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$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.
$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.
$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
$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
$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.
$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
$25,000,000
2 Beds ⋅ 7 Baths ⋅ 5066208 MLS
Set on 400+/- acres in Barnard, Vermont, Monsalvat Farm is a legacy estate where rolling pastures, stone walls, forests, and mountain views reflect the state’s timeless character. Settled in 1793, the land carries generations of stewardship, elevated by one of the finest residences in the country—an architectural masterpiece complemented by historic and companion structures that are carefully integrated into the landscape with grace and permanence. Buildings include: the primary residence called "the Sanctuary" with 12-sided cathedral great room, primary bedroom suite with 2 bathrooms, one with fireplace, 7 additional fireplaces including one in the guest suite, wine cellar, music media room known as "the Cabin" and a dining room with stunning overhead sculpture positioned as an upside down tree with nested lights; a 2 bedroom 2 1/2 bathroom charming stone guest house, known as "Gilbert's Cottage;" a restored farmhouse with 4 separate apartments each with 1 bedroom and a full bathroom; a 1 bedroom 1 bathroom cabin called "the Lodge"; a restored historic barn with attached 5 stall stable, heated tack room and farm managers office with bathroom and shower; a Gazebo with fireplace, half bathroom and shower, a detached 3-bay garage, an equipment barn, a cattle barn and a sugar house. With a private gated entrance and bridge, built to highway specifications, over a large pond, a private FAA approved heliport, orchard, fields and miles of trails, Monsalvat Farm is truly magical.

650 Francis Rd, Barnard

Listing courtesy of Christopher W. Lang from Bravynia. (Cell: 802-274-4048)
$25,000,000
6 Beds ⋅ 11 Baths ⋅ 24084663 MLS
Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding drive, revealing a breathtaking landscape of curated gardens, rolling lawns, and panoramic water views. Designed for both grand entertaining and intimate gatherings, the estate features a newly built multi-car garage with a second-floor art studio and play space, a new pool, birch garden, and an expansive patio, all seamlessly integrated with the natural beauty of the surroundings. A private dock with stairs to the secluded beach provides direct waterfront access, while a newly added wine cellar and lower-level suite with a full bathroom enhance the home's luxurious amenities. Recent upgrades, including advanced irrigation, outdoor lighting, new A/V system, ensure modern convenience without compromising the estate's historic charm.Featured in Architectural Digest as "a new house with an old soul," the interiors are a masterclass in refined elegance. Every space is thoughtfully curated with serene color palettes, exquisite craftsmanship, and breathtaking water views from nearly every room. Sasco Point is truly one of America's most distinguished waterfront estates. Luxury Perfected!

1131 Sasco Hill Rd, Fairfield

Listing courtesy of Andrew Whiteley from Brown Harris Stevens. (203) 258-1595 (203) 254-1500
$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.
$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)
$22,825,000
8 Beds ⋅ 10 Baths ⋅ 24159193 MLS
Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island Sound through dramatic walls of glass designed to flood the interiors with natural light. The home will feature 8 bedrooms, 8 full baths, and 2 half baths, with expansive living and entertaining spaces that seamlessly connect indoors and out. The architecture embraces a clean contemporary design that maximizes the stunning waterfront setting while creating an atmosphere of warmth, elegance, and effortless coastal living. Resort-inspired amenities include two pools, a cold plunge, spa, infrared sauna, and a fully equipped fitness center, offering a private retreat for wellness and relaxation. For the automotive enthusiast or collector, the property also includes garage space for up to 10 cars, a rare feature for a waterfront estate. Ideally located walking distance to the Greens Farms train station and Greens Farms Academy, and just minutes to the town centers of Westport, Fairfield, and Southport. Just 55 miles to Manhattan. Completion anticipated mid-2027, with the opportunity to collaborate with the builder to customize finishes and create a home that reflects your personal lifestyle

