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$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. ()
$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.
$9,500,000
6 Beds ⋅ 7 Baths ⋅ 5089994 MLS
Lake Winnipesaukee waterfront living at its finest. "Woodland Cove" is set on three private acres with 310 feet of pristine sandy shoreline and coveted southern exposure, this extraordinary custom estate captures sweeping views of the lake and the Belknap Mountain range while offering rare protection from prevailing winds. The sugar sand beach allows you to wade in slowly with a sandy bottom extending well off shore. The park-like grounds are a masterpiece of natural beauty, featuring mature gardens, handcrafted stonework, and multiple outdoor living spaces designed to embrace the waterfront setting. A stunning mahogany-and-fieldstone boathouse which is architecturally exceptional—stands as a true centerpiece of the property. The boathouse features a large lift to keep your boat pristine as well. Spanning more than 8,000 square feet, the 13-room residence combines timeless craftsmanship with luxurious comfort. The home features six spacious bedrooms and seven baths, with every bedroom offering its own en-suite bath for ultimate privacy and convenience. Soaring ceilings, elegant crown molding, and walls of glass create an atmosphere of light, space, and sophistication throughout. The decorator furnishings have been curated specifically for this home and are included. Designed for both relaxed lake living and entertaining, the home offers expansive decks, patios, and a beautiful screened porch that seamlessly blends indoor and outdoor living. The first-floor primary suite is a private retreat with breathtaking lake and mountain views, a generous walk-in closet, and a spa-inspired bath. Located just 10 minutes from downtown Wolfeboro, this remarkable property delivers the perfect balance of convenience, exclusivity, and complete privacy on New Hampshire’s most sought-after lake. This is truly a special property in the nations "Oldest Summer Resort."

80 Parker Island Rd, Wolfeboro

Listing courtesy of Brian Neidhardt from Four Seasons Sotheby's Int'l Realty. ()
$9,500,000
7 Beds ⋅ 8 Baths ⋅ 73485408 MLS
Magnificent estate on one of Brookline’s most beautiful residential streets, blending timeless architecture with modern luxury. Expansive first floor features elegant period details, grand entertaining rooms, an impressive foyer, custom chef’s kitchen, and spacious family room, with a covered porch and large deck extending the living space outdoors. The home offers a palatial primary suite with fireplace, multiple closets, & a spa-like bath, along with additional en-suite bedrooms and a third-floor recreation space.The fully finished lower level includes a kitchen, gym, theater, recreation room, additional bedrooms, and full bath. Additional highlights include radiant heated floors, smart home technology, and an oversized double-depth garage accommodating up to six cars. Set on nearly one acre of beautifully landscaped grounds w/ a swimming pool, clay tennis court, and heated driveway and walkways for snowmelt. An exceptional residence offering luxury, privacy, extraordinary amenities.

355 Buckminster Road, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.
$9,500,000
7 Beds ⋅ 9 Baths ⋅ 73445189 MLS
Offered fully furnished and ready to enjoy, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions.

30 East Rd, Alford

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.
$9,495,000
4 Beds ⋅ 6 Baths ⋅ 73548919 MLS
Timeless architect-designed Katama retreat made for summer living. Privately set at the end of a long drive on 1.53 acres near South Beach, this Patrick Ahearn-designed estate offers 4,605 square feet of refined Vineyard living. Built in 2022, the home blends award-winning coastal architecture with vaulted ceilings, custom shiplap, millwork, antique rough-hewn beams, Rubio Monocoat floors, high-end fixtures, and luxury finishes. The Great Room is anchored by a floor-to-ceiling gas stone fireplace, while the gourmet kitchen opens to the living, dining, and family rooms, with a Butler’s Pantry for entertaining. French doors lead to a screened porch and resort-style outdoor setting with PebbleTec gunite pool, built-in spa, bluestone patio, outdoor shower, and pergola-covered lounge with wood-burning fireplace. Four en suite bedrooms include a serene Primary Suite with pool access. An attached two-bay garage and full unfinished basement add ease and future potential.

