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327 Bedell Brook Rd, Elmore
$10,995,000
7 Beds ⋅ 8 Baths ⋅ 5108032 MLS
The Ledges represents the transformation of 209 undeveloped acres into a landmark Vermont mountain estate, where architecture, landscape, and arrival were conceived as a unified experience. Inspired by the architecture and character of Shelburne Farms, the property was created as an alpine interpretation of a traditional Vermont estate. A mile-long drive moves through dense forest, crosses Bedell Brook over a curved stone bridge, and gradually reveals the pond, main residence, and panoramic views across Mount Mansfield, Sterling Mountain, Mount Pisgah, and the Worcester Range, including clear views of Stowe Mountain Resort. The surrounding landscape includes meadows, perennial gardens, three seasonal brooks, extensive stonework, and miles of private trails adjoining Putnam State Forest conservation land. At the center of the property is a seven bedroom residence, an additional one-bedroom guest apartment, expansive living and entertaining spaces, and a clock tower overlooking the surrounding mountains. Additional buildings and amenities include a gatehouse, guest cottage, sauna cottage, inground pool, tennis court and pavilion, garage and tractor pavilion, pond with dock, and a covered lookout positioned to take in views of the mountain range and Stowe Mountain Resort trails. Together, the architecture, landscape, and progression through the property create a private mountain setting defined as much by the land as by the residence itself.

327 Bedell Brook Rd, Elmore

Listing courtesy of Wade Weathers from LandVest, Inc-Burlington. ()

123 Saddle Rock Rd, Stamford
$10,995,000
5 Beds ⋅ 6 Baths ⋅ 24181580 MLS
Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914 for inventor Thomas Robins, the main residence has been thoughtfully renovated and modernized throughout, including new electrical and plumbing systems, an expanded eat-in chef's kitchen, and beautifully reimagined open living and dining spaces designed for both grand entertaining and everyday living. Exceptional fixtures, finishes, and craftsmanship complement the home's historic pedigree, while every room is carefully oriented to capture sweeping panoramic water views. The main level is further enhanced by a stunning solarium with fireplace, offering a year-round retreat immersed in the surrounding waterfront landscape. The second floor is anchored by a newly improved primary suite featuring a private balcony with panoramic views across the gardens and Long Island Sound, a luxurious spa-inspired bath, and an expansive dressing room. Three additional bedrooms, a private office, and a versatile room complete this level, providing exceptional flexibility for family living, guests, and work-from-home needs. A charming gatehouse with guest quarters above welcomes guests to the

123 Saddle Rock Rd, Stamford

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

20 Wyman Dr, Wolfeboro
$10,950,000
7 Beds ⋅ 8 Baths ⋅ 5086004 MLS
Commanding a rare and remarkably private 6.2-acre site along the sun-drenched edge of Lake Winnipesaukee, this Wolfeboro Neck estate occupies one of the most coveted stretches in all of New Hampshire's lakes region. With an extraordinary 430 feet of frontage and uninterrupted south-to-southwest exposure, the property captures sweeping, cinematic views across the Broads, without a neighboring home in sight. It is a setting of uncommon seclusion within one of the region’s most prestigious enclaves. The residence itself, spanning nearly 15,000 square feet, was conceived on a grand architectural scale, offering 7 bedrooms and 8 baths across a layout designed for both entertaining and retreat. The home presents a compelling opportunity for a discerning owner to curate and elevate the interiors to their own high standards, transforming it into a truly bespoke lakeside compound. Outdoor living is equally ambitious, with more than 5,000 square feet of terraces, decks, and balconies that unfold toward the water, creating an effortless flow between interior and exterior spaces. A two-slip boathouse with protective breakwater anchors the waterfront experience, while the acreage affords exceptional flexibility for the addition of a guest residence, caretaker’s cottage, or recreational barn. Inside, a soaring great room wrapped in glass frames the lake as living art, flooding the home with natural light. The layout balances grand entertaining spaces with intimate retreats, including a private media room and a chef’s kitchen. Wellness amenities include a fully equipped gym, spa, and sauna, all oriented toward the tranquil lakefront. Defined by its irreplaceable combination of scale, privacy, and premier Wolfeboro Neck location, this offering represents a singular opportunity to craft a generational estate on one of New Hampshire’s most storied lakes. By appointment.

