Feature Properties

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.

$16,500,000

7 Beds ⋅ 8 Baths ⋅ 22505725 MLS

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all. This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

155 Irving Avenue, Hyannis Port

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

$16,500,000

7 Beds ⋅ 8 Baths ⋅ 73457530 MLS

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all.This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

155 Irving Avenue, Barnstable

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

$16,250,000

6 Beds ⋅ 8 Baths ⋅ 22603861 MLS

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

25 Brickyard Road, Chilmark

Listing courtesy of Listing Agent: Peyton Wallace (peyton@studiorealty.com) from Listing Office: Studio Realty LLC.

$16,000,000

6 Beds ⋅ 8 Baths ⋅ 73480812 MLS

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Debby Belt from Listing Office: Hammond Residential Real Estate.

$15,900,000

7 Beds ⋅ 10 Baths ⋅ 24107072 MLS

Introducing one of New York's most prestigious estates: a rare opportunity to own a historic piece of history elegantly nestled atop 11+ park-like acres in Purchase. This illustrious and stately turn-of-the-century residence, was the setting for the blockbuster film "Goodbye Columbus." A quiet country manor that's exceptionally private and secure, the estate is a stunning work of art, beautifully situated behind a gated entry at the end of a long, meandering driveway. The property boasts acres of lush rolling lawns adorned with over 35 years of seasonal perennials in year-round bloom, a glorious fenced saltwater pool and patio, multiple-hole practice golf green, zen-like meditation garden, and a one-acre freshwater pond with koi and carp. Encircling the property is a half mile jogging path with a grove of weeping willows, a spectacular oasis of hydrangeas, indigenous stone walls, a shady gazebo, and a charming life-size dollhouse. Inside, the home is breathtaking, with 11,792 sq ft of custom-crafted beauty featuring 7 bedrooms, 6.4 bathrooms, and 3 offices spread over three sunlit floors.

1619 Purchase St, Harrison

Listing courtesy of Leslie McElwreath from Sotheby's International Realty. (917) 539-3654 (203) 869-4343

$15,700,000

7 Beds ⋅ 10 Baths ⋅ 73342079 MLS

Modern luxury meets history in this completely renovated home on coveted Brattle St in Harvard Square. Completely transformed by a local respected builder, this property seamlessly blends historic charm w/ modern convenience in its impeccable design and finishes. The main floor offers a grand staircase, high ceilings, spacious living and dining rooms, chef's kitchen w/ top appliances and adjacent family room, an oversized mudroom off the attached garage and 2 half baths. The 2nd level has a luxurious primary suite w/ spa-like bath and gracious dressing room, 5 ensuite bedrooms (or offices) and a large laundry room. The top floor hosts a versatile office/loft space and a half bath. The lower level is fully equipped w/ a gym, game room, family room, full bath, ample storage and guest suite w/ direct exterior access. The outdoor and indoor spaces blend seamlessly for easy living, w/ a spacious patio and beautiful yard designed by a celebrated landscape architect. A true Harvard Square gem

172 Brattle Street, Cambridge

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

$15,400,000

6 Beds ⋅ 9 Baths ⋅ 22602961 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: Brian W Dougherty (brian.dougherty@corcoranadvisors.com) from Listing Office: Corcoran Property Advisors.

$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.

$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.

$15,000,000

7 Beds ⋅ 7 Baths ⋅ 73531926 MLS

Introducing Windover, a grand Georgian estate, meticulously restored and reimagined for modern living. Approached through 5 acres of conservation land, and set atop a private, tree-lined drive, the property commands an immediate sense of arrival. Refined outdoor features include expansive terraces, a secluded walled garden, and a dogwood orchard. A pool house and heated saltwater pool overlook a tranquil pond, creating a resort-like setting. The interior is expansive yet remarkably intimate. A dramatic Mediterranean-style ballroom anchors the entertaining spaces, while the living and dining rooms open to terraces, framing the surrounding landscape at every turn. The luxurious primary suite offers a private retreat; a versatile third-floor suite accommodates guests or live-in staff with ease. A dedicated media room and home gym — with steam shower and sauna — round out the experience. Windover is a property of architectural distinction, enduring beauty, and total seclusion.

15 Farm Street, Dover

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

$15,000,000

7 Beds ⋅ 10 Baths ⋅ 24104335 MLS

The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

4800 Congress St, Fairfield

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

$14,995,000

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

33 Sears Rd, Brookline

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

$14,900,000

5 Beds ⋅ 9 Baths ⋅ 24179641 MLS

Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. First floor rooms facing the water include the living room and office, both with fireplaces, the formal dining room and the open kitchen/family room. This floor also has a billiard/media room, full bar, refrigerated wine room, two powder rooms and laundry. Idyllic second floor primary suite features waterfront balcony and sitting room, 3 walk-in closets and marble bathroom. Three additional en-suite bedrooms, each with balconies, complete this level. Perched on the third floor is a home gym with waterfront balcony, full bath and sauna. Newly added wing above attached two-car garage with one-bedroom guest suite. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawns, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Side yard with secluded outdoor shower, exterior-access powder room and kayak storage rack. Spacious two-bedroom guest cottage with 1.5 baths, kitchen, laundry and attached one-car garage. Commercial-sized generator powers main house & cottage.

