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$14,500,000
19 Beds ⋅ 25 Baths ⋅ 73544510 MLS
The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.
$14,500,000
10 Beds ⋅ 8 Baths ⋅ 1665104 MLS
Set on 177± acres of exceptional island landscape, Waterman Farm offers spectacular panoramic views to the south and east toward the Fox Island Thorofare and Penobscot Bay. Perched on a secluded point of land, this classic saltwater farm features 8,582± feet of shorefront with access to both the protected Cubby Hole and Waterman Cove. The quintessential island setting is stunning, with open fields, woods, gardens, orchards, and five historic and distinguished residences, each fully renovated with year-round living space. Requisite estate infrastructure includes a historic barn, a sawmill where much of the wood for the property was harvested and milled, a versatile Quonset hut, and more. A dock with ramp, float, and mooring on Waterman Cove offers access to world-class boating around the island, along the Fox Island Thorofare, and throughout Penobscot Bay. Suitable for agricultural pursuits, residential living, or a family compound, Waterman Farm's significant contiguous acreage, sensitive restoration, and thoughtful stewardship present a rare opportunity to own a true piece of North Haven's legacy.

148 Waterman Farm Rd, North Haven

Listing courtesy of LandVest, Inc..

$14,500,000
5 Beds ⋅ 8 Baths ⋅ 73527740 MLS
Introducing the Alexander Forbes Mansion, a magnificent estate set on 6 beautiful acres in the historic and highly desirable Scott’s Woods district of Milton. This exceptional home showcases every modern amenity and has been meticulously renovated inside and out to the highest standards. The main level features a grand foyer, striking staircase, dramatic floor-to-ceiling windows and doors, formal living and dining rooms, an open kitchen and family room, solarium, home office, and a mudroom with access to the 3-car garage. On the 2nd floor, 5 bedroom suites include the luxurious primary suite with a spa-like bath and separate dressing rooms. The impeccably landscaped grounds offer a private utopia, featuring a heated in-ground pool, multiple patios and seating areas, garden area, grill, fire pit, tennis court, and a carriage house. Located at the foot of the Blue Hills, this outstanding home is minutes from top schools including Milton Academy and just eight miles from downtown Boston.

610 Harland Street, Milton

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$14,000,000
4 Beds ⋅ 6 Baths ⋅ 1668255 MLS
As the sun rises over Casco Bay, islands emerge through the morning mist and the day slowly comes to life. Eagles soar across the bay while a lobsterman works quietly on the water and a paddleboarder drifts along the shoreline. Watching the sun rise over Casco Bay, it is easy to understand why Maine has long been called the Land of Dawn. Connected to the mainland by a private causeway, 90 Cornfield Point extends into Casco Bay on more than seven acres and over 3,000 feet of private coastline. Ancient oaks, shaped by salt air and ocean winds, rise above the peninsula as they have for generations. Beneath their broad canopies, gentle paths lead to sandy beaches, rocky ledges, and quiet coves made for swimming. Surrounded by water on nearly every side, the land offers a remarkable sense of privacy and a deep connection to the sea, qualities rarely found together along the Maine coast. From sunrise to sunset, the beaches invite the rituals of summer - building sandcastles at the water's edge and gathering around a midsummer bonfire as the longest day slowly gives way to night. Here, the sea still sets the rhythm of the day. A deepwater dock provides access to Casco Bay at all tides, making it easy to spend the afternoon exploring the islands, dropping anchor in a quiet cove, or enjoying a picnic on a secluded beach. At the heart of the peninsula, this Maine coastal home and a timber-frame barn overlook the bay from one of the most remarkable private settings on the Maine coast. Sweeping water views in every direction create the kind of place where life's most meaningful moments seem to find their way and a family legacy is built for generations to come. Less than thirty minutes from Portland and the International Jetport, 90 Cornfield Point remains a private peninsula shaped by the sea, defined by light, and rooted in the rhythms of Casco Bay.

90 Cornfield Pt, Yarmouth

Listing courtesy of Legacy Properties Sotheby's International Realty.

