Privacy abounds in this one-of-a-kind breath-taking hilltop contemporary sited on 16+ acres that boasts captivating ocean views and lush rolling lawns. An open floor plan integrates the spacious eat-in kitchen, formal dining area, and cozy family room. Expansive windows and ceilings flood the home with natural light. A living room with a bucolic fieldstone fireplace offers elegant entertaining space and a wraparound deck to enjoy outdoor living with sea breezes and panoramas of the treetops.This 4-bedroom 3-bath home features a generous primary suite with a private ocean view balcony and 3 remodeled bedrooms. Added highlights include a tasteful home office built into the historical stone tower and an attached two-car garage. With walking trails and beaches nearby and easy access to Rte. 128, this charming home nestled in the natural beauty of a private enclave presents a unique opportunity that’s not to be missed.

Designed by noted architect Geroge W.W.Brewster, this home is a rare offering, showcasing soaring ceilings and expansive floor-to-ceiling windows that flood the open-concept living spaces with natural light. The thoughtfully crafted floor plan features five spacious bedrooms, including a luxurious primary suite and a private guest suite with a separate entrance above the garage—ideal for visitors or extended family.A cozy office with a fireplace and custom built-in bookcases provides the perfect work-from-home retreat. With four fireplaces throughout, the home exudes warmth and charm in every room.The seamless flow from the chef’s kitchen to the family room, dining room, and elegant living room creates an inviting atmosphere for both everyday living and entertaining. Each space offers stunning views of the manicured lawns, lush gardens, sparkling pool, and sun-drenched terrace.Additional highlights include a two-car garage and an unbeatable location—just moments from Singing Beach.

This gorgeous Dutch Colonial is located in the highly prized Woodholm neighborhood in Manchester-by-the-Sea. Sited on a private cul-de-sac, this home enjoys superb privacy yet is moments away from top-rated schools, village and beaches. 1 Woodholm Circle captivates you from the moment you arrive, with lush gardens and handsome stonework. The grand living room is anchored by a large wood burning fireplace, has beamed ceilings and exquisite woodwork. The dining room flows effortlessly into the chef's kitchen, which features stainless steel appliances, cherry cabinetry, granite counters and dining area. The adjacent family room opens out to the mahogany deck, complimented with retractable awning. The four-season enclosed sun room provides year-round enjoyment. Upstairs finds three bedrooms and shared bath. The primary suite has luxurious marble bath and super walk-in closet. Above the heated two-car garage is a guest suite with full bath & kitchenette. Beautifully landscaped grounds.

This distinguished 1865 Classic Colonial (accompanied by a separate Carriage House) once a Summer Retreat for the Dutch Embassy, masterfully blends refined elegance with modern living in mind. Thoughtfully renovated. 2 Harbor Street preserves its turn of the century craftsmanship while offering over 4,000 square feet of living space. Period details abound, including three graceful staircases, rich hardwood floors, soaring ceilings, crown molding, built-in bookcases and window seating. The sun-drenched layout flows seamlessly from the inviting living room to the cozy study, family room, and dining area, complemented with views of the wrap around porch. The primary suite features a large walk-in closet, while additional en suite bedrooms offer space for family and guests. A detached three-bedroom Carriage House (2A/1,023 sq ft) offers privacy for guests and rental potential. Located near the picturesque inner harbor near Tuck's Point and the idyllic village of Manchester by the Sea!

New Price! Stunning Annisquam property with rolling lawns, magnificent perennial gardens, private tidal dock and fully equipped guest house. The site of many wedding receptions as well as casual family gatherings, this is the sought after place to be! Main house with 3 bedrooms and 3.5 bathrooms offers water views from every room and is in pristine move-in condition. The perfect venue for entertaining, the updated chef’s kitchen overlooks sparkling Lobster Cove with adjoining formal dining room with French doors that open to an inviting stone terrace where guests can often view majestic blue heron on the water. Private guest suite with sitting room and fireplace graciously accommodates visitors. Kids and Grandchildren arriving? The large, fully equipped Guest House with cathedral ceilinged great room with fireplace house is the answer with accommodation to sleep 4, and a private terrace and parking. Open House Sunday July 27 1:30-3:00 p.m.

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.

