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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

  • Single Family Attached
  • Village Osterville
  • Rooms 18
  • Bathroom 14
  • Bedrooms 7

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: 5.25% last updated on May 19, 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 Green DUNES Barnstable MA 02672
Price Changed

MLS Number 72912582

  • Single Family Detached
  • Bathroom 11
  • Bedrooms 8
  • Rooms 11
  • Acreage 8.93

The is the ultimate Cape Cod luxurious private gated compound. Vibrant Rolling lawns contrast with rare Cape Cod heathlands. An unprecedented 2600ft of sandy beach frontage on Nantucket Sound and tidal pools of Halls Creek. This Bertman designed home w porte-cochere, rotunda and 4 story tower portend exceptional construction, attention to detail and opulent interior. The focal point is the great room w 20' wall of windows, southern exposure and unending views. Adjacent is the dining room & chefs kitchen with glistening water views, blue granite & dramatic oval waterfront breakfast area. Off the kitchen is the secluded family room. The west wing has 2 large ensuite bedrooms each with walls of glass.

Listed by Jonathan A. Matel of William Raveis R.E. & Home Services

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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186 Windswept Way Barnstable MA 02655

MLS Number 72880181

  • Single Family Detached
  • Bathroom 8
  • Rooms 19
  • Bedrooms 8
  • Acreage 4

Waterfront Legacy Property on Oyster Harbors! On an elevated 4-acre lot overlooking Cotuit Bay sits this striking Tudor style home built in 1933, beautifully maintained and updated in harmony with the original design. Refined architectural details set the tone in this grand home with 10,000 sq. ft. of living space, an inground pool, a boathouse with extraordinary views, fireplace, sitting area and changing rooms, 437' of water frontage and a substantial deep-water dock, combining to create an exceptional offering in one of the finest locations of Oyster Harbors. Gracious formal rooms feature well-proportioned and spacious areas with soaring ceilings, arched windows and doors and six fireplaces. This lovingly preserved estate boasts landscaped park-like grounds with garden beds, rolling green lawns, and a wraparound patio overlooking the gardens and water creating an ideal backdrop for entertaining. Exceptional design and a magnificent setting will captivate the most discerning buyer.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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

  • Single Family Detached
  • Bathroom 12
  • Rooms 20
  • Bedrooms 15
  • Square Feet 14,000

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: 5.25% last updated on May 19, 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$15,000,000

Est. Mortgage: $/month

MLS Number 72953013

  • Single Family Detached
  • Bathroom 9
  • Rooms 21
  • Bedrooms 6
  • Acreage 35.96

This spectacular Rich Levey-designed contemporary is perfectly set at the end of a long winding drive on 35.95 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: 5.25% last updated on May 19, 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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5 Louisburg Square Boston MA 02108

MLS Number 72978264

  • Single Family Attached
  • Bathroom 6
  • Bedrooms 6
  • Rooms 14
  • Square Feet 4,852

Exclusive townhouse located on Beacon Hill's famed Louisburg Square, one of Boston's most distinguished and sought-after addresses. Situated on the sunny side of the square, this magnificent, federal style residence offers almost 5,000 square feet of beautifully finished and classically scaled living space over six levels with elevator access to almost every floor. Grand double parlor entertaining level with soaring ceilings includes the impressive front-facing living room, handsome library, and wet bar. The gourmet kitchen connects to the elegant dining room and the sun filled conservatory with floor-to-ceiling windows overlooking the home's garden courtyard. The third floor is dedicated to the primary suite offering an oversized bedroom, lavish bath and dressing room. Newly renovated top floor family/media room with guest suite. This home presents an opportunity to live in an unparalleled historic residence with the ultra-modern convenience of two parking spaces at your front door.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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

  • Single Family Attached
  • Bathroom 8
  • Rooms 15
  • Bedrooms 5
  • Acreage 0.05

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: 5.25% last updated on May 19, 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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64 Dudley Brookline MA 02445

Brookline, MA64 Dudley

Price$10,999,999

Est. Mortgage: $/month

MLS Number 72955636

  • Single Family Detached
  • Bathroom 10
  • Rooms 17
  • Bedrooms 6
  • Acreage 0.81

