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5 Gap Head Rd, Rockport
$5,500,000
4 Beds ⋅ 4 Baths ⋅ 73555738 MLS
Tucked away on a private, no-through-traffic oceanfront way, this property enjoys a rare combination of tranquility, privacy, and stunning waterfront surroundings on Straitsmouth Point between Rockport’s legendary twin lighthouses on Thacher Island to the south; Sandy Bay and the Atlantic Ocean to the west and north and the rocky shoreline below. Every spacious room within the easy-flowing floor plan features an ocean view via massive windows and exudes a cozy, yet refined ambiance that meets today’s needs and desires for daily living and when entertaining. With 4 bedrooms – the primary suite has a massive closet - 3.5 baths and 4,000+ sf of air-conditioned living space, this spectacular residence with beautiful gardens, ample outdoor play spaces, palazzo-like covered patio, 2-car heated garage with a workshop, and substantial storage accommodates a multitude of must-haves as well as amenities you didn’t even know you wanted. A year-round property destined to become a generational treasure

5 Gap Head Rd, Rockport

5 Point De Chene Avenue, Rockport
$3,200,000
4 Beds ⋅ 3 Baths ⋅ 73572858 MLS
Commanding one of Rockport’s most prized and rarely available coastal enclaves, 5 Point De Chene Avenue provides a spectacular setting for the finest in seaside living and entertainment. The sun-drenched home showcases cathedral ceilings and a two-story glass wall that provides a focal point of breathtaking and unobstructed views of the open Atlantic Ocean, displaying an endless parade of marine vessels gracefully passing by. With unbroken water views at every turn, the main level features an open-concept layout, including a serene primary suite that provides the complete ease of single-level living. The second floor features three additional bedrooms to accommodate guests or dedicated lifestyle spaces alike. Outside, the grounds feature an expansive deck that flows naturally into a custom stone terrace, overlooking the lush yard and dramatic rocky shoreline. Complete with an oversized detached garage and ample parking, this meticulous property represents a premier opportunity to own an elegant oceanfront retreat equally suited for luxurious year-round living or memorable summers to spend treasured time by the sea.

5 Point De Chene Avenue, Rockport

10 Old Penzance Rd., Rockport
$2,900,000
3 Beds ⋅ 3 Baths ⋅ 73558865 MLS
An exceptional waterfront offering on Cape Ann's celebrated coastline, this property is defined by its setting. Elevated above the Atlantic on one of Rockport's most desirable stretches of shoreline, it enjoys uninterrupted views of Thatcher Island and its historic twin lighthouses. The outlook spans open ocean, rugged coastline, and an ever-changing horizon.Natural light and sweeping water views define the spaces. From sunrise over the Atlantic to the evening glow of the twin lighthouses, the scenery is constantly changing. Sailboats cross the horizon, lobster boats work the coast, and the sound of the surf and shore birds provides a peaceful backdrop. Ocean-facing decks and a stone patio extend the living space outdoors, creating inviting places to relax or entertain.Thoughtfully positioned to take full advantage of its setting, the residence features an open living and dining room anchored by a substantial stone fireplace, with walls of glass framing the Atlantic. Each of the three bedrooms has an en suite bath, while the second-floor primary suite offers a cathedral ceiling and panoramic ocean views.Comfortable and understated, the home can be enjoyed immediately while offering the flexibility to update over time. Offered for the first time, it presents a rare opportunity to own one of Cape Ann's most compelling waterfront locations. Whether preserved, thoughtfully expanded, or reimagined as a signature coastal home, its lasting value lies in the land, elevation, and extraordinary connection to the sea.Despite its privacy, the location is remarkably convenient. Loblolly Beach is just 0.1 mile away, with Pebble Beach, Cape Hedge Beach, and Long Beach all within approximately one mile. Located in Rockport's sought-after South End, the property also offers easy access to the galleries, restaurants, and harbors of both Rockport and Gloucester. Properties of this caliber rarely become available. This is more than a home—it's an irreplaceable waterfront setting.

