18,263 Brighton MA Homes Built 1990 1999

 Refine Search
Map
Sort by
$17,200,000
3 Beds ⋅ 4 Baths ⋅ 73473626 MLS
Penthouse Flat 5802 is an exquisitely renovated 3 bedroom 3.5 bathroom that has been completely customized by a premier custom home builder. This sprawling 4,152+/- sq ft home offers direct elevator access, a private balcony, sensational eastern views of Boston Harbor and northerly views of the Charles River. An exceptional floor plan is complete with large private foyer, 3 generous bedroom suites, including a large primary with 5 piece marble bathroom and 2 walk in closets. A banquet sized corner exposed living room is complete with a gas fireplace, private balcony, cascading views, and a custom wall of glass that opens to a large formal dining room. A top-of-the-line eat in kitchen has amazing views, center island and marble counters. Complete with automatic shades throughout, custom lighting, wine storage, private storage room, 24 hour Four Seasons Hotel Services available, fitness center, Access to Four Seasons Spa, Zuma and 2 Garage Parking Spaces!

1 Dalton St Unit 5802, Boston

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$17,000,000
3 Beds ⋅ 4 Baths ⋅ 73467086 MLS
Rare, front-facing corner residence on the 11th floor of The Carlton House in Back Bay, Boston’s premier full service building located directly above the Public Garden and connected to the Newbury Hotel. This 3-bed, 3.5 bath home offers 3,870 SQFT of living space with oversized, picture windows that frame breathtaking Back Bay views from every room. The entire residence just underwent a complete renovation by renowned builder Payne Bouchier and architect Steve Hart. Outstanding features include a gracious entry foyer, spectacular front-facing entertaining rooms, elegant custom built-ins, gourmet eat-in kitchen, ample closets, and a luxurious primary suite complete with a marble bath, expansive walk-in closets and dazzling views. Available to residents are a complete array of exclusive services including 24 hour concierge, valet parking, elegantly appointed common areas and Newbury Hotel services. Complete with 3 garage parking spaces, this residence is among the finest in the city.

2 Commonwealth Avenue Unit 11BCD, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$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.
$16,000,000
49 Beds ⋅ 43 Baths ⋅ 73546201 MLS
Rare Portfolio Offering: 36 College Avenue in Somerville is part of a three-building portfolio for sale, which also includes 202-218 Mass Ave. in Arlington and 49–55 Davis Square in Somerville. 36 College Avenue, known as the Bryant Chambers building, is a 44-unit, five-story brick apartment building in the heart of Davis Square. Located at the corner of College Avenue and Park Avenue, the property is steps from the MBTA Red Line and within walking distance of Tufts University. Built in the 1920s, the building features classic brick architecture with windows on all four sides, providing abundant natural light. The unit mix includes (3) studios, (34) one-bedroom apartments, (6) two-bedroom apartments, and (1) commercial space. Amenities include an elevator, on-site laundry, keyless FOB entry, and storage. The property offers stable in-place cash flow, a strong occupancy history, and long-term value-add potential through strategic management. PLEASE SEE FIRM REMARKS FOR ADDITIONAL INFO

36 College Ave, Somerville

Listing courtesy of Listing Agent: Carl Christie from Listing Office: Carl Christie.
$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.
$15,800,000
3 Beds ⋅ 4 Baths ⋅ 73473565 MLS
Exquisite 58th floor 3 bed, 3.5 bath home that has been completely customized and fully renovated by premier custom builder. This "Penthouse Flat" at the top of the 1 Dalton tower boats commanding Western facing views of the Charles River to Cambridge and beyond. Offering direct elevator access into a private foyer with walk in coat room, this sensational corner home is flooded with natural light. An open concept living space has a corner exposure, large eat in kitchen with breakfast bar and window bar, onyx counters and top-of-the line appliances. Three generous bedrooms are complete with en sure baths including an ultra luxurious primary suite with 5 piece marble bathroom. 24 hour Four Seasons Hotel services available, concierge, 50th floor Residents Only club, state-of-the-art fitness center, access to the Four Seasons spa, and Zuma. This ultra luxurious home is complete with private storage and 2 garage parking spaces!

1 Dalton St Unit 5801, Boston

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$15,750,000
79 Beds ⋅ 31 Baths ⋅ 73554361 MLS
Rare opportunity to acquire a generational asset in the heart of Washington Sq., Brookline. Just a stone’s throw away from Beacon St. – 10-24 University Rd. is positioned alongside one of the most transit-oriented throughfares in/around Greater Boston, providing immediate MBTA access to major universities, like BU, Northeastern and Wentworth, the Longwood Medical Area and the many tech and engineering hubs in Kenmore Sq./Downtown Boston. Addressed as 10-12, 16-18 and 22-24 University Rd., the offering consists of three (3) 7-unit buildings and eleven (11) surface level parking spaces on contiguous parcels spanning 23,479 sq./ft. in cumulative lot size. Gross building area within the shells of all three buildings amounts to 57,928 sq./ft. but twenty-one (21) residential units comprise 35,512 sq./ft. of living space, with eighteen (18) 4-5 bedroom dwellings across the first, second and third levels and three (3) 1-2 bedroom dwellings on the garden levels. While substantial value-add potential can be achieved by preserving the current building designs, additional opportunities may also exist by tapping into unutilized space on the fourth floors/garden levels, rearranging floorplans and/or increasing the total unit count.

