Feature Properties

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

$45,000,000

7 Beds ⋅ 13 Baths ⋅ 73523462 MLS

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 Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$38,000,000

5 Beds ⋅ 7 Baths ⋅ 73517239 MLS

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

55 Commonwealth Avenue, Boston

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

$32,500,000

9 Beds ⋅ 11 Baths ⋅ 73536859 MLS

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

$29,000,000

6 Beds ⋅ 8 Baths ⋅ 73401202 MLS

Step into a world of timeless elegance in this iconic English Revival Tudor. Prominently set high on a ridge abutting a tranquil pond and the lands surrounding the Weston Golf Club. The gated entry and winding approach reveal the commanding terraced property comprising over 6 secluded acres. The 1928 estate was originally designed by architect Eric Kibbon. A balance between modern comfort, beauty and continuity with the past was re-defined by visionary architect, Peter Pennoyer. The extensive restoration goes from the exterior red-clay masonry walls to meticulously re-building the interior living spaces. The curated finishes were precisely replicated from the new steel and Mahogany wood windows to the Ohio sandstone columns and millwork. The receiving court includes a carriage house, private entry to the guest residence and garage parking for 6 cars. Truly one of New England's unique suburban estates with easy access to Boston and Logan International Airport.

4 Willow Road, Weston

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

$22,990,000

13 Beds ⋅ 18 Baths ⋅ 73537578 MLS

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

$22,500,000

10 Beds ⋅ 11 Baths ⋅ 73535394 MLS

Bayberry Farm: an unparalleled 108-acre waterfront estate. Private, mile-long laneway meanders through pristine woodlands, past a picturesque lily pond, through fields of open pasture, as the residence rises provocatively on the horizon. Substantial and brilliantly designed, this dramatic illustration of New England Vernacular architecture is set on high presiding over the Sakonnet Passage and ocean beyond. The interior is just as meticulously executed as the exterior- intentionally designed to embrace the natural landscape and fully incorporate the bucolic surroundings with exceptional appointments throughout. Expansive entertaining spaces complement more classically scaled rooms, with walls of glass and intoxicating views. Numerous guest suites are found across the home’s several distinct wings, with a secluded primary suite found on the main level. Savor the epitome of coastal New England living at this exceptional, legacy-quality estate…

441 W Main Road, Little Compton

Listing courtesy of Listing Agent: William J. Milbury from Listing Office: Milbury and Company.

$21,950,000

6 Beds ⋅ 8 Baths ⋅ 73527728 MLS

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

129 Commonwealth Avenue, Boston

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

$21,500,000

10 Beds ⋅ 14 Baths ⋅ 73517157 MLS

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

56 North Summer Street, Edgartown

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$21,500,000

13 Beds ⋅ 14 Baths ⋅ 73457530 MLS

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

$21,000,000

6 Beds ⋅ 9 Baths ⋅ 73539974 MLS

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 Listing Agent: Steven White from Listing Office: William Raveis R.E. & Home Services.

$17,999,000

5 Beds ⋅ 10 Baths ⋅ 73500949 MLS

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 Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

$17,995,000

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.

$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.

$16,980,000

7 Beds ⋅ 11 Baths ⋅ 73445544 MLS

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

$16,900,000

6 Beds ⋅ 10 Baths ⋅ 73550581 MLS

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

$16,900,000

8 Beds ⋅ 8 Baths ⋅ 73485121 MLS

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana—an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location.

114 North Water Street, Edgartown

Listing courtesy of Listing Agent: Erin Hegarty from Listing Office: Donnelly + Co..

$16,500,000

6 Beds ⋅ 10 Baths ⋅ 73540259 MLS

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

$16,500,000

7 Beds ⋅ 8 Baths ⋅ 1660105 MLS

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

6 Beds ⋅ 8 Baths ⋅ 73480812 MLS

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Debby Belt from Listing Office: Hammond Residential Real Estate.

$15,800,000

5 Beds ⋅ 8 Baths ⋅ 73487660 MLS

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

$15,700,000

7 Beds ⋅ 10 Baths ⋅ 73342079 MLS

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

$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.

$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.