$13,995,000
6 Beds ⋅ 8 Baths ⋅ 73542321 MLS
Perched atop nearly an acre of dramatic granite coastline with commanding ocean views, this extraordinary estate represents a level of craftsmanship that simply cannot be replicated today. Offered at $13,995,000 with an estimated replacement cost exceeding $37,000,000, it is a rare opportunity to own a truly irreplaceable residence. Spanning nearly 15,000 square feet, the home offers 6 bedrooms, 8 baths, an elevator, four fireplaces, a heated 5-car garage, ocean-facing infinity pool, rooftop deck, and spectacular entertaining spaces including a gallery. Every detail reflects an uncompromising commitment to artistry, from bespoke millwork and artisan stonework to exceptional materials sourced from around the world. Modern infrastructure includes 21-zone radiant heat and central air, backup generator, and state-of-the-art systems, creating a legacy estate where timeless craftsmanship meets extraordinary coastal living.

25 Rockyledge Road, Swampscott

Listing courtesy of Listing Agent: Willis + Tierney from Listing Office: Compass.
$13,950,000
10 Beds ⋅ 9 Baths ⋅ 73527306 MLS
In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with its existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon point is a special place, and with its pristine shorelines along Nantucket Sound, this property is full of opportunities for you to add your custom renovations and more.

190 Vineyard Road, Barnstable

Listing courtesy of Listing Agent: George Moussa from Listing Office: LAER Realty Partners.
$13,900,000
7 Beds ⋅ 7 Baths ⋅ 73444242 MLS
Situated between Appleton St & Riedesel Ave, this grand & prominent center entrance 7+ bed, 6.5 bath home was originally built in c.1803 has been painstakingly restored, elegantly modernized and expertly crafted for modern living. Ideally sited on a maturely landscaped 22,500+ sq ft lot, this gracious home rests behind an elegant white fence with antique walkways and restored balustrade. Welcomed onto the formal foyer by a graceful staircase, hardwood floors, restored period details and abundant natural light throughout. A large living room offers a fireplace, custom built-ins, and large winnows that overlook the front and side yards. A well placed banquet sized formal dining room offers a butlers door into the kitchen and a fireplace of its own. A sparkling eat in kitchen is complete with top-of-the-line appliances, large center island, two pantries, & a mudroom. Exquisitely finished lower level with 2 level wine storage, gym, media room, steam shower, & sauna! Oversized 1 Car Garage

153 Brattle St, Cambridge

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$12,995,000
6 Beds ⋅ 7 Baths ⋅ 73516411 MLS
A masterpiece by Cafasso Design Group, this architectural work of art redefines luxury living. Tucked within a coveted enclave off Brattle Street, this home unfolds across lush, sculpted grounds framed by mature trees, offering an unparalleled serene retreat. A striking sculptural staircase serves as the dramatic centerpiece, while interiors masterfully blend contemporary Japanese, Scandinavian, Italian, and French influences.The eat-in chef’s kitchen features custom Italian walnut cabinetry, Calacatta Gold marble counters, dual sinks & dishwashers, a Gaggenau 400 Series double oven, and walls of glass. Generous bedrooms and spa-inspired baths deliver sanctuary, complemented by a glass-enclosed office and a family room featuring a floating gas fireplace. A dedicated lifestyle level boasts a gym, guest suite, and inviting spa with a Western Red Cedar sauna & steam shower. Outside, manicured grounds surround an outdoor kitchen, expansive deck, and inviting patio perfect for entertaining.

11 Brown Street, Cambridge

Listing courtesy of Listing Agent: Beth Dickerson from Listing Office: Gibson Sotheby's International Realty.
$12,995,000
4 Beds ⋅ 8 Baths ⋅ 73499377 MLS
North Pasture is a newly built estate situated on one of Nantucket highest elevations, this turn key offering is in one of the islands most coveted settings, blends modern construction with timeless design elements and high end custom finishes. Over 6000 square feet of finished living space, the residence comprises of 4 ensuite bedrooms and 4 half bathrooms; multiple living areas spanning three floors, ideal for entertaining and all of your overflow needs, high ceilings that enhance light and volume. The architectural detail and exquisite custom millwork prioritizes clean lines, open rooms, and strong visual connections to the surrounding landscape. Outdoor living is anchored by an infinity-edge pool and spa oriented toward uninterrupted southern exposure. Cabana with outdoor kitchen, lounge area, and half bath. Garage and refined landscape design complete the property.

