South Boston Luxury Homes

South Boston, Massachusetts, more commonly known as Southie, is full of history and character. South Boston was once mostly a working-class community, but today is one of the most desirable neighborhoods in Boston. In recent years South Boston has seen several revitalization projects, adding to the beauty of the neighborhood. From quaint shops, great food, and waterfront views you can't beat South Boston. You will find a mix of housing styles for sale in South Boston from historic homes to newly constructed condos. Learn more about South Boston. 

Browse Luxury Real Estate for Sale in South Boston

Scroll to view the most luxurious real estate and homes for sale in South Boston and surrounding Massachusets towns. Search through a variety of listings which offer all the exclusivity and luxury expected by the discerning buyer. If you're looking for a specific property type or town use the criteria on the right-hand side to narrow down the results.

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231 Jerusalem Road, Cohasset, MA

Price$2,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72398718

  • Single Family
  • Parking Spaces 4
  • Year Built 1950
  • Full Bath 3
  • Bathroom 3

An exceptional opportunity to purchase what amounts to 2 buildable lots, one on Jerusalem Road and a 2nd lot on Little Harbor Road. Jerusalem Road has an existing home built in the 50's that needs extensive renovation or a complete rebuild, the Little Harbor Road lot is a separate, flat, open and ready for construction. There is a recent survey plan available and the lots are flagged. A floor plan of the house is attached. Check out the attached drone tour too.

Listed by Thomas Hamilton of Dean & Hamilton REALTORS®

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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29 Howe Street, Hingham, MA

Price$2,295,000

Est. Mortgage: $/month

MLS Number 72398825

  • Single Family
  • Parking Spaces 4
  • Village Crow Point
  • Year Built 1880
  • Full Bath 3

Beautifully renovated and expanded,this circa1880,5 BR authentic NE shingle-style home sits atop a hill on a quiet street in coveted CrowPoint. With stunning views of North Beach, the Islands and beyond as well as its curated gardens, expansive yard & gorgeous heated salt-water pool,you will be amazed! Entering through a garden gate to expansive patios and porches,relax and take in the amazing views. Serenity overcomes you in this casually elegant home. The large,gracious&open Living and Dining area is bathed in light and punctuated by the original staircase and fire place. The newly updated kitchen beautiful custom cabinetry, granite countertops and Butler's Pantry: perfect for entertaining! A Den,Laundry Room,Mudroom & Full Bath round out the first floor. The Family Room has too many custom features to mention! There are four large Bedrooms and an updated Family Bath. A gorgeous Master Suite with custom built-in's, walk-in closet, Master Bath & beautiful views. A CrowPoint Classic!

Listed by Pat Butler of Coldwell Banker Residential Brokerage - Hingham

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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49 Margin Street, Cohasset, MA

Price$14,999,000

Est. Mortgage: $/month

MLS Number 72398030

  • Single Family
  • Parking Spaces 20
  • Year Built 1932
  • Full Bath 7
  • Bathroom 11

BIG PRICE DROP!!! Searching for a magnificent oceanfront property at an incredible value? Look no further! Welcome to The Oaks, New England's finest waterfront estate. Built in 1932, The Oaks is positioned on a private 9+ acre peninsula, with over 1,800' of ocean frontage as well as a 112' deep water dock. Upon entrance, visitors will be taken aback by the impressive and well-manicured grounds, which flows seamlessly into the ocean backdrop. Centered among the backdrop, the 20,000 sq.ft. Georgian Revival mansion is a sight to behold and has been maintained to the highest degree, offering a combination of modernism and traditionalism. The Oaks also impresses with its multiple terraces, tennis court, pool, skating pond, BBQ grills, Jacuzzis, and private sandy beach. The former home of Clarence Barron and family (founders of Barron's Weekly, Dow Jones Company, and Wall Street Journal) has historical significance and has had only three owners. This is opportunity not to be missed!!

