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Featured Properties

$4,995,000
7 Beds 6 Baths 1649180 MLS
Now a Worldbid Auction for October 14th with starting bid $4,995,000. Pre-Auction Bids Possible! See attachments for Auction details. Eastern Watch, located just outside of downtown Bar Harbor, evokes a sense of the by-gone Rusticator Era of the town's Gilded Age near the old estates of the Vanderbilts, Kennedys and Acadia's founder George Dorr. The classic New England cottage perched high above Frenchman Bay on Sols Cliff has views from the Porcupine islands to the Egg Rock lighthouse and beyond. Enjoy watching cruise ships and whale watch boats passing just below the oversized 130-foot granite and bluestone terrace with outdoor kitchen and granite fireplace. The 4 bedroom main house is a John Libby timber frame with a three story cathedral living area that boasts a granite fireplace and stonework. Built in 1995, the home was totally remodeled in 2006. Beautiful master suite with views of the bay and islands; master bath with walk-in shower area with soaking tub and just around the corner is your own gym area. The second floor of the carriage house is a two bedroom apartment with a kid's bunk room and play loft above. This beautiful estate sits high on a bluff that is over 100' above the ocean so you'll always have the same shoreline and view. You can walk into town or connect on to hiking or biking trails right from the house to access Acadia National Park

62 Sols Cliff Rd, Bar Harbor

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$4,980,000
5 Beds 5 Baths 73574731 MLS
From the moment you arrive, you’ll fall in love with this much-admired white brick Colonial, beautifully sited on a charming corner in Wellesley’s coveted Cliff Estates. Set back from the road and surrounded by beautifully landscaped grounds, this exceptional home offers the perfect blend of elegance, comfort, and space for today’s lifestyle. Inside, gracious rooms unfold with everything exactly where you want it—and more than you expect. The inviting fireplaced living room opens to a light-filled sunroom, ideal as a home office or quiet retreat, with French doors leading to the stone patio. The state-of-the-art kitchen features generous stone countertops, new ovens and Sub-Zero refrigeration, a charming dining area with banquette seating, and an exceptional walk-in pantry. A gracious dining room with a window seat and custom built-ins is perfect for entertaining.The oversized family room, with its dramatic barrel ceiling, abundant windows, and doors opening to the yard, is sure to become the heart of the home. An additional study provides yet another flexible space for working from home or relaxing. A glamorous turned staircase leads to the second floor and a stunning primary suite featuring two walk-in closets and a luxurious marble spa bath. Three additional bedrooms and two full baths, including one en-suite, complete this level. The finished lower level offers even more versatile living space with a playroom, exercise area, additional bedroom, and full bath. Oversized three-car garage with added storage space is such a plus! Outside, enjoy professionally landscaped grounds with mature trees and beautiful plantings. Exceptionally maintained and beautifully decorated throughout, this elegant Cliff Estates home offers a rare combination of timeless style, generous living space, and effortless everyday comfort.

97 Arnold Road, Wellesley

Listing courtesy of Listing Agent: Bobby Morgenstern from Listing Office: Gibson Sotheby's International Realty.

$4,950,000
6 Beds 9 Baths 73576957 MLS
Set on 2.19 beautifully landscaped acres in coveted South Natick, this exceptional estate offers a rare combination of architectural refinement, privacy, and resort-caliber amenities. Encompassing more than 8,500 square feet, the 6 bedroom residence has been thoughtfully designed for both sophisticated entertaining and effortless everyday living, with seven full and two half baths and refined craftsmanship throughout. At the heart of the home, a beautifully updated chef’s kitchen anchors the main living spaces and opens to a vaulted-ceiling family room with a fireplace and direct access to a deck and expansive grounds. An elegant dining room is ideal for memorable gatherings, and the gracious living room, with fireplace, and a wall of windows frames views of the breathtaking grounds. The primary suite is a luxurious retreat unto itself. French doors open from the bedroom, creating a seamless connection to the surrounding landscape. The spa-inspired bath features a soaking tub and steam shower, plus two custom closets. Two private offices, a walk-in pantry, laundry room, and two half baths complete the main level. Upstairs, five bedrooms provide flexibility for family and guests. Four are en-suite, including a particularly spacious suite ideally suited as a second primary- an elegant solution for multigenerational living, or a private guest retreat. Designed for entertaining on a different scale, the walk-out lower level feels like a destination of its own. The recreation space features a built-in bar, fireplace, kitchen, and dedicated wine room. A gym, full bath, 2nd laundry room, and abundant storage complete the exceptional lower level. Beyond the home, the property unfolds as a private resort. A stunning swimming pool serves as the centerpiece, accompanied by a state-of-the-art outdoor kitchen + bar pavilion for effortless open-air entertaining. The cabana also has a full bath, outdoor shower; and the fireside sitting area creates an inviting retreat. Mature, thoughtfully curated plantings surround the property in privacy, while the expansive level lawn offers abundant space to play. Yet perhaps the estate’s most compelling attribute is one that simply cannot be recreated: its setting alongside the cherished Lookout Farm orchards. A rare expression of luxury in South Natick, this extraordinary estate brings together beautiful interiors, exceptional amenities, resort-inspired outdoor living, designed not simply to impress, but to be lived in + enjoyed.

