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

239 Summer, Manchester

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

207-209 Long Neck Point Rd, Darien

Listing courtesy of Shelly Tretter Lynch from Compass Connecticut, LLC. (203) 550-8508 (203) 343-0141
114 North Water Street, Edgartown
$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..
210 Monument Farm Road, Concord
$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.
143 Bayberry Way, Barnstable
$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.
143 Bayberry Way, Osterville
$16,500,000
8 Beds ⋅ 11 Baths ⋅ 22605034 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, Osterville

Listing courtesy of Listing Agent: John J Hopkins (hop5jh@msn.com) from Listing Office: Frank A Sullivan Real Estate.
155 Long Neck Point Rd, Darien
$16,495,000
10 Beds ⋅ 12 Baths ⋅ 24186570 MLS
Set on 2.93 private acres along coveted Long Neck Point, this extraordinary waterfront Colonial offers a rare combination of sweeping water views, privacy, and direct access to the water. Spanning more than 10,000 square feet, the residence is designed to embrace its spectacular setting, with expansive living spaces and breathtaking vistas from nearly every room. The eight-bedroom main residence features seven full and three half baths, eight fireplaces, and an effortless flow between gracious entertaining spaces and comfortable everyday living. A pool and private dock extend the experience outdoors, creating an idyllic setting for waterfront living and entertaining. A charming two-bedroom, two-bath guest cottage offers additional space and privacy for family and guests. Distinguished by its scale, setting, and direct water access, this remarkable Long Neck Point estate offers a rare opportunity to experience the quintessential coastal lifestyle.

155 Long Neck Point Rd, Darien

Listing courtesy of Janine Tienken from Houlihan Lawrence. (203) 246-7518 (203) 655-8238
25 Brickyard Road, Chilmark
$16,250,000
6 Beds ⋅ 8 Baths ⋅ 22603861 MLS
Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

25 Brickyard Road, Chilmark

Listing courtesy of Listing Agent: Peyton Wallace (peyton@studiorealty.com) from Listing Office: Studio Realty LLC.
154 Woodland Road, Brookline
$16,000,000
5 Beds ⋅ 7 Baths ⋅ 73598666 MLS
Exceptional new construction in Brookline’s coveted Estate Area, set on 1.02 acres with sweeping golf course views. Offering over 6,000 SF of refined living space, this residence showcases timeless architecture and exceptional craftsmanship, beginning with a striking limestone façade, custom wrought-iron entry and circular drive with grand portico. Inside, sophisticated living and entertaining spaces are complemented by two custom kitchens with top-of-the-line appliances and cabinetry. Five en-suite bedrooms, 5 full and 1 half baths, and a heated 3-car garage complete the home. Meticulously designed landscaping surrounds the property, creating a private estate setting rarely available in Brookline. Built by Brookline’s only female luxury home builder, this exceptional residence offers a rare combination of design, quality and setting.

154 Woodland Road, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.
74 Garrison Ln, Barnstable
$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: .
74 Garrison Lane, Osterville
$16,000,000
7 Beds ⋅ 13 Baths ⋅ 22604940 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. Please note: Totals for square feet, bedrooms and bathrooms include Main House, Guest House and Boat House.

74 Garrison Lane, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
141 Eel River Rd, Barnstable
$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: .
141 Eel River Road, Osterville
$15,850,000
8 Beds ⋅ 9 Baths ⋅ 22605000 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 7,700 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. Please Note: Totals for square footage, bedrooms and bathrooms include both Main House and Carriage House.

141 Eel River Road, Osterville

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
8 Snail Road, Chilmark
$15,400,000
6 Beds ⋅ 9 Baths ⋅ 22602961 MLS
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Brian W Dougherty (brian.dougherty@corcoranadvisors.com) from Listing Office: Corcoran Property Advisors.
8 Snail Road, Chilmark
$15,400,000
6 Beds ⋅ 9 Baths ⋅ 73538291 MLS
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
17 Crowninshield Road, Marblehead
$15,000,000
5 Beds ⋅ 9 Baths ⋅ 73536454 MLS
This magnificent oceanfront estate stands as one of the most significant properties in Marblehead. Located in the exclusive Peach’s Point neighborhood, this property offers stunning views of Crowninshield Island, Grace Oliver’s Beach, Marblehead Lighthouse, and the surrounding islands. “Seaside Farm” replaced the original Crowninshield estate in 1999 in a classic Georgian style, with meticulous attention to detail throughout. The home is designed to maximize ocean views while maintaining privacy. The grand 2-story foyer with a custom staircase sets the tone for the home, which features elegant living spaces ideal for both daily life and entertaining. The second floor includes an oceanfront primary suite with a fireplace, walk-in closet, modern bathroom, and a private deck with exceptional views. Three additional en suite bedrooms, a large office, and a laundry room complete the second floor. Caretakers 1 bedroom apartment over 4-car garage offering views of Grace Oliver's Beach and c