Listed by Christopher Roy of Coldwell Banker Residential Brokerage - Boston - South End

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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4 Stone Bridge Lane, Milton, MA

Price$3,200,000

Est. Mortgage: $/month

MLS Number 72395973

  • Single Family
  • Parking Spaces 8
  • Year Built 2003
  • Full Bath 3
  • Bathroom 6

This estate is set along a private road of extraordinary homes. Enjoy a resort lifestyle with modern amenities and convenience. It has been meticulously updated with understated elegance and luxurious amenities: chef's kitchen with white quartz island, an adjoining living room with butler's pantry and bar, marbled fireplace in a sun-lit lounge. Excellent woodwork,crown molding and attention to details are evident. Have the privacy to work in the refined office, organize poolside entertainments or spend quiet moments strolling the grounds. After a day, retire to the upper level: the master bedroom awaits with a magnificent ensuite bath, luxurious rain shower and steam room. Guests enjoy an entire wing with private living area, ensuite bath and sauna. On weekends, retreat to nature at the Blue Hills Reservation, a state park 6 mins away. Walk its scenic trails, take in the panoramic view at summit, or ski during the winter. 4 Stone Bridge Lane is truly a home to live, work and play.

Listed by Treetop Realty Group and Sid Gehlot of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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10 Crescent Avenue, Scituate, MA

Price$2,195,000

Est. Mortgage: $/month

MLS Number 72393712

  • Single Family
  • Parking Spaces 6
  • Village Second Cliff
  • Year Built 2008
  • Full Bath 4

Walk to Peggotty Beach & stroll to Scituate Harbor from this custom-designed shingle style home inspired by grand turn-of-the-century coastal retreats, yet newer construction w/ the highest amenities throughout. Located on COVETED Second Cliff with SPECTACULAR views of the harbor and Scituate's coastline. OPEN concept floor plan w/beautiful natural light so the kitchen, dining & living room blend into one another, yet still provides plenty of private space for mudroom, study, pantry & sunroom w/FP & phenomenal views. There are 5 BRs including a private 3rd floor MBR suite w/balcony to relax & enjoy the SUNSETS. Designed for an active & entertaining lifestyle, w/ finished walkout LL w/11 ft ceilings, full bar & wine cellar, lounge/game space, exercise room, full bath & more. PROFESSIONALLY landscaped exterior with patios, garden areas, outdoor shower & lush lawn. Loads of storage, workshop & THREE+ dedicated garage spaces PLUS a separate apartment w/private entry. Ultimate Cliff Living!

Listed by Poppy Troupe of Coldwell Banker Residential Brokerage - Norwell

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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14 Chestnut, Boston, MA

Price$7,200,000

Est. Mortgage: $/month

MLS Number 72393739

  • Single Family
  • Year Built 1899
  • Full Bath 4
  • Bathroom 6
  • Bedrooms 8

This gracious Beacon Hill residence boasts stunning architectural details throughout. Currently configured as a triplex penthouse with two additional apartments, this home is complete with multiple living spaces in addition to two terraces and a private garden.

Listed by Tracy Campion of Back Bay Office

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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354 Brush Hill Road, Milton, MA

Price$2,395,000

Est. Mortgage: $/month

MLS Number 72393099

  • Single Family
  • Parking Spaces 6
  • Village Brush Hill
  • Year Built 2018
  • Full Bath 4

Exquisite new construction house by KNK studios on 1-acre corner lot in one of Milton's most desired neighborhoods. The privately gated driveway leads to a beautiful estate that captures unique architecture with every contemporary amenity. Luxurious comfort, craftsmanship, the home offers 7 bedrooms, 4 bathrooms and a 2 car garage. Dramatic 2 story open living room, grand wood-burning fireplace, large covered deck. Designer's kitchen, huge stone countertop island, high end appliances. Oversized family room with 12' ceilings, dramatic views with floor to ceiling windows. Master suite on 2nd fl. private wing, spa-feeling master bath, his-hers master closet, large balcony. 2 bedrooms, full bath on the 1st fl. 4 bedrooms with 2 full baths on 2nd fl. Ground level wet-bar, wine room, gym, media area. Open floor plan throughout, 4 zones AC / heating, walkout basement, stone patio, outdoor fireplace. Top of the line designer finishes or the buyer may pick their own. The ultimate dream home!

