Feature Properties

Presenting 55 Commonwealth Avenue, a rare opportunity to acquire one of Back Bay's finest turnkey single-family homes, an address that rarely, if ever, comes to market. Spanning nearly 11,000 SF on the sunny side, this exceptional home offers a combination of scale, natural light, and turnkey living. Designed for both entertaining and everyday living, the home features formal living and dining rooms, an expansive family room, chef’s kitchen, library, multiple offices,media room, catering kitchen, and a wellness level with fitness studio, and sauna. The residence offers 5+ bedrooms with multiple ensuite baths, three private terraces, nine fireplaces, temperature-controlled wine room, multiple laundry rooms, and a best-in-class elevator with access to every level. Complete with 2 private garage spaces and 1 gated outdoor space, this home stands as the only turnkey single-family residence available on the sunny side of the second block of Comm Ave, a genuine once-in-a-generation offering.

55 Commonwealth Avenue, Boston

Listing courtesy of Listing Agent: Khoury Group from Listing Office: Serhant.

$34,990,000

5 Beds ⋅ 9 Baths ⋅ 73577894 MLS

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

128 Commonwealth Avenue, Boston

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

$34,000,000

7 Beds ⋅ 16 Baths ⋅ 73590483 MLS

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

55 Singletree Rd, Brookline

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

$34,000,000

12 Beds ⋅ 18 Baths ⋅ 73584065 MLS

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

341 Standish St, Duxbury

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

$32,000,000

7 Beds ⋅ 10 Baths ⋅ 73576533 MLS

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

141 Main Street, Nantucket

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

$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.

$23,000,000

6 Beds ⋅ 12 Baths ⋅ 73576839 MLS

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

381 Warren Street, Brookline

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

$22,500,000

4 Beds ⋅ 4 Baths ⋅ 73582414 MLS

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

102 Sesuit Neck Rd, Dennis

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

$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.

$19,995,000

6 Beds ⋅ 8 Baths ⋅ 73527728 MLS

Exquisite, wide Back Bay townhouse on the sunny side of Commonwealth with large private roof deck, magnificent views, Juliet balcony, and 6 outdoor parking showcases exceptional bones and timeless character. Expansive windows provide outstanding natural light, highlighting the home's historic charm and original detail. The property offers a versatile floor plan for customization, with approximately 10,000+/-sf to create luxurious spaces and exceptional entertaining space. Currently exhibiting an open and airy kitchen, soaring ceilings, a stately dining room, beautiful paneled library, 5+ well-proportional bedrooms, abundant closets, and a separate au pair suite, it is one of only a few single family homes in this highly coveted neighborhood. Its distinguished façade, irreplaceable location, and palatial scale present an extraordinary canvas for a discerning buyer. Elevator to all floors, 8 fireplaces, and grandeur complete this home’s spectacular offering. Some photos virtually staged.

129 Commonwealth Avenue, Boston

Listing courtesy of Listing Agent: Jeannemarie Conley from Listing Office: Compass.

$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: .

$18,000,000

6 Beds ⋅ 7 Baths ⋅ 73585235 MLS

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

15 Vinson Circle, Winchester

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

$17,675,000

7 Beds ⋅ 8 Baths ⋅ 73584705 MLS

Featured in The Wall Street Journal’s Mansion section, this nearly 10,000 SF Back Bay townhouse blends contemporary design with classical character across five full floors. With seven bedrooms, six full baths, and two half baths, it offers a thoughtful layout for everyday family life and entertaining. Its unusually wide footprint allows for generous rooms, while light from three sides gives the home an airy feel. A marble foyer leads to a chef’s kitchen, sunlit family room, dining room, and expansive living room, where soaring ceilings, floor-to-ceiling windows, and fireplaces bring warmth and scale. The second floor is anchored by a primary suite with a fireplace, dual dressing rooms, and a spa-inspired bath with a soaking tub and glass rain shower. An office or nursery and a dedicated laundry room add flexibility and convenience. The third floor features four oversized bedrooms and two full baths, giving children or guests a space of their own. On the top floor, a bright living or game room offers space for movie nights, entertaining, or a quiet evening in. This level also includes a kitchen, full bath, and roof access with potential for a private roof deck. The garden level adds flexibility and function, with a home gym, a two-bedroom, two-bath suite with its own kitchen for extended family or guests, an office with a fireplace, laundry, a private patio, and abundant storage. A large elevator serves every level, and four direct parking spaces complete the home. With room to gather, retreat, and grow, this home offers a rare kind of townhouse living in the heart of Back Bay.

