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South Shore 5-Bed Homes

View 5 bedroom homes for sale on the South Shore of Massachusetts. Contact Lindo Realty Group for more information about a specific property, or if you'd like to schedule a private showing. Create an account to save your favorite listings and we'll send you an email when similar properties become available.

5 Bedroom Homes South Shore MA

Homes with 5 bedrooms on the South Shore cater to those seeking expansive living arrangements, combining comfort, style, and functionality. Whether it's a historic estate brimming with character or a sleek, modern colonial, these properties meet a wide array of lifestyle needs, including ample room for large households, guest accommodations, and dedicated home offices. Nestled in sought-after neighborhoods, these homes not only offer spacious interiors but also boast features such as finished basements, in-law suites, and large yards, perfect for outdoor activities and entertaining. 

354 High Street Pembroke MA 02359

Pembroke, MA354 High Street

Price$600,000

Est. Mortgage: $/month

Open House

MLS Number 73532559

  • Residential
  • Next Open House: Sat 06/13 11:00 am. to 1:00 pm.
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,066

What a unique opportunity! Explore the Old Cider Mill, a legal 2 family residence filled with charm and beautiful renovations. In the last 10 years the current owner has renovated both kitchens, added new windows throughout, installed a new gas and hot water system, completed electrical upgrades and added new flooring in the living room and sunroom. Enjoy a mini-split for first floor cooling as well. The main house offers 3-4 bedrooms and spaces for living, dining, office and a unique sitting room. Boasting a grand stone fireplace plus a slate floor and wooden cathedral ceiling this room could be the winning feature of this house. Natural cedar shingles and newer paint on the exterior. Most of the roof has been replaced since 2020. The sunny 2 room apartment has a renovated kitchen area and bathroom with shower stall. Use this space for additional income, small in law apartment or personal retreat. An expansive and private yard adds to the enjoyment of this special country home!

Listed by Nancy Kleber of Coldwell Banker Realty - Norwell - Hanover Regional Office

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$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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140 Drew Road Plymouth MA 02360

Plymouth, MA140 Drew Road

Price$3,995,000

Est. Mortgage: $/month

MLS Number 73532558

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,500

Experience unparalleled privacy in this gated, fully fenced 10-acre estate built in 2023, boasting over 600 feet of pristine water frontage on Great South Pond and abutting 40+ acres of protected conservation land with walking trails. Crafted with quality 2x6 framing, the main home features oak hardwood floors, quartz countertops, an open floor plan with a gas fireplace, a game room, and breathtaking views from every room. Enjoy a private sandy beach on crystal-clear, peaceful waters where gas-powered boats are restricted. A separate apartment above the three-car garage includes a full kitchen, bath, and laundry. Modern essentials include a generator, a Trex deck, and robust keypad security and video monitoring. An older waterfront guest cottage offers incredible potential. Located minutes from Pinehills Golf Club and under four miles from historic downtown Plymouth, this sanctuary perfectly blends secluded natural luxury with everyday convenience.

Listed by Mark Anderson of Redfin Corp.

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$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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 Forbes Road Milton MA 02186

Milton, MA85 Forbes Road, Milton Hill

Price$7,800,000

Est. Mortgage: $/month

MLS Number 73532470

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 10,054
  • High School Milton

Set discreetly on Milton Hill, this architecturally significant contemporary is defined by intention, proportion, and light. Clean, modern lines are softened by warm materials, creating a residence that feels both striking and deeply livable. Expansive glass frames elevated views while preserving privacy, allowing the landscape and skyline to become part of the design. Interior spaces unfold with purpose - dramatic yet calm, open yet grounded, balancing moments for gathering with spaces for retreat. Custom millwork, thoughtful sightlines, and seamless indoor-outdoor connections reflect a level of craftsmanship rarely found. This is not trend-driven design, but architecture with permanence and presence. For those who value modern living without compromise, and the distinction of Milton's most coveted setting, this home offers a rare and considered opportunity.

