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$49,000,000

Great Point is an unprecedented coastal estate encompassing a total of ~32 acres and 5 individual parcels within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. This extraordinary property offers location, scale, privacy, and natural beauty, with architecturally significant residences and the rare opportunity to create three additional homes. More than 2,500 feet of private shoreline frame pristine waters, sweeping Atlantic Ocean views, and a private walking path to the South Shore's miles of unspoiled sandy beaches. Mature trees, open pastures, organic gardens, and a protected waterfront setting create one of Martha's Vineyard's most remarkable landscapes. Recently completed residences blend natural materials, expansive walls of glass, and exceptional craftsmanship, creating a seamless connection between architecture and nature. Great Point offers a multi-generational coastal compound in a setting that could not be replicated today.

12 Beds ⋅ 14 Baths

Great Point is an unprecedented coastal estate encompassing a total of ~32 acres and 5 individual parcels within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. This extraordinary property offers location, scale, privacy, and natural beauty, with architecturally significant residences and the rare opportunity to create three additional homes. More than 2,500 feet of private shoreline frame pristine waters, sweeping Atlantic Ocean views, and a private walking path to the South Shore's miles of unspoiled sandy beaches. Mature trees, open pastures, organic gardens, and a protected waterfront setting create one of Martha's Vineyard's most remarkable landscapes. Recently completed residences blend natural materials, expansive walls of glass, and exceptional craftsmanship, creating a seamless connection between architecture and nature. Great Point offers a multi-generational coastal compound in a setting that could not be replicated today.

15 Forever Wild Way, Edgartown

Listing Courtesy of : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$45,000,000

A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

7 Beds ⋅ 13 Baths

A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

18 Point Inner Way, Chilmark

Listing Courtesy of : Alyssa Halisky ---- Wallace & Co. Sotheby's International Realty

$38,000,000

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.

5 Beds ⋅ 7 Baths

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 : Antonio Khoury ---- Serhant

$32,500,000

Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, private beaches, a rare walking path to the pristine South Shore, and a short bike ride to Edgartown Village. The estate is set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and open meadows. Bordering both the 900-acre Edgartown Great Pond and the Atlantic Ocean, Beach Farm includes a six-bedroom main residence completed in 2023 with expansive walls of glass that frame dramatic, panoramic views across the pond and ocean. Built to the highest standards by master craftsmen, the home is complemented by a three bedroom surf house with outdoor sauna, cold plunge, a workout barn, private walking trails, and secluded beaches.

9 Beds ⋅ 11 Baths

Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, private beaches, a rare walking path to the pristine South Shore, and a short bike ride to Edgartown Village. The estate is set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and open meadows. Bordering both the 900-acre Edgartown Great Pond and the Atlantic Ocean, Beach Farm includes a six-bedroom main residence completed in 2023 with expansive walls of glass that frame dramatic, panoramic views across the pond and ocean. Built to the highest standards by master craftsmen, the home is complemented by a three bedroom surf house with outdoor sauna, cold plunge, a workout barn, private walking trails, and secluded beaches.

61 Butlers Cove Road, Edgartown

Listing Courtesy of : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$29,000,000

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.

6 Beds ⋅ 8 Baths

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 : ---- Gibson Sotheby's International Realty

$22,990,000

Commanding one of the most extraordinary waterfront settings on Beverly’s famed Gold Coast, Rock Edge is a legendary Georgian Revival estate perched atop a dramatic rocky bluff with 400± feet of private beachfront and breathtaking ocean views. Originally built in 1904, this iconic residence has been masterfully restored and reimagined, seamlessly blending Gilded Age grandeur with exceptional modern luxury while preserving the estate’s remarkable architectural pedigree. Soaring 16-foot ceilings, richly scaled interiors, elegant oceanfront formal living and dining rooms, a stunning oceanfront veranda, and a spectacular 1,500± SQFT gourmet marble kitchen are just a few of the outstanding features of this magnificent property. Complete with a private guest wing, a separate carriage house, private beach access, restored cabanas, a pool and san unmatched seaside setting, Rock Edge represents a once-in-a-generation opportunity to own one of the North Shore’s most impressive waterfront estate.