279 Saugatuck Ave, Westport

Listing courtesy of Joseph Barbieri from Sotheby's International Realty. (203) 618-3112 (203) 869-4343

$14,900,000

7 Beds ⋅ 10 Baths ⋅ 5066210 MLS

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner’s quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

355 Greene Rd, Woodstock

Listing courtesy of Christopher W. Lang from Bravynia. ()

$14,900,000

5 Beds ⋅ 8 Baths ⋅ 73363224 MLS

Commanding ocean views from nearly every room, this extraordinary six acre estate sits on the historic site of a 1900s Manor House. Blending classic New England architecture with modern luxury, the stone-and-shingle residence features incredible design, custom mahogany, paneled walls and exquisite millwork throughout. The Primary Suite boasts panoramic ocean views, a domed gable ceiling, fireplace, walk-in closet with wet bar, and spa-like bath. All bedrooms are en suite with ocean views and closets with custom shelving. Formal gardens transition elegantly to sweeping seascapes directly above the beach. Enjoy the beach and the privacy Prides Crossing has to offer. A large,custom-built Poolhouse with kitchen and bath offers perfect indoor outdoor space. Designed for both grand entertaining and everyday comfort, this exceptional property captures the timeless beauty and elegance of Boston’s North Shore estates. A rare opportunity to own a legacy estate in an unmatched coastal setting.

53 Paine Avenue, Beverly

Listing courtesy of Listing Agent: Krista Julian from Listing Office: Coldwell Banker Realty - Manchester.

$14,889,000

6 Beds ⋅ 9 Baths ⋅ 5105837 MLS

Set along prestigious, bucolic Runnymede Drive, this exceptional seventeen-room legacy estate is privately sited on 4.6 park-like acres along a quiet side street within the only riverfront neighborhood east of I95 offering direct frontage on the Little River, distant ocean views, and the soothing sound of crashing surf. From the moment you arrive via the cobblestone driveway, it is clear this is a truly extraordinary property. Impeccably maintained grounds are thoughtfully designed to provide complete privacy while beautifully landscaped gardens deliver color and seasonal interest throughout the year. The riverside pool and pool house create an exceptional retreat for family and guests. Designed for effortless entertaining, the custom pool house features a gourmet kitchen rivaling that of the main residence and formal dining for ten overlooking the pool and river. The main home showcases timeless architecture, exquisite period craftsmanship, and custom millwork rarely found in today's luxury homes. Grand entertaining spaces include a distinguished library, elegant formal dining room, richly paneled lounge with intricate moldings, home theater, raised bar with walk-in wine cellar, and seamless access to outdoor living areas. Six beautifully appointed bedroom suites each feature luxurious en-suite tiled baths, including an expansive three-room primary suite with an extraordinary custom island dressing room and luxury marble bath with tub. Outstanding mechanical systems include multi-zone central air, automatic standby generator, sophisticated security system, and seven fireplaces, six of which have never been used. The remarkable craftsmanship and attention to detail throughout must be experienced firsthand. Seldom does an estate of this caliber, offering such exceptional privacy and meticulous care, become available just minutes from Abenaqui CC, the seaside boardwalks, shopping, Port City Air FBO terminal and under an hours drive from Logan International Jetport.

15 Runnymede Dr, North Hampton

Listing courtesy of Patrick Carey from Carey Giampa, LLC/Seabrook Beach. (Cell: 603-583-1000)

$14,850,000

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

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

$14,850,000

7 Beds ⋅ 12 Baths ⋅ 73493889 MLS

Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic walls of glass. The property is a haven for entertaining, featuring a resort-style pool, pool house, orchard, indoor basketball court, private theater, and a space-themed arcade. Custom elements and unique spaces add sophistication, while a wine cellar, billiards/ping pong area, and expansive granite patios elevate the experience. Every inch of this masterpiece is crafted with exquisite attention to detail, offering a seamless fusion of elegance and comfortable living! A true destination home where art, design, and luxury converge to create an amazing property!

67 Byron Road, Weston

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

$14,500,000

11 Beds ⋅ 13 Baths ⋅ 73552898 MLS

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence—an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleball—offering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today.

10 & 12 Boldwater Road, Edgartown

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.

$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.

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