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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3 Jerusalem Lane, Cohasset, MA

MLS Number 72345945

  • Single Family
  • Parking Spaces 4
  • Year Built 2002
  • Full Bath 5
  • Bathroom 6

Perched atop one of Cohasset's signature granite rock outcroppings, with vistas of Massachusetts Bay, this Victorian-style home is a mere 25 miles south of Boston. This custom designed home boasts ten and twelve-foot high ceilings with walls of windows that frame expansive views of Minot's Lighthouse. Gracious living can be had among family and friends in the large open floor plan with an epicurean kitchen, a spacious family room with Gothic windows or in the formal dining and living rooms. The second floor, the master bedroom includes a sitting area fireplace, walk-in closet and a private deck. Radiant heated flooring runs throughout the bedrooms and baths. Enjoy inspiring sunrises on several exterior elevated decks including a rooftop deck! The lower level offers a 3-tiered media room w/10' drop-down screen, billiard room and full bath. Ample storage is provided within a three-bay heated garage. A quaint pool and patio for summer gathering. Live in a home that inspires you!

Listed by Mary Beiche and William Tierney of Gibson Sotheby's International Realty

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Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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33 Beaver, Boston, MA

Price$7,990,000

Est. Mortgage: $/month

MLS Number 72344842

  • Single Family
  • Parking Spaces 2
  • Year Built 1899
  • Full Bath 4
  • Bathroom 5

Beautifully renovated interiors, a spectacular private roof deck, and attached garage with additional outdoor parking make 33 Beaver Place one of Boston’s most exceptional residential offerings. Once a Carriage House on the Flat of Beacon Hill, this extra wide single-family encompasses over 4,000 SF with 4 beds and 4.5 baths. The gracious foyer leads to the open concept living and dining room with elegant gas fireplace. The kitchen is just beyond with large walk-in pantry, 6-burner gas stove and wet bar. All bedrooms feature en-suites, including the 2nd floor master whose spa-like bath has a large steam shower, jetted tub, and gas fireplace. There is also a wood paneled library, alcove desk space off one of the bedrooms, and oversized skylight that fills the home with natural light. The walk-out private roof deck is impeccably landscaped and complete with fire pit and grill. 2 cars plus extra storage fit comfortably in the garage and there are 2 extra parking spaces at the front door.

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

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Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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185 DOWNER Avenue, Hingham, MA
Active With Contract

MLS Number 72344698

  • Single Family
  • Parking Spaces 2
  • Village Crow Point
  • Year Built 1900
  • Full Bath 2

CROW POINT WATERFRONT! Shingled styled 5 bedroom home offering panoramic views of Hingham Harbor and beyond!Custom details throughout complement the gracious, fireplaced living room with its magnificent views of the Harbor from almost every room. Amazing professionally landscaped grounds and 180 feet of direct waterfront offers numerous possibilities.Updated Gourmet kitchen along with sundrenched living room with expansive water views,dining room with beautiful built-ins, half bath, family room with cathedral ceiling and a bank of windows complete the first level. Second floor consists of master bedroom with expansive waterviews, two additional bedrooms & 2 full baths.Third floor- guest bedroom and another bedroom/office with large picture window showcasing the waterviews. Private floating dock offers direct water access for boating and water sports.This fabulous CROW POINT location allows a SHORT WALK to downtown restaurant, yacht club and 5 minute drive to Commuter Boat and Train!