7 Pegan Ln, Natick

Listing courtesy of Listing Agent: Beyond Boston Properties Group from Listing Office: Compass.

$4,950,000
6 Beds 6 Baths 73575312 MLS
Rare quarter-acre retreat in the heart of Brookline Village, this fully renovated Victorian offers 5,487 square feet of exceptional living space, a large private backyard, and the character of a historic home paired with modern luxury. Completely renovated to the studs in 2025, the six-bedroom, six-bath residence is just steps from the shops, restaurants, and Green Line in Brookline Village, minutes from Longwood, and only three miles from downtown Boston. Inside, soaring ceilings, white oak hardwood floors, and extensive custom millwork, cabinetry, built-ins, and vanities create a timeless, sophisticated interior. The chef’s kitchen features high-end appliances, including a paneled Sub-Zero refrigerator and 36-inch Wolf convection range, complemented by a butler’s pantry, dedicated coffee bar, and additional under-counter wine refrigerator. Designed for both everyday living and entertaining, the home offers expansive living, dining, and family spaces, four fireplaces, radiant heated floors, two laundry rooms, and an impressive full-height lower level. A private wellness retreat includes a dedicated gym, cedar sauna, and steam shower, while a wet bar with a full-height Sub-Zero wine refrigerator and adjoining recreation space provides an additional setting for entertaining. Two oversized decks, an outdoor gas fireplace, and hot tub extend the living space outdoors and overlook the expansive, fully fenced backyard. Behind the historic exterior, the residence has been comprehensively modernized with new-construction-level infrastructure, including all-new electrical, plumbing, and mechanical systems and five-zone central heating and cooling. A rare opportunity to enjoy substantial private outdoor space, beautifully preserved Victorian character, and the comforts of a complete modern renovation in one of Brookline’s most desirable and convenient locations. See more at 220Aspinwall.com

220 Aspinwall Ave, Brookline

Listing courtesy of Listing Agent: Christopher Roy from Listing Office: Gibson Sotheby's International Realty.

$4,950,000
3 Beds 4 Baths 73570275 MLS
Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural lines, light wood floors, and custom built-ins. At the heart of the home lies a soaring vaulted great room anchored by a large stone fireplace, framed by double-height windows and glass French doors that capture panoramic water views.Designed for effortless entertaining and everyday comfort, the main level flows between open gathering areas and quiet retreats. The eat-in chef's kitchen features custom cabinetry and professional-grade appliances, including a Sub-Zero refrigerator, double ovens, and a Thermador range. Adjoining the kitchen, the formal dining room serves as a centerpiece for hosting, complete with built-in display shelving and a cozy window seat, illuminated by a custom glass pendant light fixture suspended from a recessed ceiling. A first-floor en suite bedroom completes the main level, providing refined accommodations for guests or family. On the second level, a light-filled den is equipped with a wet bar, a built-in alcove day bed, and a private balcony overlooking the water. The primary suite serves as a true sanctuary, complete with vaulted ceilings, expansive windows framing water views, and a contemporary fireplace. The spa-like primary bath boasts a deep soaking tub with a wood surround, a glass shower with textured wall tiling, dual-sink vanities with under-cabinet lighting, and connects to a spacious walk-in closet. The lower level offers endless possibilities with a stone fireplace, built-in workstations, additional guest space, and a fully appointed bath with a deep soaking tub. Outside, multi-tiered outdoor spaces - including covered decking, a stone patio, and manicured lawns running down toward the water's edge - offer front-row seats to Chatham's iconic maritime landscape. Whether setting off by kayak for a day on the water or enjoying al fresco entertaining amidst unsurpassed natural beauty, this property represents coastal Cape Cod living at its absolute finest.