4 Gloucester Street, Boston

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

$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.

$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

8 Beds ⋅ 11 Baths ⋅ 73586293 MLS

Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.

143 Bayberry Way, Barnstable

Listing courtesy of Listing Agent: John Hopkins from Listing Office: Frank Sullivan Real Estate, LLC.

$16,000,000

7 Beds ⋅ 13 Baths ⋅ 73584008 MLS

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef’s kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence, the property takes on the character of a private coastal compound. A separate two-bedroom guest house with three-car garage and pool house overlooks the expansive pool and surrounding grounds. Multiple terraces and outdoor rooms lead toward the water, where a private sandy beach and substantial deep-water dock provide direct access to Eel River and Nantucket Sound. The setting is quintessentially Osterville: private, deeply connected to the water, and minutes from the village, its beaches, harbor, shops, and restaurants. With its scale, architectural pedigree, guest accommodations, and exceptional boating access, this is a distinctive waterfront offering in one of Cape Cod’s most sought-after enclaves. 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.

74 Garrison Ln, Barnstable

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

$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.

$15,850,000

8 Beds ⋅ 9 Baths ⋅ 73585729 MLS

Set on 2.35 beautifully landscaped acres along Eel River, this exceptional Osterville waterfront estate enjoys western exposure, sweeping water views, and a substantial deep-water dock with direct access to Nantucket Sound. The setting is defined by an extraordinary combination of privacy, scale, and waterfront amenities, creating a rare sense of arrival and an exceptional connection to the water. The six-bedroom main residence offers approximately 7,000 square feet of living space, with a gracious floor plan designed to take full advantage of the setting. From the grand foyer, panoramic water views immediately draw the eye through the home and toward the expansive grounds and waterfront beyond. The main level offers generous living and entertaining spaces, while the second floor features a spacious primary suite with fireplace, walk-in closet, and private bath, along with five additional bedrooms. The lower level includes a recreation room, exercise room, and abundant storage, with an attached two-car garage. The waterfront grounds are the centerpiece of the property. An expansive pool, glass-enclosed pool house, and substantial deep-water dock create an exceptional setting for summer living, boating, and entertaining. The western exposure brings beautiful afternoon and evening light across the water, while the location provides direct access to Nantucket Sound. A separate two-bedroom carriage house with attached two-car garage and private patio provides comfortable accommodations for guests and extended family. Osterville Village, with its high-end shops and refined dining, is close at hand, as are the area’s renowned golf clubs. With its extraordinary acreage, western water views, deep-water access, pool, guest accommodations, and exceptional privacy, this is a waterfront estate of uncommon scale and presence. 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.

141 Eel River Rd, Barnstable

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

$14,950,000

6 Beds ⋅ 10 Baths ⋅ 73583424 MLS

The architect’s vision for this exceptional 2025 residence was to preserve the timeless elegance of Georgian Revival architecture while reimagining the floor plan for contemporary living. The result is a beautifully balanced home with sun-filled, visually connected spaces that flow seamlessly to outdoor terraces, gardens, a 15' x 38' pool, and cabana. The design thoughtfully combines beauty and functionality, pairing classic architectural details with innovative building systems and energy-efficient technology. Distinctive elements include graciously proportioned rooms, symmetry, finely crafted millwork, a red-brick Georgian façade with limestone accents, French doors with transom windows, fireplaces with custom surrounds, and expansive wrap-around terraces. The result is a timeless yet thoroughly modern home—warm, inviting, and designed for effortless everyday living and entertaining, with exceptional connectivity between the interior and outdoors. Set in one of Newton’s most sought-after locations, the property is just steps from Newton Centre, minutes from The Street at Chestnut Hill, and approximately 15 minutes from Boston.