25 North Pasture Lane, Nantucket

Listing courtesy of Listing Agent: Karen Moreshead from Listing Office: Craigville Realty, Inc..
$12,985,000
7 Beds ⋅ 11 Baths ⋅ 73511402 MLS
This sensational oceanfront estate is located in the coveted, gated beachfront community of Nonquitt. The 7+ bed Main House boasts breathtaking water views through expansive walls of glass, while the guest and pool houses are seamlessly integrated to create a one-of-a-kind coastal retreat. Light-filled living and dining spaces are designed for effortless indoor-outdoor living and entertaining, flowing beautifully onto patios and poolside areas. The detached garage includes the fully equipped guest suite with a bedroom, sitting room, full bath, washer and dryer. Set behind a tall privet hedge and surrounded by natural beauty, this custom home was recently built by Parker Construction with top finishes throughout. Resort-style grounds include level lawns, elegant hardscapes, and a stunning infinity-edge pool and spa overlooking a private beach and the shimmering sea beyond. Nonquitt blends laid-back coastal charm with exclusive amenities including golf, tennis, and sailing.

1 Mattarest Lane, Dartmouth

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$12,950,000
5 Beds ⋅ 7 Baths ⋅ 73489042 MLS
Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool area. The main living spaces balance comfort and sophistication with warm wood floors, curated finishes, and multiple gathering areas, including a lower level with a glass-enclosed wine room, custom bar, game area, and media lounge. The kitchen features sleek cabinetry, open shelving, and picture windows overlooking the landscape, while bedrooms serve as private retreats complemented by spa-quality baths. Outside, panoramic water views unfold as a private stairway leads to the shoreline. A detached two-car garage with a guest suite above adds flexibility, completing this exceptional offering.

301 Whidah Road, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$12,900,000
5 Beds ⋅ 8 Baths ⋅ 73473428 MLS
Grand iconic corner building has just undergone a complete restoration into one of the finest single family homes on Beacon Hill. An extremely rare corner home has stood in this location since 1870 and still posses the papyrus capitals on the entryway columns to mark the style. This sun filled corner property maintains three exposures, 65 windows, ceiling heights ranging from 9-11 to 11-7, three roof decks, courtyard and a sweeping top to bottom staircase that begins in a grand entryway and ends at a dramatic 8 window cupola that truly must be seen. This tremendous home offers substantial curb appeal, three magnificent bays, gracious rooms and architectural detail. Property amenities include elevator, two wet bars, three gas fireplaces, entertainment club level with roof deck, three laundries, top floor media room, three parking spaces, and much more. Spectacular opportunity in one of Boston's most historic and desirable neighborhoods.

55-57 Hancock St, Boston

Listing courtesy of Listing Agent: Glenn Forger from Listing Office: Olde Forge Realty.
$12,750,000
10 Beds ⋅ 11 Baths ⋅ 1655480 MLS
Just imagine spending Summers in the magical village of Seal Harbor on Mount Desert Island. The current residents named this extraordinary place Wanakiwin. Which means '' harmony, peace and tranquility.'' This enchanting estate by the sea transports you with its secluded driveway that winds through a pristine woodland of mosses and lichen-covered boulders as the majestic residence comes into view. You have arrived at this architectural tour-de-force. Distinctly drawn in the highest order of shingle-style the home is dramatically anchored to what is perhaps the most magnificent parcel along the entire Maine coastline. Upon entering, the three-story fir-paneled hall is flanked by a massive staircase fashioned from white oak. Two steps down into the grand living room reveal a pleasing fireplace to the left and a pair of French doors leading out to the sprawling covered porch. Take in the sweeping panoramic views of 780' glittering ocean frontage that merges with the rugged pink granite bluff known as Ingraham Point. All while perched high and dry above the bold Atlantic. Welcome multiple generations to partake in all of the captivating ocean view bedrooms. Here, the Owners' suite boasts cathedral ceilings and its very own waterside balcony. A charming country kitchen with a gas-fired range adjoins a soaring breakfast space. The dining room features a boxed-beamed ceiling and offers yet another cozy fireplace. A library with built-ins is paired next to the den which is trimmed in mahogany and beadboard reminiscent of the captains' quarters aboard a ship. There is an arts & crafts space, a lower-level gym, and an extensive wine cellar. Explore the epic grandeur of nearby Acadia, including Sand Beach, nature hikes, popovers at the Jordan Pond House and amazing sunsets atop Cadillac Mountain. Invite company over for a Gatsby era soiree' in the gardens while overlooking the majestic surf below. Embrace it all and make it yours. Three room staff quarters.