13 Beds ⋅ 18 Baths

Commanding one of the most extraordinary waterfront settings on Beverly’s famed Gold Coast, Rock Edge is a legendary Georgian Revival estate perched atop a dramatic rocky bluff with 400± feet of private beachfront and breathtaking ocean views. Originally built in 1904, this iconic residence has been masterfully restored and reimagined, seamlessly blending Gilded Age grandeur with exceptional modern luxury while preserving the estate’s remarkable architectural pedigree. Soaring 16-foot ceilings, richly scaled interiors, elegant oceanfront formal living and dining rooms, a stunning oceanfront veranda, and a spectacular 1,500± SQFT gourmet marble kitchen are just a few of the outstanding features of this magnificent property. Complete with a private guest wing, a separate carriage house, private beach access, restored cabanas, a pool and san unmatched seaside setting, Rock Edge represents a once-in-a-generation opportunity to own one of the North Shore’s most impressive waterfront estate.

34 Paine Avenue, Beverly

Listing Courtesy of : Tracy Campion ---- Campion & Company Fine Homes Real Estate

$21,950,000

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.

6 Beds ⋅ 8 Baths

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 : Jeannemarie Conley ---- Compass

$21,500,000

Perched dramatically along the pristine Rye coastline, the oceanfront estate at 24 Straws Pointstands as a masterpiece of luxury on New Hampshire’s highly coveted and tightly held 18 miles of direct waterfront. Enjoying a rare geographic orientation, this legacy property commands breathtaking, sweeping panoramic views looking south all the way to the Massachusetts North Shore coastline. Adding to its unmatched exclusivity, the residence is one of only nine historic homes that directly abuts a magnificent, protected oceanfront common right to its front, ensuring an estate-like setting and a lifetime of unobstructed coastal beauty. Spanning over 7,000 SF of architectural craftsmanship, this residence presents an elegant 3-story silhouette from the front while cascading into 4 complete levels of oceanfront living from the back. The main entry level features a grand entry, sophisticated sitting room, private office, and a gourmet kitchen flowing into dining and family spaces facing the water. The home boasts 16 rooms, including 4 second-level en-suite bedrooms (septic officially approved for 4 bedrooms) and 6.5 baths. The incredibly versatile floor plan offers expansive flexible-use spaces for multi-generational living. The second floor includes a sitting room landing with a hall bath and a dedicated guest overflow room. The third floor reveals a private 3-room suite complete with an en-suite bath and laundry. The walk-out lower level adds an exercise room, full bath, and a spacious bunk room for guest overflow—exiting at grade to the oceanfront grounds. Inside, majestic living halls feature soaring ceilings. Outside, the private sanctuary is anchored by a heated, built-in swimming pool positioned to catch the sea breeze. 24 Straws Point offers privacy, timeless elegance, and a generational Seacoast living experience.

4 Beds ⋅ 7 Baths

Perched dramatically along the pristine Rye coastline, the oceanfront estate at 24 Straws Pointstands as a masterpiece of luxury on New Hampshire’s highly coveted and tightly held 18 miles of direct waterfront. Enjoying a rare geographic orientation, this legacy property commands breathtaking, sweeping panoramic views looking south all the way to the Massachusetts North Shore coastline. Adding to its unmatched exclusivity, the residence is one of only nine historic homes that directly abuts a magnificent, protected oceanfront common right to its front, ensuring an estate-like setting and a lifetime of unobstructed coastal beauty. Spanning over 7,000 SF of architectural craftsmanship, this residence presents an elegant 3-story silhouette from the front while cascading into 4 complete levels of oceanfront living from the back. The main entry level features a grand entry, sophisticated sitting room, private office, and a gourmet kitchen flowing into dining and family spaces facing the water. The home boasts 16 rooms, including 4 second-level en-suite bedrooms (septic officially approved for 4 bedrooms) and 6.5 baths. The incredibly versatile floor plan offers expansive flexible-use spaces for multi-generational living. The second floor includes a sitting room landing with a hall bath and a dedicated guest overflow room. The third floor reveals a private 3-room suite complete with an en-suite bath and laundry. The walk-out lower level adds an exercise room, full bath, and a spacious bunk room for guest overflow—exiting at grade to the oceanfront grounds. Inside, majestic living halls feature soaring ceilings. Outside, the private sanctuary is anchored by a heated, built-in swimming pool positioned to catch the sea breeze. 24 Straws Point offers privacy, timeless elegance, and a generational Seacoast living experience.

24 Straws Pt, Rye

Listing Courtesy of : Florence Ruffner ---- Ruffner Real Estate, LLC florenceruffner@gmail.com

$21,500,000

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.

