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18 Point Inner Way, Chilmark
$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.

55 Commonwealth Avenue, Boston
$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: Khoury Group from Listing Office: Serhant.

518 New Castle Ave, Portsmouth
$35,000,000
6 Beds ⋅ 9 Baths ⋅ 5114173 MLS
There are properties that simply cannot be replicated. Privately sited on 7.7 waterfront acres on Portsmouth's coveted Shapleigh Island, 518 New Castle Avenue is a once-in-a-generation New England estate, an extraordinary convergence of scale, privacy, architecture, and waterfront living just moments from the heart of downtown Portsmouth. With 13,450± square feet, this magnificent Shingle Style residence was conceived on a grand scale, pairing timeless coastal architecture with exceptional craftsmanship and sophisticated modern living. Georgian-inspired millwork, stately Tuscan columns, intricate wainscoting, and beautifully proportioned interiors create a residence of remarkable presence, while walls of windows capture sweeping water views and an ever-changing maritime landscape. Across 17 rooms, the estate offers 6 bedrooms, 7 full and 2 half baths, and an impressive collection of formal and informal living spaces equally suited for everyday living and grand-scale entertaining. A newly added balcony overlooking the pool creates an elevated vantage point of the estate's sweeping water views. Beyond the home, manicured grounds descend toward the Piscataqua River, where a private deep-water dock provides direct access to Portsmouth Harbor and the open Atlantic beyond. An attached 3-car garage is complemented by a separate 3-car garage with a finished 1-bedroom, 1-bath guest accommodation above, creating a private and flexible retreat for visitors. Nearly 6,000 square feet of unfinished lower-level space offers exceptional flexibility and storage, while a new roof completed in 2025 represents a significant recent improvement. Yet perhaps the estate's greatest luxury is one that cannot be recreated: complete seclusion across 7.7 waterfront acres while remaining connected to downtown Portsmouth and its cultural, culinary, and coastal lifestyle. 518 New Castle Ave is a landmark NH estate and a rare opportunity to steward one of the region's defining legacy properties.

518 New Castle Ave, Portsmouth

Listing courtesy of Mitch Varley from Compass New England, LLC. ()

215 Uncas Point Rd, Guilford
$35,000,000
6 Beds ⋅ 5 Baths ⋅ 24034137 MLS
Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa & Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

215 Uncas Point Rd, Guilford

Listing courtesy of Joseph Piscitelli from Coldwell Banker Realty. (203) 982-3511 (203) 878-7424

128 Commonwealth Avenue, Boston
$34,990,000
5 Beds ⋅ 9 Baths ⋅ 73577894 MLS
A rare Back Bay masterpiece, this extraordinary Parisian-inspired Beaux Arts single-family residence on Commonwealth Avenue commands one of Boston’s most prestigious addresses with timeless grandeur and unrivaled scale. One of the famed “Commonwealth Avenue Sisters,” the home features a magnificent limestone façade, richly detailed interiors, ornate moldings, and dramatic entertaining spaces throughout, making it an unmatched jewel of the Back Bay neighborhood. Grand formal living and dining rooms, a stunning gourmet kitchen, and a sensational family room with Juliet balcony overlooking the Commonwealth Avenue Mall create an exceptional setting for both refined entertaining and everyday living. Complete with commercial elevator access to every floor, multiple private decks, 5+ bedrooms, 6 full and 3 half baths, and 2 heated garage and 4 heated outdoor parking, this is a singular opportunity to own one of Back Bay’s most iconic single-family residences.