10 Old Penzance Rd., Rockport

82 Marmion Way, Rockport
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 73588001 MLS
OPEN HOUSE FOR 10/11/26 IS CANCELED OFFER ACCEPTED. This charming Marmion Way home offering ocean views is set back from the street with professionally landscaped, irrigated gardens, raised vegetable beds and a brand new composite wrap around deck with a private outdoor shower overlooking a deep back yard abutting conservation land. This lovely home exudes everything today's homeowner demands from the zero clearance walled fireplace with a cozy seating area and media center. Relax & entertains a crowd catering to the flow of the first floor plan ample in space with vaulted ceilings, exposed beams & multiple skylights lending itself to loads of sunshine and ocean breezes. The first floor home office could alternatively be used as a first floor bedroom with the convenience of an adjacent full bathroom with laundry. The oversized kitchen with seasonal water views offers a new stainless steel refrigerator, Bosch dishwasher and newer Jenn - Air stove. If you like to cook you'll love the ample sized walk in pantry and a granite nook with cubby shelving to print recipes and keep track of your daily to do list. The expansive living room with beamed cathedral ceiling opens to a dining room with skylights off an upgraded kitchen with water views. Upstairs there are two bedrooms and an oversized main bedroom suite with a large walk in closet and a changing room adjacent to the bathroom. The spiral staircase leading to a large family room with picture windows looking out to open ocean and Thatcher's Island Twin Lights. Other specialties include an oversized 2 car garage, garage door opener, underground sprinkler system, well water, loft space, access to the deck from various points on the first level and an overly generous sized basement offering potential workout space or an at home theatre. In addition, a roomy, sky lit guest suite with a full bathroom located above the oversized attached garage. In close proximity to Straitsmouth Cove Landing, Old Garden Beach and Cape Hedge Beach.

82 Marmion Way, Rockport

4 Lee Way, Rockport
$1,799,900
5 Beds ⋅ 5 Baths ⋅ 73586745 MLS
FIRST TIME OFFERED FOR SALE! A truly exceptional opportunity to own a custom-built 5-bedroom, 3 full and 2 half-bath home set on over 4 acres; an extraordinary offering in Rockport. Thoughtfully designed with an open, bright floor plan and quality craftsmanship throughout, this home offers both elegant entertaining spaces and comfortable everyday living. The main level features beautiful hardwood flooring throughout, a formal dining area, dedicated office space, and an impressive chef’s kitchen complete with a Wolf range and oven, dual sinks, and a convenient breakfast nook. The spacious family room showcases high vaulted ceilings and a fireplace, with wonderful views and direct access to the back patio, creating an ideal space for gatherings and relaxing. Upstairs, the expansive primary suite offers cathedral ceilings, a comfortable sitting area, and a private outdoor balcony; your own peaceful retreat overlooking the property. With five bedrooms, generous living spaces, and thoughtfully designed amenities, there is room for everyone. Outside, the property truly sets itself apart. More than 4 acres provide exceptional privacy and space, while the large barn adds versatility and character rarely found in Rockport. A 3-car garage provides ample parking and storage. A rare combination of custom construction, substantial acreage, exceptional indoor and outdoor living spaces, and a location in Rockport this is a property you will not want to miss.

4 Lee Way, Rockport

19 Old Garden Rd, Rockport
$1,795,000
3 Beds ⋅ 2 Baths ⋅ 73508055 MLS
Located in Rockport’s desirable Old Garden Beach neighborhood, this classic renovated shingle style home offers seasonal ocean views of the water and effortless coastal living. The light filled interior features an open layout with a custom kitchen, marble counters, and a living room with beamed ceiling and fireplace. The first floor includes a bedroom and full bath allowing for single level living, while two additional bedrooms and a full bath are located upstairs along with a balcony capturing ocean views. Professionally landscaped grounds designed by an accomplished gardener create exceptional outdoor living with a fire pit and private garden spaces. A full height walk out basement offers expansion potential. Moments to Old Garden Beach and ideal as a year round home or seasonal retreat.

19 Old Garden Rd, Rockport

51 South St, Rockport
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73581735 MLS
Welcome to your private coastal oasis in Rockport’s highly desirable South End. Situated just one mile from downtown and .4 miles to Old Garden Beach. This gracious three-bedroom home combines serene suburban living with effortless access to art galleries, restaurants, sandy beaches, and the renowned Shalin Liu Performance Center. A lovely entryway welcomes you into a nicely appointed interior designed for comfortable everyday living and easy entertaining. The heart of the home features an open-concept kitchen and family room with a ceramic pellet stove, surrounded by windows offering sweeping views of the lush backyard. For more formal gatherings or quiet relaxation, the distinct dining room and cozy den maintain a harmonious connection to the main layout while offering privacy. Not to be forgotten, a beautiful covered porch extends the family room and den indoor living spaces in the summer months. Upstairs, the generous primary suite serves as a peaceful sanctuary, complete with walk in closet, en-suite bathroom and a private balcony. Two additional well-proportioned bedrooms with custom closets and a full guest bath complete the second floor, providing plenty of comfort for family, guests, or a dedicated home office. Stepping outside reveals a true highlight of the property: a massive, country-like backyard anchored by a large, private patio with stone firepit. Back yard also consisted of a flat yard with beautiful shed, play structure and adorable chicken coop. Surrounded by nature, it’s an ideal setting for summer barbecues, evening relaxation, or hosting large gatherings. Adding versatility and potential to the property is the massive, detached two-car garage. Beyond vehicle storage, this flexible structure offers extensive space for workshop activities or recreational gear, topped by a large upper loft with endless potential—perfect for a studio, gym, home office, or extra storage. This is a private oasis with easy access to all that Rockport has to offer.