Majestic Georgian Revival Estate with bucolic views of The Brookline Reservoir. It was recently restored & renovated to the highest standards blending yesterday's character with today's lifestyle. Significant entertaining spaces as well as spacious, yet intimate family spaces. With high ceilings and abundant sunlight, this home offers 6 bedrooms, 7 full/3 half baths & an elevator, large gourmet Chef's kitchen is custom designed with an oversized island, top of the line appliances, & breakfast area with water views. The primary suite includes a gracious bedroom, dressing room & marble bath w/ steam shower & free-standing spa like tub, 3 bedrooms with on-suite bathrooms plus a laundry room & a family room finish up the third-floor family area. In addition, there is an indoor heated swimming pool The lower level has an attached 2 car garage, huge entertaining area & gym. Outside there is an Expansive back patio and a large tennis/sports court plus detached carriage house

Listed by The Power of Two Holly & Jerry of Classic Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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

160 Peppercorn Lane Barnstable MA 02635

MLS Number 72784318

  • Single Family Detached
  • Bathroom 8
  • Rooms 16
  • Bedrooms 5
  • Acreage 3.78

Experience the ultimate lifestyle in this custom designed waterfront home with expansive views of Popponesset Bay. Nearing completion, this stunning residence, sited on 3.78 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: 5.25% last updated on May 19, 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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352 Marlborough Street Boston MA 02115

MLS Number 72725281

  • Single Family Attached
  • Bathroom 7
  • Rooms 11
  • Bedrooms 4
  • Square Feet 4,754

Exquisite new construction Marlborough St single family! This 24' wide brick townhouse has been gut renovated and expertly designed by Boston's famed CBT Architects and constructed with the finest craftsmanship and materials by Pegasus Luxury Homes. Recently completed, this 4+ bedroom home offers 4 full baths, 3 half baths, 2 wet bars, elevator access to every floor, enormous private patio plus top floor family room with deck. Chic parlor level kitchen with top-of-the-line paneled appliances, abundant storage and southern exposure! Chevron flooring, walnut built-ins, large formal dining room and a generous living room with custom mantle. Second level master suite has a private office, front facing views and offers a massive dressing room with custom milled built-ins with lighting, storage island, and access to an ultra chic marble clad bathroom with oversized wet room/steam shower. Brand new furnishings & art available for purchase. Complete with 3 full heated parking spaces!

Listed by Michael Harper of MGS Group Real Estate LTD

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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355 Buckminster Brookline MA 02445

Brookline, MA355 Buckminster

Price$9,500,000

Est. Mortgage: $/month

MLS Number 72944714

  • Single Family Detached
  • Bathroom 8
  • Rooms 20
  • Bedrooms 7
  • Acreage 0.86

Magnificent estate home on one of Brookline's most beautiful residential streets.This home is not only an architectural masterpiece, but also a luxurious "home base" replete with all of the modern features one could want. Enormous first floor with period details, huge entertaining rooms, grand foyer, custom kitchen, and large family room.Covered porch, and large deck round out the entertaining space.Second floor has palatial master suite with multiple closets, fireplace, and large bathroom.Two additional en suite bedrooms round out the second floor.Large third floor with two more en suite bedrooms, and rec room. Basement is "fully loaded" with Kitchen, workout room, rec room, theater, & 2 additional bedrooms and one full bathroom. Enormous double depth garage with space for up to 6 cars. Heated floors throughout, smart house technology, and more.Beautifully landscaped on almost 1 acre with swimming pool,clay tennis court and heated driveway/walkways for snowmelt. A one of a kind home!

Listed by Samantha Stumpo of New Brook Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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

Boston, MA18 Commonwealth Avenue

Price$9,250,000

Est. Mortgage: $/month

MLS Number 72965888

  • Single Family Attached
  • Bathroom 11
  • Bedrooms 11
  • Rooms 40
  • Acreage 0.05

We are pleased to present the extraordinary opportunity to acquire 18 Commonwealth Avenue. Located on the south side of Commonwealth Avenue in the Back Bay, between Arlington and Berkeley Street, 18 Commonwealth is situated on one of the most revered blocks in all of Boston, MA. 18 Commonwealth currently consists of 11 studio apartments, ~8,000 gross square feet of space and has four exterior parking spaces in the rear. 18 Commonwealth Avenue is a trophy address by every measurable standard. The spectacular location offers residents an unimaginable living experience with the proximity to classic Boston amenities such as the Boston Public Garden, The Commonwealth Avenue Mall, a wealth of shopping options along Newbury Street as well as access to a multitude of transportation options. 18 Commonwealth is uniquely positioned to be converted to luxury condominiums or a single family residence.

Listed by Kevin Benzinger of Boston Realty Advisors

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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. from third party sources, including sellers, lessors 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 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. 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.