Homes with In-Law Suites for Sale on the South Shore

MLS Number 73519050

• Residential
• Next Open House: Sat 05/16 11:00 am. to 1:00 pm.
• Bedrooms 5
• Bathroom 4
• Square Feet 5,022

Discover this stunning contemporary retreat set on 1.5 private acres at the end of a cul-de-sac, offering 5 bedrooms, 4 bathrooms and 13 rooms designed for year-round enjoyment. A private in-law/au-pair suite with its own entrance, laundry and kitchenette adds exceptional versatility. The expansive custom kitchen opens to a sun-filled family room with wood stove, complemented by an inviting game room with vaulted ceilings and a formal living room with fireplace. Each room captures beautiful natural views, enhancing the home's connection to its surroundings. Enjoy staycation-worthy amenities including a gunite pool and generous outdoor spaces ideal for relaxing and entertaining. The primary suite features a private balcony and spa-like bath, while three additional bedrooms, a full bath, and second laundry complete the upper level. Unique architecture, a flexible layout and a private setting make this home a rare find.

Listed by Deb Jones McIntyre of Coldwell Banker Realty - Milton

MLS Number 73518988

• Residential
• Next Open House: Sat 05/16 1:30 pm. to 3:00 pm.
• Bedrooms 6
• Bathroom 5
• Square Feet 4,784

Welcome to 25 Towpath Dr, a legacy estate in one of Wilmington's most coveted neighborhoods. This stunning 6-bed, 5-bath Colonial sits on nearly an acre of manicured grounds and was built to bring people together. Step inside to a sun-drenched main level featuring a chef's kitchen with granite counters, a formal dining room with wainscoting, and a cozy fireplace in the family room.The crown jewel? A rare, bi-level in-law suite complete with 2 bedrooms, 1.5 baths, a full kitchen, private entry, and a private elevator-perfect for multi-generational living. Outside, your private resort awaits. Entertain on the expansive deck or unwind in the heated gunite pool and spa. Surrounded by lush landscaping and steps from the scenic Towpath trail, this home offers unparalleled privacy. With a 3-car garage, updated central air & heating, and meticulous care, this isn't just a home-it's a lifestyle. Rare, refined, and ready for its next chapter.

Listed by The Avenue and Thomas McKenna of Serhant

MLS Number 73518909

• Residential
• Next Open House: Sat 05/23 12:00 pm. to 2:00 pm.
• Bedrooms 4
• Bathroom 5
• Square Feet 4,066

Tucked behind a canopy of mature trees on 1.37 private acres, this stunning Cape Cod rambler delivers the space, style, and substance today's discerning buyer demands. With 4,066 sq. ft. of thoughtfully designed living space, 5 bedrooms, and 4 full baths, this home lives large - and the upgrades list is exceptional. The chef's kitchen anchors the main level, featuring a professional Wolf range and flowing into generous entertaining spaces dressed with wide-plank pine floors. In-law potential adds flexibility rarely found at this price point. A 4-year-old Harman pellet stove and a 3-year-old HVAC system mean efficiency and comfort are already dialed in - as is the fully paid Evergreen solar system.; laundry room w walk-in closet, new HVAC, well-water irrigation, Dehumidifier in basement, The 3-year-old roof, updated electrical panel, and battery-powered security cameras with local hard drive backup round out a home that's been maintained like a product. ****READ ATTACHED DESCRIPTION*

Listed by James Aldred of Keller Williams Realty Signature Properties

MLS Number 73518661

• Residential
• Next Open House: Sat 05/16 11:00 am. to 12:45 pm.
• Bedrooms 4
• Bathroom 3
• Square Feet 2,226