10 Beds ⋅ 14 Baths

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 : Alyssa Halisky ---- Wallace & Co. Sotheby's International Realty

$21,500,000

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. This inimitable compound features a seven-bedroom main residence and a guest house with four bedrooms and two separate apartments with private entrance, providing refined accommodations for multi-generational living and staff. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

13 Beds ⋅ 14 Baths

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. This inimitable compound features a seven-bedroom main residence and a guest house with four bedrooms and two separate apartments with private entrance, providing refined accommodations for multi-generational living and staff. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

151 & 155 Irving Avenue, Barnstable

Listing Courtesy of : Paul E. Grover ----

$21,000,000

20 Crowninshield Road offers a rare chance to own an exceptional waterfront estate on 2.25 oceanfront acres in one of the North Shore's most coveted settings. Designed to maximize ocean views from nearly every room, this completely rebuilt, six-bedroom residence features six full baths, three half baths, 10-ft ceilings, radiant & central air, a chef's kitchen, private office, and a dramatic ribbon staircase with custom millwork and a seamless coplanar design throughout, offering effortless indoor-outdoor entertaining. An elevator and threshold-free layout offer effortless accessibility. The primary suite offers sweeping water views, 2 gas fireplaces, dual walk-ins, an Ipe deck, and a private outdoor shower. Amenities include a wine cellar, sauna, steam room, pool, grill station, and a hot tub beneath a retractable Ipe deck. Complete with a guest/staff suite, 4-car garage, landscaped grounds, and exclusive access to a neighborhood beach, dock, and mooring. Not in the FEMA flood zone.

6 Beds ⋅ 9 Baths

20 Crowninshield Road offers a rare chance to own an exceptional waterfront estate on 2.25 oceanfront acres in one of the North Shore's most coveted settings. Designed to maximize ocean views from nearly every room, this completely rebuilt, six-bedroom residence features six full baths, three half baths, 10-ft ceilings, radiant & central air, a chef's kitchen, private office, and a dramatic ribbon staircase with custom millwork and a seamless coplanar design throughout, offering effortless indoor-outdoor entertaining. An elevator and threshold-free layout offer effortless accessibility. The primary suite offers sweeping water views, 2 gas fireplaces, dual walk-ins, an Ipe deck, and a private outdoor shower. Amenities include a wine cellar, sauna, steam room, pool, grill station, and a hot tub beneath a retractable Ipe deck. Complete with a guest/staff suite, 4-car garage, landscaped grounds, and exclusive access to a neighborhood beach, dock, and mooring. Not in the FEMA flood zone.

20 Crowninshield Road, Marblehead

Listing Courtesy of : Steven White ---- William Raveis R.E. & Home Services

$17,999,000

Designed for both everyday living and exceptional entertaining, this rare new construction oceanfront estate offers a privately owned sandy beach & access to a deep-sea mooring. A dramatic double-height entry opens to light-filled living spaces with sweeping Atlantic views. The chef’s kitchen features dual Taj Mahal quartzite islands, professional-grade appliances, & butler’s pantry. Flow into a sunlit breakfast nook & family room w/ a cozy fireplace. Additional highlights include an oceanfront living room, full bar w/ wine storage, & a first-floor primary suite. A three stop elevator connects all levels. Upstairs, a stunning primary retreat offers a spa bath, dual closets, fireplace, balcony, beverage bar, & an office. Three additional en-suites, a 2nd floor sitting room & rooftop terrace complete this level. Lower level offers theater, golf simulator, gym, sauna, & wine room options. Pool, outdoor kitchen, fire pit, & 2 - (2) car garages complete this exceptional coastal offering.

5 Beds ⋅ 10 Baths

Designed for both everyday living and exceptional entertaining, this rare new construction oceanfront estate offers a privately owned sandy beach & access to a deep-sea mooring. A dramatic double-height entry opens to light-filled living spaces with sweeping Atlantic views. The chef’s kitchen features dual Taj Mahal quartzite islands, professional-grade appliances, & butler’s pantry. Flow into a sunlit breakfast nook & family room w/ a cozy fireplace. Additional highlights include an oceanfront living room, full bar w/ wine storage, & a first-floor primary suite. A three stop elevator connects all levels. Upstairs, a stunning primary retreat offers a spa bath, dual closets, fireplace, balcony, beverage bar, & an office. Three additional en-suites, a 2nd floor sitting room & rooftop terrace complete this level. Lower level offers theater, golf simulator, gym, sauna, & wine room options. Pool, outdoor kitchen, fire pit, & 2 - (2) car garages complete this exceptional coastal offering.

63 West St, Beverly

Listing Courtesy of : The Marrocco Group ---- Coldwell Banker Realty - Lexington

$17,995,000

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.

7 Beds ⋅ 10 Baths

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 : Beth Dickerson ---- Gibson Sotheby's International Realty

$17,500,000

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.