20 Wyman Dr, Wolfeboro

Listing courtesy of Jamieson Duston from Duston Leddy Real Estate. (Cell: 603-365-5848)

495 Hugh Cargill Rd, Concord
$10,890,000
6 Beds ⋅ 9 Baths ⋅ 73458705 MLS
SEE VIDEO VISUALLY DESCRIBING GROUNDS AND HOME DURING THE DAY AND AT NIGHT. Georgian Revival architectural masterpiece is sited on 23.5 acres less than 3 miles from the center of Concord and its many renowned public and private schools. Acres of level manicured gardens feature specimen plantings, lawns, waterfall and a koi pond, granite terraces, and walkways of stone and antique bricks. The sunken European-style garden features a central swimming pool designed to resemble a reflecting pond with fountain. Surrounding these formal gardens are acres of private woodlands with trails for walking, riding, snow shoeing, and cross-country skiing. These estate acres abut hundreds of acres of conservation land and provide tranquility rarely found so close to Boston. Constructed by master craftsmen using only the finest materials, the 10,375sf residence offers 6 bedrooms, fully integrates smart-house technology, and is in new construction condition. Do not approach house as driveway is alarmed.

495 Hugh Cargill Rd, Concord

Listing courtesy of Listing Agent: Jonathan Radford from Listing Office: Coldwell Banker Realty - Boston.

139 Chappaquiddick Road, Edgartown
$10,750,000
7 Beds ⋅ 4 Baths ⋅ 73563263 MLS
Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

139 Chappaquiddick Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

4 Sherwood Island Ln, Westport
$10,500,000
7 Beds ⋅ 7 Baths ⋅ 24160355 MLS
Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come.

4 Sherwood Island Ln, Westport

Listing courtesy of Andrew Whiteley from Brown Harris Stevens. (203) 258-1595 (203) 254-1500

114 Quaker Road, West Falmouth
$10,300,000
4 Beds ⋅ 5 Baths ⋅ 22605061 MLS
Spectacular new construction on Buzzards Bay in coveted West Falmouth. Privately set on 4.5 acres at the end of a long drive, this exceptional waterfront residence offers 350' of private, soft white sandy beach and breathtaking 180° west-facing views with unforgettable sunsets. Quality built by a respected local builder, the home is elevated and constructed to today's flood standards. Featuring 4 bedrooms, 4.5 baths, elevator and 2-car garage. A gorgeous chef's kitchen with generous island opens to a dramatic great room with soaring ceilings. Expansive windows capture stunning water views from nearly every room. The beach is protected by jetties and adjacent to Little Island Beach and preserve. An extraordinary private coastal setting close to West Falmouth Harbor, Shining Sea Bikeway and West Falmouth Tennis Club. A rare combination of new construction, acreage, privacy and exceptional beachfront.

114 Quaker Road, West Falmouth

Listing courtesy of Listing Agent: O'Neill Group (oneillgroup@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

114 Quaker Rd, Falmouth
$10,300,000
4 Beds ⋅ 5 Baths ⋅ 73586679 MLS
Spectacular new construction on Buzzards Bay in coveted West Falmouth. Privately set on 4.5 acres at the end of a long drive, this exceptional waterfront residence offers 350’ of private, soft white sandy beach and breathtaking 180° west-facing views with unforgettable sunsets. Quality built by a respected local builder, the home is elevated and constructed to today’s flood standards. Featuring 4 bedrooms, 4.5 baths, elevator and 2-car garage. A gorgeous chef’s kitchen with generous island opens to a dramatic great room with soaring ceilings. Expansive windows capture stunning water views from nearly every room. The beach is protected by jetties and adjacent to Little Island Beach and preserve. An extraordinary private coastal setting close to West Falmouth Harbor, Shining Sea Bikeway and West Falmouth Tennis Club. A rare combination of new construction, acreage, privacy and exceptional beachfront.

114 Quaker Rd, Falmouth

Listing courtesy of Listing Agent: O'Neill Group from Listing Office: .