$15,000,000

7 Beds ⋅ 7 Baths ⋅ 73531926 MLS

Introducing Windover, a grand Georgian estate, meticulously restored and reimagined for modern living. Approached through 5 acres of conservation land, and set atop a private, tree-lined drive, the property commands an immediate sense of arrival. Refined outdoor features include expansive terraces, a secluded walled garden, and a dogwood orchard. A pool house and heated saltwater pool overlook a tranquil pond, creating a resort-like setting. The interior is expansive yet remarkably intimate. A dramatic Mediterranean-style ballroom anchors the entertaining spaces, while the living and dining rooms open to terraces, framing the surrounding landscape at every turn. The luxurious primary suite offers a private retreat; a versatile third-floor suite accommodates guests or live-in staff with ease. A dedicated media room and home gym — with steam shower and sauna — round out the experience. Windover is a property of architectural distinction, enduring beauty, and total seclusion.

15 Farm Street, Dover

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

$14,995,000

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

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

$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.

$14,850,000

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

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

$14,850,000

7 Beds ⋅ 12 Baths ⋅ 73493889 MLS

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

$14,500,000

11 Beds ⋅ 13 Baths ⋅ 73552898 MLS

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 Listing Agent: Michael Carucci from Listing Office: Serhant.

$14,500,000

19 Beds ⋅ 25 Baths ⋅ 73544510 MLS

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.

$14,500,000

10 Beds ⋅ 8 Baths ⋅ 1665104 MLS

Set on 177± acres of exceptional island landscape, Waterman Farm offers spectacular panoramic views to the south and east toward the Fox Island Thorofare and Penobscot Bay. Perched on a secluded point of land, this classic saltwater farm features 8,582± feet of shorefront with access to both the protected Cubby Hole and Waterman Cove. The quintessential island setting is stunning, with open fields, woods, gardens, orchards, and five historic and distinguished residences, each fully renovated with year-round living space. Requisite estate infrastructure includes a historic barn, a sawmill where much of the wood for the property was harvested and milled, a versatile Quonset hut, and more. A dock with ramp, float, and mooring on Waterman Cove offers access to world-class boating around the island, along the Fox Island Thorofare, and throughout Penobscot Bay. Suitable for agricultural pursuits, residential living, or a family compound, Waterman Farm's significant contiguous acreage, sensitive restoration, and thoughtful stewardship present a rare opportunity to own a true piece of North Haven's legacy.

148 Waterman Farm Rd, North Haven

Listing courtesy of LandVest, Inc..

$14,500,000

5 Beds ⋅ 8 Baths ⋅ 73527740 MLS

Introducing the Alexander Forbes Mansion, a magnificent estate set on 6 beautiful acres in the historic and highly desirable Scott’s Woods district of Milton. This exceptional home showcases every modern amenity and has been meticulously renovated inside and out to the highest standards. The main level features a grand foyer, striking staircase, dramatic floor-to-ceiling windows and doors, formal living and dining rooms, an open kitchen and family room, solarium, home office, and a mudroom with access to the 3-car garage. On the 2nd floor, 5 bedroom suites include the luxurious primary suite with a spa-like bath and separate dressing rooms. The impeccably landscaped grounds offer a private utopia, featuring a heated in-ground pool, multiple patios and seating areas, garden area, grill, fire pit, tennis court, and a carriage house. Located at the foot of the Blue Hills, this outstanding home is minutes from top schools including Milton Academy and just eight miles from downtown Boston.