Listed by Denise Marshall and Sheila Creahan of William Raveis R.E. & Home Services

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Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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127 Nichols Road, Cohasset, MA

Price$4,999,000

Est. Mortgage: $/month

MLS Number 72340312

  • Single Family
  • Parking Spaces 10
  • Year Built 1900
  • Full Bath 4
  • Bathroom 5

This is a must see home to appreciate the 180 degree views of Little Harbor, the Ocean & Sunrises. Spectacularly sited Villa on Little Harbor with water views from most rooms, 175 feet of water frontage, Stone Pier and Gangway to the dock. Curved sheltered terrace to further take in the views. The Villa is a warm light beige stucco with additional walls of stone. The roofs are a handsome slate or copper. A cobblestone circular driveway. The Villa has 11 rooms featuring high ceilings with 4 or 5 en-suite Bedrooms, large entertainment size Living Room with imported stone fireplace. Dining Room with oversized skylight, tile floor, slider to balcony, buffet with built-in wet bar. Custom cabinets in the Kitchen with granite island, Family Room with a fireplace of stone with spiraled pillars. Half Bath, Media/Exercies/Music Room in the new Round Tower. Second floor has 4th Bedroom with Full en-suite Bath. Third floor Sitting Room with balcony.

Listed by Claire Watts of Coldwell Banker Residential Brokerage - Cohasset

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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11 Saint Charles Street, Boston, MA

MLS Number 72341133

  • Single Family
  • Year Built 1875
  • Full Bath 2
  • Bathroom 3
  • Bedrooms 4

Bright & sunny home in idyllic, park-like setting. Elegant parlor-level rooms have high ceilings and marble mantel. Pretty bow front overlooks quaint St Charles Street, while the rear rooms have views of lovely gardens and trees. Sleek "Arclinea Italia" professional kitchen has top-the-line appliances, wine fridge & abundant cabinetry. The open floor plan on this level allows for flexible dining/living layout options. A dramatic wall of French doors opens to an incredible one-of-a-kind enormous garden with beautiful plantings & flowering trees. This tranquil haven with decking, gardens, benches and a shed is beautiful throughout the year and changing seasons. Four large king-size bedrooms. Two full marble bathrooms: one with double vanity & walk-in shower, the other with beautiful glass tiles & deep tub. Additional half bath. Hardwood floors throughout. New boiler. Fujitsu split AC system. Last house on quiet dead-end street on Back Bay/South End border.One block to BB Station.

Listed by Laura Spence of Gibson Sotheby's International Realty

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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143 Atlantic Avenue, Cohasset, MA

Price$7,250,000

Est. Mortgage: $/month

MLS Number 72338820

  • Single Family
  • Parking Spaces 10
  • Bathroom 6
  • Full Bath 5
  • Bedrooms 5

Magnificent direct oceanfront on exclusive Sandy Cove, this spectacular custom built home has been designed and built with entertaining and family living in mind. Built in 2002 this exquisite 14 room home boasts 7,600 sq feet of living space with 5 bedrooms, 5 full baths and 1 half bath. Updated by Architect Patrick Ahearn and builder Steven Colclough in 2014 with several additions including a four season porch. The custom built kitchen is state of the art with every detail through out for the inspired chef. This private retreat location overlooks 1.5 acres of lush green lawns & gardens manicured to perfection. Living here is an unmatched lifestyle on the Ocean with your own private beach. A year round paradise!

Listed by Frank Neer of Coldwell Banker Residential Brokerage - Cohasset

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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 Saint CHARLES, Boston, MA

Price$2,595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72338978

  • Single Family
  • Village Charming Cul de Sac
  • Year Built 1890
  • Full Bath 2
  • Bathroom 3

Absolutely stunning single family on a charming cul de sac in the desirable South End. Sunny throughout, this home is perfect for entertaining or having a quiet evening at home. Garden level features an impressive gourmet kitchen, dining area, fireplace, half bath, leading to outside patio equipped with garden sprinkler system. Parlor level offers an inviting foyer leading to a lovely open floor plan with formal dinning-living room area with high ceilings, hardwood floors and elegant fireplace. Second floor contains two well proportioned bedrooms, generous closets and full bath. Top floor features the master bedroom suite and bath with sauna, custom designed closets, entertainment center and wet bar. A full size staircase leads to an expansive roof deck with creative sitting areas, and fantastic views of Boston! Of special consideration: Two AC and heating systems in the building. One services master bedroom suite only and one system for remaining floors. A true gem and must see!