128 Commonwealth Avenue, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

55 Singletree Rd, Brookline
$34,000,000
7 Beds ⋅ 16 Baths ⋅ 73590483 MLS
There are exceptional homes, and then there are properties conceived on an entirely different scale. 55 Singletree is the latter. Perched atop a secluded hill on more than two private acres in Brookline, adjacent to the reservoir, this extraordinary estate offers a rare sense of privacy and tranquility just minutes from Boston. Its elevated position and naturally sheltered setting create remarkable seclusion, with no neighboring homes overlooking the pool or private outdoor spaces. Years of vision, craftsmanship, and investment have been brought to life through an extensive two-phase construction project by Thoughtforms, one of New England’s most respected custom home builders. The result is not simply a residence, but a world unto itself—an estate with the scale and experience of a private resort. The property's commanding elevation captures views toward the Boston skyline, culminating at a rooftop terrace overlooking the city. Across the grounds, architecture and landscape have been conceived as one experience. Water features introduce movement and serenity, expansive outdoor spaces invite both gathering and escape, and a private tennis and sports court creates a level of recreation rarely found so close to the city. Inside, monumental scale meets intimate refinement, with exceptional materials, custom craftsmanship, and thoughtfully designed spaces equally suited for grand entertaining and everyday family life. An estate of this scale, caliber, and extraordinary privacy would be exceptionally difficult to replicate today. 55 Singletree represents a singular opportunity: a secluded residential sanctuary offering remarkable sophistication, recreation, and proximity to Boston.

55 Singletree Rd, Brookline

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

341 Standish Street, Duxbury
$34,000,000
12 Beds ⋅ 18 Baths ⋅ 22604952 MLS
One of the finest coastal properties to exist across New England, Goose Point is a multigenerational family compound that has been thoughtfully designed and curated over decades of loving stewardship. Set across nearly 25 acres with more than 1,000 feet of direct waterfront and private beach, Goose Point features an established and extraordinary landscape that feels more like a private London park with mature trees, nature trails, a 2 acre lake, private gardens and orchards. Created by the master artisans, stone masons, craftsmen and landscape designers, Goose Point is a rare expression of permanence and place. A collection of stunning residences and gathering spaces are carefully sited throughout the property, ensuring ideal entertaining and private guest spaces from the Main House to the Beach House, Dock House, Pavilion, pools, gardens, Boat House and Barn. Goose Point confers a profound sense of belonging, and a place designed not simply for living, but legacy. Remarkably, this private coastal world lies just 35 miles from Boston and within easy reach of Logan Int'l Airport, world renowned medical, academic, and cultural institutions.

341 Standish Street, Duxbury

Listing courtesy of Listing Agent: Brian W Dougherty (brian.dougherty@corcoranadvisors.com) from Listing Office: Corcoran Property Advisors.

341 Standish St, Duxbury
$34,000,000
12 Beds ⋅ 18 Baths ⋅ 73584065 MLS
One of the finest coastal properties to exist across New England, Goose Point is a multigenerational family compound that has been thoughtfully designed and curated over decades of loving stewardship. Set across nearly 25 acres with more than 1,000 feet of direct waterfront and private beach, Goose Point features an established and extraordinary landscape that feels more like a private London park with mature trees, nature trails, a 2 acre lake, private gardens and orchards. Created by the master artisans, stone masons, craftsmen and landscape designers, Goose Point is a rare expression of permanence and place. A collection of stunning residences and gathering spaces are carefully sited throughout the property, ensuring ideal entertaining and private guest spaces from the Main House to the Beach House, Dock House, Pavilion, pools, gardens, Boat House and Barn. Goose Point confers a profound sense of belonging, and a place designed not simply for living, but legacy. Remarkably, this private coastal world lies just 35 miles from Boston and within easy reach of Logan Int'l Airport, world renowned medical, academic, and cultural institutions.