9 The Ledges, Newton

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$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.

$14,000,000

5 Beds ⋅ 8 Baths ⋅ 73487660 MLS

Set amongst the stately residences of West Cambridge, this Tudor/Shingle style home, built around 1895, is the perfect marriage of timeless architectural character & modern sophistication. Completely renovated, while keeping intact the original details, like grand wooden entry door, floor to ceiling windows & awe-inspiring millwork, this pristine home offers approximately 9,594 SF of elegant living space set across 4 floors. A pristine chef’s kitchen with island seating & casual dining area provide great space for family gatherings, while the grand, open formal living/dining/foyer area is perfect for entertaining. A comfortable family room and separate den flow effortlessly to the outdoors and connect to a double mudroom with abundant storage. The upper levels host 5 bedrooms, all with ensuite bathrooms. The lower level, with exterior access, finishes off the home, complete with billiard area and new wet bar, playroom, media room, gym, and sauna. Other features include: 9' ceilings; hardwood floors and detailed tiled flooring; 8 fireplaces; geothermal heat and much more. Enjoy private outdoor space with fenced-in yard, sport court, outdoor kitchen, and covered porch overlooking the lush backyard. A separate, heated and oversized 2 car garage with driveway provides ample parking. Situated on a rare 0.41-acre corner lot in a highly sought-after tree-lined neighborhood, it's just moments from Harvard Square and Charles River. A timeless beauty in its own private setting, yet still close to the bustle of the city and all it has to offer, this property has it all!

157 Brattle Street, Cambridge

Listing courtesy of Listing Agent: Cort LaBonte Coldren Coopersmith Group from Listing Office: Compass.

$12,995,000

6 Beds ⋅ 7 Baths ⋅ 73516411 MLS

The privacy and grounds of a suburban estate, two blocks from the Charles River and minutes from Harvard Square. A masterpiece by Cafasso Design Group, this architectural work of art redefines luxury living. Tucked within a coveted enclave off Brattle Street, this home unfolds across lush, sculpted grounds framed by mature trees, offering an unparalleled serene retreat. A striking sculptural staircase serves as the dramatic centerpiece, while interiors masterfully blend contemporary Japanese, Scandinavian, Italian, and French influences.The eat-in chef’s kitchen features custom Italian walnut cabinetry, Calacatta Gold marble counters, dual sinks & dishwashers, a Gaggenau 400 Series double oven, and walls of glass. Generous bedrooms and spa-inspired baths deliver sanctuary, complemented by a glass-enclosed office and a family room featuring a floating gas fireplace. A dedicated lifestyle level boasts a guest suite and inviting spa with a Western Red Cedar sauna & steam shower. Outside, manicured grounds surround an outdoor kitchen, expansive deck, and inviting patio perfect for entertaining. You won't believe whats behind the front door!

11 Brown Street, Cambridge

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

$12,900,000

6 Beds ⋅ 10 Baths ⋅ 73560074 MLS

12 Foxcroft Lane | East SandwichA once-in-a-generation waterfront estate, 12 Foxcroft Lane represents the pinnacle of Cape Cod coastal luxury. Set on beautifully manicured grounds with sweeping lawns, a pristine private sandy beach, and panoramic views of Cape Cod Bay from Plymouth to Provincetown, this extraordinary 16,000± sq. ft. residence offers six bedrooms and ten baths designed for generations to enjoy.Light-filled living spaces flow seamlessly to exceptional outdoor entertaining areas, while the chef's kitchen opens to an inviting family room anchored by a magnificent stone fireplace - the heart of the home, where stories are shared, celebrations unfold, and a lifetime of memories begin. The luxurious first-floor primary suite is a private retreat with breathtaking views. World-class amenities include a private theater, professional fitness center, resort-style infinity pool, poolside cabana, putting green, and a private boardwalk leading directly to the beach.More than a home,12 Foxcroft Lane is a legacy estate--an irreplaceable waterfront sanctuary offering unmatched privacy, extraordinary craftsmanship, and one of the finest beachfront settings on the Eastern Seaboard