5 Beds ⋅ 6 Baths

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 : Lanse Robb ---- LandVest, Inc., Manchester -by-the-Sea

$16,980,000

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

7 Beds ⋅ 11 Baths

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

Listing Courtesy of : Tracy Campion ---- Campion & Company Fine Homes Real Estate

$16,900,000

A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the luxurious main level master suite, 7 full bathrooms, 3 half bathrooms, and an expansive 4-car garage. Designed by Thoughtforms, this home boasts an expansive open floor plan and luxurious craftmanship and attention to detail throughout. The fully finished lower level is equipped with a recreation room, wine cellar, full theater room, wet bar, steam room, and sauna. On the second floor, four bedrooms offer private en suite bathrooms. This exceptional home is a unique grand colonial estate for the discerning buyer set in one of the most highly desired locations in all of Weston

6 Beds ⋅ 10 Baths

A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the luxurious main level master suite, 7 full bathrooms, 3 half bathrooms, and an expansive 4-car garage. Designed by Thoughtforms, this home boasts an expansive open floor plan and luxurious craftmanship and attention to detail throughout. The fully finished lower level is equipped with a recreation room, wine cellar, full theater room, wet bar, steam room, and sauna. On the second floor, four bedrooms offer private en suite bathrooms. This exceptional home is a unique grand colonial estate for the discerning buyer set in one of the most highly desired locations in all of Weston

50 Winsor Way, Weston

Listing Courtesy of : Rose Hall ---- Blue Ocean Realty, LLC

$16,900,000

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.

8 Beds ⋅ 8 Baths

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 : Erin Hegarty ---- Donnelly + Co.

$16,500,000

Presenting an offering of rare distinction. Refined coastal living, classic architecture and impeccable craftsmanship blend to create a unique sense of privacy, elegance, and pleasure. Nestled upon the shores of iconic Bass River, bask in waterfront living in this exclusive legacy estate replete with exquisite gardens, spectacular pool and deep-water dock capable of accommodating a 90' yacht with additional space for two vessels. Beyond the gates, this private enclave encompasses a main house, carriage house, guest house and boathouse. The estate is set among lush plantings, intimate gardens, curated vistas, and secluded courtyards. The sun-drenched interiors boast a peaceful balance of function and modern refinement. Custom appointments, outstanding finishes and bespoke details, furnish exceptional continuity. A deep-water dock and elaborately designed pier, capable of welcoming a substantial yacht, offer direct access to Nantucket Sound and the Atlantic.

6 Beds ⋅ 10 Baths

Presenting an offering of rare distinction. Refined coastal living, classic architecture and impeccable craftsmanship blend to create a unique sense of privacy, elegance, and pleasure. Nestled upon the shores of iconic Bass River, bask in waterfront living in this exclusive legacy estate replete with exquisite gardens, spectacular pool and deep-water dock capable of accommodating a 90' yacht with additional space for two vessels. Beyond the gates, this private enclave encompasses a main house, carriage house, guest house and boathouse. The estate is set among lush plantings, intimate gardens, curated vistas, and secluded courtyards. The sun-drenched interiors boast a peaceful balance of function and modern refinement. Custom appointments, outstanding finishes and bespoke details, furnish exceptional continuity. A deep-water dock and elaborately designed pier, capable of welcoming a substantial yacht, offer direct access to Nantucket Sound and the Atlantic.

57 Uncle Barneys Rd, Dennis

Listing Courtesy of : Paul McCormick ---- Gibson Sotheby's International Realty

$16,500,000

As you pass through the gates of Staples Point, a sense of anticipation builds. The driveway winds past manicured lawns, hinting at the grandeur ahead. Then, the estate reveals itself--arguably the finest residence in Maine--where endless feet of bold ocean frontage meet the crashing waves in a dramatic, unforgettable scene. The expansive grounds unfold like a story of their own. Sculpted lawns flow toward the rugged coastline, and every turn offers a new view of the sea. The sound of surf, the scent of salt air, and the endless horizon create a rhythm that is both powerful and peaceful. A place where you can find complete relaxation. Envisioned by acclaimed architect Joe Waltman and masterfully constructed by Wright-Ryan, the home rises with quiet confidence. Seven bedrooms and many expansive living spaces are arranged to capture sweeping bold ocean views, while every detail reflects masterful craftsmanship and thoughtful design. At Staples Point, the coastline becomes more than a view--it's a way of life. Each wave, each breeze, and every sunlit moment reflects the rare beauty and timeless elegance of this extraordinary Maine estate. A once-in-a-lifetime opportunity to own a private coastal sanctuary where every detail has been crafted for a unique experience.