29 Slough Cove Rd, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
$9,250,000
6 Beds ⋅ 9 Baths ⋅ 24179744 MLS
Exceptional new construction estate by K&C Builders Inc., set on over 2.5 private acres on coveted Brookside Road. Offering approximately 11,000 SF across four finished levels, this stunning residence features 6 bedrooms, 8 full baths, and 1 half bath. Designed for elegant entertaining and everyday living, the home showcases a spectacular great room, gourmet chef's kitchen, private study, cabana-style room opening to the pool area, finished lower level, and finished attic. Premium Rhea European Windows flood the home with natural light while providing exceptional energy efficiency and modern sophistication. Extensive custom millwork, architectural ceiling details, designer lighting, detailed interior paneling, custom cabinetry, and bespoke finishes reflect the superior craftsmanship and attention to detail that define every K&C Builders project. The luxurious primary suite offers a spa-inspired bath and oversized custom walk-in closets. Outdoor amenities include professionally landscaped grounds, a resort-style pool, outdoor kitchen, and expansive entertaining spaces designed for seamless indoor-outdoor living. Ideally located minutes from downtown Darien, Metro-North, beaches, country clubs, and Darien schools, this extraordinary residence presents a rare opportunity to own a signature home built to the highest standards of quality, design, and craftsmanship.

175 Brookside Rd, Darien

Listing courtesy of Sylwia Kozlowski from William Raveis Real Estate. (203) 984-6945 (203) 227-4343
$9,200,000
6 Beds ⋅ 9 Baths ⋅ 24190177 MLS
A bold expression of sculptural architecture and modern organic design, this exceptional Green's Farms estate is set on 1.19 artfully layered acres with stacked stone walls, gardens, and a striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds and heated pool. 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 den showcasing architectural millwork and custom built-ins, private office, and an expansive living room which extends to a covered outdoor terrace with fireplace, creating a exquisite setting for effortless entertaining and relaxed outdoor living. The kitchen is defined by architectural 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, private terrace, 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, sixth bedroom, and full bath. Moments from beaches, train, shopping, and 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
$9,100,000
5 Beds ⋅ 3 Baths ⋅ 5104599 MLS
Commanding 485' of Lake Winnipesaukee shoreline at the end of its own peninsula, 65 Tips Cove is a generational offering of rare provenance in America's oldest summer resort. Frontage of this scale on a point lot cannot be replicated. Set on 2.75± level, landscaped acres between Tips Cove and Jockey Cove - with a separate .51± acre garden lot available — the property is enveloped by water on nearly every side. Mature white pine buffers behind; ahead, lawn falls to a granite shoreline where the water runs clear. Privacy here is measured not in hedgerows but in open water and quiet. Multiple docking options serve the property: a granite breakwater dock, a U-shaped covered slip, and open-water docking off the deck. Capacity at this scale is difficult to permit anew, and places the Broads, Winter Harbor, and downtown Wolfeboro moments away by boat. The southwesterly exposure is the signature. From a lakeside deck cantilevered above the rocks, summer sunsets fall down the open lake, swinging through autumn to settle behind the Belknap Range, with Rattlesnake Island anchoring the view to the northwest. It is the orientation this lake pays a premium for. The residence is itself a landmark, its red roof recognizable from the summit of Mount Major. Gracious single-level living unfolds beneath soaring ceilings, where grand hallways lead to four private sleeping quarters set apart from a primary suite with en-suite bath. Stone fireplaces anchor the principal rooms, beadboard and natural woodwork frame the ever-present water views, and a formal dining room stands ready for the gatherings to come — an enduring plan, built for multigenerational use and for owners measuring the next thirty years, not the next three. Days begin at the shoreline; nights belong to loon calls and unlit skies. A singular opportunity to acquire one of Winnipesaukee's defining shorefront estates.

65 Tips Cove Rd, Wolfeboro

Listing courtesy of Adam Dow from KW Coastal and Lakes & Mountains Realty/Wolfeboro. (Phone: 866-525-3946)
$9,000,000
4 Beds ⋅ 7 Baths ⋅ 73476388 MLS
Behind its classic Village façade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and thoughtfully curated finishes define every level of the home. The backyard is a true extension of the home, anchored by a fully equipped cabana, heated saltwater pool, sunken fire pit, and striking custom glass wall. A strong rental history further enhances the property's appeal, offering exceptional flexibility as a private family retreat or a compelling investment opportunity. A home where exceptional quality meets effortless living, offering a fresh and relaxed interpretation of luxury in the heart of Edgartown Village.