341 Standish St, Duxbury

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

141 Main Street, Nantucket
$32,000,000
7 Beds ⋅ 10 Baths ⋅ 73576533 MLS
Town & Country. The one you’ve been waiting for has arrived.Singular in its setting, scale, and design, 141 Main Street is unlike anything else on Nantucket. A grand approach from Upper Main Street introduces the celebrated George C. Gardner House, an elegant 1835 Greek Revival and one of the island’s most treasured historic residences. Meticulously preserved in keeping with its architectural significance, the property brings together historic grace, thoughtful design, and gracious modern living.Extraordinary natural light fills every level of the main residence, while beautifully conceived living spaces create an effortless, open flow among the kitchen, dining, family, and sitting rooms, all extending naturally to the gardens and grounds. Four en suite bedrooms enjoy individual access to the pool, while the exceptional separation of space provides privacy for family and guests. The primary living space encompasses the entire third floor and is distinguished by a sensational outdoor living room with expansive decking overlooking the pool, gardens, and privately owned open space beyond. A private primary suite and office or sitting room complete this remarkable retreat.Believed to have been Nantucket’s first pool, it was reoriented on the grounds by the current owners and now sits perfectly at the back of the property. Easily accessible from both the main residence and the separate three-bedroom guest cottage, the pool and surrounding grounds create an exceptional setting for outdoor living and entertaining.Set on more than half an acre with mature gardens, a private courtyard, pool, and guest cottage, the estate offers the scale and seclusion of a country property in the heart of Town. A stroll down Main Street’s cobblestones leads to Nantucket’s celebrated restaurants, boutiques, galleries, museums, waterfront, and enduring island culture.It is impossible to compare 141 Main Street to anything else on the island. Its setting, provenance, privacy, and pristine condition place it in a category of its own—the ultimate expression of gracious in-Town living and your own private island resort in downtown Nantucket.

141 Main Street, Nantucket

Listing courtesy of Listing Agent: Marybeth Gilmartin from Listing Office: Compass.

38-48-58 Quaker Ln, Greenwich
$30,000,000
5 Beds ⋅ 7 Baths ⋅ 24210105 MLS
Behind iron gates, a private drive winds to a stately shingle-style residence set high above the landscape, with sweeping western views. Exquisitely renovated, the home offers five bedrooms, five full and two half baths, and seven fireplaces. The French country kitchen, with its hand-laid wood-inlay floors, sets the tone for a home of rare craftsmanship. The grounds are a private retreat of orchards, a vineyard, a raised vegetable garden, and open fields. An infinity-edge pool and spa are complemented by a one-bedroom guest cottage that also serves as garage and pool house. The residence is offered furnished, with select exclusions. Available together with the adjoining 12 horse stable equestrian property with a beautiful Mediterranean 5 bedroom home, the three parcels form a complete estate of exceptional scale and privacy. Showings by private appointment.

38-48-58 Quaker Ln, Greenwich

Listing courtesy of Christian Perry from Serhant Connecticut, LLC. (818) 321-0539 (203) 489-7800

Rogers Is, Branford
$29,995,000
10 Beds ⋅ 8 Baths ⋅ 24172874 MLS
A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, and support space, making access to the island with a 5-minute boat ride, seamless and effortless. Just offshore, the island unfolds into a peaceful, panoramic retreat surrounded by water views in every direction. Designed for both relaxation and entertaining, the estate features a 10-bedroom main residence with 6 full and 2 half baths, a 4-bedroom/2.5 bathroom guest house, artist's studio with half bath, and dedicated staff quarters. A mahogany wraparound porch invites you to take in the scenery, while meandering granite pathways guide you thru the grounds which offer an exceptional collection of amenities: an in-ground heated pool with pool house and separate bath house, tennis court, Nicklaus-designed putting green, koi pond, greenhouse and two docks. A charming gazebo sits at the edge of the property-perfectly positioned to capture sweeping views for miles. Quiet, expansive and thoughtfully designed, Rogers Island is a legacy property where generations can gather with ease, hosting everything from intimate weekends to large-scale entertaining, all set against a backdrop of uninterrupted water views, timeless coastal beauty and a sense of privacy that's increasingly impossible to find.

Rogers Is, Branford

Listing courtesy of Alicia Hale from Coldwell Banker Realty. (203) 913-8719 (203) 878-7424

4 Willow Road, Weston
$29,000,000
6 Beds ⋅ 8 Baths ⋅ 73401202 MLS
Step into a world of timeless elegance in this iconic English Revival Tudor. Prominently set high on a ridge abutting a tranquil pond and the lands surrounding the Weston Golf Club. The gated entry and winding approach reveal the commanding terraced property comprising over 6 secluded acres. The 1928 estate was originally designed by architect Eric Kibbon. A balance between modern comfort, beauty and continuity with the past was re-defined by visionary architect, Peter Pennoyer. The extensive restoration goes from the exterior red-clay masonry walls to meticulously re-building the interior living spaces. The curated finishes were precisely replicated from the new steel and Mahogany wood windows to the Ohio sandstone columns and millwork. The receiving court includes a carriage house, private entry to the guest residence and garage parking for 6 cars. Truly one of New England's unique suburban estates with easy access to Boston and Logan International Airport.