70 Possum Rd, Weston
$9,990,000
5 Beds ⋅ 10 Baths ⋅ 73475863 MLS
This peerless modern 2-acre estate is located in a highly desired private neighborhood in Weston. Exterior features a beautiful, flat landscaped yard, patio w/grill, and a full sports court. The luxurious 5 bed, 7f/3h bath interior features lofty 12’ high ceilings with walls and ceilings of glass, opening the space to the exterior and drenching this home in sunlight. Smart home features include Lutron shades to provide unmatched comfort. Unmatched detail throughout,with main level foyer, floating staircases, and an open flow to the main dining and living areas. Chef’s kitchen w/top of the line appliances & breakfast bar opens to the large family room with fireplace. Huge office, mudroom, and large 3car garage finish the main level. 2nd floor features an amazing master suite, w/2 large baths and dressing rooms. 4 additional bedroom suites and laundry finish the 2nd floor. The lower level features a large gym, pickleball/sportsroom, playroom/media room, cedar closet, and amazing storage.

70 Possum Rd, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

68 Clyde Street, Brookline
$9,985,000
5 Beds ⋅ 8 Baths ⋅ 73478330 MLS
Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

68 Clyde Street, Brookline

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

4800 Congress St, Fairfield
$9,975,000
7 Beds ⋅ 10 Baths ⋅ 24161896 MLS
The former home of Richard Rodgers, composer of The Sound of Music, this 10.92 acre estate with a stunning modern residence was recently fully renovated and expanded, and offers curated one floor living. Generous main rooms are enhanced by lofty ceilings, skylights and walls of glass. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. Separate residential wings include 7 bedrooms and 7 full baths, each with a unique design. All property systems have been upgraded and integrated to work seamlessly .The barn pool house includes a full eat-in kitchen and lounge, bath ,and full gym steps from the pool. An office pavilion is set privately in a quiet garden area. The park like property is surrounded by high stone walls, a nature preserve, open land, a heated paddle tennis court, and an orchard. Live in ultimate style and easy elegance just a quick commute to NYC and airports. This private haven surrounded by a 155 acre nature preserve is minutes to Fairfield, Westport and Greenwich dining and shopping.

4800 Congress St, Fairfield

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

57 Hancock St, Boston
$9,900,000
5 Beds ⋅ 7 Baths ⋅ 73585937 MLS
Grand iconic corner building has just undergone a complete restoration into one of the finest single family homes on Beacon Hill. An extremely rare corner home has stood in this location since 1870 and still posses the papyrus capitals on the entryway columns to mark the style. This sun filled corner property maintains three exposures, 65 windows, ceiling heights ranging from 9-11 to 11-7, three roof decks, courtyard and a sweeping top to bottom staircase that begins in a grand entryway and ends at a dramatic 8 window cupola that truly must be seen. This tremendous home offers substantial curb appeal, three magnificent bays, gracious rooms and architectural detail. Property amenities include elevator, two wet bars, three gas fireplaces, entertainment club level with roof deck, three laundries, top floor media room, three parking spaces, and much more. Spectacular opportunity in one of Boston's most historic and desirable neighborhoods.

57 Hancock St, Boston

Listing courtesy of Listing Agent: Glenn Forger from Listing Office: Olde Forge Realty.

50 Poplar Hill Dr, Farmington
$9,900,000
21 Beds ⋅ 40 Baths ⋅ 24120482 MLS
Once home to both Mike Tyson and 50 Cent, this extraordinary estate sits on more than 17 private acres in Farmington, Connecticut-a historic town just 10 miles west of Hartford and ideally positioned between Boston and New York City. Spanning an impressive 51,000 square feet, the residence embodies unmatched opulence, with over $3 million in recent renovations elevating it to a world-class standard. Inside, discover an indoor pool and spa, a lavish nightclub, recording studio, billiards room, casino room, multiple game rooms, a racquetball court, state of the art fitness center, grand foyer, elevator and seven kitchens serving 21 bedrooms and 40 bathrooms. There is a boardroom, library and offices. Outside, the grounds are equally captivating with a resort-style pool, grotto, waterfall, private bridge, 4 bedroom guesthouses, pool house, a pond with fountain, basketball and tennis courts and an 8 car garage. This is more than a home-it is a rare opportunity to own a legacy estate of iconic distinction.

