Colonial Homes for Sale on the South Shore

MLS Number 73518305

• Residential
• Bedrooms 4
• Bathroom 2
• Square Feet 2,688
• High School Oliver Ames

This stately home sits high on a hill backing up to a mature neighborhood with plenty of space for outdoor entertaining with it's updated and reimagined landscaping and new fence. Known as the Dickerman Estate on almost an acre of land, this home boasts historic charm & character while having the conveniences of today's needs: an updated kitchen, fresh interior paint, newer cabintry in the bathrooms & recessed lighting in the office. Wide pine floors, claw foot tub, & a dutch style door creates a sense of nostalgia that only a cared for antique home can offer. The roof on the main house, front door, fence and oil tank have all been replaced. Many structural items have been addressed as needed for it's age. The attached carriage house/shed/mudroom/workshop needs your vision & touches to match the elegance of the rest of the home. Conveniently located near the highway (Rt24) and shopping: Roche Bros, Beanery, Langwater Farm, Farmer's Daughter & more. Open house 5/16 11-2pm!

Listed by Karly Graham of eXp Realty

MLS Number 73518281

• Residential
• 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, one of which, is the primary bedroom with it's own bath.The fourth room offers the flexibility to be 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 to downtown Boston.

Listed by Paul Hurley of Coldwell Banker Realty - Milton

MLS Number 73518247

• Residential
• Bedrooms 5
• Bathroom 2
• Square Feet 2,088
• High School Mhs/ Amsa

Offer Deadline Tuesday at 12pm - Welcome to this beautifully maintained and well cared for home in the heart of Marlborough - filled with character and charm. Zoned multi-family, yet utilized as a single-family home for decades, offering wonderful potential for in-law or extended family. While some cosmetic updates may be desired, many major improvements have already been completed, including all new windows, roof, boiler, water heater, updated electrical, and much more. Features include abundant natural light throughout, classic baseboard and crown molding details throughout, potential for additional living space in the basement, and walk-up attic with high ceilings offering nearly 500 sqft of additional bonus space. Private level backyard. Conveniently located on a side street near downtown, walk to the new public library, parks, local amenities, and the Marlborough Boardwalk. Open House Friday 4-6 PM & Sunday 1-3 PM.

Listed by Kassia Silva of REMAX Executive Realty

MLS Number 73518241

• Residential
• Bedrooms 4
• Bathroom 2
• Square Feet 1,838

Beautifully maintained 4-bedroom, 1.5-bath Colonial blending timeless character with thoughtful updates throughout. Step inside through the inviting front entry into a sun-filled foyer showcasing gleaming hardwood floors, soaring ceilings, decorative radiators, elegant French doors, detailed trim work, and stunning built-ins that add warmth and character throughout the home. The spacious living and dining areas flow seamlessly, creating the perfect setting for entertaining or everyday living. The updated eat-in kitchen features granite countertops, stylish cabinetry, stainless steel appliances, decorative tile backsplash, and direct access to the rear deck and backyard. Upstairs offers generously sized bedrooms and updated baths, while the walk-up attic provides exceptional storage and future expansion potential. Conveniently located near shopping, dining, parks, and commuter routes. Timeless character, modern updates, and room to grow in a beautifully maintained home.

Listed by Christian Doherty of Doherty Properties

MLS Number 73518197

• Residential
• Bedrooms 5
• Bathroom 1
• Square Feet 1,325

Rare opportunity at 104 Bedford Ave! Generationally owned by one family, this 5-bedroom, 1-bath home is ready for its next chapter! Endless potential for investors, contractors, or buyers looking to restore and reimagine a property with history and character. Convenient first-floor layout offers 2 bedrooms on the main level, with 3 additional bedrooms upstairs, including closets with custom built-ins. Close to Route 113 for easy commuting. Conveniently located near major routes, shopping, restaurants, and public transportation, and just in time to enjoy summer festivals and scenic walks along the Merrimack River! With vision and renovation, this home could truly shine once again. Property sold as-is. *OFFER DEADLINE SET FOR WEDNESDAY MAY 20TH 10:00 a.m.

Listed by Kristy Schiavo of Lamacchia Realty,Inc.

MLS Number 73518174

• Residential
• Bedrooms 3
• Bathroom 3
• Square Feet 2,244

Tucked along a private road at the edge of the Arboretum, this beautifully rebuilt 2009 single family offers a rare sense of calm within a connected urban setting. Rebuilt by master builder Chris DeSisto of Maplehurst Builders, the home reflects the sensibility of someone who understood not only how to build, but how to live. There is a feeling that is hard to name, something between a cabin in the woods and a well crafted boat, where every inch is thoughtfully considered and deeply comfortable. Warm natural wood, soaring ceilings, and abundant light define the main living space, anchored by a fireplace and an open, well designed kitchen with custom cabinetry. A first floor bedroom and full bath offer flexibility, with two bedrooms above. The finished lower level adds living space, a full bath, and room for work or recreation. Set on a 4,185 sq ft lot with a small yard, ample parking, and a Tesla charger, this 2,244 sq ft home lives with ease, shaped by both nature and neighborhood.

Listed by The May Group, Abigail Clutz, Anne Fantasia and Lisa May of Gibson Sotheby's International Realty

MLS Number 73518168

• Residential
• Bedrooms 4
• Bathroom 3
• Square Feet 2,252
• High School Holliston

In a setting and location like no other, this sunny four bedroom home offers unparalleled privacy at the end of a cul-de-sac, with access to Lake Winthrop, close to Patoma Park, and just a short walk to charming downtown Holliston, the Upper Charles Rail Trail, schools, cafes & playground. Granite, eat-in kitchen with stainless appliances and slider out to lovely composite deck and backyard; inviting family room with gas fireplace and hickory flooring; spacious dining and living rooms; great mudroom with cabinetry; powder room with marble vanity. Upstairs are all four bedrooms, including the primary with hickory wood flooring, walk-in closet and updated bathroom with granite countertops. Walk-up attic provides both great storage and expansion possibilities. *Brand new roof in 2025* Newer Buderus boiler (9 yrs); new oil tank (3 yrs); freshly painted interior (2026); driveway (2021). Gorgeous, flat lot provides privacy, recreation & relaxation. Stroll downtown on the new sidewalk!

Listed by Kathy Chisholm of Realty Executives Boston West