South Shore Homes with In-Ground Pools

MLS Number 73568734

• Residential
• Bedrooms 5
• Bathroom 5
• Square Feet 4,800

Own a rare piece of local 19th Century history with this iconic historical home custom built for P.T. Barnum entertainer, General Tom Thumb. Sitting in front of 114 acres of conservation land, with its distinctive Mansard roof, this nearly 4761 square foot Victorian is full of architectural character throughout, where 10 foot ceilings, exquisite original plasterwork, oversized hardwood doors, ornate hand turned railings and balusters, built ins, crown moldings, ceiling medallions and custom wall alcoves showcase craftsmanship rarely found today. A striking main staircase anchors the home, while a separate original servant staircase connects its four finished levels and offers a fascinating glimpse into the home's history. Thoughtfully updated over the years, the home blends historic character with modern comfort. The renovated chef's kitchen features custom cabinetry, high end appliances including a Viking gas stove and oven, and dramatic brick archways opening to the family room. A working dumbwaiter connects to the dining room and butler's pantry, while the original lower height stove is another unique reminder of the home's past. With 5 bedrooms, 4.5 bedrooms including a spacious primary suite, multiple gathering spaces, gas heating and central air, this property is as functional as it is nostalgic. Outside, the nearly 1.5 acre property was designed for entertaining. The fenced grounds feature an oversized in-ground pool, expansive patio, and a pool house with kitchenette and bath offering exciting potential for future ADU use, subject to buyer due diligence and required approvals. A separate cabana with built-in grill and Italian brick oven creates another destination for outdoor gatherings, while an awesome garden shed adds charm and useful storage. A heated and insulated three car garage provides abundant parking and storage. Rich in history, architectural detail and scale, the Tom Thumb House offers the rare opportunity to own a home with a story unlike any other, while still enjoying the space, amenities and comfort today's lifestyle demands.

Listed by Ashley Trapp of The Simply Sold Realty Co.

MLS Number 73565003

• Residential
• Bedrooms 3
• Bathroom 1
• Square Feet 1,532
• High School Holbrook Ms & Hs

Welcome home to this well-maintained single-level ranch in Holbrook, offering easy one-floor living with 3 bedrooms, 1 full bath and plenty of space to enjoy both indoors and out. The bright interior features a spacious living room, an updated white kitchen with granite countertops, a built-in island & seating, and stainless appliances, plus an additional family room for flexible everyday living. A fantastic enclosed porch extends the living area and overlooks the unbelievable backyard, perfect for summer entertaining with an in-ground pool and fenced-in yard. Outside is where this property really shines! The fully fenced lot creates a private backyard retreat centered around the in-ground pool, extensively updated in May 2026 with resurfacing, a new liner, new piping, and new stairs. There's plenty of surrounding patio and yard space for entertaining, grilling, and relaxing by the pool. Additional highlights include low-maintenance vinyl siding, solar panels, ample off-street parking, and a nicely landscaped yard. A comfortable, move-in-ready ranch with a backyard built for summer, just unpack and enjoy!

Listed by Kristen M. Dailey of The Firm

MLS Number 73559531

• Residential
• Bedrooms 4
• Bathroom 3
• Square Feet 2,011

Beautifully maintained and offered fully furnished, this 4-bedroom, 2.5-bath home is tucked away on a quiet double cul-de-sac just off Route 53, offering exceptional convenience to Derby Street Shops, Route 3, South Shore Hospital, and the commuter boat and commuter to Boston. Designed for flexibility, the main level features two bedrooms and a full bath, ideal for single-level living or guests. The open-concept living and dining area centers around a cozy fireplace, while the chef's kitchen boasts a Wolf 6-burner range, Sub-Zero refrigerator, radiant heated floors, and quality finishes throughout. Upstairs are two additional bedrooms and a half bath. The finished walk-out lower level offers over 1,100 sq. ft. with a full bath and direct access to the backyard and the pool. Enjoy a professionaly landscaped backyard resurfaced in-ground pool, expansive deck, paver patio, fire pit, custom shed, new roof (2025), new garage door, and beautifully landscaped fenced yard.