93 Cooksey Dr, Mount Desert

Listing courtesy of Legacy Properties Sotheby's International Realty.

$12,500,000
8 Beds ⋅ 7 Baths ⋅ 1667981 MLS
Perched high atop dramatic granite cliffs on Maine's Bold Coast, 'Sea Ledges' is an extraordinary 172-acre compound with over 1.2 miles of diverse ocean frontage. Few homes on the Eastern Seaboard sit as high over the open ocean. Because the deep Atlantic runs straight to the rock face, massive storm swells hit with unfiltered force, exploding into the air for an unbelievable front-row spectacle. The acoustic backdrop is captivating, defined by the deep-ocean surge. During rough seas, the home provides the ultimate experience of the Atlantic's raw power, allowing you to hear the thunderous boom resonating through the cliffs right from inside the house, joined by the whistle of coastal winds and nesting seabird calls. It feels like a private national park, boasting over 8 miles of maintained trails for world-class hiking and rugged rock traversing. This multi-tiered network lets you climb upper ridges for vast horizons, navigate technical descending pathways to conquer the granite face, or step onto unique, private cobble beaches tucked between coves where you can safely enter the ocean waters. The meticulously renovated main residence frames these views from every room, crowned by a 4th-story 'Eagles Nest' tower sitting top of the tree canopy. Enjoy cinematic views of Old Man Island--showcasing a striking, emerald-green Scottish grassland aesthetic--alongside Cross Island and the horizon toward Machias Seal Island, a famous sanctuary for bald eagles, puffins, and rare razorbills. For monumental upside, 5 additional premier cliffside lots feature grandfathered, pre-approved building footprints that are already blasted and cleared. An unmatched legacy estate.

214 Sea Ledges Rd, Cutler

Listing courtesy of www.HomeZu.com. 877-249-5478
$12,500,000
5 Beds ⋅ 4 Baths ⋅ 73516310 MLS
Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops, custom cabinetry, premium appliances, and a walk-in pantry. Spacious living areas and a serene primary suite capture breathtaking Atlantic Ocean views. Additional bedrooms occupy a separate wing for added privacy. Outdoors, organic landscaping, historic stone walls, colorful gardens, fenced pasture, and expansive decks create a peaceful setting for entertaining or stargazing. Ownership includes exclusive access to scenic trails, pond launches, and a private beach. Smart features include Nest thermostats and a HEOS sound system, completing this exceptional Vineyard lifestyle to treasure always.

18 Spruce Gate Road, Chilmark

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$12,500,000
8 Beds ⋅ 10 Baths ⋅ 73496953 MLS
Set on exquisitely landscaped, private grounds overlooking Brae Burn Country Club, this stunning estate delivers sophisticated living at every turn. The first floor flows through gracious living and dining rooms, a handsome paneled library, chef's kitchen, family room, two powder rooms, mudroom, and garage. The primary suite is a sanctuary — dressing room, spa bath, bonus room, and a private balcony with sweeping views. Five additional bedroom suites complete the second floor; a third-floor guest suite with ensuite offers privacy and comfort for visitors. The lower level is extraordinary: indoor pool, regulation squash court, gym, sauna, wet bar, home theatre, game room, and guest suite. Elevator to three main floors. A heated three-car garage and heated driveway complete the home. Easy access to the Pike and Route 128, while maintaining a peaceful, private setting. Few properties in the area offer this level of scale, finish, and amenity.

