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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.
$7,950,000
5 Beds ⋅ 6 Baths ⋅ 73543062 MLS
Nestled in the highly coveted enclave of Acoaxet and Westport Harbor, this magnificent coastal estate at 169 Atlantic Ave offers the pinnacle of New England waterfront living. Meticulously reimagined from top to bottom, this home underwent a complete, high-end remodel completed in 2021. Sited flawlessly to maximize panoramic views of the open Atlantic Ocean, sandy shorelines, and the Elizabeth Islands, this property seamlessly blends classic Shingle-style architecture with unparalleled private luxury.

169 Atlantic Avenue, Westport

Listing courtesy of Listing Agent: Kirk Schryver Team from Listing Office: Compass.
$8,625,000
7 Beds ⋅ 8 Baths ⋅ 73543017 MLS
Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

63 Main Street, Barnstable

Listing courtesy of Listing Agent: Christa Zevitas from Listing Office: .
$6,900,000
5 Beds ⋅ 5 Baths ⋅ 73542564 MLS
Set 150 feet above sea level on nearly 13 acres in one of Manchester-by-the-Sea’s most coveted locations, 370 Summer Street offers a rare opportunity to own an extraordinary North Shore estate. Reached by a long private drive, the property commands sweeping views of Kettle Cove and Crow Island. Designed by Marcus Gleysteen of MGA with interiors by Lena Fransioli of Zoe Design, the home blends organic modern architecture with timeless craftsmanship. Stone, wood, and metal leaf finishes include a striking copper leaf wall, live-edge maple stairs, bubinga paneling, and a stainless steel freestanding fireplace beneath arched ceilings soaring to 23 feet. Abutting Hooper Trask Conservation Pasture, the estate enjoys access to 2,000+ acres of protected land, trails, beaches, the harbor, village center, top-ranked schools, and the commuter rail.

370 Summer Street, Manchester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.
$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.
$9,890,000
5 Beds ⋅ 4 Baths ⋅ 73540605 MLS
A rare opportunity to own one of Duxbury's most extraordinary waterfront estates on Eagle's Nest Point. Sited on a private 7.6-acre peninsula extending into Duxbury Bay, this classic shingle-style residence offers sweeping water views on three sides, deep-water dock access, and the kind of privacy that simply cannot be replicated. The main house has been thoughtfully updated while preserving its architectural integrity with generous principal rooms, gracious flow, and natural light throughout. A separate guest cottage provides comfortable accommodations for visitors while maintaining the quiet of the main residence. Whether arriving by land or by sea, 160 Marshall Street makes an unmistakable impression. Seven and a half acres, three sides of water, and a setting that defines the finest of coastal New England living. This property is being sold as a commissioner's sale pursuant to a Massachusetts Land Court partition action.

160 Marshall Street, Duxbury

Listing courtesy of Listing Agent: Kristin Thompson from Listing Office: Keller Williams Realty Signature Properties.
$21,000,000
6 Beds ⋅ 9 Baths ⋅ 73539974 MLS
20 Crowninshield Road is set on 2.25 oceanfront acres in one of Marblehead's most coveted waterfront settings. This exceptional estate offers approximately 7,013 square feet of finished living area and 8,620 square feet of gross area, combining timeless coastal elegance with modern luxury. Completely rebuilt to the highest standards, this six-bedroom residence features six full baths and three half baths, sweeping ocean views, 10-foot ceilings, radiant heat, and central air conditioning. At the heart of the home, a dramatic ribbon staircase serves as a stunning architectural centerpiece, rising gracefully through all levels and complementing the seamless coplanar design. Remarkable craftsmanship is on display throughout, anchored by extensive millwork in old-growth white oak and a continuous installation of large-format stone running both inside and outside the home. A full-size elevator serves every floor, and the threshold-free design offers full accessibility to all living spaces. An intuitive, easy-to-use home control system governs the property, engineered with multiple layers of redundancy for reliable performance and security.The primary suite serves as a private retreat, featuring two gas fireplaces, dual walk-in closets, direct access to an expansive Ipe deck, and an outdoor shower. An extensive wine cellar offers precision climate-controlled display racking. Spa-inspired amenities include a sauna, steam room, an outdoor hot tub concealed beneath a retractable Ipe deck, and a pool surrounded by granite and Ipe decking.A separate staff or guest suite provides flexibility for extended family or live-in assistance. The four-car garage offers substantial vehicle storage capacity.The beautifully landscaped grounds frame expansive panoramic Atlantic ocean views and provide exceptional privacy. Ownership includes access to a neighborhood beach, dock, and mooring field, offering a rare opportunity to enjoy Marblehead's renowned boating and waterfront lifestyle. Just minutes from Marblehead's historic harbor, yacht clubs, shops, and restaurants, this rare legacy property offers exceptional craftsmanship in one of New England's most desirable oceanfront settings.The dwelling is not located in the FEMA flood zone.