4 Willow Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

104 Dans Hwy, New Canaan
$25,500,000
9 Beds ⋅ 14 Baths ⋅ 24103956 MLS
Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a 2014 transformation. The volume of the rooms, soaring ceilings, proportion of the windows and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Adjacent to the dining room gallery is a walled garden with a custom pavilion for entertaining. The 52 acres were transformed in collaboration with noted landscape architect Perry Guillot into a private park with a dramatic meandering approach, a great lawn, and woodland trails amongst streams and waterfalls. A 60 x 22 pool and tennis court were also added. At the discrete entrance to the property are twin cottages; a caretaker residence and a gym. Privacy and proximity to NYC and airports along with this caliber of property make this a world class offering and a rarity by any standards.

104 Dans Hwy, New Canaan

Listing courtesy of Leslie Razook from William Pitt Sotheby's Int'l. (203) 918-4452 (203) 966-2633

16 Nathan Hale Dr, Norwalk
$24,000,000
5 Beds ⋅ 6 Baths ⋅ 24041087 MLS
This commanding estate has extraordinary 240% views of the Long Island Sound Archipelago. The custom renovation by the esteemed firm S.R. Gambrel, Inc. was created with an intention for comfortable, gracious living, with a woven theme of health and wellness providing seamless indoor/outdoor living and entertaining spaces. The combination of stunning finishes, high ceilings, breathtaking views, and natural light makes this offering one of a kind and irreplaceable.The two-story entry hall reflects interior spaces that are both grand and intimate. The great room, expansive dining room, and chef's kitchen with its massive marble island are designed for entertaining. The breakfast room, den, and two private offices provide intimate spaces. The primary suite, with breathtaking views, has two dressing rooms and a marble bathroom.Three additional bedrooms are on the east wing. A hidden gym,wine room, and laundry room are all located on the entry floor. with a tandem 4-car garage.The property has 265 feet of private shoreline with a deepwater pier, gangway, and 30'x15' floating dock,low-tide sandy beach and a separate mooring. Designed as a private waterfront oasis, the sound view pool and pool pavilion are tucked under an ancient ledge.The outdoor living room with fireplace, jaccuzzi, infrared sauna and cold plunge are connected by a wide terrace across the entire house. A private association beach club with two tennis courts and tennis pro is just moments away.

16 Nathan Hale Dr, Norwalk

Listing courtesy of Leslie Razook from William Pitt Sotheby's Int'l. (203) 918-4452 (203) 966-2633

381 Warren Street, Brookline
$23,000,000
6 Beds ⋅ 12 Baths ⋅ 73576839 MLS
An extraordinary opportunity to own one of Brookline's most prestigious estates, set on nearly 1.75 acres in the most coveted location. This majestic brick Georgian Colonial has been masterfully renovated with museum-quality craftsmanship and timeless architectural detail. Offering over 16,000 sq. ft. of elegant living space, the home features a grand two-story foyer, 6 bedrooms, 9 full and 3 half baths, a gourmet kitchen, oversized fireplaced living room, formal dining room, Parisian-inspired bar, tea room, mahogany library, and a dramatic two-story family room with a spiral staircase leading to a private office. The exceptional primary suite offers dual spa-like baths, two walk-in closets, and a private office.The lower level features a media room,50's billard and bar area, wine cellar ,en suite bedroom with sitting area ,fitness room and indoor pool. Resort-style grounds include professionally landscaped park-like gardens, a 4-car garage, 2 swimming pools, a full pool cabana with kitchen, living room and full bathroom and a lighted tennis court. A truly iconic estate offering unparalleled luxury and timeless elegance.

381 Warren Street, Brookline

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.

