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Multi-Generational Homes with In-Law Suites on the South Shore

Explore South Shore homes designed for multi-generational living, complete with in-law suites and private living areas. These homes often include separate kitchens, bathrooms, and entrances, offering flexibility for long-term guests, live-in support, or private workspaces. View available properties and contact Lindo Realty Group to schedule a private tour or get more information.

South Shore MA Homes with Private Living Quarters

Homes with in-law setups on the South Shore come in a range of layouts—from finished basements with full amenities to separate guesthouse-style additions. These spaces are ideal for flexible living arrangements and long-term comfort. Towns like Braintree, Milton, and Scituate offer a variety of options with features like full kitchens, independent entrances, and dedicated utilities. Want to stay updated on new listings? Sign up for alerts or reach out to a Lindo Realty Group expert.

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354 High Street Pembroke MA 02359

Pembroke, MA354 High Street

Price$600,000

Est. Mortgage: $/month

MLS Number 73532560

  • MultiFamily
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,066
  • Parking Spaces 4

One of a kind antique cranberry/cider mill now a 2 family residence filled with charm and boasting beautiful renovations. In the last 10 years the owner has renovated both kitchens, added new windows throughout, installed a new gas heat and hot water system, completed electrical upgrades and added new flooring in the living room and sunroom. First floor cooling with mini-split. The main house offers 3+ 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 in last 6 years. The sunny 2 room apartment has a renovated kitchen and bathroom with shower plus a separate bedroom. The space is perfect for additional income or small in-law apartment. The expansive and private yard is where you can relax and enjoy this special 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: 6.66% last updated on Jul 30, 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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555 Webster Street Marshfield MA 02050

Marshfield, MA555 Webster Street

Price$1,150,000

Est. Mortgage: $/month

MLS Number 73530220

  • MultiFamily
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,765
  • Parking Spaces 12

Welcome to 555 Webster Street in Marshfield! This renovated, expansive custom Cape offers approximately 4,765 square feet of living space with two separate wings, providing outstanding flexibility for short-term rental, owner-occupied income, extended family, or in-law living. The home features 7 bedrooms, 4 full bathrooms - blending antique character with modern updates throughout. Situated on a 0.8-acre lot, the property includes a wraparound deck, new stone patio and firepit, and a two-car garage. This property is ideal for the multi-generational living or a savvy investor seeking strong returns utilizing it for short or long-term rental in a prime coastal location. Close to Marshfield beaches, Green Harbor Golf across from property, Levitate Music Venue, dining, and local amenities - this is a rare opportunity to own a high-yield property in desirable Marshfield. Must see to fully appreciate the value and versatility.

Listed by Paul Preziosi of William Raveis R.E. & Home Services, Colin Garvey of William Raveis R.E. & Home Services

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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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$724,900

Est. Mortgage: $/month

MLS Number 73530129

  • Residential
  • 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

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$
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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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52 Ridgewood Road Milton MA 02186

Milton, MA52 Ridgewood Road

Price$1,699,900

Est. Mortgage: $/month

MLS Number 73529479

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,077

One of Milton's most desirable neighborhoods. Extensively updated in 2023, this property underwent a comprehensive gut renovation, including all-new plumbing, electrical systems, heating system, roof and numerous high-quality improvements throughout, offering the perfect blend of modern efficiency and timeless charm.The spacious kitchen and living areas provide excellent functionality for both everyday living and entertaining. The walk-out basement, offering tremendous potential for a future Accessory Dwelling Unit (ADU), in-law suite, guest quarters, home office, or additional income-producing space, subject to local approvals. The direct exterior access creates endless possibilities for multi-generational living or investment opportunities. Located near top-rated schools, parks, shopping, restaurants, and major commuter routes.