17 Crowninshield Road, Marblehead

Listing courtesy of Listing Agent: Traci Howe from Listing Office: Gibson Sotheby's International Realty.
9 The Ledges, Newton
$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.
53 Paine Avenue, Beverly
$14,900,000
5 Beds ⋅ 8 Baths ⋅ 73363224 MLS
Commanding ocean views from nearly every room, this extraordinary six acre estate sits on the historic site of a 1900s Manor House. Blending classic New England architecture with modern luxury, the stone-and-shingle residence features incredible design, custom mahogany, paneled walls and exquisite millwork throughout. The Primary Suite boasts panoramic ocean views, a domed gable ceiling, fireplace, walk-in closet with wet bar, and spa-like bath. All bedrooms are en suite with ocean views and closets with custom shelving. Formal gardens transition elegantly to sweeping seascapes directly above the beach. Enjoy the beach and the privacy Prides Crossing has to offer. A large,custom-built Poolhouse with kitchen and bath offers perfect indoor outdoor space. Designed for both grand entertaining and everyday comfort, this exceptional property captures the timeless beauty and elegance of Boston’s North Shore estates. A rare opportunity to own a legacy estate in an unmatched coastal setting.

53 Paine Avenue, Beverly

Listing courtesy of Listing Agent: Krista Julian from Listing Office: Coldwell Banker Realty - Manchester.
15 Runnymede Dr, North Hampton
$14,889,000
6 Beds ⋅ 9 Baths ⋅ 5105837 MLS
Set along prestigious, bucolic Runnymede Drive, this exceptional seventeen-room legacy estate is privately sited on 4.6 park-like acres along a quiet side street within the only riverfront neighborhood east of I95 offering direct frontage on the Little River, distant ocean views, and the soothing sound of crashing surf. From the moment you arrive via the cobblestone driveway, it is clear this is a truly extraordinary property. Impeccably maintained grounds are thoughtfully designed to provide complete privacy while beautifully landscaped gardens deliver color and seasonal interest throughout the year. The riverside pool and pool house create an exceptional retreat for family and guests. Designed for effortless entertaining, the custom pool house features a gourmet kitchen rivaling that of the main residence and formal dining for ten overlooking the pool and river. The main home showcases timeless architecture, exquisite period craftsmanship, and custom millwork rarely found in today's luxury homes. Grand entertaining spaces include a distinguished library, elegant formal dining room, richly paneled lounge with intricate moldings, home theater, raised bar with walk-in wine cellar, and seamless access to outdoor living areas. Six beautifully appointed bedroom suites each feature luxurious en-suite tiled baths, including an expansive three-room primary suite with an extraordinary custom island dressing room and luxury marble bath with tub. Outstanding mechanical systems include multi-zone central air, automatic standby generator, sophisticated security system, and seven fireplaces, six of which have never been used. The remarkable craftsmanship and attention to detail throughout must be experienced firsthand. Seldom does an estate of this caliber, offering such exceptional privacy and meticulous care, become available just minutes from Abenaqui CC, the seaside boardwalks, shopping, Port City Air FBO terminal and under an hours drive from Logan International Jetport.

15 Runnymede Dr, North Hampton

Listing courtesy of Patrick Carey from Carey Giampa, LLC/Seabrook Beach. (Cell: 603-583-1000)
280 Warren St, 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.
532 Round Hill Rd, Greenwich
$14,495,000
7 Beds ⋅ 11 Baths ⋅ 24178299 MLS
Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence.

532 Round Hill Rd, Greenwich

Listing courtesy of Ian Defronze from Serhant Connecticut, LLC. (646) 637-8161 (203) 489-7800
157 Brattle Street, Cambridge
$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.
25 Rockyledge Road, Swampscott
$13,995,000
6 Beds ⋅ 8 Baths ⋅ 73542321 MLS
Perched atop nearly an acre of dramatic granite coastline with commanding ocean views, this extraordinary estate represents a level of craftsmanship that simply cannot be replicated today. Offered at $13,995,000 with an estimated replacement cost exceeding $37,000,000, it is a rare opportunity to own a truly irreplaceable residence. Spanning nearly 15,000 square feet, the home offers 6 bedrooms, 8 baths, an elevator, four fireplaces, a heated 5-car garage, ocean-facing infinity pool, rooftop deck, and spectacular entertaining spaces including a gallery. Every detail reflects an uncompromising commitment to artistry, from bespoke millwork and artisan stonework to exceptional materials sourced from around the world. Modern infrastructure includes 21-zone radiant heat and central air, backup generator, and state-of-the-art systems, creating a legacy estate where timeless craftsmanship meets extraordinary coastal living.