34 Paine Avenue, Beverly
$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.

1044 Grosse Point Rd, Ferrisburgh
$22,900,000
11 Beds ⋅ 9 Baths ⋅ 5011908 MLS
‘Grosse Pointe’ in Ferrisburgh, Vermont is an extraordinary New England estate on the shores of Lake Champlain. It offers 1.5 miles of pristine shoreline, where panoramic views stretch across the lake to the majestic Adirondack Mountains. Spanning nearly 345 acres of verdant fields and tranquil forests, this estate offers a rare blend of natural beauty and serene isolation. At its heart stands a magnificent 10,000-square-foot French Colonial Revival mansion, a timeless marvel completed in 1906. Constructed with fossil-laden local Panton Stone, its grand façade and richly detailed interior echo the elegance of a bygone era. Perched on the property's highest point, the residence offers breathtaking vistas of the lake and mountains in three directions. Golf has been revitalized at the estate, honoring its history. Two exclusive courses exude beauty that will astound any golfer. The courses navigate pastures and woodlands, along and over the lake, engulfing players in picturesque water and mountain views, and creating an experience to be remembered. The estate also features five additional residences and 'Bradford Farm,' a beautifully renovated farmhouse with two expansive barns. Three concrete piers along the lakeshore offer deep-water access for boating and world-class fishing. This unparalleled summer retreat is a rare legacy opportunity, promising a sanctuary of tranquility, a haven for wildlife, a playground for recreation, and a timeless testament to a life well-lived.

1044 Grosse Point Rd, Ferrisburgh

Listing courtesy of Jessica Bridge from Element Real Estate. (Cell: 802-233-9817)

102 Sesuit Neck Rd, Dennis
$22,500,000
4 Beds ⋅ 4 Baths ⋅ 73582414 MLS
An exceptional East Dennis estate spanning nearly 22 private acres, this extraordinary waterfront property offers a rare combination of scale, seclusion, and breathtaking coastal beauty. Beyond a gated entrance, a long, bucolic drive unfolds to a magnificent setting, bordered by protected conservation land and overlooking sweeping vistas of Cape Cod Bay. With 200 feet of private beach, the property enjoys a level of privacy and direct waterfront access rarely found on Cape Cod. The four-bedroom main residence captures the beauty of its surroundings with stunning water views, while a detached barn adds versatility and character to the estate. Perhaps most remarkable is the potential for an additional substantial residence, offering the rare ability to create a true multigenerational compound. With nearly 22 acres of private waterfront land virtually impossible to replicate in East Dennis, this is a finite opportunity to own one of Cape Cod's most impressive coastal estates.

102 Sesuit Neck Rd, Dennis

Listing courtesy of Listing Agent: Paul McCormick from Listing Office: Gibson Sotheby's International Realty.

102 Sesuit Neck Road, East Dennis
$22,500,000
4 Beds ⋅ 4 Baths ⋅ 22604415 MLS
An exceptional East Dennis estate spanning nearly 22 private acres, this extraordinary waterfront property offers a rare combination of scale, seclusion, and breathtaking coastal beauty. Beyond a gated entrance, a long, bucolic drive unfolds to a magnificent setting, bordered by protected conservation land and overlooking sweeping vistas of Cape Cod Bay. With 200 feet of private beach, the property enjoys a level of privacy and direct waterfront access rarely found on Cape Cod. The four-bedroom main residence captures the beauty of its surroundings with stunning water views, while a detached barn adds versatility and character to the estate. Perhaps most remarkable is the potential for an additional substantial residence, offering the rare ability to create a true multigenerational compound. With nearly 22 acres of private waterfront land virtually impossible to replicate in East Dennis, this is a finite opportunity to own one of Cape Cod's most impressive coastal estates.

102 Sesuit Neck Road, East Dennis

Listing courtesy of Listing Agent: Paul McCormick (paul.mccormick@gibsonsir.com) from Listing Office: Gibson Sotheby's International Realty.