Listed by Derek Greene of The Greene Realty Group

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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85 Warren Avenue, Boston, MA

Price$4,275,000

Est. Mortgage: $/month

MLS Number 72393240

  • Single Family
  • Parking Spaces 1
  • Year Built 1890
  • Full Bath 3
  • Bathroom 6

Totally renovated & exquisitely deigned 4+ bedroom townhouse offers an ideal location. A granite stoop leads into a gracious bow front double parlor. Welcomed into this ultra luxurious home by a gracious living room that features a gas fireplace, elegant crown moldings, tall ceilings and hardwood floors. A rear facing study is complete with a wall of built-ins, a gas fireplace and a private deck. The street level offers a formal dining that is adjacent to an enormous gourmet eat-in kitchen. Top-of-the-line appliances, marble counters, and abundant storage, this spectacular kitchen is the heart of the home. The garden level offers a large media room & abundant storage. The master suite occupies the 4th fl with a front facing bedroom, en-suite marble bath, a mirrored dressing room, plus home office/4th bed. Top floor offers 2 guest suites each with a full bath. Lushly landscaped roof top deck is an urban oasis with mature plantings & skyline views! 1 oversized direct access parking!

Listed by Michael Harper of Coldwell Banker Residential Brokerage - Boston - Newbury St.

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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370 Hillside Street, Milton, MA

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72391395

  • Single Family
  • Parking Spaces 10
  • Year Built 1999
  • Full Bath 4
  • Bathroom 5

Stately Georgian colonial sited on a 2.76 plush private parcel of land in the sought after Bucolic Scott Woods area. This custom blt 6,000 sq. ft.HR colonial offers 10 rms, 5 Bdrms, 4 full & 1 h bth w/ a 3 car htd garage. A stunning two-story foyer w/sweeping bridal staircase is flanked by a fire placed LR & DR. Superior craftsmanship throughout w/detailed crown moldings & wainscoting. The centerpiece of the home is the dramatic 2-story cathedral Great Room w/custom built-ins, stone firepl & expansive windows that joins a wonderful chef's kitchen w/high-end SS appl., butler's pantry, & huge island perfect for family & friends to gather. A sun-filled office w/ custom built-ins, half bth & laundry rm. finish the 1st. fl. The 2nd fl offers a master-suite w/ frpl, his & her walk in cl & a spa-like bth that provides a private oasis. 4 Addt Bdrms w/ great closet space & walk up attic. Relax in your lush backyd w/ inground pool, patio & expansive deck. Country living ! Only 9 miles to Boston

Listed by Francine Jeffers and Paul Rege of Kelley & Rege Properties, Inc.

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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173 Main Street, Hingham, MA

Price$2,395,000

Est. Mortgage: $/month

MLS Number 72391463

  • Single Family
  • Parking Spaces 4
  • Village Bachelor's Row
  • Year Built 1888
  • Full Bath 3

Much admired shingle style home with over 5700+ SF on coveted Lower Main Street, just a short stroll to the harbor and Hingham's restaurants and shops. The second you approach this gracious home of yesteryear you are smitten by the spacious front porch overlooking Main Street. The architectural details in this home are exquisite. Stunning 10' ceilings with oversized windows and many period details throughout, including a dramatic center staircase which gracefully winds up to the third floor. House was moved to the center of the lot and placed on a new foundation, providing a great finished lower level space not often found in homes of this era. Dramatic, sun filled family room addition off the back with luxurious master suite above to suit current day living needs. The back yard is private and beautiful, complete with Gunite pool, spa and plenty of yard space. Two car detached garage with storage above. Watch the 4th of July parade from your own front lawn!

Listed by Tara Coveney of Coldwell Banker Residential Brokerage - Hingham

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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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.