25 Rockyledge Road, Swampscott

Listing courtesy of Listing Agent: Willis + Tierney from Listing Office: Compass.
28 Aunt Ediths Rd, Yarmouth
$13,900,000
7 Beds ⋅ 10 Baths ⋅ 73580848 MLS
Set along the shores of historic Bass River, this extraordinary waterfront estate captures the rare combination of deep-water boating, exceptional privacy, and sweeping views toward Nantucket Sound. Set on .84 acres, the property offers 134 feet of private deep-water dockage, a private sandy beach, and direct access to one of Cape Cod's most distinctive waterways, where the river opens to Nantucket Sound. In addition to its own private beach and deep-water dock, the property also enjoys access to an association beach and secondary deep-water dock. An inground Gunite pool, oversized hot tub, and three-car attached garage complete an exceptional waterfront setting. Designed to embrace its spectacular waterfront setting, the residence is distinguished by beautiful architectural details, refined finishes, and exceptional craftsmanship throughout. The open floor plan features coffered ceilings and an abundance of waterside doors with transom windows, bringing natural light and the beauty of the river into the living spaces. The main level centers around an exceptional chef's kitchen with generous seating and top-of-the-line appliances, while elegant formal and informal spaces flow naturally to the waterside pool and entertaining areas. A luxurious first floor primary suite with a walk-in closet and beautifully appointed bathroom embrace the water views, while a second bedroom suite and home office complete the first floor. The second-floor features three waterside suites with private balconies and beautiful water views, along with two additional en-suite bedrooms and a generous media/game room. The third floor is designed for entertaining, with two bonus rooms and a full bar uniquely crafted in the style of a classic boat. Outside, the waterfront setting is designed for effortless summer living, with a Gunite pool, oversized hot tub, built-in grill, gas fire pits, and multiple seating areas overlooking the river. The grounds are beautifully landscaped and thoughtfully designed to create a sense of privacy, with mature natural screening surrounding the property. With its deep-water dock and boat lift, private beach, expansive river views, and easy access to Nantucket Sound, this remarkable estate offers a rare opportunity to experience Bass River at its finest—where Cape Cod's rich maritime heritage meets sophisticated contemporary waterfront living.

28 Aunt Ediths Rd, Yarmouth

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
28 Aunt Ediths Road, South Yarmouth
$13,900,000
7 Beds ⋅ 10 Baths ⋅ 22604811 MLS
Set along the shores of historic Bass River, this extraordinary waterfront estate captures the rare combination of deep-water boating, exceptional privacy, and sweeping views toward Nantucket Sound. Set on .84 acres, the property offers 134 feet of private deep-water dockage, a private sandy beach, and direct access to one of Cape Cod's most distinctive waterways, where the river opens to Nantucket Sound. In addition to its own private beach and deep-water dock, the property also enjoys access to an association beach and secondary deep-water dock. An inground Gunite pool, oversized hot tub, and three-car attached garage complete an exceptional waterfront setting. Designed to embrace its spectacular waterfront setting, the residence is distinguished by beautiful architectural details, refined finishes, and exceptional craftsmanship throughout. The open floor plan features coffered ceilings and an abundance of waterside doors with transom windows, bringing natural light and the beauty of the river into the living spaces. The main level centers around an exceptional chef's kitchen with generous seating and top-of-the-line appliances, while elegant formal and informal spaces flow naturally to the waterside pool and entertaining areas. A luxurious first floor primary suite with a walk-in closet and beautifully appointed bathroom embrace the water views, while a second bedroom suite and home office complete the first floor. The second-floor features three waterside suites with private balconies and beautiful water views, along with two additional en-suite bedrooms and a generous media/game room. The third floor is designed for entertaining, with two bonus rooms and a full bar uniquely crafted in the style of a classic boat. Outside, the waterfront setting is designed for effortless summer living, with a Gunite pool, oversized hot tub, built-in grill, gas fire pits, and multiple seating areas overlooking the river. The grounds are beautifully landscaped and thoughtfully designed to create a sense of privacy, with mature natural screening surrounding the property. With its deep-water dock and boat lift, private beach, expansive river views, and easy access to Nantucket Sound, this remarkable estate offers a rare opportunity to experience Bass River at its finest—where Cape Cod's rich maritime heritage meets sophisticated contemporary waterfront living. 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.