148 Dartmouth Street, Newton

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$12,250,000
7 Beds ⋅ 9 Baths ⋅ 73551533 MLS
Perched within ''The Cliffs''--West Falmouth's most coveted private seaside enclave--this custom shingle-style estate offers over 11,000 square feet of exquisitely finished living space in pristine condition. From its elevated vantage overlooking Buzzards Bay, the residence commands panoramic water views toward the Elizabeth Islands and Vineyard Sound--permanently protected by a perpetual view easement, ensuring unobstructed western sunsets for generations. An opulent foyer with sweeping curved staircase opens to soaring volumes, rich hardwoods, and custom millwork throughout. Seven bedrooms, eight full and one half baths are arranged for privacy, while a formal dining room and multiple living areas open through French doors to landscaped grounds and four expansive decks. Recent improvements include a new roof and whole-house generator. Residents enjoy The Cliffs' private sandy association beach, minutes from West Falmouth Harbor, yacht clubs, golf, and the Shining Sea Bikeway.

39 Naushon S, Falmouth

Listing courtesy of Listing Agent: Diana Lucivero from Listing Office: Compass.
$12,250,000
5 Beds ⋅ 6 Baths ⋅ 73342640 MLS
Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite center island, custom built-ins, and a charming breakfast nook with wraparound picture windows framing the breathtaking waterfront vistas. The sumptuous first-floor primary suite is a sanctuary of relaxation, offering private patio access, a spacious walk-in closet, and a spa-inspired en-suite with dual vanities, a luxurious soaking tub, and a glassless double-headed rain shower. The sun-drenched sunroom complete with a full wet bar and sliders on three sides opens directly to the meticulously designed outdoor living areas. The second level hosts four additional spacious bedrooms, a generous family room, and a bonus room with a private balcony, designed for both comfort and relaxation. This exceptional residence also features a partially finished lower level, thoughtfully designed to enhance both convenience and functionality with direct outdoor access perfect for accommodating small boats, golf carts and other recreational essentials. Set on 1.37 acres of pristine coastal land, this estate is an outdoor enthusiast's paradise. The meticulously landscaped grounds feature a built-in fire pit, an outdoor shower, a waterside in-ground pool, a sandy beach, and a private dock. A rare opportunity to own a world-class waterfront residence, this home delivers unparalleled elegance, modern luxuries, and the very best of Cape Cod's coastal living.

71 Sand Pt, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$12,000,000
4 Beds ⋅ 3 Baths ⋅ 73556482 MLS
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$11,995,000
5 Beds ⋅ 4 Baths ⋅ 73537406 MLS
Tracing its roots to a classic Cape house and fishing shack in Provincetown's historic West End, this remarkable waterfront residence was elevated and transformed through an extensive restoration that preserved its authentic architectural character while reimagining the property for a new generation. Structural pilings and timbers salvaged from Boston's famed Jimmy's Harborside Restaurant were masterfully incorporated into the staircase and ceiling details. Rich pine floors, a rugged fieldstone fireplace, a custom Vermont marble kitchen with a soapstone island, a generous pantry, a waterfront dining room, and a harbor-facing sitting room define the interior layout. A rare and defining feature is the property's extraordinary private dock--the largest associated with any single-family residence in Provincetown--extending approximately 70 feet into the harbor and providing an unparalleled connection to the waterfront.

71 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.
$11,950,000
6 Beds ⋅ 8 Baths ⋅ 73531287 MLS
Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-like swimming pool and cabana, a boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. The open floor plan seamlessly flows from a fireplaced living room with coffered ceilings to a gourmet kitchen with a Sub-Zero refrigerator, Wolf range, and Danby natural stone counters. Glass doors line the waterside of the home, opening to an expansive Phoenician Buff stone terrace surrounding a Pebble Tec pool and spa. The first-floor primary boasts 2 walk-in closets and a luxurious bath with a freestanding soaking tub. Four en suite bedrooms, a family room, and an ipe deck occupy the second level, with bonus space above. A bedroom suite over the garage accommodates guests or staff. Located minutes from everything Osterville has to offer.