43 Peases Point Way S, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$8,995,000
5 Beds ⋅ 6 Baths ⋅ 24201619 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 7,000 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
$8,995,000
6 Beds ⋅ 6 Baths ⋅ 22601242 MLS
Introducing 18 Strandway, a newly constructed waterfront masterpiece located within the exclusive enclave of Old Mill Point in West Harwich. Built in 2020, this exceptional six-bedroom, six-bath estate spans nearly 5,000 sq ft on a .73 acre waterfront lot and offers a rare combination of modern craftsmanship, coastal elegance, and premier access to the salty water of Nantucket Sound and the Herring River. Perfectly positioned in a private setting, the home showcases spectacular views from nearly every room- facing North, South, and West, along with seamless indoor-outdoor living. Highlights include a private dock with water and power, suitable for a forty-foot boat, a stand-alone boat house with a rooftop sundeck, a heated saltwater resort-style pool, 2 separate laundry rooms (one on each floor), a radiant heated basement, and every modern amenity throughout the expansive living spaces with high-end finishes. This is a rare opportunity to own a true waterfront gem in one of Cape Cod's most sought-after communities.--

18 Strandway Way, West Harwich

Listing courtesy of Listing Agent: Tom McGreevy (tmcgreevy@petersonrealty.com) from Listing Office: Peterson Realty Inc..
$8,995,000
7 Beds ⋅ 6 Baths ⋅ 73496969 MLS
Discover 39 Worthington Road in Brookline's coveted Cottage Farm neighborhood. This fully renovated masterpiece boasts 7 bedrooms and 5.5 bathrooms with impeccable craftsmanship and attention to detail. The interior, designed by a renowned interior designer has been featured in various publications. Wonderful spaces for entertaining and comfortable living include a large custom-designed chef's kitchen open to a gracious family room with custom millwork built-ins along with a large library with over 12' ceilings. There is a luxurious primary suite with a spa-like bath, walk-in closets, a sun-filled study, & access to a terrace. The lower level includes a gym, playroom, and more. Nestled on a double, extra-large expansive landscaped lot complete with a hockey rink (and equipment) and full outdoor kitchen, privacy and serenity, and indoor/outdoor living abound. The ideal setting and location that defines urban-suburban living close to all Boston/Cambridge/Brookline has to offer.

39 Worthington Rd, Brookline

Listing courtesy of Listing Agent: Rachel Goldman from Listing Office: MGS Group Real Estate LTD.
$8,995,000
5 Beds ⋅ 7 Baths ⋅ 73485860 MLS
Exquisite fully renovated 5+ bedroom townhouse! An ideal South End location on West Canton St between Warren Ave & Tremont St, this special home has been totally customized by the Lagasse Group and has been finished with the highest level of craftsmanship. A parlor level kitchen offers an oversized island, abundant storage, a beverage center, gas cooking and is open to a large dining space and a bow front living area with views east down Montgomery St. A double entry, half bath, private deck with floor to ceiling wall of glass, and tall ceilings complete the parlor level. A 2nd level primary suite is complete with 5 piece bath with ample storage, 2 walk in dressing rooms and a large bedroom. A 3rd floor is complete with 3 bedrooms, 2 full baths, auxiliary laundry & storage. Under the stoop entrance boats a large mudroom AND a walk in coat closet, the bedroom/home gym with en suite bath and a kids play room. Garden level media room with wine storage, private garden, laundry room.

158 W Canton St, Boston

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$8,995,000
6 Beds ⋅ 7 Baths ⋅ 73479457 MLS
Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef’s kitchen features a center island, butler’s pantry & dining nook—truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

188 Heath St, Brookline

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.
$8,990,000
5 Beds ⋅ 6 Baths ⋅ 73333444 MLS
No. 86 Mount Vernon is a spectacular corner residence overlooking the coveted Louisburg Square in Boston’s most storied neighborhood. Built circa 1875, this 20’ wide townhouse offers 4,492 SQFT of classically scaled living space across 4 levels. The gracious floor plan has been reconfigured for today’s modern lifestyle, all while preserving the beauty and integrity of the magnificent historic details throughout the home. A grand double parlor living room, soaring ceiling heights, exquisite crown molding and ironwork, 70 windows and 6 original fireplaces serve as a lasting testament to a golden age of living. The 3rd floor living area opens to an expansive rooftop garden terrace with stunning views of Beacon Hill and the Back Bay skyline. Atop it all is a luxurious primary suite with multiple closets and a lavish 5-piece marble bath. Additional features include radiant heated mahogany floors throughout, direct elevator access to all floors and 1 parking space at the Brimmer St. Garage.

86 Mount Vernon Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$8,950,000
6 Beds ⋅ 6 Baths ⋅ 73575562 MLS
Reintroducing this newly RENOVATED rare 30-foot wide single-family home in the heart of the Back Bay and Boston’s most coveted neighborhood. Boasting 6 bedrooms, 5.5 bathrooms, and an expansive 5,700 square feet, this home mixes it's historical brownstone charm with contemporary luxuries of a newly installed elevator, exquisite custom wood flooring and state-of-the-art appliances throughout the home. This single-family includes a private entrance in-law/guest suite adorned with lofty 9' ceilings and comes equip with two private parking spaces and option to buy one garage parking.