20 Crowninshield Road, Marblehead

Listing courtesy of Listing Agent: Steven White from Listing Office: William Raveis R.E. & Home Services.
$15,400,000
6 Beds ⋅ 9 Baths ⋅ 73538291 MLS
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$22,990,000
13 Beds ⋅ 18 Baths ⋅ 73537578 MLS
Commanding one of the most extraordinary waterfront settings on Beverly’s famed Gold Coast, Rock Edge is a legendary Georgian Revival estate perched atop a dramatic rocky bluff with 400± feet of private beachfront and breathtaking ocean views. Originally built in 1904, this iconic residence has been masterfully restored and reimagined, seamlessly blending Gilded Age grandeur with exceptional modern luxury while preserving the estate’s remarkable architectural pedigree. Soaring 16-foot ceilings, richly scaled interiors, elegant oceanfront formal living and dining rooms, a stunning oceanfront veranda, and a spectacular 1,500± SQFT gourmet marble kitchen are just a few of the outstanding features of this magnificent property. Complete with a private guest wing, a separate carriage house, private beach access, restored cabanas, a pool and san unmatched seaside setting, Rock Edge represents a once-in-a-generation opportunity to own one of the North Shore’s most impressive waterfront estate.

34 Paine Avenue, Beverly

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$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.
$7,900,000
4 Beds ⋅ 6 Baths ⋅ 73536744 MLS
Set along one of Back Bay's most picturesque tree-lined streets, this distinguished single-family residence pairs timeless architectural elegance with thoughtfully updated interiors and modern amenities. Grand living spaces are defined by soaring ceilings, oversized bay windows, elegant custom built-ins, handsome fireplaces, and abundant natural light. The beautifully renovated kitchen features custom cabinetry, top-of-the-line appliances, and a spacious butler's pantry designed for effortless entertaining. Crowning the home is a spectacular roof deck with sweeping views of the Back Bay skyline and city beyond. Recent improvements include updated HVAC systems and lighting throughout. Additional amenities include an elevator servicing all floors, a wine room, and a versatile lower level with kitchenette and full bath, ideally suited for a guest suite. Complete with an outdoor patio and 2 full parking spaces, this residence offers a rare opportunity in Boston's most coveted neighborhood.

122 Marlborough Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$6,200,000
4 Beds ⋅ 5 Baths ⋅ 73536732 MLS
Set on a private street in Brant Point just steps from Downtown, this beautifully appointed home features 4 bedrooms all w/en suite bathrooms, a den & powder room across a thoughtfully designed floor plan. The chef's kitchen boasts a 6 burner Wolf range, Sub Zero refrigerator, island, built-in desk, pantry & sink overlooking the yard. The generous sized, sunlight filled living room w/3 exposures offers a fireplace & french doors onto a covered porch overlooking the professionally landscaped yard. A 1st floor bedroom w/en suite bath is ideal for guests, while the primary suite features a balcony, vaulted ceilings & spa-inspired marble bath. A 2nd floor bar w/beverage cooler is located for easy access to the bedrooms & widows walk offering sweeping views & stargazing. Outside, enjoy a yard, covered porch, outdoor shower, shed, & parking for two. Steps to Childrens & Jetties Beach, & world-class dining including Lola 41,The White Elephant & The Nantucket Hotel who has private memberships.