51 South St, Rockport

2 Smith Rd, Rockport
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 73585059 MLS
Refined coastal living just moments from Old Garden Beach. This pristine 3 bedroom, 2 bath ranch offers effortless single level living in one of Rockport's most coveted neighborhoods. At the center of the home, a well-appointed kitchen flows seamlessly into two inviting living areas. Perfect for both relaxed daily life and elegant entertaining. A partially finished basement adds valuable flex space, while outside, a beautifully landscaped, full fenced yard with sunny south-facing deck creates an ideal private retreat. With every major system updated and meticulously maintained, this home is truly move-in ready, combining turnkey convenience, with timeless charm. A rare opportunity to enjoy coastal living at its finest all just minutes from the beach, town, and schools.

2 Smith Rd, Rockport

1 Spring Lane, Rockport
$950,000
4 Beds ⋅ 3 Baths ⋅ 73541989 MLS
MOVE RIGHT INTO THIS CHARMING 10 ROOM, HIP ROOF COLONIAL IN ONE OF ROCKPORTS MOST DESIRABLE NEIGHBORHOODS. FEATURING 4 BEDROOMS, 3 NEWLY RENOVATED FULL BATHS, UPDATED KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, SLIDER LEADING OUT TO AN OVERSIZED DECK AND BEAUTIFUL GARDENS, PLUS 2 BONUS ROOMS ON THE THIRD FLOOR. THE WALKOUT BASEMENT CAN BE FINISHED TO PROVIDE ADDITIONAL SPACE. ALL THIS WITHIN WALKING DISTANCE TO ROCKPORT CENTER, FRONT BEACH, SHOPS, RESTURANTS AND BEARSKIN NECK. ENJOY AN EVENING OF ENTERTAINMENT AT THE SHALEN LIU PERFORMANCE CENTER A CULTUAL JEWEL OF CAPE ANN. ALSO, ENOY THE MANY OF ROCKPORTS OUTDOOR PERFORMANCES DURING THE SUMMER. YOU WILL NOT BE DISAPPOINTED WHEN YOU VISIT AND VIEW THIS HOME.

1 Spring Lane, Rockport

33 Highview Rd, Rockport
$898,000
3 Beds ⋅ 3 Baths ⋅ 73454882 MLS
Fully Renovated 3BD/3BA in Rockport – Walk to the BeachWelcome to 33 Highview Road—a fully updated coastal home featuring a new roof, new siding, new hardwood floors, and a modern kitchen with quartz counters and stainless appliances. 4 fire places! The bright, open layout includes3 refreshed full bathrooms and turnkey finishes throughout.Located in a desirable neighborhood just a short walk to the beach, this property delivers everyday convenience with true coastal living.Newly installed septic-Title V has passed, and renovations are complete. Move-in ready and low-maintenance—perfect for buyers seeking clean design and strong long-term value. Street taken over by Town, brand new street and sidewalk in progress.

33 Highview Rd, Rockport

22 High St, Rockport
$869,000
2 Beds ⋅ 2 Baths ⋅ 73581355 MLS
Charming 2–3 bedroom antique ideally located just steps from the heart of Rockport. Lovingly renovated over the years, this inviting home thoughtfully blends original period details with modern updates while offering the flexibility of single-level living if desired. The first floor features a kitchen and dining area overlooking the beautiful gardens, a cozy living room with gas fireplace, and a versatile bedroom or den with fireplace conveniently located near a full bath. Upstairs are two additional bedrooms and a second full bath. A sunny garden room and recently upgraded outdoor patio provide wonderful spaces to relax and enjoy the gorgeous gardens, with mature plantings offering both beauty and privacy from early spring through late fall. Additional features include two-car parking and a garden shed. Enjoy this special setting in the heart of town, just blocks from Rockport’s galleries, restaurants, shops, waterfront and the Shalin Liu Performance Center.