1 Fairfield St, Boston

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.
$8,950,000
4 Beds ⋅ 3 Baths ⋅ 73556482 MLS
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$8,950,000
4 Beds ⋅ 3 Baths ⋅ 22603612 MLS
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

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

1722 Monument St, Concord

Listing courtesy of Listing Agent: Jonathan Radford from Listing Office: Coldwell Banker Realty - Boston.
$8,875,000
6 Beds ⋅ 8 Baths ⋅ 24126255 MLS
Perched on more than seventy acres of rolling meadows and sculpted gardens, Linden Hill Farm stands as one of the most distinguished country estates in the region. A tree-lined allee of Linden trees leads to the Georgian Revival residence, built in 1929, where timeless architecture is seamlessly paired with modern luxury. The six-bedroom main residence opens with a dramatic double-height entrance hall that flows onto a stone terrace spanning the rear facade. Sunlight illuminates the grand living room, where French doors lead outside to a western-facing, glass-enclosed sunroom that overlooks the manicured boxwood garden and dining pavilion. The richly paneled library provides a private retreat, while the elegant dining room-with its own terrace access-offers an ideal setting for gathering with family and friends. At the center of the home, the chef's kitchen is outfitted with professional-grade appliances, a butler's pantry, and an inviting dining area that opens to the patio and kitchen garden. Upstairs, the primary suite is a sanctuary, complete with a fireplace, two dressing rooms, dual baths, a sitting room, and a terrace with views of the formal gardens. Additional guest suites with fireplaces and a separate wing with a game room ensure comfort and privacy for both residents and visitors. The estate's amenities are exceptional, a 60' x 30' swimming pool with bluestone surround, pool house, a lighted Omni-Turf tennis court, charming guest house,

406 Wells Hill Rd, Salisbury

Listing courtesy of Elyse Harney Morris from Elyse Harney Real Estate. (860) 318-5126 (860) 435-0120
$8,800,000
5 Beds ⋅ 6 Baths ⋅ 22603271 MLS
Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors.

25 Oyster Way, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$8,800,000
5 Beds ⋅ 6 Baths ⋅ 73544944 MLS
Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors. 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.

25 Oyster Way, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$8,800,000
7 Beds ⋅ 8 Baths ⋅ 73457104 MLS
Set at the end of a long winding drive, this remarkable 16+ acre estate abuts more than 100 acres of conservation land, creating a rare sense of privacy and natural beauty. Suited for formal entertaining, intimate gatherings, and gracious family living, it includes a welcoming main entrance hall, a wonderful living room with an attached library, a spacious formal dining room with adjoining butler’s pantry, and a stunning chef’s kitchen that overlooks a fireplaced family room and a covered patio. There are 7 bedrooms highlighted by a stunning primary suite, as well as two offices, a playroom, an exercise room, and an attached, heated three-car garage. Outdoor amenities include a heated pool with a well-appointed pool house, a sport court, a stream-fed pond, and a barn-garage with a greenhouse and two horse stalls, along with a charming two-bedroom cottage. This exceptional property offers access to excellent public and private schools, Legacy Place, the train, and Boston via Rte. 95/128

401 Sandy Valley Rd, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..
$8,795,000
6 Beds ⋅ 10 Baths ⋅ 24177074 MLS
Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sun room, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

55 Calhoun Dr, Greenwich

Listing courtesy of Barbara Wells from Houlihan Lawrence. (203) 912-5644 (203) 869-0700
$8,750,000
5 Beds ⋅ 5 Baths ⋅ 5103915 MLS
Hart’s Crossing is a home and a haven featuring a custom 21st-century residence and a comprehensively restored Civil War-era guest house, set on 418 acres of private land. The property provides a refuge in nature, with a kingdom-sized backyard to explore and adventures that change with the seasons. Located at the end of a town-maintained road, the property is a 10-minute drive from either Woodstock Village or the Upper Connecticut River Valley to access the conveniences and necessities of life, yet a century away from the inconveniences, in a peaceful sanctuary. The airy and light-filled 5-bedroom main residence sits on a plateau overlooking the Ottauquechee and White River Valleys to the east and north, with sweeping views to the south along the Connecticut River through walls of windows. The historic farmhouse has been reimagined as a comfortable 2-bedroom guest cottage, featuring exposed timber framing accented by a modern kitchen and bath, with a screened porch and wide deck alongside a refreshing, spring-fed swimming pond. Nearby is a multipurpose barn with a caretaker’s apartment for farm and recreational purposes. The property is enrolled in Vermont’s Current Use program, intended to help large landowners preserve the working landscape with a professional land management plan and a reduction in property taxes as consideration. There are miles of trails enabling access to the entire property for hiking, biking, snowmobiling, and simply wandering without a watch. At the end of Sugar House Road, you’ll discover the best of today, thoughtfully combined with the timeless values of yesterday.