24 Straws Pt, Rye
$21,500,000
4 Beds ⋅ 7 Baths ⋅ 5101732 MLS
Perched dramatically along the pristine Rye coastline, the oceanfront estate at 24 Straws Pointstands as a masterpiece of luxury on New Hampshire’s highly coveted and tightly held 18 miles of direct waterfront. Enjoying a rare geographic orientation, this legacy property commands breathtaking, sweeping panoramic views looking south all the way to the Massachusetts North Shore coastline. Adding to its unmatched exclusivity, the residence is one of only nine historic homes that directly abuts a magnificent, protected oceanfront common right to its front, ensuring an estate-like setting and a lifetime of unobstructed coastal beauty. Spanning over 7,000 SF of architectural craftsmanship, this residence presents an elegant 3-story silhouette from the front while cascading into 4 complete levels of oceanfront living from the back. The main entry level features a grand entry, sophisticated sitting room, private office, and a gourmet kitchen flowing into dining and family spaces facing the water. The home boasts 16 rooms, including 4 second-level en-suite bedrooms (septic officially approved for 4 bedrooms) and 6.5 baths. The incredibly versatile floor plan offers expansive flexible-use spaces for multi-generational living. The second floor includes a sitting room landing with a hall bath and a dedicated guest overflow room. The third floor reveals a private 3-room suite complete with an en-suite bath and laundry. The walk-out lower level adds an exercise room, full bath, and a spacious bunk room for guest overflow—exiting at grade to the oceanfront grounds. Inside, majestic living halls feature soaring ceilings. Outside, the private sanctuary is anchored by a heated, built-in swimming pool positioned to catch the sea breeze. 24 Straws Point offers privacy, timeless elegance, and a generational Seacoast living experience.

24 Straws Pt, Rye

Listing courtesy of Florence Ruffner from Ruffner Real Estate, LLC. (florenceruffner@gmail.com)

20 Crowninshield Road, Marblehead
$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.

2575 Weeks Hill Rd, Stowe
$20,000,000
6 Beds ⋅ 10 Baths ⋅ 5051127 MLS
Holistically designed and meticulously crafted, reminiscent of a European country estate, Pristine Meadow is one of New England’s most spectacular properties, perfectly sited on 110 park-like acres in the heart of Stowe. Comprised of gently rolling hills, meadows, woodland, swimming pond, hiking and skiing trails, and breathtaking vistas, this quintessential estate provides the utmost privacy. The 14,000 sqft residence features six bedrooms and ten baths, highlighted by Italian-inspired interiors, imported materials, and magnificent architectural millwork. The symbiosis of design and functionality is exemplified by the great room, both grand and comfortable. A state-of-the-art Boffi kitchen with the best appliances, custom cabinetry, walk-in pantry, and charming breakfast room with fireplace and solarium. A wood-paneled study sits just off the main dining room. The second-level primary suite affords dramatic views, spa-like baths, and two dressing rooms. A secondary suite equal in its design and three ensuite bedrooms and a guest apartment complete the sleeping quarters. The finest example of Italian craftsmanship is the indoor pool constructed with hand-laid tile and beautiful travertine, evoking the experience of an Italian palazzo. A fitness room, wine cellar, and laundry room round out the lower level. Not to be understated are a four-bay garage, car/implement barn, and lovely unfinished cottage that could be utilized in so many ways. Pristine Meadow must be experienced!

2575 Weeks Hill Rd, Stowe

Listing courtesy of Meg Kauffman from LandVest, Inc.. ()

58 Shore Rd, Greenwich
$19,995,000
5 Beds ⋅ 7 Baths ⋅ 24164225 MLS
You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a facade clad in premium Thermory wood siding beneath a Spanish slate roof an exterior that feels both grounded and enduring.. Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence; featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances and a fully equipped secondary prep kitchen designed for effortless entertaining at scale. Upstairs, European white oak introduce warmth, while radiant heat continues throughout all main spaces and baths reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural

58 Shore Rd, Greenwich

Listing courtesy of Danielle Malloy from Serhant Connecticut, LLC. (203) 921-9987 (203) 489-7800

129 Commonwealth Avenue, Boston
$19,995,000
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.

16 Doubling Rd, Greenwich
$19,950,000
9 Beds ⋅ 13 Baths ⋅ 24207664 MLS
MOVE RIGHT IN- Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly sophisticated modern lifestyle.The residence is distinguished by its extensive integration of advanced technology systems, seamlessly embedded throughout the home. Smart-home infrastructure (lighting, climate, security,and entertainment).State-of-the-art environmental and wellness technologies (air, water, energy efficiency,and comfort). Attached 2 car garage + 5 car carriage house w lifts. 45'x20' pool Features: Full house generator. Venetian plaster walls, bleached white oak and porcelain floors throughout, radiant heated floors (including garage), self cleaning glass beaded stucco exterior with composite slate roof, imported windows/doors and stone, and expansive property for sports and entertaining. Pet grooming room with separate laundry. Chef's kitchen and additional family kitchen. Separate staff quarters. Plans available for an additional indoor pool and underground parking garage for 8 more vehicles with a car elevator.