Listed by Katie Norton and Joanne Conway of William Raveis R.E. & Home Services

MLS Number 73559145

• Residential
• Bedrooms 2
• Bathroom 2
• Square Feet 1,756

Nestled along the tranquil Eel River in Plymouth's highly sought-after Chiltonville neighborhood, this beautifully updated contemporary ranch embodies the best of sophisticated one-level living. Thoughtfully renovated with timeless style and quality craftsmanship, this exceptional residence offers two bedrooms and two full baths, blending comfort, functionality, and refined design in an idyllic waterfront setting. The heart of the home is a breathtaking cathedral-ceiling newly remolded (2026) kitchen where exposed beams and a dramatic floor-to-ceiling white brick wood-burning fireplace create a striking architectural centerpiece in the spacious living room with walls of windows to enjoy the natural light. The adjacent dining room with closet and French doors is perfect flex space. Beautifully refinished hardwood flooring flows throughout the light-filled living spaces, while the open-concept design captures peaceful views of the surrounding landscape. A beautifully crafted three-season room with custom molding and bead board ceiling provides a private retreat, while an expansive porch and oversized deck with a custom retractable awning invite effortless indoor-outdoor living. Outside, a sparkling in-ground pool with surrounding patios & storage shed overlooks a sweeping rolling lawn that gently extends to the Eel River, creating a private setting for entertaining or quiet relaxation.Additional highlights include a two-car garage under and a Title V-approved four-bedroom septic system, providing outstanding potential for a future addition or accessory dwelling unit (ADU), subject to local approvals. The lower level has a heated private office area or play room. Offering contemporary flair, exceptional outdoor amenities, waterfront beauty with the ever changing season and room to grow, this remarkable Chiltonville property is just minutes from Plymouth's historic waterfront, beaches, shopping, restaurants, golf, and commuter routes.

Listed by Lynne Morey of Coldwell Banker Realty - Plymouth

MLS Number 73553456

• Residential
• Bedrooms 5
• Bathroom 8
• Square Feet 5,650
• High School Canton Sr

Welcome to 480 York Street, an extraordinary custom-built estate being offered for sale for the very first time. Privately nestled on an impressive 5.93-acre parcel, this one-of-a-kind property combines timeless craftsmanship, exceptional living space, and a breathtaking natural setting to create the ultimate private retreat.From the moment you arrive, you'll appreciate the home's commanding presence, complemented by an attached three-car garage and an additional detached three-car garage featuring a spacious lofted bonus room-perfect for a home office, studio, guest suite, recreation space, or the ultimate car enthusiast's workshop.Designed for both grand entertaining and comfortable everyday living, the residence offers 13 thoughtfully designed rooms, including five generous bedrooms and an inviting open-concept floor plan. At the heart of the home is a spectacular chef's kitchen, beautifully appointed with custom cabinetry, high-end appliances, granite countertops, an oversized center island, and a large walk-in pantry. The adjoining sunroom is flooded with natural light, creating the perfect place to enjoy your morning coffee while overlooking the picturesque grounds.Exceptional craftsmanship is evident throughout, with rich hardwood flooring, elegant decorative moldings, custom millwork, and three fireplaces adding warmth, character, and sophistication. Expansive windows line the rear of the home, allowing sunlight to pour into the living spaces while showcasing the beautiful backyard and surrounding landscape.The luxurious primary suite is a true private sanctuary, offering a spacious sitting room, two oversized walk-in closets, and separate his-and-her bathrooms, providing comfort and privacy rarely found in today's homes. Each additional bedroom is generously sized, making the home ideal for family living and hosting overnight guests.The expansive lower level presents endless possibilities. Whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, golf simulator, or additional living quarters, this finished space is ready to be customized to fit your lifestyle.Step outside and experience your own private resort. The beautifully landscaped backyard features a stunning in-ground pool surrounded by an expansive patio, offering the perfect setting for summer entertaining. Call for your private tour!

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