11 Beachside Cmn, Westport

Listing courtesy of Andrew Whiteley from Brown Harris Stevens. (203) 258-1595 (203) 254-1500
$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.
$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.
$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)
$21,500,000
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.
$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.
$20,000,000
11 Beds ⋅ 6 Baths ⋅ 5104776 MLS
Commanding an extraordinary stretch of Winnipesaukee shoreline, on approximately 30 acres, North Ledges at Welch Island is one of the lake’s most compelling island estates. Encompassing three distinct waterfront parcels with roughly 3,000 feet of shoreline, this remarkable compound combines exceptional privacy and panoramic views, on a scale rarely found on Winnipesaukee. The estate unfolds across a beautifully wooded landscape, with walking trails connecting its residences, recreational amenities and extensive waterfront. A magnificent stone boathouse, substantial breakwater docking, expansive Ipe deck with integrated seating and McIntosh audio system, multiple sandy-bottom swimming areas and exceptional water access create a waterfront environment designed for generations of boating, swimming and gathering. A tennis/pickleball court, private gym, formal garden, and numerous outbuildings further distinguish the property. At the heart of North Ledges is a timeless six-bedroom lake house offering more than 4,000 square feet of classic Winnipesaukee character. Rich wood interiors, a grand wood-burning fireplace and gracious gathering spaces are complemented by an expansive chef’s kitchen designed for entertaining and a spacious sunroom overlooking the lake. Several bedrooms open to private sleeping porches, creating quiet retreats surrounded by water and nature. Two additional waterfront cottages provide exceptional flexibility for family and guests. A charming three-bedroom cottage features a spacious lakeside deck with hot tub, substantial breakwater docking and an established rental history. A staff cottage on the third parcel preserves the simplicity and character of traditional island living. North Ledges is more than a remarkable collection of waterfront properties. It is a private island estate of uncommon scale and beauty, offering the rare ability to gather generations together while preserving the space, privacy and authentic connection to Winnipesaukee.

15 Welch, Gilford

Listing courtesy of Becky Fuller from Four Seasons Sotheby's Int'l Realty. ()
$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.. ()
$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
$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: .
$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.
$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.
$17,500,000
3 Beds ⋅ 2 Baths ⋅ 73559053 MLS
This remarkable 5+ acre waterfront estate is one of the most extraordinary coastal offerings to come to market in generations. Perched on the southwest tip of an exclusive community, it is Cape Cod's southernmost private residential land. The property commands panoramic, unobstructed views across Buzzards Bay to Naushon and the Elizabeth Islands, and then onto Vineyard Sound and Martha's Vineyard. The estate features more than 611 feet of shoreline, anchored by a substantial protective seawall that ensures both privacy and structural permanence, as well as a private, pristine sandy beach. A charming three-bedroom cottage currently rests on the grounds, offering immediate enjoyment while serving as an unparalleled canvas for a world-class waterfront masterpiece. Future development allows for a two-story residence designed to capture expanded views toward Great Harbor, subject to local approvals.

187 Penzance Rd Unit Lot 1C, Falmouth

Listing courtesy of Listing Agent: Kerrie Marzot from Listing Office: Sotheby's International Realty.
$17,500,000
3 Beds ⋅ 2 Baths ⋅ 22603752 MLS
This remarkable 5+ acre waterfront estate is one of the most extraordinary coastal offerings to come to market in generations. Perched on the southwest tip of an exclusive community, it is Cape Cod's southernmost private residential land. The property commands panoramic, unobstructed views across Buzzards Bay to Naushon and the Elizabeth Islands, and then onto Vineyard Sound and Martha's Vineyard. The estate features more than 611 feet of shoreline, anchored by a substantial protective seawall that ensures both privacy and structural permanence, as well as a private, pristine sandy beach. A charming three-bedroom cottage currently rests on the grounds, offering immediate enjoyment while serving as an unparalleled canvas for a world-class waterfront masterpiece. Future development allows for a two-story residence designed to capture expanded views toward Great Harbor, subject to local approvals. This is more than a property - it is a private sanctuary where sea breezes, sunrises and dramatic sunsets define daily life. Representing an unrepeatable investment in New England's most authentic and unspoiled coastal landscape, it offers a level of prestige and natural beauty that is impossible to replicate. Breathtaking. Timeless. Truly Irreplaceable.