16 Doubling Rd, Greenwich

Listing courtesy of Jill Kelly from Sotheby's International Realty. (203) 536-6280 (203) 869-4343

56 North Summer Street, Edgartown
$19,750,000
10 Beds ⋅ 14 Baths ⋅ 73517157 MLS
A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

56 North Summer Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

47 Sunset Point, Barnstable
$18,500,000
7 Beds ⋅ 11 Baths ⋅ 73563501 MLS
Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and beach. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck invites al fresco dining and entertaining. Elevated quality and craftsmanship are found throughout, from rich hardwood floors to custom built-ins and crown moldings.The expansive primary suite encompasses an entire wing of the home with a private balcony overlooking the water, a sumptuous bathroom with a built-in soaking tub, and two walk-in closets. Four well-appointed en suite bedrooms complete the second level, offering refined accommodations for family and friends. Designed to embrace outdoor living, the resort-inspired pool and terrace are the perfect gathering place for summer days, complete with an outdoor kitchen and cabana. A rolling lawn leads to the water, where the private dock offers endless possibilities for days spent on the ocean. Additional highlights include a sports court and a car barn that's sure to please the discerning automotive enthusiast. A rare combination of luxury, privacy, and natural beauty, this one-of-a-kind estate is ready to be enjoyed.

47 Sunset Point, Barnstable

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

47 Sunset Point, Osterville
$18,500,000
7 Beds ⋅ 11 Baths ⋅ 22603952 MLS
Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and beach. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck invites al fresco dining and entertaining. Elevated quality and craftsmanship are found throughout, from rich hardwood floors to custom built-ins and crown moldings. The expansive primary suite encompasses an entire wing of the home with a private balcony overlooking the water, a sumptuous bathroom with a built-in soaking tub, and two walk-in closets. Four well-appointed en suite bedrooms complete the second level, offering refined accommodations for family and friends. Designed to embrace outdoor living, the resort-inspired pool and terrace are the perfect gathering place for summer days, complete with an outdoor kitchen and cabana. A rolling lawn leads to the water, where the private dock offers endless possibilities for days spent on the ocean. Additional highlights include a sports court and a car barn that's sure to please the discerning automotive enthusiast. A rare combination of luxury, privacy, and natural beauty, this one-of-a-kind estate is ready to be enjoyed.

47 Sunset Point, Osterville

Listing courtesy of Listing Agent: Paul E Grover (paul@paulgrover.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

15 Vinson Circle, Winchester
$18,000,000
6 Beds ⋅ 7 Baths ⋅ 73585235 MLS
A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

63 West St, Beverly
$17,999,000
5 Beds ⋅ 10 Baths ⋅ 73500949 MLS
Designed for both everyday living and exceptional entertaining, this rare new construction oceanfront estate offers a privately owned sandy beach & access to a deep-sea mooring. A dramatic double-height entry opens to light-filled living spaces with sweeping Atlantic views. The chef’s kitchen features dual Taj Mahal quartzite islands, professional-grade appliances, & butler’s pantry. Flow into a sunlit breakfast nook & family room w/ a cozy fireplace. Additional highlights include an oceanfront living room, full bar w/ wine storage, & a first-floor primary suite. A three stop elevator connects all levels. Upstairs, a stunning primary retreat offers a spa bath, dual closets, fireplace, balcony, beverage bar, & an office. Three additional en-suites, a 2nd floor sitting room & rooftop terrace complete this level. Lower level offers theater, golf simulator, gym, sauna, & wine room options. Pool, outdoor kitchen, fire pit, & 2 - (2) car garages complete this exceptional coastal offering.

63 West St, Beverly

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

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