2 Sky Top Dr has been lovingly transformed into a showcase of modern living and timeless charm. Since the current owners arrived, virtually every inch of this gorgeous residence has been thoughtfully updated and refined to reflect a true sense of home. The transformation began with the installation of a stunning stone fireplace, now the centerpiece of the inviting family room - a space that radiates comfort and style. On the main level, you'll discover an airy open concept design with fabulous kitchen featuring a waterfall counter, living room and dining area that effortlessly accomodates everything from fesitve gatherings around the dining table to intimate dinners perched at the kitchen counter. Sunlight spills through oversized windows, casting a golden glow across each curated detail. The upstairs baths have been recently reimagined, offering sleek finishes. The expansive lower level presents endless possibilities, now a vibrant rec room and home office. Location is prime!

Nothing could be finer! This exceptional split-level home is moments away from the pristine sands of Wingaersheek Beach, one of the finest beaches on the North Shore. Chic and contemporary finishes grace this fully renovated property and the attention to detail is evident throughout. The open concept living room/dining room is well-suited for entertaining, with sliders leading out to the deck. The kitchen is spectacular! Outfitted with top-of-the line stainless steel appliances, custom cabinetry, quartz counters, island with waterfall edges and coffee bar, this is the true heart of the home. The oversized primary bedroom has excellent closet space & sitting/dressing area. The bathroom has lovely tile and double sinks. A second bedroom and laundry complete this level. On the lower, walk out level, you will find an excellent family room, sumptuous tiled floors, bedroom, fabulous bath, in-law kitchen and second laundry. The fenced yard is complete with jacuzzi, shed and seaside gardens.

Build your dream home on this 1.55 acre cleared lot with water and power at street, and approved 5 bedroom septic plan. Lovely building site atop curved drive with hiltop location. Prime location close to White and Black Beaches, Trustees of Reservation hiking trails and short distance to Village, resaurants an shops.

THERE'S NO PLACE LIKE HOME! Cozy and comfortable this darling 2 bedroom plus ranch is a rewarding escape peacefully situated on a quiet street located close to town and Gloucester's beautiful beaches. Wake up in the morning and begin the day by sipping your coffee out on your private deck. The basement is finished with room for guests. This home is move in ready and has been lovingly cared for by the same family for many years. The Seller is waiting for another group to make new memories in this wonderful one level living home. Come see for yourself. You will love it!

Coastal Living at Its Best! Located in the beautiful Magnolia Village! This is a first-floor unit rare to find!! It is perfect for downsizers, first-time home buyers, or anyone seeking a coastal getaway. This charming 1-bedroom, 1-bath condo offers a comfortable living space just moments from the ocean. Enjoy the convenience of in-building laundry, assigned parking, and a private patio for relaxing outdoors. With restaurants, shops, beaches, and public transportation nearby, plus easy access to the highway and train, this condo offers the ideal blend of tranquility and convenience.  Don’t miss your chance to own a slice of Gloucester’s seaside charm!

A Rare Rockport Gem. The condo you've been waiting for all summer long has arrived. Come home to this darling 1 bedroom condo at the Mt. Pleasant House, only a whisper away from Dock Square. This sun drenched cozy unit fits the bill with several interesting elements: an exposed brick chimney, an artisan cut glass window divider between rooms, historic paned windows & a room with a view. The condo fee covers, heat, hot water & electric, and laundry a rare offering indeed. The Mt. Pleasant House is situated in the Historic District. Relish in anything Rockport from our crystal clear beaches to the Shalin Liu Performance Center. Treat yourself to 5 star dining, art galleries & jewelry shops dotted along Bearskin Neck up to Captain's Bounty. Kayak or SUP along the harbor & the craggy coast from The Headlands to Halibut Point. If it's ancient quarries and woodland trails you like, we have that too. OH SAT & SUN 12-2. Offers due Tuesday at 5pm.

Perfectly located near the center of Manchester by the Sea, this beautiful three story separate residence near the water has a spacious layout, incredible high end finishes and three floors of spacious living. A rare find on the Northshore, Three Sawmill Circle has marble countertops, stainless steel appliances, a gas fireplace, four large bedrooms (one with a walk-in closet) and three full baths. Designed and well-thought out with modern living in mind, you will love the bonus room on the first floor that could be a great office space. Extra storage, closets, mudroom, attached garage and private use side yard with patio. Conveniently located near commuter rail and routes, great shops and restaurants in idyllic Manchester by the Sea. Enjoy the perks of living on the Northshore in a picturesque seaside town with parks by the water, nature trails and sunsets on Manchester's own Singing Beach to enjoy!

