Southampton Homes with Colonial Style

Welcome to Southampton, Massachusetts, a charming town nestled in the picturesque Hampshire County. Known for its scenic landscapes and tight-knit community, Southampton offers a serene lifestyle that perfectly balances rural charm with modern conveniences. With its rich history and vibrant local culture, this quaint town is an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

One of the standout features of Southampton is its stunning array of Colonial-style homes. These classic residences exude timeless elegance, showcasing beautiful architectural details that reflect the town's historical roots. With their symmetrical facades, gabled roofs, and inviting front porches, Colonial homes in Southampton provide a warm and welcoming atmosphere. Many of these properties are situated on spacious lots, offering ample outdoor space for gardening, entertaining, or simply enjoying the serene surroundings.

Living in Southampton means embracing a lifestyle that values community, nature, and history. Residents benefit from access to local parks, walking trails, and recreational activities, making it easy to enjoy the great outdoors. The town also hosts a variety of community events throughout the year, fostering connections among neighbors and creating a vibrant social scene.

If you're seeking a home that combines historical charm with modern comfort, look no further than the Colonial-style residences in Southampton. These homes not only provide a beautiful backdrop for your life but also a sense of belonging in a community that values its heritage and welcomes newcomers with open arms. Come discover the allure of Southampton and find your dream home today!

Newest Southampton Homes with Colonial Style

$479,900

3 Beds ⋅ 3 Baths ⋅ 73585185 MLS

This sturdy Colonial offers timeless character, flexible living spaces, and a backyard filled with established beauty. Enjoy easy access to the Southampton Public Library and Conant Park, offering pickleball, basketball, tennis, and youth sports. Lovingly maintained and thoughtfully improved by the same family for nearly 50 years, this home offers a wonderful sense of history and pride of ownership. Enter from one of two covered porches into a bright family room, where beautiful Andersen wood sliding doors bring the outdoors in. With views of the backyard, this inviting space is perfect for relaxing, watching football, enjoying nature, or gathering with family and friends. The functional galley kitchen features a pantry, built-in hutch, and abundant cabinet space, with an adjoining breakfast nook for morning coffee or casual conversation. The main level also includes a formal living room and dining room, gorgeous, pegged oak flooring, and a convenient half bath. Upstairs, the flexible layout offers three or four generously sized bedrooms. The spacious primary bedroom, located in the newer section of the home, features vaulted ceilings and an adjoining room ideal for an additional bedroom, walk-in closet, or home office. Two additional full baths and convenient bedroom-level laundry complete the second floor. The expansive yard features mature dogwood, black walnut, elm, maple, a London Plane tree, along with established blueberry bushes, creating a beautiful natural setting. Recent improvements include a brand-new roof on the house and detached garage, completed in September 2026, fresh paint, duct and furnace cleaning, and a state-of-the-art septic system to be installed. A well-loved home with character, flexibility, and a beautiful setting, ready for its next chapter.

13 East St, Southampton

Listing courtesy of Listing Agent: Kristin Brodeur from Listing Office: Taylor Agency.

$599,900

4 Beds ⋅ 2 Baths ⋅ 73568186 MLS

Stately 3 Story Colonial Home proudly situated on a 1.3 acre in town lot close to Conant Park and Edwards Public Library. Bright, spacious & modern interior flows comfortably throughout the house. Kitchen looks out to the calming backyard and inground pool. Dining Room perfect for casual or formal dining. The Sunroom open to the Dining Room is perfect for relaxing with a good book, favorite beverage and friendly conversations. Front Entry has built-in storage and coat rack. Spacious Living Room shines with a wonderful large bow window looking out to the backyard. Gas fireplace great for those cozy cool evenings. The Living Room is open to another Sunroom with sliding doors to access the block patio. There is a convenient Half Bath downstairs. Upstairs are 4 Bedrooms (pending new septic design). The Main Bedroom enjoys beautiful wood floors, natural light & a stairway to a big Bonus Room with a large walk-in closet. The other 3 Bedrooms have pine floors, closets and ceiling lights. The Full Bath with tile flooring.Basement is partially finished with a bar. Wine racks and bar can stay. There is a Laundry Area with a sink. Holyoke Gas Heat-hot air & Natural Gas water heater. The 3 car garage enjoys extra space for workshop, smalll studio or a great seasonal gathering space. The inground pool is set nicely on the lot with natural screening for privacy. New pool liner 2024, new pool pump Aug. 2026. pool filters 2025 & a new pool solar cover Aug. 2026. Walking in the yard gives you a park like feel with wooded privacy. There is a wooden observation deck overlooking a stream. This home has been loved and cared for and now its your turn to enjoy this wonderful home and property!