103 Aunt Nabby's Lane, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$4,950,000
5 Beds 8 Baths 73556306 MLS
Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every room, from the chef's kitchen with professional grade appliances to the exquisitely appointed first-floor primary suite featuring custom-designed closets and a luxurious bathroom with a jetted Grohe shower system. Four additional bedrooms, including a second-floor primary suite, ensure refined accommodations for family and guests, while a finished lower level provides flexible bonus space. Set amidst park-like grounds with manicured landscaping, the backyard features multiple gathering spaces, including an expansive poolside terrace with a summer kitchen and fire pit. The stunning pool house caters to resort-style living and offers endless possibilities. Meticulously appointed with no detail overlooked, additional highlights include a whole-home generator, state-of-the-art security, and Lutron smart lighting. Minutes from everything Osterville has to offer, this exceptional family compound is ready to be enjoyed.

313 Bridge Street, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$4,950,000
3 Beds 5 Baths 1672341 MLS
Don't let this once-in-a-generation waterfront masterpiece pass you by. Rarely does a property combine an architect-caliber, modern-transitional residence, and an irreplaceable true deepwater dock, located within walking distance of two of the Seacoast's most beloved downtowns. Set directly on the Piscataqua River with sweeping views of Portsmouth and three iconic bridges, this approx 3,400-square-foot custom home was designed by Amy Dutton Home and built by Haven Hill Builders -- conceived from the water in. Outdoor space is the property's crown jewel. An expansive 24/7 deepwater dock is outfitted for serious entertaining and boating alike. A 40-foot float accommodates larger vessels and the Japanese-style hibachi kitchen is built for waterside cooking. A private cabana with half-bath creates a self-contained retreat right on the water. Three bedrooms and two-and-a-half baths unfold across a light-filled, open-concept layout. The kitchen is a showpiece, anchored by a Thermador range and a waterfall-edge quartz island with a built-in insert for fresh herbs or party ice. Custom lamp-black cabinetry with fluted glass inserts adds understated drama to the main living area. The primary suite is framed by custom doors that open to a rooftop-terrace with water views for effortless indoor-outdoor living. A dramatic third-floor space is wrapped in a triple-glazed curtain wall of glass overlooking the Portsmouth skyline -- the home's defining architectural feature. Above the garage, a light-filled studio with its own water-facing windows provides flexible space for work or art. Outside, a granite patio and firepit overlook the water, surrounded by coastal gardens cascading toward the shoreline. Built to a high-performance standard with a steel substructure, continuous exterior insulation, and 98%-efficient heating and cooling -- extraordinary design meets extraordinary durability. This is an extremely rare opportunity to acquire one of the Seacoast's signature propert

31 Water St, Kittery

Listing courtesy of Keller Williams Coastal and Lakes & Mountains Realty.

$4,950,000
6 Beds 6 Baths 1659543 MLS
Experience the pinnacle of luxury living with this breathtaking waterfront estate on Long Lake. Nestled on an expansive private lot with 800 feet of pristine shoreline, this extraordinary property offers a sandy beach, private dock, and a stunning boardwalk, creating the ultimate lakeside retreat. The 5,122 sq. ft. custom-designed main home features 4 bedrooms and 4.5 bathrooms, showcasing impeccable craftsmanship and high-end finishes throughout. Step into the grand living room, where cathedral ceilings and a dramatic floor-to-ceiling stone fireplace set the tone for elegant relaxation. Walls of floor-to-ceiling windows frame breathtaking panoramic lake views, bathing the home in natural light. A gourmet chef's kitchen, adorned with rich stonework and premium appliances, makes entertaining effortless. The luxurious primary en-suite offers a serene escape with a double-sided fireplace, spa-inspired bath, and a private balcony overlooking the water. Beautiful multi-functional den/office/bedroom with full bath, floor to ceiling windows and built-ins. This property includes an attached 3-car garage and a detached 3-car carriage house topped with a 1,384 sqft, 2 bedroom open concept in-law suite with a beautiful full kitchen and center island, perfect for guests or multi-generational living. Blending timeless elegance with modern luxury, this Long Lake masterpiece offers an unparalleled waterfront lifestyle. Ideal for both private enjoyment and lavish entertaining.