Great opportunity to see what living on the Northshore is like and settle in Manchester-by-the-Sea by this Fall! This beautifully renovated 3-bed, 2-bath home offers 2,300plus square feet of flexible living space across two levels. Enjoy an open floor plan filled with natural light, terraced decks, and a serene wooded setting. Three bedrooms on second floor plus additional room on first floor for bedrooms and offices. Set back on over an acre of land and conveniently located near the commuter rail Rockport Line, major commuter routes (Route 128) and the town’s charming shops and restaurants. Embrace the outdoors with nearby trails, parks, and iconic Singing Beach. A perfect blend of nature, comfort, and coastal living awaits!

This attractive property presents an exceptional residential rental opportunity. Sweetly located between Black and White Beach, just a short distance to highly rated local schools, shopping, Singing Beach, and all things Manchester! A sunroom invites relaxation and enjoyment of natural light throughout the seasons. Outside, the property truly shines with its deck and patio, providing spaces for outdoor enjoyment, relaxation, and entertaining. The outdoor dining area is perfect for meals enjoyed in the fresh air. Seasonal ocean views are a bonus!

Pristine and private large residence awaits you in Manchester by the Sea! High quality finishes and hardwood floors throughout this sunny three bedroom two story residence in the historic center of Manchester. This unit has an incredible marble kitchen, stainless steel appliances, two marble tiled baths with glass enclosures and washer and dryer in unit. Thoughtfully designed with flexible living and work spaces. The main level has a large living room, dining room, kitchen, office or bonus room with turret and a large bedroom with bath. The upper level has two bedrooms, a full bathroom and family room. Plenty of room for storage with oversized closets. Two off street parking spaces in back near entrance . A great view of the village and outdoor patio space overlooking Sawmill Brook. . Conveniently located near train, commuter routes, shops, restaurants and idyllic Singing Beach. A perfect location to enjoy the beauty of this Northshore gem of a town! Available September 1st.

Located just steps from White and Black Beaches, and a very short drive to Landmark School, Brookwood and highly rated public schools, this is a new opportunity to enjoy the off season in Manchester by the Sea. ALL UTILITIES INCLUDED. This comfortable home is very well maintained. Available September 1, 2025 - July 1, 2026.

ONE SCHOOL STREET. Newly renovated second floor one bedroom apartment in the heart of Manchester-by-the-Sea. This unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with marble tile and a glass-enclosed shower. Additional highlights for R5 include sunny inner courtyard second floor views, in-unit washer and dryer and all-new systems and luxury finishes throughout. Enjoy views of the town center in this perfect location just across the street from the inner harbor. Conveniently located near cafe,shops, restaurants, parks, the Rockport Line commuter rail, commuter routes and iconic Singing Beach. Leasing immediately for November 1st move in. One School Street, Unit R5 offers a rare opportunity to live in a professionally designed space in one of the North Shore's most desirable coastal towns. Near the inner Harbor with nearby Tucks Point and incredible Singing Beach to enjoy!

ONE SCHOOL STREET. Newly renovated sunny ttop floor one bedroom apartment in the heart of Manchester-by-the-Sea. This top floor spectacular unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with double sinks, and marble tile and a glass-enclosed shower. Additional highlights for R4 include vaulted ceiling, double closets, large living room, top floor inner courtyard views, in-unit washer and dryer and all-new systems and finishes throughout. Enjoy views of the town center in this perfect location across the street from the inner harbor. Conveniently located near the Rockport Line commuter rail, shops, restaurants, parks, and the iconic Singing Beach. Leasing now so don't miss it for November 1st move in. One School Street, Unit R4 tow offers a rare opportunity to live in a professionally designed space in one of the North Shore's most desirable coastal towns.

ONE SCHOOL STREET. Newly renovated top floor one bedroom apartment in the heart of Manchester-by-the-Sea. This unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with marble tile and a glass-enclosed shower. Additional highlights for R3 include top floor views, central air conditioning, in-unit washer and dryer and all-new systems and finishes throughout. Enjoy views of the town center in this perfect location just across the street from the inner harbor. Conveniently located near the Rockport Line commuter rail, shops, restaurants, parks, and the iconic Singing Beach. This property is being fully renovated inside and out with incredible design and high end finishes. Leasing now so don't miss it for November 1st move in. One School Street, Unit R3 offers a rare opportunity to live in a professionally designed space in one of the North Shore's most desirable coastal towns.