3 Dolphin Ct, Nantucket

Listing courtesy of Listing Agent: Cort LaBonte Coldren Coopersmith Group from Listing Office: Compass.
$15,000,000
5 Beds ⋅ 9 Baths ⋅ 73536454 MLS
This magnificent oceanfront estate stands as one of the most significant properties in Marblehead. Located in the exclusive Peach’s Point neighborhood, this property offers stunning views of Crowninshield Island, Grace Oliver’s Beach, Marblehead Lighthouse, and the surrounding islands. “Seaside Farm” replaced the original Crowninshield estate in 1999 in a classic Georgian style, with meticulous attention to detail throughout. The home is designed to maximize ocean views while maintaining privacy. The grand 2-story foyer with a custom staircase sets the tone for the home, which features elegant living spaces ideal for both daily life and entertaining. The second floor includes an oceanfront primary suite with a fireplace, walk-in closet, modern bathroom, and a private deck with exceptional views. Three additional en suite bedrooms, a large office, and a laundry room complete the second floor. Caretakers 1 bedroom apartment over 4-car garage offering views of Grace Oliver's Beach and c

17 Crowninshield Road, Marblehead

Listing courtesy of Listing Agent: Traci Howe from Listing Office: Gibson Sotheby's International Realty.
$6,500,000
10 Beds ⋅ 10 Baths ⋅ 73535185 MLS
Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. The property was divided into three townhouse residences, but has since been used as a single-family home. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$6,150,000
10 Beds ⋅ 11 Baths ⋅ 73535142 MLS
Iconic “Egg Rock” Estate—a rare oceanfront legacy property set on 3 private acres in Nahant’s prestigious East Point. Overlooking Egg Rock and the Atlantic, this grand 9,000+ SF residence offers 10 bedrooms and 8 baths, showcasing exceptional period craftsmanship. Elegant interiors feature soaring 11’ ceilings, intricate plaster moldings, refined millwork, gleaming hardwood floors, and a dramatic central staircase. Nine fireplaces, a stately library, billiard room, mural room, and classic butler’s pantry enhance its timeless appeal, while a third-floor guest suite provides added privacy for extended stays. Expansive windows capture sweeping ocean vistas. Outdoors, enjoy a heated cliffside pool and pool house, ideal for relaxation or direct access via a rebuilt seawall to a private shared beach. A distinguished offering of coastal grandeur and historic significance.

374 Nahant Road, Nahant

Listing courtesy of Listing Agent: Annie Wachtel from Listing Office: Coldwell Banker Realty - Marblehead.
$6,500,000
4 Beds ⋅ 5 Baths ⋅ 73534024 MLS
Set along one of N.E. most coveted waterfront corridors, this extraordinary 13 acre estate represents a rare convergence of architectural pedigree, unrivaled privacy and enduring coastal elegance. Bordered by over 200 acres of protected land & commanding sweeping views of the North River, the property offers an irreplaceable setting of remarkable beauty & serenity. Inspired by the celebrated coastal architecture of Robert A.M. Stern, the custom Nantucket-style 14 room residence is a masterwork of timeless design and exceptional craftsmanship. Beyond the home, resort-caliber amenities elevate the estate experience. Meticulously landscaped grounds unfold to a private heated swimming pool, fully appointed cabana, lush lawns, and outdoor living spaces designed for relaxation and entertaining. A private deep-water dock capable of handling vessels up to 45' provides direct access to the Atlantic Ocean, offering an unparalleled lifestyle for boating enthusiasts and waterfront purists alike.

12 and 0 Hunter Dr., Marshfield

Listing courtesy of Listing Agent: Janet Koelsch from Listing Office: Coldwell Banker Realty - Scituate.
$6,750,000
5 Beds ⋅ 9 Baths ⋅ 73533214 MLS
Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on 3 acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast beautiful granite floors for fine entertaining. Additionally, rich oak wood floors are throughout the house. Three custom marble fireplaces grace the sitting areas. A first floor primary suite, private office and sunroom complete the main level. Upstairs has 4 large bedroom suites while the finished 3rd floor is ideal for a dual in-home office or guest bedroom. The tremendous lower level features a sauna, steam and home theater. This exceptional home embodies an elevated blend of refined and recreational living. This location provides excellent proximity to Boston and top-ranked schools.