50 Poplar Hill Dr, Farmington

Listing courtesy of Sherry Borgeson from Berkshire Hathaway NE Prop.. (860) 334-0095 (860) 537-6699

9 Over Rock Ln, Westport
$9,860,000
6 Beds ⋅ 9 Baths ⋅ 24205443 MLS
Newly completed, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating staircase anchors four finished levels featuring soaring ceilings, custom millwork, and engineered white oak flooring. The chef's kitchen showcases dual quartzite waterfall islands, custom rift white oak cabinetry, a walk-in pantry, and a professional appliance suite. The primary suite offers cathedral ceilings, a fireplace, private balcony, dual dressing rooms, and a spa-inspired bath with heated floors and a soaking tub. Designed for seamless indoor-outdoor living, the nearly 950-square-foot covered terrace features granite flooring, a wood-burning fireplace, outdoor kitchen, heated 20' 40' saltwater pool, 10-person spa, and room for a future tennis or pickleball court. The walk-out lower level includes a family room, wet bar, fitness studio, guest suite, and flexible space for a theater, golf simulator, or media lounge. Prepare to fall in love.

9 Over Rock Ln, Westport

Listing courtesy of Danna Rogers from Higgins Group Bedford Square. (917) 282-6292 (203) 226-0300

14 Indian Trail, Osterville
$9,850,000
5 Beds ⋅ 5 Baths ⋅ 22503092 MLS
Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of coastal legacy. This waterfront estate offers 1.78 acres of private grounds, a beautifully preserved five-bedroom residence, and a substantial deep-water dock with direct access to Nantucket Sound—accommodating six or more vessels with ease. Inside, the home exudes understated charm with a seamless connection to outdoor living—screened porch, expansive deck, and water views from most rooms. A welcoming main-level primary suite with adjoining study anchors the floor plan, while the heart of the home features a stone fireplace, an open-concept kitchen, and a screened porch that opens to an expansive deck—perfect for entertaining or quiet reflection. Upstairs, guest bedrooms are enhanced by gracious proportions and stunning vistas. With additional buildable parcels from the same legacy estate also available, this is a rare opportunity to establish a private compound in one of New England's most exclusive waterfront enclaves. A sanctuary of coastal beauty and historic significance, all within the beloved village of Osterville - home to world-class golf, protected waters, and the timeless allure of Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

14 Indian Trail, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

14 Indian Trail, Barnstable
$9,850,000
5 Beds ⋅ 5 Baths ⋅ 73395925 MLS
Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of coastal legacy. This waterfront estate offers 1.78 acres of private grounds, a beautifully preserved five-bedroom residence, and a substantial deep-water dock with direct access to Nantucket Sound—accommodating six or more vessels with ease. Inside, the home exudes understated charm with a seamless connection to outdoor living—screened porch, expansive deck, and water views from most rooms. A welcoming main-level primary suite with adjoining study anchors the floor plan, while the heart of the home features a stone fireplace, an open-concept kitchen, and a screened porch that opens to an expansive deck—perfect for entertaining or quiet reflection. Upstairs, guest bedrooms are enhanced by gracious proportions and stunning vistas. With additional buildable parcels from the same legacy estate also available, this is a rare opportunity to establish a private compound in one of New England's most exclusive waterfront enclaves. A sanctuary of coastal beauty and historic significance, all within the beloved village of Osterville - home to world-class golf, protected waters, and the timeless allure of Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

14 Indian Trail, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

606 And 607 N Main St, Wolfeboro
$9,800,000
3 Beds ⋅ 1 Baths ⋅ 5095854 MLS
A truly rare offering on the shores of Winter Harbor, this remarkable 40± acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of two distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. Across the road, rolling fields and open meadows surround an antique Cape, forming a timeless pastoral landscape rich with character and possibility. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, an equestrian estate, a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, open fields, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events.

606 And 607 N Main St, Wolfeboro

Listing courtesy of Lobin Frizzell from KW Coastal and Lakes & Mountains Realty/Meredith. ()

38 Prospect Rd, Westport
$9,675,690
6 Beds ⋅ 10 Baths ⋅ 24190177 MLS
A bold expression of sculptural architecture and modern organic design, this one-of-a-kind Green's Farms estate with stone cottage is set on 1.19 artfully layered acres with stacked stone walls, gardens, and striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds with heated pool and spa. Every space is composed with architectural precision, balancing dramatic scale with warmth and livability. The main level features a statement dining room anchored by a dramatic fireplace, sophisticated living room and private office showcasing elevated millwork and custom built-ins, and an expansive family room which extends to a covered outdoor terrace with fireplace, creating an exquisite setting for effortless entertaining and relaxed outdoor living. The kitchen is defined by sleek wood cabinetry, striking natural stone, a curated suite of professional-grade appliances, and a fully appointed scullery. Upstairs, five ensuite bedrooms include a serene primary suite with fireplace, 2 private terraces, dual walk-in closets, and a spa-inspired bath finished in natural stone and refined wood detailing. The finished lower level offers a gym, recreation/game room, media lounge, 6th bedroom, and 1 1/2 baths. Moments from beaches, train, shopping, & dining, this extraordinary residence offers exceptional craftsmanship and an effortless indoor-outdoor lifestyle in Westport's most coveted neighborhood.