Listed by Tracy Kok and Jonathan Keith of Keith Brokerage,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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73 Washington Street Milton MA 02186

Milton, MA73 Washington Street

Price$1,240,000

Est. Mortgage: $/month

Open House

MLS Number 73532297

  • Residential
  • Next Open House: Thu 06/11 5:00 pm. to 6:30 pm.
  • Bedrooms 6
  • Bathroom 3
  • Square Feet 2,954

Great location! This classic Garrison Colonial sits on a desirable corner lot and features a cozy fireplace living room, hardwood floors, and an eat-in kitchen. The main level also offers a deck, formal dining room, and a flexible first-floor bedroom or home office. Upstairs you will find four generously sized bedrooms and a tiled full bath. Additional highlights include a partially finished basement, updated windows, central A/C, and a fenced, private yard. An attached two-car garage is topped by a full in-law apartment with its own kitchen/living room, hardwood floors, two bedrooms, and a full bath. All this just a short walk to Andrews Park and conveniently close to East Milton Square, restaurants, and highway access.

Listed by Robert Mcauliffe of Duhallow Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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320 Little Sandy Pond Road Plymouth MA 02360

Plymouth, MA320 Little Sandy Pond Road

Price$2,360,000

Est. Mortgage: $/month

MLS Number 73531550

  • Residential
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 9,000

Minutes from the Cape Cod Canal and a half a mile from Atlantic country club lies this beautiful 9,000 sqf 6 bed 6 bath colonial home that sits on over 3 acres of private pond front land. The house was built for the builders own family and no shortcuts were taken. Enjoy the peaceful sounds of the peepers on the pond at night and the star lit sky over the cape from the grand deck or one of the two Juliet balcony's. The home also features a 40' farmers porch on the front side of home. Additional rooms on the inside of the house are a spacious full walk in pantry, large laundry room with a sink and plenty of countertop and storage areas, a mudroom with closets and built ins, guest en suite with walk in closet and full bathroom, gym, office, dining room, work shop and a 1,200 sqf barroom/game room area with a 21' wet bar, custom lighting and built in Bluetooth speaker system.

Listed by Darin Thompson of Stuart St James,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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90 Liberty Street Randolph MA 02368

Randolph, MA90 Liberty Street

Price$1,099,000

Est. Mortgage: $/month

MLS Number 73530960

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,925

NEW CONSTRUCTION!!! This beautifully designed Colonial features 5 bedrooms, 3.5 baths which sits on an expansive lot, perfect for summer gatherings. On the main level you have an open floor plan with your living room, dining room, kitchen with sliders leading out to your private deck, half bath and access to your two car garage. Second floor has four bedrooms including a primary suite another full bath and laundry. The lower level is completely finished with a generous size family room/playroom, fifth bedroom with sliders leading to the back yard, full bathroom and lots of storage. Hardwood flooring is throughout the home, luxury vinyl plank flooring is in the lower level, central air throughout and convenient location. Buyer will pick out kitchen cabinets, vanities, quartz counter tops, appliances, lighting, tile and paint colors. ~~~Easy to Show~~~

Listed by Kim Curtin of Todd A. Sandler REALTORS®

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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 Grist Mill Lane Hingham MA 02043

Hingham, MA1 Grist Mill Lane

Price$3,295,000

Est. Mortgage: $/month

MLS Number 73530777

  • Residential
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5,473
  • High School Hingham

Nestled on the shores of Cushing Pond, 1 Grist Mill Lane offers an exceptional lifestyle in one of Hingham's most sought-after neighborhoods. This expansive home features an open floor plan with sun-filled living and dining rooms, gleaming hardwood floors, and walls of picture windows showcasing breathtaking water views. The main living spaces flow seamlessly into the custom Faneuil kitchen, private home office, and fireplaced family room with custom wet bar, built-ins, and dining/game area. The luxurious primary suite features a newer gas fireplace, custom cabinetry, lovely views, while well appointed bedrooms with hardwood floors and a newly designed California Closets laundry room adds convenience. The finished lower level offers flexible living space with a wood-burning fireplace and room for a second office. Outside, enjoy a heated pool, hot tub, gazebo, putting green with lighted holes, and direct pond access for kayaking in summer and ice skating in winter. Welcome Home!