15 Brown Street, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$6,500,000
4 Beds ⋅ 5 Baths ⋅ 73532634 MLS
This magnificent townhouse on picturesque Beacon Street offers the perfect combination of modern conveniences and historic grandeur in the heart of Back Bay. An elevator serves all levels of the home, which is topped by a dramatic skylight and private roof deck with stunning views. The tastefully appointed interiors include a grand double parlor living level with striking historic details and soaring ceilings, a living or entertaining room with full wet bar and direct access to the outdoor deck, an open kitchen, dining and family room with endless storage and high-end appliances, expansive mudroom with access to the patio and parking, and a home office. The entire 4th floor was renovated and includes the luxurious primary suite. Additional features include a whole-house water filtration system, new HVAC, ERV system for continuous fresh air, new lighting controls, and the entire home was deleaded. This wonderful home is steps from all Back Bay has to offer and includes 3 parking spaces.

321 Beacon Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$8,950,000
6 Beds ⋅ 11 Baths ⋅ 73531786 MLS
Purposefully designed for entertaining on every scale, this remarkable 2.07-acre estate offers approximately 12,000 square feet of luxurious living where family and friends naturally gather. From children's pool parties and lawn games to elegant dinners, corporate events and celebrations, every indoor and outdoor space is designed to create unforgettable experiences. Resort-quality amenities include a spectacular swimming pool, newly constructed four-season pool house, covered outdoor kitchen, bar, wine room, games room, home theatre, fitness center, spa, and expansive entertaining terraces. Extensively renovated and modernized, the residence features enterprise-grade WiFi, Crestron Home automation, distributed digital audio/video, advanced security, whole-house generators, upgraded mechanical systems, high-performance HVAC, designer lighting, custom millwork, and exceptional finishes throughout. Landscaped grounds with manicured lawns, stone walls, mature trees, and ultimate privacy.

1722 Monument St, Concord

Listing courtesy of Listing Agent: Jonathan Radford from Listing Office: Coldwell Banker Realty - Boston.
$11,500,000
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: .
$6,250,000
6 Beds ⋅ 6 Baths ⋅ 73528490 MLS
Set high on nearly an acre in one of Marblehead Neck's most prestigious locations, this 6 bedroom, 5.5 half bathroom exceptional Colonial captures lovely views of Marblehead Harbor while offering privacy, elegance, and timeless architectural appeal. A circular driveway and extraordinary landscaping introduce beautifully curated living spaces where a top-to-bottom renovation has seamlessly blended classic architectural detail with superior designer finishes throughout. From Belgium bluestone flooring to German imported glass on the bar, every detail was thoughtfully selected to the highest standard. Rich wood detailing, crisp moldings, soaring ceilings, and expansive windows frame harbor views and fill the home with natural light. Grandly scaled rooms open effortlessly to a wraparound porch, deck, and bluestone patios. A stunning pool and hot tub are perfectly positioned beside an expansive flat lawn — creating an exceptional private setting for relaxation and entertaining.

48 Harbor Ave, Marblehead

Listing courtesy of Listing Agent: Haley Paster Scimone from Listing Office: Gibson Sotheby's International Realty.
$21,950,000
6 Beds ⋅ 8 Baths ⋅ 73527728 MLS
Exquisite, wide Back Bay townhouse on the sunny side of Commonwealth with large private roof deck, magnificent views, Juliet balcony, and 6 outdoor parking showcases exceptional bones and timeless character. Expansive windows provide outstanding natural light, highlighting the home's historic charm and original detail. The property offers a versatile floor plan for customization, with approximately 10,000+/-sf to create luxurious spaces and exceptional entertaining space. Currently exhibiting an open and airy kitchen, soaring ceilings, a stately dining room, beautiful paneled library, 5+ well-proportional bedrooms, abundant closets, and a separate au pair suite, it is one of only a few single family homes in this highly coveted neighborhood. Its distinguished façade, irreplaceable location, and palatial scale present an extraordinary canvas for a discerning buyer. Elevator to all floors, 8 fireplaces, and grandeur complete this home’s spectacular offering. Some photos virtually staged.