22 High St, Rockport

17 Highland Street Unit 1, Rockport
$849,000
3 Beds ⋅ 3 Baths ⋅ 73558821 MLS
The light post in the front yard guides you into this charming New England home. Step inside to find beautiful hardwood flooring, expansive rooms, and a gorgeous McCormick kitchen. A large, wood-burning fireplace in the living offers a warm retreat on cold winter evenings, while the fenced back-yard and expansive side yard allow ample room for gardening in the summer months. A mud / laundry room in the back of the home offers direct entry to the backyard, allowing you to avoid tracking mud and dirt into the main living space. The dining and living rooms have large built-ins perfect for displaying your favorite pieces. The full bathroom on the first floor offers the option for single floor living - a rare find in the area.Upstairs you'll find 3 large bedrooms and 2 bathrooms. There is a finished flex room space on the 3rd floor, and the opportunity to fully finish the attic which would add an additional 500+ square feet of living space to the home. A truly unique feature to this home is the extensive closet space including 4 total hall closets (2 on the first floor, 2 on the second), and double closets in 2 of the bedrooms. The unfinished basement and small shed in the backyard offer additional storage. Located off the main road, with 2 assigned parking spaces, it is a quick 5 - 10 minute walk to downtown Rockport, Front Beach, and the MBTA. This quiet oasis maintains all the charm of the Rockport home, with parking, living spaces, and a private outdoor yard that cannot be beat at this price point.Open houses Saturday, August 8, 10:30am-12pm & Sunday, August 9, 10:30am-12pm

17 Highland Street Unit 1, Rockport

17 Highland Street Unit 1, Rockport
$849,000
3 Beds ⋅ 3 Baths ⋅ 73558794 MLS
The light post in the front yard guides you into this charming New England home. Step inside to find beautiful hardwood flooring, expansive rooms, and a gorgeous McCormick kitchen. A large, wood-burning fireplace in the living offers a warm retreat on cold winter evenings, while the fenced back-yard and expansive side yard allow ample room for gardening in the summer months. A mud / laundry room in the back of the home offers direct entry to the backyard, allowing you to avoid tracking mud and dirt into the main living space. The dining and living rooms have large built-ins perfect for displaying your favorite pieces. The full bathroom on the first flooroffers the option for single floor living - a rare find in the area.Upstairs you'll find 3 large bedrooms and 2 bathrooms. There is a finished flex room space on the 3rd floor, and the opportunity to fully finish the attic which would add an additional 500+ square feet of living space to the home. A truly unique feature to this home isthe extensive closet space including 4 total hall closets (2 on the first floor, 2 on the second), and double closets in 2 of the bedrooms. The unfinished basement and small shed in the backyard offer additional storage. Located off the main road, with 2 assigned parking spaces, it is a quick 5 - 10 minute walk to downtown Rockport, FrontBeach, and the MBTA. This quiet oasis maintains all the charm of the Rockport home, with parking, living spaces, and a private outdoor yard that cannot be beat at this price point.Open houses Saturday, August 8, 10:30am-12pm & Sunday, August 9, 10:30am-12pm

17 Highland Street Unit 1, Rockport

1 C Pigeon Hill Ct Unit C, Rockport
$799,000
3 Beds ⋅ 3 Baths ⋅ 73528956 MLS ⋅ ['Quarry Commons Condominium'] BLDG.
Spacious custom Colonial set in a tranquil Pigeon Cove location, framed by a natural granite wall for privacy and charm. The open, flexible floor plan features a cherry kitchen with island breakfast bar, dining area with sliders to the deck and backyard, plus a formal living room and separate dining room or family room option.The large primary bedroom includes a walk-in closet and private bath. Outside, enjoy a charming granite garden house and established perennial gardens. This is an ideal spot for nature lovers, with trails and paths to quarries and Dogtown just steps away, and Pigeon Cove Harbor only two blocks down the street for launching boats and kayaks. Additional highlights include a one-car attached garage, propane gas heat, and an existing gas line for easy conversion to gas cooking if desired. Convenient to the nearby commuter rail with service to North Station.