48 Starboard Lane, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$11,750,000
6 Beds ⋅ 9 Baths ⋅ 73536353 MLS
A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.
$11,750,000
5 Beds ⋅ 7 Baths ⋅ 73516055 MLS
EXCEPTIONAL WATERFRONT ESTATE with 2.29 acres of land, a DOCK, 200' of frontage on Hingham Harbor, and spectacular views of Boston skyline. Designed by acclaimed architect, Tom Catalano, known for his creation of homes representative of a by-gone era, yet suited for modern living. The natural light is incredible and the views are mesmerizing. The finishes and millwork are truly MASTERFUL with coffered ceilings, wainscotting, arched openings, custom cabinetry and quarter sawn oak floors throughout. The staircases are a graceful work of art, with gentle rises and walls of windows. The exterior spaces are as exquisite as the interior. The back of the house features gorgeous stone terraces with beautiful pergolas, a heated Gunite pool and sweeping lawn to the dock and waters edge. The front "garden" sets the stage for this stunning property with a torch lit fountain, expansive level lawn, an English conservatory and gardens.

5 Bare Cove Ln, Hingham

Listing courtesy of Listing Agent: Tara Coveney from Listing Office: Coldwell Banker Realty - Hingham.
$11,750,000
6 Beds ⋅ 6 Baths ⋅ 73485239 MLS
One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.
$11,700,000
4 Beds ⋅ 6 Baths ⋅ 1663284 MLS
Welcome to Sea Haven, a breathtaking oceanfront estate where modern luxury meets the raw beauty of the Atlantic coastline. Perched majestically above dramatic rocky cliffs, this extraordinary residence commands over 2.5 acres, offering panoramic ocean views & an unparalleled sense of tranquility & seclusion. From the moment you arrive, Sea Haven captivates with its architectural elegance & seamless integration into the natural landscape. Designed to maximize views, the estate features walls of glass that blur the line between indoor & outdoor living, bathing every room in sunlight & framing sweeping vistas of the Atlantic Ocean. At the heart of the property lies the infinity-edge pool, seemingly spilling into the sea below--an awe-inspiring centerpiece that provides a front-row seat to the ever-changing tides, morning sunrises, and coastal wildlife. Multiple balconies, patios & an expansive outdoor dining area invite you to soak in the salt air & savor the coastal lifestyle, whether you're entertaining guests or enjoying a peaceful evening. Inside, no detail has been overlooked. The home boasts custom finishes throughout, from custom-crafted cabinetry, soaring sloped ceilings & designer lighting to natural stone surfaces & premium appliances that reflect the highest standards of contemporary luxury. Sea Haven features four spacious bedrooms, each thoughtfully positioned for privacy & ocean views. The primary suite is a true retreat, complete with a spa-inspired bath, private balcony, and floor-to-ceiling glass walls that invite the sea indoors. Additional amenities include a home office with ocean views--perfect for remote work or creative pursuits - and theatre room, designed for cinematic experiences in the comfort of your home. Whether you're seeking a serene personal retreat or a show-stopping setting for unforgettable coastal events, Sea Haven is the epitome of refined oceanfront living.

5 Fairbourne Ln, York

Listing courtesy of Anchor Real Estate.

