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South Shore MA Luxury Homes

Luxury HomeView current real estate listings for luxury homes on Massachusetts' South Shore below. You'll find a variety of beautiful homes in Milton, Quincy, Dorchester, South Boston, Weymouth, and beyond.

South Shore Luxury Homes for Sale

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835 Sea View Avenue Barnstable MA 02655

MLS Number 72933462

  • Residential
  • Bedrooms 7
  • Bathroom 14
  • Square Feet 15,500

Set on Osterville’s exclusive Sea View Avenue with commanding views over Nantucket Sound and an unprecedented 280 feet of private sandy beach, a once-in-a-lifetime coastal oasis awaits. Magnificent landscaping sets the stage, with specimen trees and lush plantings that offer total privacy across 3.66 acres. Designed in perfect harmony with its surroundings, virtually every room has ocean views and direct access to the outdoors. A thoughtful layout divides the residence into a main house and attached guest house with a total of 7 en suite bedrooms. Outdoor living is highlighted by a resort-style swimming pool, summer kitchen, and expansive terrace for sunbathing and al fresco dining. Additional amenities include a 5,000-bottle wine cellar, golf simulator, gym, massage room, 7 garage spaces, and a separate staff house. Located in one of New England’s most sought-after waterfront communities, this grand estate is minutes away from everything Osterville has to offer, yet a world apart.

Listed by Paul E. Grover of Berkshire Hathaway HomeServices Robert Paul Properties

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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151 Grove Street Westwood MA 02090

Westwood, MA151 Grove Street

Price$15,500,000

Est. Mortgage: $/month

MLS Number 72950372

  • Residential
  • Bedrooms 15
  • Bathroom 12
  • Square Feet 14,000
  • High School Westwood High

Welcome to Acorn Hill. This private gem is hidden right off of RT. 95. 27+ acres and one of the finest Estate properties in New England. Designed for family and friends, this "homey pastoral estate" provides comfortable spaces in the main house, in-law house, guest house, and caretaker house.Main house offers sunny foyer, his/her home offices, large living room, dining room with fireplace, cooks kitchen with fireplace and eat-in area, dog room and two pantry's. Adirondack room as it is called, is a slice of Vermont with a bar and outdoor fire pit.Second level offers Master suite includes Boudoir, his/her walk-in closets, large master bath with fireplace and roof deck access. Eight additional bedrooms, and third floor recreational space are offered.Enclosed breezeway to the separate in-law house is convenient and essential for live in family, it has three bedrooms, baths and more.Caretaker house, Barn (4 stall), tennis court/pool. This property is extremely private MUST be experienced.

Listed by Wendy Fox of Compass

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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395 Commonwealth Boston MA 02115

Boston, MA395 Commonwealth, Back Bay

Price$14,995,000

Est. Mortgage: $/month

MLS Number 73057384

  • Residential
  • Bedrooms 23
  • Bathroom 12
  • Square Feet 15,000

The Ayer Mansion is the only Tiffany-designed home in the world. Standing five stories on both Commonwealth Ave and Marlborough St, this is a rare opportunity to match a buyer’s vision with a uniquely modern design. Designed by Louis Comfort Tiffany, the sleek, pale façade with bright mosaic detail challenges the Boston streetscape as much now as it did at its unveiling in 1902. Entering the great hall, the eye is drawn to the tall fireplace, vaulted ceiling and up the imperial stairs under the proscenium arch of Tiffany mosaics tiles. At the top of the first landing and seen from the foot of the stairs, a trompe l’oeil Greek temple reflects unusual depth and light. With designs in place and an award-winning team of developers and architects assembled, this private residence will offer its next occupant the opportunity to reimagine this livable work of art. With each floor ranging in size from 2700sf to 3000sf, the conceptual redesign accommodates 6 bedrooms, 13 baths and 3-Car garage.

Listed by Greta Gustafson and Ruth Kennedy Sudduth of LandVest,Inc.