1 C Pigeon Hill Ct Unit C, Rockport

1 Pigeon Hill Ct Unit C, Rockport
$799,000
3 Beds ⋅ 3 Baths ⋅ 73528952 MLS
Spacious custom Colonial set in a tranquil Pigeon Cove location, framed by a natural granite wall for privacy and charm. The open, flexible floor plan features a cherry kitchen with island breakfast bar, dining area with sliders to the deck and backyard, plus a formal living room and separate dining room or family room option.The large primary bedroom includes a walk-in closet and private bath. Outside, enjoy a charming granite garden house and established perennial gardens. This is an ideal spot for nature lovers, with trails and paths to quarries and Dogtown just steps away, and Pigeon Cove Harbor only two blocks down the street for launching boats and kayaks. Additional highlights include a one-car attached garage, propane gas heat, and an existing gas line for easy conversion to gas cooking, if desired. Convenient to the nearby commuter rail with service to North Station.

1 Pigeon Hill Ct Unit C, Rockport

28 Pleasant St, Rockport
$729,000
2 Beds ⋅ 2 Baths ⋅ 73547965 MLS
Well loved two-story home in a prime downtown Rockport location, close to shops, restaurants, schools, and the commuter rail. The first floor offers a spacious kitchen with updated appliances, a large dining area, and a generous living room, all with hardwood floors, with a sliding door leading to the deck and large fenced backyard. In the yard you'll find mature concord grapevines, perfect for making jam! A convenient half bath with first-floor laundry completes the main level. Upstairs you'll find two oversized bedrooms, a full bath with jacuzzi tub, and pull-down attic access for additional storage. The primary bedroom has hardwood floors, 2 large closets and a slider out to a balcony overlooking the back yard. The second bedroom is large enough to convert into 2 bedrooms. The second floor was added in the late 1990s and features quality 2x6 construction with engineered roof trusses, providing a well-built addition and the flexibility of no interior load-bearing walls. The full basement offers both interior and exterior access, providing ample storage or workspace. A wonderful opportunity to enjoy downtown living with plenty of indoor and outdoor space. Additional features include central vacuum, outdoor sprinkler system., large driveway and storage shed.

28 Pleasant St, Rockport

85 Long Beach, Rockport
$599,999
2 Beds ⋅ 1 Baths ⋅ 73572999 MLS
Just steps from the boardwalk and one of Cape Ann’s most beautiful beaches, this charming seaside Long Beach cottage is the perfect seasonal escape. Enjoy spectacular sunsets, refreshing ocean breezes, and the quintessential Rockport lifestyle from this inviting two-bedroom, one-bath retreat. An open floor plan, screened in porch and two decks creates an easy, comfortable flow for relaxed beach days and effortless entertaining. The cottage’s warm coastal character and ideal location make it a wonderful place to gather with family and friends or simply escape and unwind. The unfinished lower level offers incredible versatility and adds to the cottage’s appeal. Currently featuring laundry facilities, a ping pong table, and plenty of beach gear storage, it provides an ideal space for a fun bunk room, game room, or overflow space for guests—an opportunity to customize it to suit your lifestyle. The lower level also has a covered patio, outdoor shower and beautiful garden area. Spend your days swimming, strolling the shoreline, or enjoying the boardwalk, then head into Rockport village to explore its galleries, boutiques, cafés, restaurants, and iconic harbor. Sunbathing, swimming and surfing the waves, this Long Beach cottage offers endless ways to enjoy the coast. Whether you’re looking for an investment property with a proven rental history, summer sanctuary, weekend getaway, or a place to create generations of seaside memories, this special cottage puts you where you want to be—by the water, surrounded by beauty, and close to everything Rockport has to offer. All offers if any due on Monday,September 14 by 5pm.

85 Long Beach, Rockport

14-1/2 Story Street Unit A, Rockport
$575,000
2 Beds ⋅ 2 Baths ⋅ 73562718 MLS ⋅ ['14 1/2 Story Street Condominium'] BLDG.
Charming and affordable opportunity to own in Pigeon Cove! This townhouse-style condominium offers a thoughtfully designed layout with comfortable living space, abundant natural light and modern updates throughout. The spectacular renovated kitchen is a standout, complemented by an inviting living room, designer colors and updated bathrooms. The basement offers potential for additional living space in the future. Outside you will find a mahogany deck, providing plenty of room to relax or entertain. Situated on a tree-lined street directly across from Pingree Park with a playground and sports fields. Located between Halibut Point State Park and downtown Rockport's beaches, shops and waterfront dining. A wonderful opportunity for year-round living, a weekend getaway or investment.

14-1/2 Story Street Unit A, Rockport

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