Welcome to Easton! Set on a picturesque and private 1.87-acre lot surrounded by beautiful gardens, this home is just a short walk to Borderland State Park. Thoughtfully updated for energy efficiency, it features newer owned solar panels, upgraded insulation, a high-efficiency Lennox Signature heating system, new central air, UV sanitation, heat pump water heater, water filtration system, whole-house humidification/dehumidification, Hardie Plank siding, new windows, a young roof, and a newer septic system. The sun-filled kitchen, dining, and living areas showcase soaring ceilings and an open feel. All three full baths are tastefully renovated with high-end finishes and custom tile. The primary suite includes an oversized soaking tub with a rain shower. This 4-bedroom home offers in-law potential with a lower level featuring a bedroom, full bath, kitchenette, and family room. Relax on the expansive new deck overlooking your private, wooded backyard. New interior doors/trim. EV Charger

Listed by Lisa Cranshaw of William Raveis R.E. & Home Services

MLS Number 73518561

• Residential
• Next Open House: Sat 05/16 11:00 am. to 12:30 pm.
• Bedrooms 6
• Bathroom 4
• Square Feet 3,840

Welcome to the 8 Charles St compound., a stately Victorian-style home showcasing timeless period architecture and unforgettable curb appeal. This absolutely breathtaking property is the one you drive by and wonder what the inside looks like-and it does not disappoint. Inside, original stained glass windows and rich architectural details blend beautifully with modern updates throughout, including a thoughtfully renovated kitchen. The expansive floor plan spans four finished levels, offering multiple living spaces, a dedicated dining room and an incredible enclosed porch perfect for year-round enjoyment. The second floor features a sun-filled primary suite with walk-in closet, along with two well-appointed bedrooms, a full bath, and convenient laundry. The walk-up third level provides two additional flexible bedroom options. A rare bonus is the detached two-car garage with an in-law suite or private guest quarters, complete with bedroom, bathroom, and living space. Truly one-of-a-kind.

Listed by The Allain Group, Jessica Allain and Gabby Nunez of Compass

MLS Number 73511844

• Residential
• Next Open House: Sat 05/16 11:00 am. to 12:30 pm.
• Bedrooms 5
• Bathroom 4
• Square Feet 4,788

An original owner, custom built distinguished residence offers an exceptional opportunity for an elevated lifestyle. Set on a generous 4+ acres lot at the end of the cul-de-sac to enjoy the serenity and privacy. A modern kitchen with a large island, a separate eating area and open concept family room with a beautiful stone fireplace. A formal dining room for entertaining ensures convenience & comfort for hosting or quiet dinners. Gorgeous, custom built-in cabinetry, w/wet bar & fireplace in formal living rm/office. A first fl. primary bedroom, cathedral ceiling & sky light. 3 bdrms, loft, full bath on the 2nd floor. Bonus of in-law suite that sits over the 3 car garage providing ample flexible space for various living or generational arrangements. A common mud room entrance provides a separate, private entrance to each living space. A Huge unfinished basement with endless possibilities await. Explore the possibilities &envision your future in this remarkable, sought after home.

Listed by Maria Varrichione of REMAX Executive Realty

MLS Number 73518281

• Residential
• Next Open House: Thu 05/14 5:30 pm. to 7:00 pm.
• Bedrooms 3
• Bathroom 3
• Square Feet 2,288

Cary Hill Area is home for this custom oversized Colonial newly built in 2000. This eight room home features a well-designed open and airy floor plan which is perfect for large gatherings. The kitchen is equipped with new stainless appliances and leads to a spacious family room with a gas fireplace. The first floor includes a dining room and formal living room with French doors. The sunny deck overlooks a nice backyard and two car garage.The second level offers three + bedrooms, two bathrooms, with the fourth room offering flexibility for an office, nursery, or a laundry room. The spacious attic has good ceiling height with great potential for two extra bedrooms and a bathroom.The basement of this home also offers expansion possibilities with an expansive space and headroom for a potential in-law or an ADU.The Cary Hill area is proximate to East Milton Square with its shops and restaurants, Milton Academy, and major highways including to and from downtown Boston.

Listed by Paul Hurley of Coldwell Banker Realty - Milton