32 East Street, Southampton

Listing courtesy of Listing Agent: Dan Schachter from Listing Office: DCS Real Estate, LLC.

$999,000

5 Beds ⋅ 5 Baths ⋅ 73557767 MLS

NEW PRICE! Exceptional 4271 sq.ft. custom Colonial offering resort-style outdoor living on nearly one private acre in Red Brook Estates. The gorgeous backyard features a sparkling in-ground pool, multiple entertainment areas from the deck, patios or finished pool house with outdoor living room and 1/2 bath, creating your own private oasis at home. The attached covered seating area creates the perfect outdoor living room, set for a comfortable area and TV, ideal for relaxing or entertaining throughout the season. Inside, this spacious 5 bedroom, 4.5 bath offers soaring ceilings, abundant natural light and an impressive primary suite with dramatic two-story ceiling, gas fireplace, private deck, spa-inspired ensuite bath, huge walk in closet and impressive private loft, ideal for a home office, fitness or sitting area.This beautifully maintained home seamlessly blends timeless elegance, everyday comfort, and resort-style outdoor living. The open-concept main level offers a grand sense of space, hardwood floors, a warm and welcoming living room, inviting kitchen with dining area, dining room, flex room, primary suite, full bath, 1/2 bath, laundry room and mudroom. Designed with comfort and privacy in mind, you'll find 5 bedrooms, including TWO Primary Suites!! A third bedroom features a private ensuite bath and 3 bedrooms have walk-in closets. Car enthusiasts, hobbyist will appreciate the rare convenience of 2 separate 2 car garages, offering room for 4 vehicles, workshop space or recreational equipment. With its generous living space, flexible floor plan, and exceptional amenities, this home also offers outstanding multi-generational potential, providing privacy and versatility for extended family, guests, or evolving lifestyle needs. Conveniently located near area amenities while offering privacy and tranquility. This remarkable property is a rare opportunity to enjoy luxury living with resort-style amenities right at home.

2 Kevin Dr, Southampton

Listing courtesy of Listing Agent: Goodlife Dream Team from Listing Office: Goodlife Capital Group LLC.

$749,500

4 Beds ⋅ 3 Baths ⋅ 73543429 MLS

Private 1.95 Acre Colonial in a lovely neighborhood offering an Unbeatable Price-Per-Sq-Ft. Escape to your own private sanctuary. Nestled in a highly sought-after Southampton neighborhood, this immaculate 2,800-square-foot, 4-bedroom, 2.5-bath Colonial sits on a gorgeous,1.95 acre lot. Enjoy complete peace, quiet, and privacy, all while benefiting from a significantly lower price-per-square-foot than comparable local listings. Inside, you'll find an open floor plan with custom woodwork, gleaming hardwood floors, a sun-filled living room with a fireplace, dining room, and a spacious family room with French doors leading to a 14x25 deck. The updated kitchen features quartz countertops and a breakfast bar. A ½ bath, laundry room, and mudroom with garage access complete the first floor. Upstairs offers a spacious primary suite with a walk-in closet, jetted tub, and separate shower, plus 3 additional bedrooms and a full bath. The walk-out basement provides excellent potential for future living space, plumbing has been roughed in for a future full bath. The home is surrounded by beautiful landscaping with stone walls and goshen stone walkways Additional highlights include Andersen windows, quality 2x6 construction, a new roof (2025), repointed chimney, economical HG&E natural gas heat, and a convenient location 10 minutes from I-90/91

2 Eastwood Dr, Southampton

Listing courtesy of Listing Agent: Darcie Gasperini from Listing Office: Taylor Agency.

$785,000

5 Beds ⋅ 3 Baths ⋅ 73541332 MLS

Welcome home to privacy in a fantastic neighborhood! Settled high above the street on almost 6 acres is this stunning 5-bed Southampton Colonial with plenty of space for everyone! Crown molding & hardwood flooring are just some of the gorgeous features of this 11-year young home. Highly sought-after first floor primary suite also contains the laundry area as well as a huge primary bath with walk-in shower, Jacuzzi tub & double vanity! Four remaining bedrooms are located on the second floor with overflowing closets for all. The kitchen features granite countertops, white cabinetry, and a gas range for the chef enthusiast. Holyoke Gas & Electric is the gas heat provider for cost savings! The home office off the foyer will be your sanctuary and host dinner parties with ease in the designated dining room. Need more room for a playroom, home gym or gaming area, the partially finished basement will provide just that. Tons of potential on this lot with tiered yard, firepit and pool with deck!

34 Bissonnette Cir, Southampton

Listing courtesy of Listing Agent: Danielle Langevin from Listing Office: Lock and Key Realty Inc..

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