Listed by Jennifer Girvin of Keller Williams Realty Boston-Metro | Back Bay

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

481 Jerusalem Road, Cohasset, MA

MLS Number 72338817

  • Single Family
  • Parking Spaces 10
  • Year Built 1920
  • Full Bath 5
  • Bathroom 8

Spectacular sunrises and sunsets from this colonial on Jerusalem Road's Gold Coast featuring ocean views from every room. Rebuilt in 2001 to custom design by Carr, Lynch and Sandell Inc. and recently updated. 200+ feet of oceanfront property looking out to Minot’s Light, Marblehead and Massachusetts Bay. Open floor plan that is great for entertaining and family living. First floor has Chef’s Kitchen with deck and pergola, Dining Room with carved ceiling moldings surrounding ornate fireplace, Living Room with fireplace and deck, large Guest Suite or Home Office with deck, plus ensuite Bedroom with Kitchenette. Second floor has Master Suite with private deck providing panoramic views, plus two additional Ensuite Bedrooms. Third floor comprises Observatory/Media/Family Room with deck. Lower level has Game and Media rooms, Mudroom with Laundry and Studio/Exercise Room with walkout to patio, lawn and ocean access. Spectacular ocean front home providing vacation lifestyle all year round!

Listed by Frank Neer of Coldwell Banker Residential Brokerage - Cohasset

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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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100 Beach Street, Cohasset, MA

Price$5,100,000

Est. Mortgage: $/month

MLS Number 72337919

  • Single Family
  • Parking Spaces 6
  • Year Built 1920
  • Full Bath 6
  • Bathroom 8

"Harbourstead" Direct waterfront, Victorian estate on Cohasset's Little Harbor. Classic elegance and architectural detail are evident in this exceptional offering. Totally renovated and updated home features substantial and well proportioned entertaining rooms, library, office, siting room, sun room, luxurious master suite, three additional bedroom suites and lovely two bedroom, in law apartment. All rooms have exceptional water views. The foyer opens to formal living room and dining room, each access large deck. Chef's kitchen with large work island three subzero fridges, Wolf double oven range, Shaw farmer sinks, dining area, additional siting area, access to library and covered porch. Master suite features; spa bath, dressing room with wet bar and large sitting room. Three more bedroom suites and laundry on this level. Private office, sunroom, mud room, full bath, exercise room on lower level. Heated pool, sun deck, patio, private dock, 3 car garage, back up generator system.

Listed by Fred Alibrandi of Douglas Elliman Real Estate

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

30 Black Horse Lane, Cohasset, MA

Price$7,595,000

Est. Mortgage: $/month

MLS Number 72336738

  • Single Family
  • Parking Spaces 20
  • Year Built 1906
  • Full Bath 5
  • Bathroom 6

Situated on 6.75 acres on a picturesque peninsula, 30 Black Horse Lane in Cohasset is the quintessential family retreat. This 7-bedroom, 7.5 bath estate with over 1600 feet of direct Gulf waterfront has easy harbor access. The perfectly situated sprawling grounds consist of endless lawn, natural granite outcroppings, grassy knolls, whispering trees and a wide variety of flowers and plantings. The personal luxuries such as a private causeway, terraced patios overlooking the grounds, custom tennis court, outdoor heated pool with spa, pool house, boathouse, and private dock right on the Gulf create a waterside country-club elegance in your backyard. The property also includes a four car garage with a guest home above. Secluded as its setting may be, this rare estate is within walking distance of downtown Cohasset and only a short drive, boat or train ride to Boston. One of the last remaining grand Cohasset estates, it is a perfect blend of useable waterfront luxury and privacy.

Listed by Kevin Lewis of Compass

{$office->Name}

Perry DiNatale Realty
91 N Street
South Boston MA, 02127
Office: 617.765.8747

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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