10-24 University Rd., Brookline

Listing courtesy of Listing Agent: Joe Danisch from Listing Office: Coelho Realty Group LLC.
$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.
$15,500,000
3 Beds ⋅ 4 Baths ⋅ 73370409 MLS ⋅ ['Four Seasons Residences | One Dalton'] BLDG.
Welcome to the 56th floor of the Four Seasons Private Residences at One Dalton, New England’s tallest and most prestigious residential address. This 3-plus bedroom, 3.5 bath home encompasses over 4,000 SQFT wrapped in floor-to-ceiling windows providing unmatched and unobstructed views of Boston’s skyline including Back Bay, the Charles River, Cambridge, the South End and Boston Harbor. Exceptional features include a striking custom fireplace, custom overhead lighting, and expansive floor-to-ceiling windows that frame unobstructed vistas of the city and river. The thoughtfully designed floor plan includes private elevator access, an elegant entry rotunda, and a spacious living area that flows seamlessly into a custom gourmet kitchen. Residents will delight in the white glove services of the Four Seasons, access to 20,000 sqft of world-class amenities spanning three floors, and exquisite in-residence dining at the renowned Zuma restaurant.

1 Dalton St Unit U5602, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$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.
$14,800,000
3 Beds ⋅ 5 Baths ⋅ 73546677 MLS ⋅ ['Raffles Boston Back Bay Residences'] BLDG.
Welcome to Raffles Boston, the first North American residential destination from the world-renowned five-star Raffles Hotels & Resorts brand. This extraordinary corner penthouse residence pairs sophisticated interiors with panoramic views of Back Bay and the Charles River from its private terrace, all complemented by the impeccable service and elevated lifestyle synonymous with Raffles. An elegant formal entry welcomes you into beautifully appointed living spaces framed by floor-to-ceiling windows and anchored by a walnut kitchen with Stevali cabinetry, marble countertops, and a wet bar. The luxurious primary suite features expansive walk-in closets and a spa-inspired six-fixture bath. Residents enjoy an unmatched collection of world-class amenities, including acclaimed dining venues and bars, the renowned Guerlain Spa, a state-of-the-art fitness center with a 20-meter indoor pool, dedicated butler service, 24-hr concierge, and the legendary hospitality that defines the Raffles brand.

430 Stuart Street Unit PH35B, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$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
25 Baths ⋅ 73544528 MLS
The Wheatleigh: Former 5 Star Forbes Travel Property and 'Leading Hotel of the World', this Gilded Age masterpiece sits on over 21 acres overlooking Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. At Tanglewood's doorstep, this 25,000+SF architectural sanctuary marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, Parlors, 3 formal Dining Rooms, Wine Cellar (6,500-bottle capacity), meeting rooms, massage room, Gym, and 19 Guest suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the Pool and Tennis Court. This iconic Inn 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
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
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
73483108 MLS
Offers due May 12th, 2026. This is a combined sale including two buildings, 283-293 Second Ave and 179 & 202 Bear Hill Road in Waltham, MA. Additionally, 283-293 Second Ave is available to purchase individually (MLS #73483110). 179 & 202 Bear Hill Road in Waltham, MA can also be purchased individually.

283-293 Second Avenue, Waltham

Listing courtesy of Listing Agent: Jeremy Freid from Listing Office: 128 CRE.
$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.
$13,955,000
3 Beds ⋅ 5 Baths ⋅ 73549089 MLS ⋅ ['Millennium Residences @ Winthrop Center'] BLDG.
The life you want to live is here - The Millennium Residences at Winthrop Center Penthouse Collection. 61st floor 3 BR + Den + Flex Room, 4.5 BA home offers 12’ ceilings w/ panoramic West Sunset, to Boston Common, Charles River and City views. Christopher Peacock kitchen & bath cabinetry, wide-plank oak floors, marble baths, custom architectural details. Combining 5-star services with unprecedented residential amenities including stunning entry lobby & exclusive vehicle accessed lobby for weather-free arrival & departure, Winthrop Center offers 8 food & beverage spots, a next-generation office club & unrivaled live/work amenities including: 35th floor CLUB with owner’s lounge & bar; 2 sprawling outdoor terraces, screening room, FLX fitness, 75-foot indoor lap pool; Club VIPets, THE COLLECTIVE & more as the most evolved living experience Millennium has ever created transcends everything on the market today.

240 Devonshire Street Unit PH-MC 1B, Boston

Listing courtesy of Listing Agent: MP Boston Marketing Team from Listing Office: MP Boston Marketing LLC.
$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
3 Beds ⋅ 6 Baths ⋅ 73489081 MLS
A once in a generation opportunity to own a full floor at Le Jardin! Occupying more than 4,600 sq ft on a single living level this gracious home offers 20 oversized windows that wrap the home on 3 sides and flood the home with natural light. An unmatched 40' of frontage overlooking the historic Boston Public Garden, this one of a kind home has been exquisitely renovated and professionally maintained. Offering 3 bedroom suites + a den/4th bedroom, including an elegant primary suite with dual bathrooms, dual dressing rooms, a private library and an intimate sitting room with gas fireplace. A well designed layout offers grand entertaining spaces overlooking the park, a large eat-in kitchen with stone counters and abundant storage, many custom builtins throughout, a well designed wet bar located off the formal dining room, a large laundry room, & beautiful hardwood floors. 24-hour concierge, private elevator foyer, 4 garage parking spaces w Valet!

250 Boylston St Unit 2, Boston

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.