12 Foxcroft Ln, Sandwich

Listing courtesy of Listing Agent: Michael Harney from Listing Office: Sotheby's International Realty.

$12,900,000

7 Beds ⋅ 7 Baths ⋅ 73444242 MLS

Situated between Appleton St & Riedesel Ave, this grand & prominent center entrance 7+ bed, 6.5 bath home was originally built in c.1803 has been painstakingly restored, elegantly modernized and expertly crafted for modern living. Ideally sited on a maturely landscaped 22,500+ sq ft lot, this gracious home rests behind an elegant white fence with antique walkways and restored balustrade. Welcomed onto the formal foyer by a graceful staircase, hardwood floors, restored period details and abundant natural light throughout. A large living room offers a fireplace, custom built-ins, and large winnows that overlook the front and side yards. A well placed banquet sized formal dining room offers a butlers door into the kitchen and a fireplace of its own. A sparkling eat in kitchen is complete with top-of-the-line appliances, large center island, two pantries, & a mudroom. Exquisitely finished lower level with 2 level wine storage, gym, media room, steam shower, & sauna! Oversized 1 Car Garage

153 Brattle St, Cambridge

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.

$12,500,000

8 Beds ⋅ 11 Baths ⋅ 73579095 MLS

Nestled privately on one of Greater Boston's most coveted streets, this magnificently detailed Victorian home was restored, expanded, and completely reimagined for modern living in 2020 — and stands in a class of its own. As you enter through the handmade mahogany front door, the grand entryway opens on either side to a glorious living room and a stunning library. The first floor boasts 10'7" ceilings, two gas fireplaces with custom handmade mantels, and an extraordinary level of craftsmanship in the woodworking details throughout. The sprawling kitchen great room is wrapped in large windows, with French doors that open to the yard. Natural stone countertops, a Viking range, and top-of-the-line appliances are integrated seamlessly with the custom cabinetry. It's an exceptionally generous space that doubles effortlessly as a catering kitchen for entertaining at scale. On the second floor, an original Palladian window greets you at the landing. Three bedrooms — each with its own ensuite bath and multiple exposures — include a primary suite with marble bath. Every room enjoys a privacy that feels almost impossibly serene for a home this close to the heart of Harvard Square — a true urban oasis. The third floor adds two more bedrooms with ensuite baths, plus a spectacular home office or hangout room anchored by sweeping views. The top floor is a magical space. Eight skylights and an original half-moon window fill the room with light. This studio-like haven is ideally suited for inspiring creative work. An open staircase connects the kitchen great room to the lower level, where a playroom (or media room), mudroom, powder room, and gracious bedroom suite complete the main house. Beyond them sits an entirely separate one-bedroom apartment spanning approximately 950 sq ft, with its own exterior access — full kitchen, living and dining areas, bedroom, and bath — an exceptional arrangement for guests, extended family, an au pair, or staff. Outside, a two-car garage with additional parking easily accommodates a crowd. Mature landscaping on a level lot of nearly a quarter acre delivers a degree of privacy that is rare this close to Harvard Square. Ideally located within a quarter mile of Huron Village and BB&N's Middle School, and under a mile from Longfellow Park and Shady Hill School.

68 Sparks Street, Cambridge

Listing courtesy of Listing Agent: Michael Glenmullen from Listing Office: Coldwell Banker Realty - Cambridge.