38 Prospect Rd, Westport

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300

145 Forest St, Sherborn
$9,500,000
5 Beds ⋅ 10 Baths ⋅ 73592555 MLS
Welcome to “Kettle View Cottage,” a truly one-of-a-kind estate where timeless architecture, extraordinary craftsmanship, and an incomparable connection to nature come together. Originally built in 2012 and the recipient of the distinguished Bulfinch Award in 2014, this exceptional 8,715-square-foot residence has since been extensively reimagined and expanded by the current owners for comfortable everyday living and grand entertaining. Set on 3.4 acres overlooking Farm Pond with one-third ownership of the island, this private retreat offers a lifestyle rarely found in Sherborn. Stroll through the gardens and orchard, follow the fern-lined woodland path, or make your way to the newly renovated boathouse, dock, and private pond access for swimming, kayaking and enjoying the water. Inside, walls of glass, soaring ceilings, elegant architectural details, and thoughtful custom spaces create an inviting sense of scale. Throughout the home, the views are intentionally focused toward the outdoors, bringing the landscape into the heart of the home. The kitchen is complemented by high-end Viking and Miele appliances, a wood-burning fireplace, and a warm, inviting eat-in setting that connects seamlessly to the butler’s pantry, dining room, and family room. A dramatic second staircase, added as part of the expansion, leads to a refined second level. The expanded primary suite features dual baths and dressing rooms, with four additional bedrooms and baths upstairs. One bedroom is currently being used as a handsome office overlooking the pond with custom built-ins. Designed for wellness and recreation, the home offers a gym, sauna, massage room, salon, billiard room, media spaces, and multiple gathering areas. Outdoors, extensive new landscaping, stone patios, an outdoor kitchen, fire pit, hot tub, gardens, and more come together to create a true private resort. With four heated garage bays, a whole-house generator, extensive infrastructure upgrades, and impeccable attention to detail throughout, Kettle View Cottage is an extraordinary expression of sophisticated country living.

145 Forest St, Sherborn

Listing courtesy of Listing Agent: The Bohlin Group from Listing Office: Compass.

12 Boldwater Road, Edgartown
$9,500,000
8 Beds ⋅ 11 Baths ⋅ 73584420 MLS
A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

12 Boldwater Road, Edgartown

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

15 Pickering Ave, Portsmouth
$9,500,000
4 Beds ⋅ 4 Baths ⋅ 5109617 MLS
Pickerings Neck. A truly rare opportunity on the waterfront in Portsmouth’s historic South End. Pickerings Neck is more than a property, it is a piece of Portsmouth’s maritime history and an opportunity to create a family compound unlike anything else in the city. Located on historic Pickering’s Neck, whose story reaches back to John Pickering’s arrival in 1633, this waterfront site later became part of Portsmouth’s important shipbuilding tradition. Today, the property offers an extraordinary collection of buildings and waterfront amenities, including a principal residence with an apartment, small warehouse, waterfront decks, docks, mooring and a separate building currently home to the South End Yacht Club.The real opportunity may lie in what comes next. Situated in the Commercial zoning district and within Portsmouth’s Historic District, the property presents a compelling canvas for creating an exceptional private family compound. Envision expanding and reimagining the existing residence or exploring the potential for a larger estate home, while repurposing the distinctive yacht club building into a remarkable waterfront guest residence or complementary living space. Few properties combine this degree of waterfront access, multiple existing structures, boating amenities, history and proximity to downtown Portsmouth. Step from your home to your dock, explore the Piscataqua and Portsmouth Harbor, or walk into the heart of the city. 15 Pickering offers something that simply cannot be recreated: the opportunity to write the next chapter of an extraordinary Portsmouth waterfront property.