3 & 4 Trestle Ln, Harrison

Listing courtesy of Landing Real Estate.

$4,900,000
5 Beds 3 Baths 1671727 MLS
The Driftwood: Exceptional oceanfront retreat on the coveted shores of Goose Rocks Beach captures the timeless charm of coastal Maine living with an unrivaled private beachfront setting. Nestled at the desirable west end of the beach, the property enjoys direct private access to the soft white sands and sweeping Atlantic vistas that stretch endlessly beyond its doorstep. Sunlight pours through expansive windows, illuminating inviting living spaces designed for both relaxation and entertaining. The stunning oceanside living room, anchored by a classic wood-burning fireplace, provides a warm and welcoming gathering place while framing breathtaking views of the beach and sea. The home's Town Effective Age is 2001. With five bedrooms and three full baths, including a serene oceanside primary suite overlooking the beach, this residence is designed to embrace its extraordinary setting. Thoughtfully appointed gathering spaces include a sunroom, den, dining room, and spacious living areas that effortlessly connect with the beauty of the surrounding landscape. Outside, a lush seaside yard creates the perfect setting for lawn games, evening cocktails, and memorable gatherings. An outdoor rinsing area, central air conditioning, and private stairway to the beach enhance the effortless coastal lifestyle this property affords. Steeped in nostalgia yet rich in opportunity, this is a truly special beachfront sanctuary where the Atlantic Ocean serves not simply as a view, but as an ever-present companion. The protected cove further enhances this remarkable property, with calm waters ideal for swimming, boating, sailing, paddleboarding, kayaking, and beachcombing. For boating enthusiasts, the sheltered location presents the potential to obtain a mooring, providing convenient access to the waters of Cape Porpoise and the Gulf of Maine. An extraordinary chance to experience one of Maine's most treasured stretches of coastline from a private and irreplaceable oceanfront setting.

669 Kings Hwy, Kennebunkport

Listing courtesy of Landvest, Inc..

$4,895,000
4 Beds 4 Baths 1660620 MLS
Glidden Ledge - an outstanding 13.35± acre waterfront property with panoramic views over Fitch Cove, the Damariscotta River, and out to Glidden Ledge. This landholding includes a beautifully designed main residence, three-car garage, guest cottage, and a charming shed. The four-bedroom home features a refined yet comfortable layout with high-end materials and systems, centered around a dramatic timber-frame great room with a coffered ceiling and two-story stone fireplace. Additional highlights include a main-floor primary suite and a spacious screened porch with its own stone fireplace. A winding drive leads through thoughtfully cultivated grounds with over a mile of walking paths, mature gardens, and scenic outdoor spaces, including a unique point of land with a small private island as part of this estate. The property offers 2,716± feet of varied shoreline, a dock with three floats, and a mooring. Wildlife is abundant, from bald eagles to daily seal visits on the western ledges, and the fishing is excellent. This is remarkably an entire non-public peninsula with unparalleled beauty, peace and quiet spaciousness. Private yet convenient, the property is near Wawenock Golf Club, Pemaquid Beach, and Pemaquid Point Lighthouse, with the coffee shops, dining, stores and culture of Damariscotta and Newcastle just six miles up the road.

16 Glidden Ledge Rd, South Bristol

Listing courtesy of Camden Coast Real Estate. info@camdencoast.com

$4,800,000
6 Beds 7 Baths 73466199 MLS
Over the past century, The Loring-Atherton House has been owned by just two families. Now, this distinguished Cottage Farm residence presents a rare opportunity for its next owner to thoughtfully reinterpret it for a new era. Set on a prominent corner lot in the heart of Brookline’s Cottage Farm Historic District, the residence is an exceptional example of Georgian Revival architecture. Its stately brick exterior is defined by a slate roofline, dormer windows, tall chimneys and a classically detailed entrance crowned by an arched fanlight. At the rear, a broad brick terrace, graceful curved staircases and a multi-paned bay overlook the mature, tree-canopied grounds. Inside, the home reveals an extraordinary collection of architectural details. A dramatic great room features a soaring exposed timber ceiling, hand-painted decorative friezes, richly paneled walls, built-in bookcases and window seating, and a substantial marble fireplace. Elsewhere, a beautifully crafted wood staircase, patterned tile floors, ornamental ironwork, additional fireplaces and a mural-lined library speak to the artistry and character carried throughout the residence. Together, these elements provide a compelling architectural language from which something entirely personal can be created. Currently offering six bedrooms and six and a half bathrooms across approximately 8,326 square feet of finished living space, the property encompasses more than 10,000 square feet of finished and unfinished space in total. The opportunity is not simply to restore what was, but to consider how its most distinctive elements can inform what comes next, creating a home that feels relevant to the present while remaining connected to its remarkable history. Directly across from Mason Square Park and moments from the Longwood Medical Area, Fenway, Boston University, leading schools and many of the region’s finest cultural and green spaces, 180 Ivy Street offers the architectural character and greenery of Brookline while keeping Back Bay, downtown Boston, Cambridge and Harvard University all within easy reach. More than a significant address, it is an opportunity to carry forward a century-long legacy while defining its next era.