7 Beds ⋅ 8 Baths

As you pass through the gates of Staples Point, a sense of anticipation builds. The driveway winds past manicured lawns, hinting at the grandeur ahead. Then, the estate reveals itself--arguably the finest residence in Maine--where endless feet of bold ocean frontage meet the crashing waves in a dramatic, unforgettable scene. The expansive grounds unfold like a story of their own. Sculpted lawns flow toward the rugged coastline, and every turn offers a new view of the sea. The sound of surf, the scent of salt air, and the endless horizon create a rhythm that is both powerful and peaceful. A place where you can find complete relaxation. Envisioned by acclaimed architect Joe Waltman and masterfully constructed by Wright-Ryan, the home rises with quiet confidence. Seven bedrooms and many expansive living spaces are arranged to capture sweeping bold ocean views, while every detail reflects masterful craftsmanship and thoughtful design. At Staples Point, the coastline becomes more than a view--it's a way of life. Each wave, each breeze, and every sunlit moment reflects the rare beauty and timeless elegance of this extraordinary Maine estate. A once-in-a-lifetime opportunity to own a private coastal sanctuary where every detail has been crafted for a unique experience.

19 Cunner Ln, Cape Elizabeth

Listing courtesy of Legacy Properties Sotheby's International Realty.

$16,000,000

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.

6 Beds ⋅ 8 Baths

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 : Debby Belt ---- Hammond Residential Real Estate

$15,800,000

Set among the stately residences of historic Brattle Street, this completely renovated & pristine home offers approximately 9,594 square feet of elegant living space on a rare 0.41-acre corner lot in sought-after West Cambridge—moments from Harvard Squar/Charles River. Beautiful private yard w/ sports court, outdoor kitchen,heated garage. The interior blends timeless architectural character w/ modern sophistication, featuring nine-foot ceilings, custom millwork, wood floors, beautiful windows, 8 fireplaces that bring warmth throughout. A gracious foyer opens to expansive formal living & dining rooms ideal for entertaining, complemented by a fully renovated chef’s kitchen with island seating & casual dining area. A comfortable family room and den flow effortlessly to the outdoors & connect to a double mudroom offering abundant storage. The upper levels host 5 host 5 bedrooms all with ensuite baths, finished lower level, playroom, media, gym, sauna. Geothermal heat.

5 Beds ⋅ 8 Baths

Set among the stately residences of historic Brattle Street, this completely renovated & pristine home offers approximately 9,594 square feet of elegant living space on a rare 0.41-acre corner lot in sought-after West Cambridge—moments from Harvard Squar/Charles River. Beautiful private yard w/ sports court, outdoor kitchen,heated garage. The interior blends timeless architectural character w/ modern sophistication, featuring nine-foot ceilings, custom millwork, wood floors, beautiful windows, 8 fireplaces that bring warmth throughout. A gracious foyer opens to expansive formal living & dining rooms ideal for entertaining, complemented by a fully renovated chef’s kitchen with island seating & casual dining area. A comfortable family room and den flow effortlessly to the outdoors & connect to a double mudroom offering abundant storage. The upper levels host 5 host 5 bedrooms all with ensuite baths, finished lower level, playroom, media, gym, sauna. Geothermal heat.

157 Brattle Street, Cambridge

Listing Courtesy of : Cort LaBonte Coldren Coopersmith Group ---- Compass

$15,700,000

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

7 Beds ⋅ 10 Baths

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

172 Brattle Street, Cambridge

Listing Courtesy of : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$15,400,000

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.

6 Beds ⋅ 9 Baths

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 : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$15,000,000

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

5 Beds ⋅ 9 Baths

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 : Traci Howe ---- Gibson Sotheby's International Realty

$15,000,000

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.

7 Beds ⋅ 7 Baths

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 : Tracy Campion ---- Campion & Company Fine Homes Real Estate

$14,995,000

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

6 Beds ⋅ 8 Baths

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

33 Sears Rd, Brookline

Listing Courtesy of : The Sarkis Team ---- Douglas Elliman Real Estate - The Sarkis Team

$14,900,000

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.

5 Beds ⋅ 8 Baths

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 : Krista Julian ---- Coldwell Banker Realty - Manchester

$14,850,000

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.

6 Beds ⋅ 8 Baths

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 : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$14,850,000

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

7 Beds ⋅ 12 Baths

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

67 Byron Road, Weston

Listing Courtesy of : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$14,500,000

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

11 Beds ⋅ 13 Baths

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

10 & 12 Boldwater Road, Edgartown

Listing Courtesy of : Michael Carucci ---- Serhant