$12,500,000

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.

$12,250,000

7 Beds ⋅ 9 Baths ⋅ 73551533 MLS

Perched within ''The Cliffs''--West Falmouth's most coveted private seaside enclave--this custom shingle-style estate offers over 11,000 square feet of exquisitely finished living space in pristine condition with multiple family suites. From its elevated vantage overlooking Buzzards Bay, the residence commands panoramic water views toward the Elizabeth Islands and Vineyard Sound--permanently protected by a perpetual view easement, ensuring unobstructed western sunsets for generations. An opulent foyer with sweeping curved staircase opens to soaring volumes, rich hardwoods, and custom millwork throughout. Seven bedrooms, eight full and one half baths are arranged for privacy, while a formal dining room and multiple living areas open through French doors to landscaped grounds and four expansive decks. Recent improvements include a new roof and whole-house generator. Residents enjoy The Cliffs' private sandy association beach, minutes from West Falmouth Harbor, yacht clubs, golf, and the Shining Sea Bikeway.

39 Naushon S, Falmouth

Listing courtesy of Listing Agent: Diana Lucivero from Listing Office: Compass.

$11,900,000

5 Beds ⋅ 7 Baths ⋅ 73570207 MLS

Privately gated and exquisitely appointed, 540 Harland Street presents a rare opportunity to own an extraordinary equestrian estate set on approximately 8 acres within the Blue Hills Reservation. Surrounded by protected natural beauty and offering direct riding access to approximately 7,000 acres of preserved landscape, this exceptional property combines complete privacy, sophisticated living, and an unparalleled connection to the outdoors—yet remains conveniently close to Boston.The approximately 8,250-square-foot main residence is designed for grand-scale living and effortless entertaining, featuring five bedrooms, five full baths, and two half baths, complemented by soaring 10-foot ceilings throughout. The spectacular chef’s kitchen is outfitted with premium Wolf appliances, while a dedicated home gym and state-of-the-art home theater elevate the everyday experience. An in-home elevator provides seamless access throughout the residence.Outdoor living is equally impressive, with a 350-square-foot patio and a fully equipped Wolf outdoor kitchen, creating an exceptional setting for entertaining, dining, and enjoying the surrounding landscape.The estate’s remarkable carriage house adds an extraordinary layer of versatility, offering an 8–16+ car garage and approximately 1,750 square feet of guest living space above. Ideal for car enthusiasts, collectors, guests, or extended family, this separate structure provides an exceptional combination of utility and luxury.At the heart of the property’s equestrian amenities is an approximately 2,000-square-foot state-of-the-art multi-stall equestrian center, thoughtfully complemented by an adjacent exercise pen. The direct access to miles of protected Blue Hills terrain allows riders to leave the property on horseback and immediately experience one of the region’s most spectacular natural settings.This is far more than a luxury residence—it is a private equestrian compound and lifestyle estate, offering an extraordinary level of scale, privacy, amenities, and access to protected land rarely found in Greater Boston. A truly distinctive retreat where refined living and the freedom of the countryside exist in perfect harmony.

540 Harland St, Milton

Listing courtesy of Listing Agent: Signature Collective Team from Listing Office: Serhant.

$11,750,000

6 Beds ⋅ 6 Baths ⋅ 73570794 MLS

One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$11,750,000

6 Beds ⋅ 9 Baths ⋅ 73536353 MLS

A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$11,750,000

5 Beds ⋅ 7 Baths ⋅ 73516055 MLS

EXCEPTIONAL WATERFRONT ESTATE with 2.29 acres of land, a DOCK, 200' of frontage on Hingham Harbor, and spectacular views of Boston skyline. Designed by acclaimed architect, Tom Catalano, known for his creation of homes representative of a by-gone era, yet suited for modern living. The natural light is incredible and the views are mesmerizing. The finishes and millwork are truly MASTERFUL with coffered ceilings, wainscotting, arched openings, custom cabinetry and quarter sawn oak floors throughout. The staircases are a graceful work of art, with gentle rises and walls of windows. The exterior spaces are as exquisite as the interior. The back of the house features gorgeous stone terraces with beautiful pergolas, a heated Gunite pool and sweeping lawn to the dock and waters edge. The front "garden" sets the stage for this stunning property with a torch lit fountain, expansive level lawn, an English conservatory and gardens.