Listed by Rebecca Huang of William Raveis R.E. & Home Services

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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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2 Seabiscuit Drive Plymouth MA 02360

MLS Number 73526741

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,688

Welcome to South Plymouth! Built just two years ago, this custom Cape is in excellent, move-in-ready condition and features a sought-after first-floor primary suite. Located on a private cul-de-sac acre lot, the property offers a fenced backyard, full irrigation system, professional landscaping, and a wide driveway. Inside, you'll find custom tile work, detailed woodwork, and a flexible floor plan with an in-law-ready area on the second floor. Two laundry locations, one on each floor, add everyday convenience. With modern construction, quality finishes, and a private setting, this home offers a great combination of comfort, functionality, and style.

Listed by Stephen Webby of Vaux Realty,LLC

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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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10 Cedarcrest Canton MA 02021

Canton, MA10 Cedarcrest

Price$850,000

Est. Mortgage: $/month

MLS Number 73525550

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,304
  • High School Canton Sr

Located in the highly desirable Spring Valley neighborhood, this meticulously maintained home is ready for its new owners. Conveniently located within walking distance to the Kennedy Elementary School and playground, and just a short distance to town, the train, and shopping.The home features a beautiful sun-filled kitchen with granite countertops, a spacious family room, versatile dining area, and four generously sized bedrooms. Need space for extended family or in-laws? You'll love the attached inlaw unit offering flexibility and endless possibilities.Set in an incredible neighborhood, the property also boasts a large yard, deck, and patio perfect for entertaining or relaxing outdoors. Storage is never a concern with the impressive six-car garage addition. A wonderful opportunity to enjoy comfort, space, and outdoor living all in one exceptional home.

Listed by Britta Reissfelder Group and Britta S. Reissfelder of Coldwell Banker Realty - Canton

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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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15 D Street Hull MA 02045

Hull, MA15 D Street

Price$764,990

Est. Mortgage: $/month

MLS Number 73524260

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,236
  • High School Hull High School

NEW TO MARKET !!! Check out this 4 bedroom, 2 full bath expanded Ranch style home located in the Alphabet section of town and just steps to the Bay and a few minute walk to sandy Nantasket Beach. The interior of the home features beautiful hard wood flooring on main floor, wood burning fireplace in the large Living Room area with upgrades to the roof and a majority of the windows as well as care-free vinyl siding and new heating system in 2025. There is a 1-car BONUS garage area with extra storage. There is a huge walk out finished lower level PERFECT for in-law setup. There are multiple commuter options incl the Train service AND ferry service into the City of Boston. This home is right around the corner from Sunset Marina where you can park your Yacht, and very close to one of the best restaurants in town, Local 02045 for fine dining and gorgeous and stunning sunsets. Enjoy the private back yard patio for entertaining family and friends. This home has it all. Don't miss your chance!

Listed by Brian S. McCarthy of McCarthy & Gratta RE

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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6 Sunnyside Avenue Randolph MA 02368

Randolph, MA6 Sunnyside Avenue

Price$749,900

Est. Mortgage: $/month

MLS Number 73523454

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,775

Amazing Opportunity to own this one of a kind 4 BR 3 Bath Custom Log Cabin Ranch with Central Air located in Randolph. Best of all this Home also has a legal 1BR In-Law. This one is set on a beautiful, wooded lot. It's hard to believe you are just a short drive to Boston. Gleaming Hardwood floors throughout this open floor plan are accented w beautifully finished plank walls & exposed beams. Spacious Living Room features Cathedral Ceilings and a beautiful Stone Fireplace. This Home would be the perfect place to Host the Holidays or Entertain Family & Friends. A covered Farmer's porch stretches along the front of the Home and really offers a rustic outdoor living space perfect for grilling, relaxing after a long day, or just enjoying the serenity of the location. A perfect fit for buyers seeking expanded living space or independent living as the In-Law unit is connected to the main house. City Water & Sewer. Commuter's Delight just minutes to MBTA Stations & Southeast Expressway.

