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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: 6.29% last updated on Sep 22, 2022
* 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: 6.29% last updated on Sep 22, 2022
* 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: 6.29% last updated on Sep 22, 2022
* 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 and less than 5 minutes to Rte.128/95.

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

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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: 6.29% last updated on Sep 22, 2022
* 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$12,500,000

Est. Mortgage: $/month

MLS Number 72972183

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 6,830

Amongst the most prestigious of addresses in Boston, 39 Union Park is a gracious and impressive townhome that presents a unique opportunity to acquire a trophy property of the highest caliber set on the finest park in South End. The current owner completed a years-long, painstaking renovation and restoration at the helm of renowned design firm StudioDykas, creating a distinctive and unparalleled living experience. This 24-foot wide Italianate-style home features a classic brick bow front facade and spans over 6,800 square feet on six levels with five bedrooms, six full and two half bathrooms, and two distinct outdoor living areas, including a private tiered garden and terrace. Elegant proportions abound with an unusually wide floor plate and impressive ceiling heights throughout. Constructed with integrity and imbued with a rare combination of scale, quality, and location, this home is the perfect showplace for art and high design. One off-site deeded garage parking space included.

Listed by Hanneman + Gonzales Team, Chris Gonzales, John Gould, Nick Hanneman, Penney Gould Team and Daisy Penney of Compass

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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251 Commonwealth Avenue Boston MA 02116

MLS Number 73034159

  • Residential
  • Bedrooms 8
  • Bathroom 9
  • Square Feet 11,793

A storied Back Bay location, 251 Commonwealth Avenue was built in 1880.The home has only had a handful of owners, and much of the original interior architecture and design remain intact. At 28 feet wide, the building has a commanding presence along Commonwealth Ave. Grand formal rooms are adorned with quartersawn oak paneling, carved fireplaces (16 total), and period lighting fixtures forged in bronze, crystal and brass. There are embossed ceilings, built-ins crafted from cherry, and a museum quality central staircase connecting the floors. The building measures 11,793 gross square feet*. Currently configured as four separate apartments, there is a brick and granite parking court for six vehicles in the rear. The parlor, second, and third floors are used as the current owner’s palatial private quarters. The other three apartments are single floor residences, and the penthouse includes a walk-out deck overlooking the city. Located on the sunny side w/ exceptional light.

Listed by Rene Rodriguez and Jack Lavanchy of Cabot & Company

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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 73000231

  • Residential
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 10,410
  • High School Brookline Hs

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 five 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 and Emily Sullivan of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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160 Peppercorn Lane Barnstable MA 02635

MLS Number 72784318

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 7,504

Experience the ultimate lifestyle in this custom designed waterfront home with expansive views of Popponesset Bay. This stunning residence, sited on 3.79 acres, incorporates elegant and functional architecture and offers 7,500 sq ft of uniquely designed living space. Interior spaces, rich with modern comforts and extraordinary views, feature dramatic vaulted ceilings, custom fireplaces, exceptional millwork, expansive windows and an elevator. A stunning chef's kitchen with granite center island, handsome home library and a fabulous entertainment/great room create an ideal setting for family and friends. Five en suite bedrooms include the stunning master suite with magnificent water views, private balcony, custom fireplace and his and hers bathrooms with adjoining dressing rooms. A fabulous wrap-around porch offers multiple areas to relax and enjoy the sweeping views and this special property is further highlighted by a tennis court, in-ground pool and private dock.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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1825 S County Road Barnstable MA 02655

MLS Number 73028756

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 7,854

There is something special about the peaceful seclusion of Warren's Cove that makes you want to settle back and escape from it all. Ideally situated on 12 waterfront and salt marsh acres with a private island, this estate includes a spacious main house and guest quarters comprised of the finest finishes to complement the beautiful modern architecture. The open outdoor spaces and stunning views provide the perfect backdrop for entertaining or spending time with family and friends. Multiple decks, patios and infinity pool tempt you to stay outside and get lost in the scenic views. Highlights of the custom-built home include water views from every room, soaring 2-story ceilings, three fieldstone fireplaces, gourmet kitchen open to family room, library/office, home theatre, exercise room, game room, lavish primary suite, koi pond. Guest quarters include kitchen, living area, two bedrooms, full bath. Enjoy the epitome of a carefree lifestyle!

Listed by Kathleen Byrne of Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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18 Commonwealth Avenue Boston MA 02116

MLS Number 73035727

  • Residential
  • Bedrooms 5
  • Bathroom 11
  • Square Feet 7,950

Generational opportunity on the first block of Commonwealth Avenue in the Back Bay. Built in 1864 as a grand residence, this 8,000+/- sq/ft brownstone presents a rare opportunity to create a custom home in one of the most sought-after locations in Boston. Available for the first time in 50 years, this six-story property with elevator overlooks the Commonwealth Avenue Mall and is steps to Public Garden & Newbury Street. 18 Commonwealth is a design / build opportunity for 5+ bedrooms / 6+ bathroom single family home with potential to add a roof terrace & garage parking. Original details include grand staircase illuminated by sky-light, intricate mill work & moldings, 10-12 foot ceilings, ornate fireplaces & hardwood floors. 4 outdoor parking spaces. Endless possibilities for renovation & restoration of this historic residence on the first block on Commonwealth Avenue.

Listed by Dave Costello & Scott Accorsini Team of Advisors Living - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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31 Chestnut Street Boston MA 02108

MLS Number 73039064

  • Residential
  • Bedrooms 9
  • Bathroom 7
  • Square Feet 8,979

31 Chestnut Street, a classic, Greek Revival home, rich with history yet existing comfortably in Boston’s 21st century, boasts an exceptionally rare combination of features and amenities that afford the owner with a stunning showplace in our City’s most storied neighborhood. The main entertaining level features a grand living room offering spectacular views overlooking Chestnut Street with a glimpse to the Common and leads to a formal fireplaced dining room with adjoining Butler's Pantry. A spacious great room with a one-of-a-kind skylight/cupola opens to the home’s two-tiered patio. The third floor is dedicated to the expansive master suite with walk-in closet, his and her baths and separate studies. The garden level functions as an oversized au pair suite with open living/dining area, kitchen and access to the lower level of the home’s picturesque patio. Grand in every facet, this home is located steps from the shops and restaurants of Charles Street, Public Garden, and the Common.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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.