180 Ivy St, Brookline

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$4,795,000
4 Beds 6 Baths 1659121 MLS
Pint Cove Cottage offers a full sensory experience on 1.24 acres, with sweeping views that let you see and hear the ocean's beauty. Elevated to maximize ocean vistas, it is a coastal gem. The private estate features premium amenities, including an outdoor heated pool, a cabana bar with a TV and grill, a chipping and putting green, an elevator, and an ocean-view platform with its own staircase leading down to Pint Cove's rugged shoreline. The first floor showcases open living spaces with breathtaking views framed by large windows—French doors open to covered seating areas and an open sun deck, ideal for outdoor dining. Coastal charm is evident throughout, with maple floors, coffered ceilings, and a gas fireplace surrounded by built-ins, paneling, and polished stone. The gourmet kitchen includes an island with bar seating, a stainless-steel refrigerator, a double-oven gas range, and custom cabinets. Additional first-floor features include a billiard room with a bar, a screened seaside porch, a guest suite with private deck access, and an overflow guest room with a nearby bath. The grand turret staircase, adorned with twisted balustrades and a wood tray ceiling, leads to the primary suite, which offers a large living area, a wet bar, a gas fireplace, and a balcony overlooking the sea. The primary bath includes double vanities, a jetted tub, and a custom-tiled shower. The level also has two more guest suites and a workout nook. Downstairs, the media room has tiered seating, a wet bar with two refrigerators, and a bar island. The temperature-controlled wine cellar features backlit storage, a tasting table, ample space, and a bathroom. The garage offers custom closets for added organization. Sandy Cape Neddick Beach is just a walk away.

1 Cove Rd, York

Listing courtesy of Anne Erwin Sotheby's International Realty. 207-363-6640

$4,700,000
4 Beds 5 Baths 1673190 MLS
Perched atop one of Ogunquit's most extraordinary natural landmarks, 24 Ho Hum Hill commands a setting that simply cannot be replicated. Rising approximately 110 feet above sea level on a ridge in the heart of the village, this remarkable estate captures panoramic views stretching from Ogunquit's vibrant village center to its world-famous beach and the Atlantic beyond. It is a perspective few will ever experience, changing beautifully with every season, tide, and sunset. With more than 4,000 square feet of living space, the home blends grand entertaining with everyday comfort. A beautiful modern kitchen flows into a spacious family lounge, while separate formal living and dining rooms provide elegant gathering spaces. The primary suite offers a peaceful retreat with an ensuite bath and fireplace, complemented by generous guest accommodations. The home includes four designated bedrooms, three full baths, and one half bath. Buyers should note the existing septic system is designed for three bedrooms. A private two-bedroom in-law apartment adds exceptional flexibility for extended family, guests, or valuable rental income in one of Maine's most desirable coastal destinations. Outside, every level of the property embraces its extraordinary setting. The crown jewel is the private ridgetop deck--a breathtaking sanctuary suspended above Ogunquit, where sunrise coffee, evening cocktails, and summer nights are framed by one of southern Maine's most spectacular vistas. Car enthusiasts will appreciate the 3 car garage, plus an additional 1 car garage equipped with a vehicle lift, offering storage and versatility rarely found in coastal properties. Properties of this caliber are defined not only by their craftsmanship, but by their rarity. There are beautiful homes, there are exceptional views, and then there are once-in-a-generation opportunities. 24 Ho Hum Hill is one of Ogunquit's landmark residences, where elevation and breathtaking scenery create an extraordinary offering

24 Ho Hum Hill, Ogunquit

Listing courtesy of RE/MAX Realty One. (207)252-1775

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