Listed by Molly Hall and Maureen Doran of Coldwell Banker Realty - Hingham

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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 Sapphire Circle Canton MA 02021
Open House

MLS Number 73530656

  • Residential
  • Next Open House: Sun 06/14 12:00 pm. to 3:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,634

Exceptional New Construction set on a new private cul-de-sac. First of four homes, this 5 bedroom, 4 full bath Craftsman residence showcases sophisticated design and elevated finishes. Chef's kitchen features Thermador appliances w/48" gas range, island, farmers sink, quartz countertops. Large custom pantry. Kitchen flows into a dramatic cathedral family room anchored by a stunning floor-to-ceiling stone fireplace. 1st floor bedroom or office with 3/4 bath. The expansive primary suite offers dual walk-in closets and a spa-inspired bath with a spectacular porcelain glass shower and 5'5" soaking tub. Illumination package,Jack and Jill, town water and sewer, lawn irrigation. Pella windows, board & batten Hardee siding, 3 HVAC zones, EV charging station, 3 car garage and so much more! Walk to Canton's downtown,shops,restaurants, and commuter rail T-station. Fantastic local builder

Listed by Darla M. Prentice of Prentice Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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190 Washington Street Duxbury MA 02332

Duxbury, MA190 Washington Street

Price$4,850,000

Est. Mortgage: $/month

MLS Number 73530636

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 4,828
  • High School Duxbury

Move right in to this beautifully updated, all en-suite 5 bedroom family home - new baths 2020, situated across the street from popular Shipyard Beach for water access, boating and recreation. Enjoy the chef's kitchen by Christopher Peacock, Wolf Range, Sub-Zero, with 2 islands, designer marble and soap stone counters, wet bar, and beverage pantry. Open floor plan flows into the vaulted family room with custom built-ins and gas fireplace. Dining room with coffered-ceiling creating ideal spaces for everyday living and entertaining. State of the art heating and cooling (2020). Walkout basement with playroom and full bath. Superb landscape design surround the 20' x 40' gunite pool with waterfall, hot tub, gas fire pit, outdoor kitchen, and stunning pool house complete with vaulted ceilings, wood-burning fireplace, and beautifully appointed full bath.

Listed by Timothy E. Driscoll and Suzanne Stevens of South Shore Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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20 Cherry Lane Braintree MA 02184

Braintree, MA20 Cherry Lane

Price$1,250,000

Est. Mortgage: $/month

MLS Number 73530434

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,388

A rare opportunity to own an expansive home located in a highly sought-after neighborhood, is being offered for the first time in nearly 30 years. It's perfect for multi-generational living, accommodating a legal in-law. The house boasts two full kitchens, two fireplaces, six spacious bedrooms, and four full bathrooms. Each floor features open living and dining rooms, while the second floor offers a massive bonus room and first floor features a deck for convenient outdoor access. Full basement with great ceiling height and access to inground pool offer a possibility to add additional living space. An attached two-car garage and a fenced-in backyard complete this home.

Listed by Kristen Heffron of Village Realty HM,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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36 Spruce Middleboro MA 02344

Middleboro, MA36 Spruce

Price$749,900

Est. Mortgage: $/month

Open House

MLS Number 73530129

  • Residential
  • Next Open House: Sat 06/13 11:30 am. to 2:00 pm.
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 2,382

Beautifully remodeled home in Middleboro retains its old charm with modern updates .This 2 level main residence with attached 2 bedroom Accessory dwelling Unit is perfect for an In-Law set up or to bring in extra rental income. Both units showcase all newly remodeled kitchen with new stainless steel appliances and new hardwood floors as well as newly remodeled tiled bathrooms. Large barn on property can be used as storage or a bonus workshop area on a beautiful spacious lot with parking for 8 cars. Conveniently located near shopping, dining, schools and highway access. located 8 miles from Middleboro center.

Listed by Tracy Rappa of KAM Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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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7 Howe Street Hingham MA 02043

Hingham, MA7 Howe Street, Crow Point

Price$2,899,000

Est. Mortgage: $/month

MLS Number 73530131

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,545

A well appointed Colonial in coveted Crow Point. Curated finishes define an open plan with 9' ceilings and designer lighting. Formal living and dining rooms with coffered ceilings and custom millwork flow to an intimate bistro. The chef's white kitchen-with an oversized island, Carrara marble backsplash, Viking appliances and a pantry. The hearth-anchored family room with built-ins and oversized sliders opens to a deck and beautiful yard. The primary suite is a serene retreat with custom closets and dressing room with seasonal Walton's Cove views. Four additional bedrooms, Jack-and-Jill and family baths, laundry, office, mudroom with powder room, full high-ceilinged basement with a new HVAC zone ready to finish, two-car garage and farmer's porch. Walk to North Beach, Yacht Club and Foster School; minutes to Commuter Rail and Boat, marina dining and boutique shopping.

Listed by Gerald Mullen of NextHome Signature Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* 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.

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