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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410 Beacon Street Boston MA 02115

Boston, MA410 Beacon Street, Back Bay

Price$14,950,000

Est. Mortgage: $/month

MLS Number 73033196

  • Residential
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 10,255

Contemporary luxury meets exceptional historic details in this exquisite Back Bay Townhouse! With over 10,000 SF of impeccably renovated living and entertaining spaces, this property is in a class of its own! With exceptional views of both the Charles River and Back Bay Skyline, this home comprises 7 bedrooms and 6 full, 2 half baths and has graciously proportioned rooms and a thoughtful layout. The designer chef’s kitchen with top of the line appliances opens directly onto a spectacular deck and patio, allowing for easy “indoor/outdoor” living. The top floor primary suite has multiple private patio spaces and a stunning skylight, bathing the spaces in natural light. The spacious gym has an attached full bath. The high level of sophisticated craftsmanship, elevator, 1 car garage (w/ 2 outdoor deeded spaces) and intricate details throughout, make this home a rare find indeed! This home is ideally situated in the heart of Back Bay and is in the center of everything Boston has to offer!

Listed by Maggie Gold Seelig of MGS Group Real Estate LTD

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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300 Summer Street Westwood MA 02090

Westwood, MA300 Summer Street

Price$13,200,000

Est. Mortgage: $/month

MLS Number 72999830

  • Residential
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 10,309
  • High School Westwood

This spectacular Rich Levey-designed contemporary is perfectly set at the end of a long winding drive on 31.43 secluded acres. It offers 10,000 sq ft of open living area, which takes advantage of long views over the infinity pool to a stream-fed pond with boat house. Inside, details such as floor-to-ceiling windows that rise to 20 ft heights, and a three-season porch create a seamless flow from outdoors to in. Thoughtfully conceived, with interior design by Meichi Peng, the house includes soaring Venetian plaster walls, porcelain tile floors with radiant heat, a stunning kitchen, a beautiful primary suite, plus 5 ensuite bedrooms including a connected 2-bedroom guest house. There is also a glass-enclosed wine cellar, a home theater, and gym. A workshop and studio space can be found in the 2,800 sq ft barn across the large circular driveway from the main house. This private estate offers an ideal work-from-home environment close to Boston.

Listed by John Boyle and Ruth Kennedy Sudduth of LandVest,Inc.

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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255 Bayberry Way Barnstable MA 02655

MLS Number 73016268

  • Residential
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 4,896

“Point House”: a spectacular 5.98-acre waterfront estate on a peninsula overlooking West Bay. In an unsurpassed setting, the 4,896 sq ft residence offers exceptional water vistas, gardens, an expansive private beach, and a substantial deep-water dock. The 6-bedroom home features generous living spaces, beautiful architectural detailing, custom flooring and 5 fireplaces. The foyer welcomes you to the views and impressive deck and beckons you to step outside to take in the panoramic vistas. Highlights include a light filled, 2 story great room with a floor-to-ceiling brick fireplace, well-equipped kitchen, dining area and a family room accented by a fireplace, all opening to the outside spaces. Two bedrooms and a sitting room with fireplace are on the 1st level. The primary bedroom features beautiful water views, a spacious bath, walk in closet and a sitting room with fireplace, and 3 bedrooms and a sitting room finish the 2nd level. A detached 2 car garage includes living space above.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Fairfield Street Boston MA 02116

Boston, MA1 Fairfield Street, Back Bay

Price$12,000,000

Est. Mortgage: $/month

MLS Number 73044264

  • Residential
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5,700

Rare, 30-foot wide, corner, single-family with in-law in the heart of the Back Bay and Boston’s most coveted neighborhood. This premiere home is ready for your custom finishes and a Spring 2023 occupancy. Bespoke custom renovations adorn this 5,700 square foot home featuring 6 bedrooms and 5.5 bathrooms and private entrance in-law/guest suite. Two parking spaces.

Listed by Michael Carucci of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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39 Union Park Boston MA 02118

Boston, MA39 Union Park, South End

Price$11,500,000

Est. Mortgage: $/month

MLS Number 73072884

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 5,833

This beautifully designed townhouse has been painstakingly renovated to the highest standards by StudioDykas. Located on picturesque Union Park, the six floors reflect a balance of European design and modern finishes, making it a perfect blend of sophistication and comfort. The home encompasses 5 bedrooms and 6 full bathrooms, an elegant living and dining room floor with high ceilings, crown moldings and oversized windows. The custom kitchen offers flat paneled walnut cabinets, large island for entertaining and a beautiful adjoining family room and balcony. The primary bedroom and bath boast a calm, tranquility, reminiscent of a world class boutique hotel, featuring an oversized shower, separate standing deep soaking tub, and a large custom closet. This is truly a one-of-a-kind home. One deeded parking space at Rollins Square included.