187 Penzance Road, Woods Hole

Listing courtesy of Listing Agent: Kerrie A Marzot (kerrie.marzot@sothebys.realty) from Listing Office: Sotheby's International Realty.
$17,500,000
5 Beds ⋅ 6 Baths ⋅ 73386848 MLS
Welcome to a truly exceptional 7.4-acre oceanfront estate in Manchester-by-the-Sea, offering direct access to the soft sands of Graves Beach—your private shoreline retreat. This rare two lot property blends classic New England charm with resort-style living, featuring panoramic water views and extraordinary privacy along one of the North Shore’s most desirable coastlines. The home offers two primary suites—one on each floor—ideal for flexibility and comfort. The grounds showcase mature, curated landscaping cultivated over decades. Additional features include a stone bungalow overlooking the beach, a caretaker’s house on separate lot, detached garage, and an ocean-facing pool and jacuzzi. Enjoy unforgettable sunrises and elegant coastal entertaining—all just 45 minutes from downtown Boston.

239 Summer, Manchester

Listing courtesy of Listing Agent: Lanse Robb from Listing Office: LandVest, Inc., Manchester -by-the-Sea.
$16,995,000
5 Beds ⋅ 8 Baths ⋅ 24166336 MLS
This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property. Parcel IDs 61 10 (207) & 61 10-2 (209)

207-209 Long Neck Point Rd, Darien

Listing courtesy of Shelly Tretter Lynch from Compass Connecticut, LLC. (203) 550-8508 (203) 343-0141
$16,980,000
7 Beds ⋅ 11 Baths ⋅ 73445544 MLS
Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$16,900,000
6 Beds ⋅ 10 Baths ⋅ 73550581 MLS
A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the luxurious main level master suite, 7 full bathrooms, 3 half bathrooms, and an expansive 4-car garage. Designed by Thoughtforms, this home boasts an expansive open floor plan and luxurious craftmanship and attention to detail throughout. The fully finished lower level is equipped with a recreation room, wine cellar, full theater room, wet bar, steam room, and sauna. On the second floor, four bedrooms offer private en suite bathrooms. This exceptional home is a unique grand colonial estate for the discerning buyer set in one of the most highly desired locations in all of Weston

50 Winsor Way, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
$16,900,000
8 Beds ⋅ 8 Baths ⋅ 73485121 MLS
Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana—an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location.

114 North Water Street, Edgartown

Listing courtesy of Listing Agent: Erin Hegarty from Listing Office: Donnelly + Co..
$16,750,000
7 Beds ⋅ 10 Baths ⋅ 73505053 MLS
This exceptional 6-acre estate offers supreme privacy and tranquility on a quiet cul-de-sac bordered by conservation land and completed fenced in with 3 gated driveways. The luxurious main residence includes 7 bedrooms, a gourmet kitchen with scenic views, solarium, library, private theater, billiards room, 2025 Built state-of-the-art Fitness Center with infrared room, juice bar, club house with a connecting wing to the Indoor Outdoor Heated Pool with full spa experience. Two greenhouses, multiple fruit tree orchards, tennis court w 4 Bed guest house, 2 add'l guest houses, commercial kitchen with live in chef's suite. A multi-car garage completes the offering. Just minutes from historic downtown Concord and top equestrian destinations, this secure, secluded retreat blends unmatched luxury with convenient New England access. Within minutes to Bedford Airport and New England's premier private boarding schools. Multi-Generational Living under one roof! 29 Cycling routes nearby.

210 Monument Farm Road, Concord

Listing courtesy of Listing Agent: Beth Dickerson from Listing Office: Gibson Sotheby's International Realty.

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