Middleton Homes with Colonial Style

Welcome to Middleton, Massachusetts—a charming town nestled in Essex County that perfectly blends suburban tranquility with rich historical charm. With its picturesque landscapes, friendly community, and convenient location, Middleton is an ideal place for families and individuals looking to settle down in a serene environment while still being close to urban amenities.

One of the standout features of Middleton is its stunning collection of Colonial-style homes. These timeless residences echo the elegance of America’s past, often featuring classic architectural elements such as gabled roofs, symmetrical facades, and inviting front porches. The Colonial homes in Middleton not only exude character but also offer spacious layouts, making them perfect for both entertaining and everyday living. Many of these homes are set on generous lots, providing ample outdoor space for gardening, play, or simply enjoying the beautiful New England seasons.

Living in Middleton means embracing a lifestyle filled with community spirit and outdoor activities. The town is surrounded by lush parks and conservation areas, perfect for hiking, biking, and family picnics. With a strong sense of community, residents often come together for seasonal events, farmers' markets, and local festivals that celebrate the town's heritage.

Whether you’re drawn to the historical charm of Colonial architecture or the welcoming atmosphere of a close-knit community, Middleton offers a unique blend of both. Explore the possibilities of making this delightful town your new home, where history meets modern living in the heart of Essex County.

Newest Middleton Homes with Colonial Style

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 73575674 MLS

Single family alternative! SIMPLIFY YOUR LIFESTYLE w/out sacrificing space in this exceptional NEW CONSTRUCTION duplex townhome. Thoughtfully designed w/no expense spared, this highly sought-after floor plan features a FIRST-FLOOR PRIMARY SUITE complete w/a full en-suite bath, walk-in closet & soaring 8-foot ceilings, plus the convenience of a 1st-FLOOR LAUNDRY. Open-concept main level showcases a dramatic 2-STORY family room w/ gas fireplace, a chef’s kitchen with an oversized island, pantry, GAS range & stainless-stl appliances, all bathed in abundance of NATURAL LIGHT! Hardwood floors throughout. Upstairs you’ll find two generously sized bedrooms, each with double closets, along with a full bath featuring a tub/shower combination. Enjoy peaceful views of Boston Brook from your PRIVATE DEEDED YARD w/sliders to a composite deck. Walk out basement for future expansion! Professionally landscaped grounds, 2- car garage., wired for future electric car, along with maintenance-free exterior & a home warranty complete this stunning town home.

133 Essex Street Unit 133, Middleton

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 73575076 MLS

Welcome to 6 Zaloga Way, a stunning luxury custom home nestled in the prestigious Ryebrook Estates. This exceptional home offers the perfect blend of timeless elegance, thoughtful design, and high-end finishes throughout. Thoughtfully designed with all bedrooms located on the 1st floor. This 4 bedroom 3.5 bath home sits on a 1.29 acre lot abutting conservation land. The views out the back are spectacular – and with mature trees on each side makes this home very private and quiet. The attention to detail is the winner in this home. The coffered ceilings and gourmet chef’s kitchen hosts Thermador Professional appliances including double ovens, paneled appliances and a warming oven. This home boasts his and her separate master baths and closets. “Her” custom closet is the jewel of the home. The meticulous craftmanship throughout features crown molding, hardwood floors and wainscoting topped with a security system, professional landscaping & irrigation system.

6 Zaloga Way, Middleton

$1,649,000

5 Beds ⋅ 5 Baths ⋅ 73573444 MLS

A rare opportunity in sought-after Ryebrook Estates, offering exceptional privacy, four finished levels, and a three-car garage. Located in Middleton, a charming North Shore community known for its scenic surroundings, small-town feel, and highly regarded Masconomet school system, this home also provides convenient access to major routes, area shopping, dining, and Boston. Inside, soaring ceilings, an open floor plan, abundant natural light, and hardwood floors create an inviting atmosphere. The newly updated 2026 chef’s kitchen is designed for gathering, with quartz countertops and a Thermador five-burner cooktop. The first floor also includes a private office, half bath, laundry room, and new central A/C. Upstairs, the spacious primary suite offers two walk-in closets, along with three additional bedrooms—including one with an en-suite bath—and another full bathroom. Finished in 2021, the top floor provides flexible space for a fifth bedroom, home office, or bonus room, featuring exposed beams and a walk-in closet. Completed in 2022, the expansive lower level includes a game room, den, ¾ bath, and excellent potential for an in-law or guest suite. Surrounded by a custom-designed floral garden, this special property offers an exceptional combination of space, versatility, convenience, and privacy.