129 Commonwealth Avenue, Boston

Listing courtesy of Listing Agent: Jeannemarie Conley 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.
$10,000,000
7 Beds ⋅ 10 Baths ⋅ 73524508 MLS
Introducing 19 Bonnybrook, an exceptional new-construction estate set on over ¾ acre in Waban. Spanning 11,535 sq ft, this luxurious residence offers 7 bedrooms, 7 full baths, & 3 half baths, blending scale, elegance, modern comfort & custom millwork. A spectacular gourmet chef’s kitchen with premium appliances & dual islands is complemented by a fully equipped secondary kitchen for effortless entertaining. The dramatic two-story family room features 20+ft ceilings & stunning floor-to-ceiling stone fireplace. The first floor also includes formal living & dining rooms, a sun-filled breakfast area overlooking the landscaped backyard & patio, & a gracious first-floor ensuite. 2nd floor offers a presidential primary suite w spa-like bath, fireplace,& private deck, four ensuite bedrooms, office/yoga room, & laundry. The lower level features a guest suite, gym, wine cellar, theatre, steam & sauna, & recreational room. Elevator, 3-car garage, & room for pool complete this exceptional offering

19 Bonnybrook Road, Newton

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.
$45,000,000
7 Beds ⋅ 13 Baths ⋅ 73523462 MLS
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

18 Point Inner Way, Chilmark

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$9,900,000
7 Beds ⋅ 7 Baths ⋅ 73521104 MLS
319 Beacon Street is a stunning single-family residence offering impressive scale, refined finishes, and an outstanding layout for both grand entertaining and everyday living. Flooded with natural light from oversized windows, the residence features beautifully proportioned rooms with high ceilings, all connected by an elevator servicing every level. Elegant formal living and dining spaces provide a sophisticated setting for entertaining while maintaining a warm and inviting feel. A suburban-sized eat-in kitchen is outfitted with top-of-the-line appliances, custom cabinetry, and extensive storage. The expansive family room with a full bar opens to a spectacular oversized deck, creating an ideal indoor-outdoor setting for entertaining. Additional highlights include a home office and a private guest suite on the lower level. Atop it all is an incredible roof deck with sweeping city views. Complete with 2 garage and 1 outdoor parking space, all in a premier Back Bay location.

319 Beacon Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$7,500,000
3 Beds ⋅ 6 Baths ⋅ 73520995 MLS
Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas.

46 Great Bay Rd, Barnstable

Listing courtesy of Listing Agent: Chuck Tuttle from Listing Office: William Raveis R.E. & Home Services.
$6,995,000
4 Beds ⋅ 3 Baths ⋅ 73520913 MLS
Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay.

103 Edgartown Bay Road, Edgartown

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
$7,250,000
6 Beds ⋅ 6 Baths ⋅ 73520863 MLS
This exquisite New Seabury home blends natural beauty with modern luxury. Perched to capture stunning Nantucket Sound views with a pristine sandy beach right outside, the property offers Cape Cod living at its finest. The open layout includes a gourmet kitchen with premium appliances, a quartz island, and custom cabinetry. A sunlit living room boasts soaring ceilings, a stone fireplace, and glass doors leading to an outdoor oasis. The serene primary suite features a spa-like marble bath, walk-in closet, and private deck with ocean views. The finished lower level provides flexible space for a media room, gym, or guests. Outdoors, enjoy a heated pool, bluestone patio, and lush landscaping—perfect for entertaining or unwinding. Approved permits are in place for an 1,800 sq. ft. guest house. With breathtaking views and direct beach access, this property epitomizes Cape Cod luxury.

50 Coastline Drive, Mashpee

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$38,000,000
5 Beds ⋅ 7 Baths ⋅ 73517239 MLS
Presenting 55 Commonwealth Avenue, a rare opportunity to acquire one of Back Bay's finest turnkey single-family homes, an address that rarely, if ever, comes to market. Spanning nearly 11,000 SF on the sunny side, this exceptional home offers a combination of scale, natural light, and turnkey living. Designed for both entertaining and everyday living, the home features formal living and dining rooms, an expansive family room, chef’s kitchen, library, multiple offices,media room, catering kitchen, and a wellness level with fitness studio, and sauna. The residence offers 5+ bedrooms with multiple ensuite baths, three private terraces, nine fireplaces, temperature-controlled wine room, multiple laundry rooms, and a best-in-class elevator with access to every level. Complete with 2 private garage spaces and 1 gated outdoor space, this home stands as the only turnkey single-family residence available on the sunny side of the second block of Comm Ave, a genuine once-in-a-generation offering.

55 Commonwealth Avenue, Boston

Listing courtesy of Listing Agent: Antonio Khoury from Listing Office: Serhant.

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