Listed by Jayson LaPlante and Julie Cambra of Milestone Realty,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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 Morning Stroll Plymouth MA 02360
Price Changed

MLS Number 73523322

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,389

Rare opportunity for a brand new home w/garage space for 3 vehicles, steps to all amenities of the Village Green at The Pinehills! Built by Barefoot Cottage Company, this last "flex" open floor plan home in popular Summerhouse Cottages features first floor home office, primary suite w/luxurious bath, first floor laundry, half bath, luxury wide plank flooring & gas fireplace! Vaulted custom channel gap ceiling in gourmet kitchen w/quartz countertops & island perfect for entertaining! 2 additional bedrooms, full bath & loft on second floor w/ample custom closets. Covered porch off dining area & front covered porch, plus beautiful landscaped stairs to rear yard. Lower level walkout offers endless possibilities w/separate street entrance & third garage-can be finished as additional independent living space for in-law, boomerang kid, or more! Love where you live & walk to morning coffee, afternoon gelato or evening craft brew at the beer garden! Some photos virtua

Listed by Andrea Suba of Pinehills Brokerage Services LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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133 River Street Norwell MA 02061

Norwell, MA133 River Street

Price$1,500,000

Est. Mortgage: $/month

MLS Number 73519604

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,612
  • High School Norwell

This Norwell beauty has all the smart improvements: roof, HVAC, electrical and plumbing. Walk to Norwell Center or the North River from this turn-key property! The newly updated kitchen is sleek and efficient with dual appliances & so much storage. New bathrooms feature high-end finishes of marble, glass & tile. Large, beautifully proportioned spaces on the main level include a 36ft long Media Room in converted barn with wet bar, a dining room ringed by windows overlooking the rear yard, and an elegant fireplaced living room. Four sunny bedrooms (including a primary) and two full bathrooms make up the second floor reached by front or rear staircases. Who needs an in-law or multi-gen option? The converted barn has a kitchen space, dedicated entrance, + bedroom, sitting room, full bath and walk-in closet upstairs. Character and efficiency have been preserved with careful restoration of windows, floors and woodwork details. Walk out basement and deck lead to gardens and privacy. Convenient commute to Boston only 26 miles north by car, train or boat. Be in before school starts!!

Listed by The Laurie Detwiler Team and Laurie A. Detwiler of William Raveis R.E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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19 Copeland Street Marshfield MA 02050

Marshfield, MA19 Copeland Street

Price$979,000

Est. Mortgage: $/month

Price Changed

MLS Number 73519455

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,773
  • High School Marshfield High

If you are looking for space, privacy, and endless options to customize this is the home for you! With one front entrance leading to the living room and main staircase, and another leading to the above garage great room, there is a strong opportunity for an in-law suite! One full bath downstairs, and two full baths upstairs allow for added flexibility. Alternatively, the great room above the garage is spacious enough for an entertainment space, kids playroom, or studio setup. Dense foliage surrounding the property contributes to a very private and secluded living environment! Large front and back yards provide ample outdoor space to enjoy the peaceful atmosphere. Important updates include the roof replacement in 2024, hot water heater replacement in 2023, kitchen renovation in 2025, and 2 uplifted bathrooms in 2026. Just a few minutes from home, you can enjoy access to Marshfield Center, Green Harbor Golf Course, and various public beaches (Rexhame, Fieldston, Green Harbor)!

Listed by Jacob Cincotta of Paramount Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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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10-12 Drew Avenue Weymouth MA 02189

Weymouth, MA10-12 Drew Avenue

Price$690,000

Est. Mortgage: $/month

Price Changed

MLS Number 73519022

  • MultiFamily
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 1,775
  • Parking Spaces 6

Wonderful 2 unit Duplex home that has been owned by the same family for generations. Well loved and maintained thoughout the years . Main house has 3/4beds, 1 full bath, eat in kitchen, living room, walk out to enclosed porch. The Second unit has 1 bed, 1 bath, living room and eat in kitchen . Basement has laundry area and good storage space. Lovely yard , drive way for parking. gas heating system , This home is perfect for in-law, extended family situation , multi generational living or additional income. convenient to schools, walk to Jackson Square and commuter rail.

Listed by Ann Harrington of Lighthouse Realty Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 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

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