775 548 Sugar House Rd, Hartland

Listing courtesy of Laird Bradley from Williamson Group Sothebys Intl. Realty. (Phone: 802-457-2000)
$8,747,000
7 Beds ⋅ 10 Baths ⋅ 24199897 MLS
FrogPond Estate is New Canaan's most striking modern Scandinavian offering-an architectural achievement set on 2.25 private acres just moments from town and train. With 11,836+ sq. ft. of sunfilled, designdriven living space, this 7 bed, 9.5bath custom residence delivers soaring 12ft ceilings, bespoke millwork, designer lighting, and walls of glass that erase the line between indoors and out. A showstopping doubleisland gourmet kitchen anchors the open main level, perfect for quiet daily living or largescale entertaining. The estate's fully independent 1,190 sq. ft. Cottage-with separate address and utilities-adds a private bedroom, office, full bath, island kitchen, laundry, and a flexible loft ideal for guests, extended family, staff, or professional use. Thoughtfully scaled yet beautifully finished, it elevates FrogPond into a true multidwelling compound. Pool is open. Landscaping complete. Showready today. A rare modern sanctuary-private, polished, and unlike anything else in the market. This is the listing buyers will clear their schedules to see.

259 Frogtown Rd, New Canaan

Listing courtesy of Mar Jennings from Higgins Group Bedford Square. (203) 984-5203 (203) 226-0300
$8,696,000
7 Beds ⋅ 8 Baths ⋅ 24160984 MLS
Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury Homes, Fairfield County's premiere creator of bespoke residential properties, this 8,560SF masterpiece will embody uncompromising craftsmanship, globally sourced materials, and state-of-the-art systems & technology. Expansive floor-to-ceiling glass invites natural light to cascade throughout the meticulously designed interiors, framing serene views of the manicured grounds and resort-style pool w/spa. The open floor plan is ideal for elegant entertaining and effortless daily living. A chef's kitchen of unrivaled distinction is complemented by a fully appointed scullery, seamlessly supporting both private gatherings and large-scale entertaining. The great room exudes warmth and architectural presence, while the handsome parlor/office opens to an oversized covered porch. The primary suite is a sanctuary unto itself, featuring a fireplace, private terrace, and spa-inspired bath designed for true indulgence. 6 addit'l bedrooms provide luxurious accommodations for family & guests alike. LL is exceptional w/media room, golf simulator, gym, etc. 4 car garage, elevator shaft & much more.

688 Hulls Farm Rd, Fairfield

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300
$8,650,000
5 Beds ⋅ 7 Baths ⋅ 24151164 MLS
Refined Luxury. Rare Direct Lakefront Home within the Coveted Silo Ridge Community. 5 Luxurious En-suite Bedrooms Including 2 on Main Level. Jaw Dropping Great Room with Fireplace & Access to Large Covered Porch with Major Lake & Mountain Views. Extremely High Quality Construction with Numerous Luxury Appointments Including: Lutron 1-Touch Lighting; Multi-Zone Sound System; 4-Season In Ground Pool/Spa; Heated 3-Car Attached Garage; Electric Shades Throughout; 2 Screened Porches with Powered Screens & Built in Heaters. Finished Lower Level with 2 Bedrooms, 2.5 Baths & Family Room with Direct Access to Heated Pool/Spa & Cabana with Fireplace. 1-Mile to Metro North Train & Arms Distance to all the Hudson Valley has to Offer. The Best of Silo Ridge for Sale. Exceptional!

292 Wood Duck Rd, Amenia

Listing courtesy of Graham Klemm from Klemm Real Estate Inc. (860) 488-6635 (860) 868-7313
$8,625,000
7 Beds ⋅ 8 Baths ⋅ 22603124 MLS
Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Set aside any reservations of the year built...the entire foundation and structure were comprehensively reinforced and renovated by E.J. Jaxtimer. Any changes or modifications a buyer might want would be aesthetic alone. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage with vaulted ceilings and additional charm. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

63 Main Street, Osterville

Listing courtesy of Listing Agent: Christa Zevitas (czevitas@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

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