610 Harland Street, Milton

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

$14,000,000

4 Beds ⋅ 6 Baths ⋅ 1668255 MLS

As the sun rises over Casco Bay, islands emerge through the morning mist and the day slowly comes to life. Eagles soar across the bay while a lobsterman works quietly on the water and a paddleboarder drifts along the shoreline. Watching the sun rise over Casco Bay, it is easy to understand why Maine has long been called the Land of Dawn. Connected to the mainland by a private causeway, 90 Cornfield Point extends into Casco Bay on more than seven acres and over 3,000 feet of private coastline. Ancient oaks, shaped by salt air and ocean winds, rise above the peninsula as they have for generations. Beneath their broad canopies, gentle paths lead to sandy beaches, rocky ledges, and quiet coves made for swimming. Surrounded by water on nearly every side, the land offers a remarkable sense of privacy and a deep connection to the sea, qualities rarely found together along the Maine coast. From sunrise to sunset, the beaches invite the rituals of summer - building sandcastles at the water's edge and gathering around a midsummer bonfire as the longest day slowly gives way to night. Here, the sea still sets the rhythm of the day. A deepwater dock provides access to Casco Bay at all tides, making it easy to spend the afternoon exploring the islands, dropping anchor in a quiet cove, or enjoying a picnic on a secluded beach. At the heart of the peninsula, this Maine coastal home and a timber-frame barn overlook the bay from one of the most remarkable private settings on the Maine coast. Sweeping water views in every direction create the kind of place where life's most meaningful moments seem to find their way and a family legacy is built for generations to come. Less than thirty minutes from Portland and the International Jetport, 90 Cornfield Point remains a private peninsula shaped by the sea, defined by light, and rooted in the rhythms of Casco Bay.

90 Cornfield Pt, Yarmouth

Listing courtesy of Legacy Properties Sotheby's International Realty.

$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.

$13,950,000

10 Beds ⋅ 9 Baths ⋅ 73527306 MLS

In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with its existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon point is a special place, and with its pristine shorelines along Nantucket Sound, this property is full of opportunities for you to add your custom renovations and more.

190 Vineyard Road, Barnstable

Listing courtesy of Listing Agent: George Moussa from Listing Office: LAER Realty Partners.

$13,900,000

7 Beds ⋅ 7 Baths ⋅ 73444242 MLS

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

153 Brattle St, Cambridge

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

$12,995,000

6 Beds ⋅ 7 Baths ⋅ 73516411 MLS

A masterpiece by Cafasso Design Group, this architectural work of art redefines luxury living. Tucked within a coveted enclave off Brattle Street, this home unfolds across lush, sculpted grounds framed by mature trees, offering an unparalleled serene retreat. A striking sculptural staircase serves as the dramatic centerpiece, while interiors masterfully blend contemporary Japanese, Scandinavian, Italian, and French influences.The eat-in chef’s kitchen features custom Italian walnut cabinetry, Calacatta Gold marble counters, dual sinks & dishwashers, a Gaggenau 400 Series double oven, and walls of glass. Generous bedrooms and spa-inspired baths deliver sanctuary, complemented by a glass-enclosed office and a family room featuring a floating gas fireplace. A dedicated lifestyle level boasts a gym, guest suite, and inviting spa with a Western Red Cedar sauna & steam shower. Outside, manicured grounds surround an outdoor kitchen, expansive deck, and inviting patio perfect for entertaining.

11 Brown Street, Cambridge

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

$12,995,000

4 Beds ⋅ 8 Baths ⋅ 73499377 MLS

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

25 North Pasture Lane, Nantucket

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

$12,985,000

7 Beds ⋅ 11 Baths ⋅ 73511402 MLS

This sensational oceanfront estate is located in the coveted, gated beachfront community of Nonquitt. The 7+ bed Main House boasts breathtaking water views through expansive walls of glass, while the guest and pool houses are seamlessly integrated to create a one-of-a-kind coastal retreat. Light-filled living and dining spaces are designed for effortless indoor-outdoor living and entertaining, flowing beautifully onto patios and poolside areas. The detached garage includes the fully equipped guest suite with a bedroom, sitting room, full bath, washer and dryer. Set behind a tall privet hedge and surrounded by natural beauty, this custom home was recently built by Parker Construction with top finishes throughout. Resort-style grounds include level lawns, elegant hardscapes, and a stunning infinity-edge pool and spa overlooking a private beach and the shimmering sea beyond. Nonquitt blends laid-back coastal charm with exclusive amenities including golf, tennis, and sailing.