5 Bare Cove Ln, Hingham

Listing courtesy of Listing Agent: Tara Coveney from Listing Office: Coldwell Banker Realty - Hingham.

$11,500,000

6 Beds ⋅ 8 Baths ⋅ 73531287 MLS

Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-like swimming pool and cabana, a boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. The open floor plan seamlessly flows from a fireplaced living room with coffered ceilings to a gourmet kitchen with a Sub-Zero refrigerator, Wolf range, and Danby natural stone counters. Glass doors line the waterside of the home, opening to an expansive Phoenician Buff stone terrace surrounding a Pebble Tec pool and spa. The first-floor primary boasts 2 walk-in closets and a luxurious bath with a freestanding soaking tub. Four en suite bedrooms, a family room, and an ipe deck occupy the second level, with bonus space above. A bedroom suite over the garage accommodates guests or staff. Located minutes from everything Osterville has to offer.

48 Starboard Lane, Barnstable

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

$11,495,000

4 Beds ⋅ 8 Baths ⋅ 73499377 MLS

North Pasture is a newly built estate situated on one of Nantucket highest elevations, this turn key offering is in one of the islands most coveted settings, blends modern construction with timeless design elements and high end custom finishes. Over 6000 square feet of finished living space, the residence comprises of 4 ensuite bedrooms and 4 half bathrooms; multiple living areas spanning three floors, ideal for entertaining and all of your overflow needs, high ceilings that enhance light and volume. The architectural detail and exquisite custom millwork prioritizes clean lines, open rooms, and strong visual connections to the surrounding landscape. Outdoor living is anchored by an infinity-edge pool and spa oriented toward uninterrupted southern exposure. Cabana with outdoor kitchen, lounge area, and half bath. Garage and refined landscape design complete the property.

25 North Pasture Lane, Nantucket

Listing courtesy of Listing Agent: Karen Moreshead from Listing Office: Craigville Realty, Inc..

$11,000,000

15 Beds ⋅ 13 Baths ⋅ 73576414 MLS

Set amid approximately 20+ acres of sweeping grounds, 151 Grove Street is one of Westwood’s most remarkable residential offerings—a distinguished Georgian estate where architectural heritage, enduring craftsmanship, and gracious modern living come together with uncommon ease. Built in 1908 and encompassing approximately 13,754+ square feet, the residence unfolds with a sense of scale and permanence rarely encountered. Thoughtfully maintained and beautifully appointed, each room reflects a commitment to exceptional materials and timeless design. With a more recent expansion, it marries perfectly the old and the new, as every space has been perfectly renovated. At the heart of the home, the gourmet kitchen is both elegant and purposeful. Stainless-steel appliances, stone countertops, a professional-grade range with a custom hood, an island with a prep sink, and a generous peninsula create an exceptional setting for everyday living and sophisticated entertaining. Nearby, the expansive living room is defined by soaring ceilings, stately fireplaces, decorative columns, and richly toned hardwood floors—a memorable double level gathering space imbued with warmth and architectural character. Generously proportioned bedrooms feature hardwood flooring, some with their own baths. The home’s private primary quarters are equally considered. The suite creates pure serenity. Comfortable boudoir included sitting area, refrigerated drawers, integrated in custom built-in shelving. Luxurious private bath appointed with marble tile, fireplace and access to outdoor shower. The primary wing also offers oversized walk-in closets. Beyond the interiors, the estate reveals an extraordinary outdoor setting. A private swimming pool with a diving board, expansive patios, and welcoming fire pit create a resort-like atmosphere surrounded by the beauty and privacy of the property’s substantial acreage. A distinguished slate roof and six-car+ garage further underscore the home’s impressive scale and lasting quality. Grand yet inviting, historic yet entirely suited to contemporary life, 151 Grove Street is more than a residence—it is a legacy property. A private showing offers the rare opportunity to experience its extraordinary craftsmanship, remarkable proportions, and singular sense of place. Come home to a rare paradise.