28 Aunt Ediths Road, South Yarmouth

Listing courtesy of Listing Agent: Robert B Kinlin (rkinlin@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
14 & 20 Gateway Rd, Wolfeboro
$13,900,000
9 Beds ⋅ 11 Baths ⋅ 5108354 MLS
There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.

14 & 20 Gateway Rd, Wolfeboro

Listing courtesy of Margot Skelley from Compass New England, LLC. ()
157 Bridge Street, Chatham
$12,999,900
4 Beds ⋅ 7 Baths ⋅ 22601380 MLS
In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the residence is a study in refined elegance and thoughtful scale. Every detail has been curated for a sense of timeless sophistication while embracing the natural beauty of its surroundings. The main level unfolds with effortless grace, where a grand open-concept kitchen and great room--anchored by one of four gas fireplaces--serves as the heart of the home. A formal dining room, butler's pantry, and coffee bar create an environment equally suited for intimate gatherings and elevated entertaining. Bathed in natural light, the breakfast room offers serene views over the resort-caliber outdoor setting, where a 16' x 36' Gunite pool with integrated spa and sun shelf, is set against the tranquil backdrop of the Mitchell River. The first-floor primary suite is a private sanctuary, appointed with a a spa-quality bath featuring radiant heated floors, a soaking tub, and a glass-enclosed shower. The upper level reveals a dramatic loft retreat with fireplace, wet bar, and private deck--an ideal vantage point to take in sweeping water views. A second primary suite, equally refined, is complemented by two additional guest bedrooms and baths. Above the garage, a substantial bonus room with its own deck captures panoramic vistas of Stage Harbor and the historic Chatham Coast Guard Boathouse. This home is further distinguished by its exceptional level of finish and infrastructure, including Wolf appliances, curated fixtures, central vacuum, whole-house generator, 400-amp electrical service, and professionally landscaped grounds supported by a private irrigation well. An outdoor shower completes the effortless indoor-outdoor lifestyle. A singular offering of enduring quality and provenance--this is more than a home; it's a legacy property in one of Cape Cod's most treasured waterfront settings.

157 Bridge Street, Chatham

Listing courtesy of Listing Agent: The Grattan Group (dgrattan@cireab.com) from Listing Office: Christie's International Real Estate Atlantic Brokerage.
35 Raven Rock Rd, Roxbury
$12,995,000
5 Beds ⋅ 8 Baths ⋅ 24216276 MLS
Privately set at the crest of a hill beyond a gated drive, 35 Raven Rock Road commands breathtaking views across miles of bucolic Litchfield County countryside and the Shepaug River Valley. Spanning over 114 acres, this exceptional country compound offers extraordinary privacy, with 20+ acres of cultivated lawns, extensive gardens, sculptures, pond and specimen trees creating a remarkable estate setting. Built in 2002, the approximately 13,600 SF stone and slate residence pairs gracious proportions with exquisite finishes, superb custom millwork, marble floors, and 8 fireplaces. A marble entry hall leads to an elegant living room opening onto an expansive stone terrace overlooking the grounds and countryside. A formal dining room, paneled library and inviting family room adjoining a heated porch provide beautiful settings for entertaining and everyday living. The chef's kitchen features a professional range, Traulsen refrigeration and a separate cooking room with charbroilers and a stone pizza oven. The main-level primary suite offers a fireplace, dual walk-in closets, separate water closets and a marble bath. Four additional bedrooms feature en suite baths, complemented by an upstairs media/rec room. The finished lower level includes a gym, steam room, cedar closets and wine cellar. A heated pool, pool house, Har-Tru tennis court, 4-car garage with guest quarters and heated barn enrich the estate. Major infrastructure upgrade includes newly installed additional well system.

35 Raven Rock Rd, Roxbury

Listing courtesy of Jeffrey Jackson from Corcoran Centric Realty. (917) 846-5599 (203) 625-9500
209-209 Long Neck Point Rd, Darien
$12,995,000
5 Beds ⋅ 8 Baths ⋅ 24187039 MLS
This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property.

209-209 Long Neck Point Rd, Darien

Listing courtesy of Shelly Tretter Lynch from Compass Connecticut, LLC. (203) 550-8508 (203) 343-0141

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