15 Pickering Ave, Portsmouth

Listing courtesy of Tony Jalbert from Tate & Foss Sotheby's International Rlty. ()

55 Adin St, Hopedale
$9,500,000
12 Beds ⋅ 12 Baths ⋅ 73572810 MLS
Introducing The Ledges, an extraordinary historic estate set on nearly 18 acres of magnificent private grounds. Situated on the former estate grounds of Governor Eben Draper and associated with the distinguished Draper family, this remarkable stone-and-brick residence offers a rare combination of architectural significance, grand-scale living and modern comfort. Period craftsmanship is evident throughout, with imported English oak, flagstone, coffered ceilings, leaded glass windows, multiple fireplaces, a dramatic Great Hall and banquet-sized dining room. Extensive restoration and modernization have thoughtfully preserved the home's character while introducing updated central air, heating, electrical and plumbing systems, beautifully renovated marble and tile baths, and an updated kitchen with an oversized center island, dining and sitting areas, Wolf range, Sub-Zero refrigeration and Fisher & Paykel dishwasher drawers. Beyond the residence, sweeping lawns and formal gardens originally designed by landscape architect Warren Manning create an exceptional setting for an inground pool, tennis court, gazebo and pond. Rich in history yet designed to be enjoyed today, The Ledges is an offering of remarkable beauty, privacy and presence.

55 Adin St, Hopedale

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

153 Shore Rd, Chatham
$9,495,000
3 Beds ⋅ 3 Baths ⋅ 73594589 MLS
Sparkling harbor views, afternoons by the pool, and expansive, private grounds on coveted Shore Road. Offered for the first time since 1987, "Offshore" encompasses more than an acre - a rare opportunity to enjoy a remarkably private estate-like setting in the heart of Chatham. Beyond the house, a surprising expanse of lawn and gardens unfolds, its scale and privacy revealed only when you explore the grounds. Inside, gracious, generously proportioned rooms and timeless Cape Cod character create an inviting setting for entertaining, gathering with friends, or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs windows frame picture-perfect coastal scenes. A spacious first-floor primary suite offers comfort and ease. A carriage-style garage completes the property, just moments from Chatham Bars Inn, the Fish Pier, Lighthouse Beach, and Main Street. Whether enjoyed as it is today or thoughtfully reimagined, this special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Rd, Chatham

Listing courtesy of Listing Agent: Sarah Keith from Listing Office: eXp Realty LLC.

153 Shore Road, Chatham
$9,495,000
3 Beds ⋅ 3 Baths ⋅ 22603522 MLS
Sparkling harbor views, afternoons by the pool, and expansive, private grounds on coveted Shore Road. Offered for the first time since 1987, "Offshore" encompasses more than an acre - a rare opportunity to enjoy a remarkably private estate-like setting in the heart of Chatham. Beyond the house, a surprising expanse of lawn and gardens unfolds, its scale and privacy revealed only when you explore the grounds. Inside, gracious, generously proportioned rooms and timeless Cape Cod character create an inviting setting for entertaining, gathering with friends, or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs windows frame picture-perfect coastal scenes. A spacious first-floor primary suite offers comfort and ease. A carriage-style garage completes the property, just moments from Chatham Bars Inn, the Fish Pier, Lighthouse Beach, and Main Street. Whether enjoyed as it is today or thoughtfully reimagined, this special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Road, Chatham

Listing courtesy of Listing Agent: Sarah Keith (sarah@capecodbliss.com) from Listing Office: eXp Realty, LLC.

73 Chestnut Street, Weston
$9,450,000
7 Beds ⋅ 11 Baths ⋅ 73577074 MLS
Magnificent residence sited on 2.78 private and pristine acres in one of Weston’s most coveted locations. Completely renovated with the highest level of finishes offering every modern amenity. This exceptional home offers estate-like living designed equally for comfortable family life and sophisticated entertaining. The modern designer kitchen anchors the center of the home and flows seamlessly into the sumptuous fireplaced family room with access to private deck overlooking the pool and grounds and spacious screened porch, creating an inviting open floor plan. The formal dining room enhanced by a butler’s pantry is complemented by a well-proportioned formal living. Multiple home offices, a generous mudroom, dog-washing room and a large gym are just a few of the exceptional features this home offers. This home offers two luxurious primary suite options, one on each of first and seconds levels providing exceptional flexibility. All bedrooms are generously sized and feature ensuite baths. The lower level provides dedicated play, craft and billiard spaces along with ample storage. A sleek and private two-bedroom accessory dwelling with separate entrance and two-car garage offers additional accommodations. Resort-like grounds are enhanced with a beautiful pool, well equipped cabana, expansive patios, and private tennis court, creating an extraordinary setting for year-round living and entertaining. The incomparable residence provides the ultimate in private living while offering easy access to Boston and Weston’s renowned schools.