$11,495,000
4 Beds ⋅ 7 Baths ⋅ 73516512 MLS
Set along the inner harbor in prestigious Manchester, this rare waterfront estate offering over 4 acres of exceptional privacy, sweeping coastal views, and direct harbor access from a private dock. Beyond the gated entrance, the property unfolds into beautifully landscaped grounds for both grand-scale entertaining and quiet retreat, complete with a heated in-ground pool, tennis court, and multiple terraces positioned to capture breathtaking sunsets over the water. The residence blends timeless architecture with refined comfort across approximately 8,000 square feet of living space. Expansive rooms filled with natural light framed by stunning water views, while thoughtful details and elegant finishes create a sense of understated luxury throughout. The fully finished lower level features a wet bar, Spa-inspired sauna area complete with shower, enhancing the home’s resort-like atmosphere. Moments from Singing Beach, marinas, and the village, defined by scale, privacy and costal elegance

5 Proctor St, Manchester

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.
$11,250,000
7 Beds ⋅ 9 Baths ⋅ 73389616 MLS
Seaway is an exceptional coastal estate located in desirable Manchester, just 45 minutes north of Boston. Set on nearly an acre with sweeping views of the Atlantic, this grand Colonial Revival home has been masterfully restored by renowned architectural firm Carpenter & MacNeille. The residence offers a combination of classic New England charm & refined modern living. Elegant formal spaces flow seamlessly into a custom chef’s kitchen with AGA range & light-filled gathering rooms, designed for comfort & entertaining. A luxurious primary suite features ocean views, spa-style bath, dressing areas, & morning bar/kitchenette. There are 5 additional ensuite bedrooms and & 3-bay carriage house. Outdoors, manicured gardens, stone terraces, & a pool create an idyllic setting for relaxation. Seaway has private deeded access to Singing Beach, is moments to the village shops, & direct train access to Boston. An opportunity to own one of the North Shore’s most iconic seaside homes.

4 Cobb Avenue, Manchester

Listing courtesy of Listing Agent: John Farrell from Listing Office: Coldwell Banker Realty - Beverly.
$11,000,000
73543050 MLS
Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

39 Cottage St, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$11,000,000
8 Beds ⋅ 7 Baths ⋅ 1660121 MLS
Coastal Estate near Portland, Maine. Set on 2.9 private acres along esteemed Foreside Road in Falmouth, this rare waterfront estate offers exceptional privacy, direct ocean frontage, and close proximity to the city. Overlooking Mussell Cove on two sides with sweeping views to Casco Bay, the property enjoys remarkable seclusion with only one neighboring parcel-just 8 minutes from downtown Portland and 20 minutes from Portland International Jetport. The home features 8 bedrooms, 6.5 baths, a fitness gym, wine cellar, light-filled living spaces ideal for both entertaining and quiet retreat. Offered fully furnished for turnkey enjoyment including a Steinway grand piano. A newly constructed detached carriage house accommodates three cars and serves as a recreation pavilion, complete with a indoor half basketball court and pickle ball court-perfect for multi-generational living and year-round activity, The waterfront setting offers picturesque views, a private dock with direct access to Mussel Cove and Casco Bay, and excellent summer fishing. the grounds feature established English and rose gardens, mature apple trees, and a large raspberry patch, adding charm and a sense of permanence. Modern amenities include whole-house air conditioning, a full house automatic generator ensuring uninterrupted comfort and dual path internet connectivity with satellite failover.This coastal estate has both Colonial and historical farmhouse influences.The original farmhouse dates back to 1888 and remains incorporated into the modern residence today. A rare opportunity to own a coastal estate combining privacy, recreation, and convenience-just minutes from Portland.

127 Foreside Rd, Falmouth

Listing courtesy of Engel & Volkers Casco Bay.

$10,995,000
5 Beds ⋅ 6 Baths ⋅ 73540092 MLS
Not all new construction is created equal. The result of a visionary collaboration between acclaimed architecture firm Of Possible and renowned custom builder NS Builders, 45 White Oak Rd represents a rare opportunity to own a residence where design, craftsmanship, and performance were never compromised. Conceived as a showcase of what is possible when architecture and construction are executed at the highest level, this 7,200+ sq. ft. home balances architectural significance with the warmth and functionality required for everyday living. Expansive walls of glass create a seamless connection to the beautifully landscaped grounds, while custom German white oak millwork, curated natural stone finishes, and exceptional detailing reflect an uncompromising commitment to quality throughout. Designed for both grand entertaining and comfortable daily living, the home offers a level of craftsmanship, sophistication, and performance rarely found in today's market.

45 White Oak Rd, Wellesley

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

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