bedrooms with vaulted ceilings feel like a peaceful sanctuary perched among the trees, with seasonal ocean peaks that serve as a reminder of how close you are to the water's edge. Outside, a spacious second floor deck, private yard, enclosed outdoor shower, and sweet garden shed complete the coastal lifestyle experience. Offering quintessential Lanesville character, privacy, and an unbeatable location at an exceptionally attractive price point, this hidden gem is impossible to forget! A rare find that captures the essence of coastal living without compromise! Please DO NOT park in driveway.

4 Langsford Street, Gloucester

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

$1,198,000

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.

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

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.

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

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.

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.

$2,950,000

Open House SAT October 17, 2026 11:30am -1pm. EXCEPTIONAL OPPORTUNITY TO LIVE ON THE HARBOR WITH YOUR OWN DEEP WATER DOCK approx. 290 feet long with a renovated 4-bedroom 2 1/2 bath harbor front home on SMITH'S COVE. The dock 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 with all high-end appliances. There is a huge pantry off the kitchen. A spacious primary bedroom suite over the heated garage includes its own bath, while two bedrooms feature walkout decks and Harbor views. There is a fourth bedroom. Large deck off living room all overlooking this spectacular harbor. There is another room that could be an office and is next to the main bedroom. There are two baths on the second level and a half bath with a washer-dryer hook-up on the first floor. Heated garage.

4 Beds ⋅ 3 Baths ⋅ 73421894 MLS ⋅ ACTIVE Status

Open House SAT October 17, 2026 11:30am -1pm. EXCEPTIONAL OPPORTUNITY TO LIVE ON THE HARBOR WITH YOUR OWN DEEP WATER DOCK approx. 290 feet long with a renovated 4-bedroom 2 1/2 bath harbor front home on SMITH'S COVE. The dock 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 with all high-end appliances. There is a huge pantry off the kitchen. A spacious primary bedroom suite over the heated garage includes its own bath, while two bedrooms feature walkout decks and Harbor views. There is a fourth bedroom. Large deck off living room all overlooking this spectacular harbor. There is another room that could be an office and is next to the main bedroom. There are two baths on the second level and a half bath with a washer-dryer hook-up on the first floor. Heated garage.

263 East Main Street, Gloucester

Listing courtesy of Listing Agent: Jeanne Carpenter from Listing Office: J. Barrett & Company.

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