1 Mattarest Lane, Dartmouth

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

$12,950,000

5 Beds ⋅ 7 Baths ⋅ 73489042 MLS

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool area. The main living spaces balance comfort and sophistication with warm wood floors, curated finishes, and multiple gathering areas, including a lower level with a glass-enclosed wine room, custom bar, game area, and media lounge. The kitchen features sleek cabinetry, open shelving, and picture windows overlooking the landscape, while bedrooms serve as private retreats complemented by spa-quality baths. Outside, panoramic water views unfold as a private stairway leads to the shoreline. A detached two-car garage with a guest suite above adds flexibility, completing this exceptional offering.

301 Whidah Road, Chatham

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

$12,900,000

5 Beds ⋅ 8 Baths ⋅ 73473428 MLS

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

55-57 Hancock St, Boston

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

$12,750,000

10 Beds ⋅ 11 Baths ⋅ 1655480 MLS

Just imagine spending Summers in the magical village of Seal Harbor on Mount Desert Island. The current residents named this extraordinary place Wanakiwin. Which means '' harmony, peace and tranquility.'' This enchanting estate by the sea transports you with its secluded driveway that winds through a pristine woodland of mosses and lichen-covered boulders as the majestic residence comes into view. You have arrived at this architectural tour-de-force. Distinctly drawn in the highest order of shingle-style the home is dramatically anchored to what is perhaps the most magnificent parcel along the entire Maine coastline. Upon entering, the three-story fir-paneled hall is flanked by a massive staircase fashioned from white oak. Two steps down into the grand living room reveal a pleasing fireplace to the left and a pair of French doors leading out to the sprawling covered porch. Take in the sweeping panoramic views of 780' glittering ocean frontage that merges with the rugged pink granite bluff known as Ingraham Point. All while perched high and dry above the bold Atlantic. Welcome multiple generations to partake in all of the captivating ocean view bedrooms. Here, the Owners' suite boasts cathedral ceilings and its very own waterside balcony. A charming country kitchen with a gas-fired range adjoins a soaring breakfast space. The dining room features a boxed-beamed ceiling and offers yet another cozy fireplace. A library with built-ins is paired next to the den which is trimmed in mahogany and beadboard reminiscent of the captains' quarters aboard a ship. There is an arts & crafts space, a lower-level gym, and an extensive wine cellar. Explore the epic grandeur of nearby Acadia, including Sand Beach, nature hikes, popovers at the Jordan Pond House and amazing sunsets atop Cadillac Mountain. Invite company over for a Gatsby era soiree' in the gardens while overlooking the majestic surf below. Embrace it all and make it yours. Three room staff quarters.

93 Cooksey Dr, Mount Desert

Listing courtesy of Legacy Properties Sotheby's International Realty.

$12,500,000

8 Beds ⋅ 7 Baths ⋅ 1667981 MLS

Perched high atop dramatic granite cliffs on Maine's Bold Coast, 'Sea Ledges' is an extraordinary 172-acre compound with over 1.2 miles of diverse ocean frontage. Few homes on the Eastern Seaboard sit as high over the open ocean. Because the deep Atlantic runs straight to the rock face, massive storm swells hit with unfiltered force, exploding into the air for an unbelievable front-row spectacle. The acoustic backdrop is captivating, defined by the deep-ocean surge. During rough seas, the home provides the ultimate experience of the Atlantic's raw power, allowing you to hear the thunderous boom resonating through the cliffs right from inside the house, joined by the whistle of coastal winds and nesting seabird calls. It feels like a private national park, boasting over 8 miles of maintained trails for world-class hiking and rugged rock traversing. This multi-tiered network lets you climb upper ridges for vast horizons, navigate technical descending pathways to conquer the granite face, or step onto unique, private cobble beaches tucked between coves where you can safely enter the ocean waters. The meticulously renovated main residence frames these views from every room, crowned by a 4th-story 'Eagles Nest' tower sitting top of the tree canopy. Enjoy cinematic views of Old Man Island--showcasing a striking, emerald-green Scottish grassland aesthetic--alongside Cross Island and the horizon toward Machias Seal Island, a famous sanctuary for bald eagles, puffins, and rare razorbills. For monumental upside, 5 additional premier cliffside lots feature grandfathered, pre-approved building footprints that are already blasted and cleared. An unmatched legacy estate.