151 Grove Street, Westwood

Listing courtesy of Listing Agent: Wendy Fox from Listing Office: Compass.

$11,000,000

73543050 MLS

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

39 Cottage St, Brookline

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

$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.

$10,850,000

7 Beds ⋅ 9 Baths ⋅ 73569449 MLS

Few properties offer the sense of privacy, space and comfort found at 15 Claridge Drive while remaining just minutes from Boston. Encompassing 3.75 acres of beautifully landscaped grounds in one of Weston’s most desirable settings, this thoughtfully designed estate offers a rare quality of life with the ease and amenities of a private retreat. Designed by architect Thomas Catalano with landscape design by Morgan Wheelock, the home was created for comfortable family living, entertaining and multigenerational use. Set on a gentle slope overlooking rolling lawns, the property feels peacefully set apart from the pace of everyday life. Mature landscaping, specimen plantings and open grounds create a bucolic and spacious setting where children can play, family and friends can gather, and there is room to simply enjoy being at home. The main home offers five spacious bedrooms, each with an ensuite bath. A private guest apartment includes two bedrooms and a full kitchen, offering flexibility for extended family and guests. The home features multiple rooms for gathering and entertaining, along with two private offices. A four-season conservatory, fully equipped gym, state-of-the-art media room, and wine cellar with tasting room provide spaces for work, wellness, entertainment and relaxation. An elevator provides access to all four floors of the home. Outdoors, the pool, tennis court, lawns and gardens create a private setting for recreation, summer gatherings and quiet afternoons at home. The finest materials were selected to create this exceptional estate. Exterior details include stucco, Dolomitic limestone and Chelmsford granite, a Vermont slate roof and custom mahogany windows by Tischler. Inside, thoughtful materials and meticulous craftsmanship continue throughout. A stone foyer, cantilevered limestone staircase and dramatic three-story rotunda add architectural character, while generous living spaces keep the home comfortable and welcoming. With its combination of privacy, quality, space and proximity to Boston, 15 Claridge Drive offers a rare opportunity to shape daily life around what matters most, a place for family to live, gather, play and grow together.

15 Claridge Drive, Weston

Listing courtesy of Listing Agent: Dean Poritzky from Listing Office: Engel & Volkers Wellesley.

$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..

$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: .

$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.

$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.

$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.

$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: .

$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.

$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.

$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.

$9,398,000

7 Beds ⋅ 10 Baths ⋅ 73524508 MLS

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.

$9,000,000

5 Beds ⋅ 4 Baths ⋅ 73540605 MLS

A rare opportunity to own one of Duxbury's most extraordinary waterfront estates on Eagle's Nest Point. Sited on a private 7.6-acre peninsula extending into Duxbury Bay, this classic shingle-style residence offers sweeping water views on three sides, deep-water dock access, and the kind of privacy that simply cannot be replicated. The main house has been thoughtfully updated while preserving its architectural integrity with generous principal rooms, gracious flow, and natural light throughout. A separate guest cottage provides comfortable accommodations for visitors while maintaining the quiet of the main residence. Whether arriving by land or by sea, 160 Marshall Street makes an unmistakable impression. Seven and a half acres, three sides of water, and a setting that defines the finest of coastal New England living. This property is being sold as a commissioner's sale pursuant to a Massachusetts Land Court partition action.

160 Marshall Street, Duxbury

Listing courtesy of Listing Agent: Kristin Thompson from Listing Office: Keller Williams Realty Signature Properties.

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