ONE SCHOOL STREET. Newly renovated Second Floor one bedroom apartment in the heart of Manchester-by-the-Sea. This unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with marble tile and a glass-enclosed shower. Additional highlights for R2 include large bay windows,central air conditioning, in-unit washer and dryer, and all-new systems and finishes throughout. Enjoy views of the town center in this perfect location just across the street from the inner harbor. Conveniently located near the Rockport Line commuter rail, shops, restaurants, parks, and the iconic Singing Beach. This property is being fully renovated inside and out with incredible design and high end finishes. Leasing now for November 1st move in. One School Street, Unit R2 offers a rare opportunity to live in a professionally designed space in one of the North Shore's most desirable coastal towns!

ONE SCHOOL STREET. Newly renovated First Floor one bedroom apartment in the heart of Manchester-by-the-Sea. This unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with marble tile and a glass-enclosed shower. Additional highlights include central air conditioning, in-unit washer and dryer, and all-new systems and finishes throughout. Enjoy views of the town center in this perfect location just across the street from the inner harbor. Conveniently located near the Rockport Line commuter rail, shops, restaurants, parks, and the iconic Singing Beach. This property is being fully renovated inside and out with incredible design and high end finishes. Leasing now for November 1st move in. One School Street, Unit R1 offers a rare opportunity to find a first floor unit in a professionally designed space in one of the North Shore's most desirable coastal towns.

ONE SCHOOL STREET. Newly renovated first floor one bedroom courtyard facing apartment in the heart of Manchester-by-the-Sea. This unit features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with KitchenAid and Bosch appliances. The bathroom is finished with Sahara Carrera honed marble tile and a glass-enclosed shower. Additional highlights for R6 include central air conditioning, in-unit washer and dryer and all-new systems and finishes throughout. Enjoy this courtyard first floor unit in this beautifully restored building near the town center. Perfectly located just across from the Manchester Library and the inner harbor. Conveniently located near the Rockport Line commuter rail, shops, restaurants, cafe, parks and iiconic Singing Beach. Leasing now so don't miss it for November 1st move in. One School Street Unit R6 offers a rare opportunity to live in a professionally designed space in one of the North Shore's most desirable coastal towns.

Available October 1st. Located in the heart of Manchester by the Sea, this third floor sunny apartment is renovated and includes hardwood floors, custom counters and renovated bath with marble tile and glass shower. Light filled kitchen with large living room windows with views of the town square. Clean, quiet and ready to move right in. Beautiful historic building in the perfect location in town. In idyllic Manchester by the Sea, near great shops, restaurants, parks, commuter rail and routes. Close to the water, town parks and incredible Singing Beach. Come see how good living on Cape Ann can be!

ONE SCHOOL STREET. Newly renovated first floor studio apartment in the heart of Manchester-by-the-Sea. This first floor courtyard facing studio features hardwood flooring, Calacatta Grande quartz countertops and a modern kitchen equipped with Kitchen Aid and Bosch appliances. The bathroom is finished with marble tile and a glass-enclosed shower. Additional highlights for R7 include washer dryer in-unit, first floor unit with easy access, central air conditioning and all-new systems and finishes throughout. Enjoy views of the courtyard and town center in this perfect location just across the street from the inner harbor. Conveniently located near parks, trails, cafe, great restaurants, shops, the Rockport Line commuter rail, and commuter routes. Come enjoy the sand and sights of Northshore sunsets, beautiful hiking trails, Tucks Point and iconic Singing Beach. Leasing now so don't miss it for November 1st move in.

Welcome to your Winter Hideaway on Waterman Road! ALL UTILITIES INCLUDED PLUS WIFI. Come see this well maintained sun-filled furnished rental. Spend hours exploring the private side of Wingaersheek with stunning sand dunes, sand bars, sea kites & the occasional whiskered seal. This sun filled unit has a well equipped kitchen, a large open concept dining area with easy streamline access from living room to kitchen. Window A.C. in BR. There is fireplace, however it's not for tenant use, sorry! There's plenty of closet space in the over-sized bedroom and in the living room, a sparkly new bathroom, new refrigerator and a separate laundry room. Easy one floor access from your car to your door. Unit available 10/1/25- 5/29/26. non-refundable $50 on line application fee required per potential tenant via NTN Rental Decision Point. Pets considered on a case by case basis. No cats. Electric vehicles must be charged off premises. Generac on site. extra pull out bed, new wall unit A.C. in LR