214 Sea Ledges Rd, Cutler

Listing courtesy of www.HomeZu.com. 877-249-5478

$12,500,000

5 Beds ⋅ 4 Baths ⋅ 73516310 MLS

Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops, custom cabinetry, premium appliances, and a walk-in pantry. Spacious living areas and a serene primary suite capture breathtaking Atlantic Ocean views. Additional bedrooms occupy a separate wing for added privacy. Outdoors, organic landscaping, historic stone walls, colorful gardens, fenced pasture, and expansive decks create a peaceful setting for entertaining or stargazing. Ownership includes exclusive access to scenic trails, pond launches, and a private beach. Smart features include Nest thermostats and a HEOS sound system, completing this exceptional Vineyard lifestyle to treasure always.

18 Spruce Gate Road, Chilmark

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$12,500,000

8 Beds ⋅ 10 Baths ⋅ 73496953 MLS

Set on exquisitely landscaped, private grounds overlooking Brae Burn Country Club, this stunning estate delivers sophisticated living at every turn. The first floor flows through gracious living and dining rooms, a handsome paneled library, chef's kitchen, family room, two powder rooms, mudroom, and garage. The primary suite is a sanctuary — dressing room, spa bath, bonus room, and a private balcony with sweeping views. Five additional bedroom suites complete the second floor; a third-floor guest suite with ensuite offers privacy and comfort for visitors. The lower level is extraordinary: indoor pool, regulation squash court, gym, sauna, wet bar, home theatre, game room, and guest suite. Elevator to three main floors. A heated three-car garage and heated driveway complete the home. Easy access to the Pike and Route 128, while maintaining a peaceful, private setting. Few properties in the area offer this level of scale, finish, and amenity.

148 Dartmouth Street, Newton

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

$12,250,000

7 Beds ⋅ 9 Baths ⋅ 73551533 MLS

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

39 Naushon S, Falmouth

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

$12,250,000

5 Beds ⋅ 6 Baths ⋅ 73342640 MLS

Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite center island, custom built-ins, and a charming breakfast nook with wraparound picture windows framing the breathtaking waterfront vistas. The sumptuous first-floor primary suite is a sanctuary of relaxation, offering private patio access, a spacious walk-in closet, and a spa-inspired en-suite with dual vanities, a luxurious soaking tub, and a glassless double-headed rain shower. The sun-drenched sunroom complete with a full wet bar and sliders on three sides opens directly to the meticulously designed outdoor living areas. The second level hosts four additional spacious bedrooms, a generous family room, and a bonus room with a private balcony, designed for both comfort and relaxation. This exceptional residence also features a partially finished lower level, thoughtfully designed to enhance both convenience and functionality with direct outdoor access perfect for accommodating small boats, golf carts and other recreational essentials. Set on 1.37 acres of pristine coastal land, this estate is an outdoor enthusiast's paradise. The meticulously landscaped grounds feature a built-in fire pit, an outdoor shower, a waterside in-ground pool, a sandy beach, and a private dock. A rare opportunity to own a world-class waterfront residence, this home delivers unparalleled elegance, modern luxuries, and the very best of Cape Cod's coastal living.

71 Sand Pt, Barnstable

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

$12,000,000

4 Beds ⋅ 3 Baths ⋅ 73556482 MLS

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

166 Shore Road, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$11,995,000

5 Beds ⋅ 4 Baths ⋅ 73537406 MLS

Tracing its roots to a classic Cape house and fishing shack in Provincetown's historic West End, this remarkable waterfront residence was elevated and transformed through an extensive restoration that preserved its authentic architectural character while reimagining the property for a new generation. Structural pilings and timbers salvaged from Boston's famed Jimmy's Harborside Restaurant were masterfully incorporated into the staircase and ceiling details. Rich pine floors, a rugged fieldstone fireplace, a custom Vermont marble kitchen with a soapstone island, a generous pantry, a waterfront dining room, and a harbor-facing sitting room define the interior layout. A rare and defining feature is the property's extraordinary private dock--the largest associated with any single-family residence in Provincetown--extending approximately 70 feet into the harbor and providing an unparalleled connection to the waterfront.

71 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.

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