73 Chestnut Street, Weston

Listing courtesy of Listing Agent: Deena Powell from Listing Office: Gibson Sotheby's International Realty.

19 Bonnybrook Road, Newton
$9,398,000
7 Beds ⋅ 10 Baths ⋅ 73524508 MLS
OFFERING SPECIAL FINANCING OR A 2/1 BUY DOWN,Introducing 19 Bonnybrook, an exceptional new-construction estate set on over ¾ acre in Waban. Spanning 11,535 sq ft, this luxurious residence offers 7 bedrooms, 7 full baths, & 3 half baths, blending scale, elegance, modern comfort & custom millwork. A spectacular gourmet chef’s kitchen with premium appliances & dual islands is complemented by a fully equipped secondary kitchen for effortless entertaining. The dramatic two-story family room features 20+ft ceilings & stunning floor-to-ceiling stone fireplace. The first floor also includes formal living & dining rooms, a sun-filled breakfast area overlooking the landscaped backyard & patio, & a gracious first-floor ensuite. 2nd floor offers a presidential primary suite w spa-like bath, fireplace,& private deck, four ensuite bedrooms, office/yoga room, & laundry. The lower level features a guest suite, gym, wine cellar, theatre, steam & sauna, & recreational room. Elevator, 3-car garage, & room for pool complete this exceptional offering

19 Bonnybrook Road, Newton

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

78 & 92 Pastures Ln, New Canaan
$9,250,000
7 Beds ⋅ 8 Baths ⋅ 24213848 MLS
Hidden behind gates and surrounded by 5.5 acres of pristine, rolling lawns, this extraordinary stone manor estate is a masterclass in old-world craftsmanship and cutting-edge modern innovation. Anchored by a separately deeded 2 acre lot with a guest house, the property presents rare flexibility and long-term value, perfectly suited for multi-generational living, guests, or future expansion. Originally constructed in 1927, the residence has been comprehensively reimagined and renovated from the inside out, preserving its architectural integrity while delivering a fully modernized, high-tech smart home experience. With all new systems, infrastructure, and finishes including new HVAC, electrical, plumbing, septic, irrigation, generator, propane tank, fencing, landscaping and all new mechanicals offering the confidence of new construction wrapped in timeless stone. Inside, over 8,500 square feet of refined living space unfolds with remarkable craftsmanship. Radiant heated floors span the first level, complemented by hand-selected reclaimed pumpkin wood, and museum-quality lighting throughout. The heart of the home is a striking new kitchen with soaring ceilings, custom concrete countertops, a bespoke island, and hand-selected bleu chinois tilework that adds depth and character throughout the first floor. Designed to entertain and inspire, the home also features an 800+ bottle wine cellar, a private fitness and training studio, and a beautifully appointed home office/library

78 & 92 Pastures Ln, New Canaan

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

219 Scraggy Neck Road, Cataumet
$9,190,000
5 Beds ⋅ 9 Baths ⋅ 22604910 MLS
A rare waterfront compound on the protected waters of Squeteague Harbor, 219 and 221 Scraggy Neck Road combine an exceptional turnkey residence with an adjacent waterfront building parcel, encompassing 7.7 acres in one of Cataumet's most private coastal settings. The centerpiece is a beautifully renovated residence set on 4.3 acres, offering 6,500+ square feet of living space with five bedrooms and sweeping harbor views. Designed for effortless waterfront living and entertaining, the property features a private dock, boathouse, heated saltwater pool and spa, pool house, and beautifully landscaped grounds. An additional 3.4-acre waterfront parcel expands the offering, with direct harbor frontage and a completed feasibility study exploring the potential for a residence, accessory structures, and private dock. Together, the two properties present a unique opportunity to create an extraordinary multi-residence waterfront compound with exceptional privacy, acreage, and direct access to Squeteague Harbor.

219 Scraggy Neck Road, Cataumet

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

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