Listed by John Corcoran of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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194 Beacon Street Boston MA 02116

Boston, MA194 Beacon Street, Back Bay

Price$11,200,000

Est. Mortgage: $/month

MLS Number 73057659

  • Residential
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 7,339

Exceptional and extraordinary opportunity for a buyer to convert a 5 unit building into a trophy single family home. This Riverside Beacon Street building is for sale with 7339 sq feet of gross living area over 7 stories & RIVER VIEWS from 6 of the 7 living levels. 5 CAR PARKING in total w/4 garage spaces & 1 exterior space. This property currently consists of 5 units. Units 1&2 have been combined to create a striking 3 bed/3.5 bath triplex on the parlor, second and garden levels with attached garage, private patio & expansive garage rooftop deck. The 3rd and 4th floors are each floor-through 1 bedroom homes with Charles River Views & oversized living/dining & bedroom spaces. Perched at the top is the 2+ bedroom/2 bath PH duplex with 2 private decks, including rooftop deck with panoramic views. The front, South facing side, bathes the building in light, while the rear side boasts unparalleled views of the famed Charles River. Ultimate potential in an undeniable location.

Listed by Sarah Glovsky, Andrew Glovsky and Nathalie Grenet of The Charles Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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118 Woodland Road Brookline MA 02467

MLS Number 73069893

  • Residential
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 10,410
  • High School Bhs

Located in the coveted estate area of Chestnut Hill, this brick estate was built in 2003 and offers over 10,000 square feet of finished living space on over an acre of lushly landscaped grounds. Grand foyer leads to a sophisticated front-to-back living room and elegant dining room. Mahogany paneled library overlooks the backyard and patios. Spacious custom gourmet kitchen facing the Southern exposure offers state of the art appliances along with multiple pantries and attached family room. The home also offers a grand primary suite with large bath, walk-in closet, and sitting room plus six additional bedrooms, all with en suite closets and baths. Heated 3 car garage, 4 fireplaces, circular driveway, expansive finished basement, gym, two offices, wine cellar, mudroom, and more. This home is located minutes from downtown Boston, golf courses, local shopping and dining, and public transportation.

Listed by Erin Baumgartner of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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82 Sargent Road Brookline MA 02446

Brookline, MA82 Sargent Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 73060067

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,883

Harmonized with exquisite surroundings, this spectacular residence is set on just under one-acre in prestigious Sargent Estates, one of Brookline’s extraordinary locations. Built in 1994, this fourteen room, six bathroom property has since undergone many renovations and beautifully displays exceptional design and custom details throughout the 6,883 square foot interior. The marble-appointed foyer, with dramatic staircase, is a fitting introduction to the main level with stately, principal rooms. The layout is well-suited for entertaining as well as intimate gatherings. There are six bedrooms including a primary bedroom with marble fireplace and luxurious bathroom. The third floor has two bedrooms-perfect for au pair or guest suite. The lower level has a wonderful home theater plus exercise room. The floor plan is brightened by many windows and views of the picturesque grounds are breathtaking. Amenities include four fireplaces, multi-zone HVAC, slate roof, and three-car heated garage.

Listed by Mona And Shari Wiener, Mona Wiener and Shari Wiener of Hammond Residential Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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352 Marlborough Street Boston MA 02115

MLS Number 73049365

  • Residential
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 4,754

This showcase townhouse on picturesque Marlborough Street has been completely renovated and impeccably designed to create the perfect combination of modern conveniences and historic grandeur in the heart of Back Bay. An elevator serves all levels of the home, which are topped by a magnificent family/media room that opens to a spacious private deck with wonderful city views. The tastefully appointed interiors include 4 bedrooms and 4 full and 3 half bathrooms with the entire third level dedicated to the luxurious primary suite including an oversized dressing room, sitting room/home office and a lavish marble bath. Additional features include a beautiful custom eat-in kitchen on the parlor level, elegant formal living and dining rooms, 3 gas fireplaces, 2 wet bars, handsome walnut built-ins, chevron flooring, a private garden patio and a full suite on the garden level ideal for au pair or guest use. Complete with 3 heated parking spaces, this exquisite family home is not to be missed!

Listed by Tracy Campion of Campion & Company Fine Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 or leasing 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 or leasing. MLSPIN 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.