22 R Sawyer Ln, Middleton

$1,289,000

4 Beds ⋅ 3 Baths ⋅ 73567014 MLS

This home is completely transformed and truly move-in ready. This beautifully renovated Colonial combines classic New England charm with the style, comfort and convenience of a newly updated home. Ideally located in Middleton and within the highly regarded Masconomet Regional School District, this home has been thoughtfully redesigned from top to bottom, creating a fresh and sophisticated space ready for its next owners. The beautifully updated interior features 4 spacious bedrooms and 3 full bathrooms, offering plenty of room for comfortable everyday living. At the heart of the home is a stunning new gourmet chef's kitchen, thoughtfully designed for both entertaining and daily life. Fresh finishes and carefully selected details flow throughout, creating a cohesive, modern feel while maintaining the warmth and character of a traditional Colonial. A finished basement provides valuable space with endless possibilities-perfect for a family room, home office, playroom, gym or entertainment area. The transformation continues outside with an impressive list of major improvements, including a new roof, new siding, new windows and new driveway. Updated landscaping enhances the homes curb appeal, while the deck and paved patio create inviting spaces for outdoor dining, entertaining and relaxing. The renovation goes far beyond cosmetic updates. Significant improvements have also been made to the homes new HVAC, plumbing, electrical, and ventilation system, offering the piece of mind that comes with a truly comprehensive renovation. With so many major components already addressed, buyers can enjoy an exclusively renovated home without the time and expense of taking on the work themselves. Private showings upon request.

113 River St, Middleton

$1,950,000

5 Beds ⋅ 4 Baths ⋅ 73563129 MLS

Commanding a distinctive Middleton setting, this iconic New England Saltbox rises above 1.88 acres of sweeping lawns framed by mature specimen trees and historic stone walls. Believed to date to circa 1680, this remarkable post-and-beam Colonial was relocated from Salisbury Square to its present hilltop setting in 1929. Carefully preserved over the decades, the home showcases exceptional period character and early New England craftsmanship. A picturesque shared drive passes an antique barn and classic stone bridge, creating a memorable approach to the property. Interior details include five fireplaces, wide-plank floors, exposed beams, and thoughtful modern updates. A spacious country kitchen opens to sun-filled gathering spaces overlooking the grounds, while five bedrooms, a private office, and a dramatic primary suite with cathedral post-and-beam ceilings provide flexible living space. This distinctive Middleton property combines historic architectural character, expansive grounds, and modern comforts, with convenient access to major highways, Boston, and North Shore destinations. Buyers and buyers’ agents should perform their own due diligence regarding the property’s age, history, features, and any other information material to their purchase decision.

47 East St, Middleton

$799,900

4 Beds ⋅ 4 Baths ⋅ 73562452 MLS

What an amazing opportunity for the savvy investor! Known as the Philip Knight House, this remarkable circa 1753 Colonial era homestead has welcomed generations of stewards for more than 270 years. From Philip Knight to Captain Henry Quiner, the Noyes family of soapmakers, then into a working farm with fruit trees and a working cider mill, and later the beloved Blue Door Bed & Breakfast. Each owner has left a lasting mark, while preserving a piece of Middleton's history. Now, the next chapter is yours to write. Will you restore the original pumpkin pine floors and celebrate its remarkable heritage, or reimagine the property for generations to come? However you envision its future, this is a rare opportunity to leave your mark on one of Middleton's most historic homes. Set on approximately 1.29 bucolic acres, this home currently offers over 3,200 sq ft of living space with 4 beds and 3.5 baths (including a 1 bed/1 bath accessory dwelling), along with an oversized 3 car garage and extended driveway, providing the flexibility to restore, renovate, or reimagine to suit your vision. Original architectural details blend with generations of additions, creating a home that's as unique as its history. Outside, the generous lot offers mature landscaping, open space, and room to enjoy the peaceful surroundings. A commuter's dream, conveniently located minutes from several local highways to Boston or points North, while remaining close to all Middleton has to offer, including MASCO just down the road. Whether you're searching for a one-of-a-kind historic residence or envisioning something entirely new, the setting is every bit as exceptional as the opportunity. Sold "as is where is" with no repairs or improvements to be made. The property, being offered well below assessed value and in it's present condition, is not likely to qualify for financing. As applicable, obtaining Title V is solely BUYER responsibility. Listed in MACRIS historic assets database for Middleton, any significant redevelopment/teardown of the property may be subject to Middleton Building Department and Historical Commission review, and would need to adhere to potential demolition delay by-laws. Buyers should conduct their own due diligence regarding applicable demolition review requirements.

20 East Street, Middleton

$1,175,000

4 Beds ⋅ 3 Baths ⋅ 73561765 MLS

Welcome to 25 Essex Street, a beautifully maintained 4-bedroom Colonial offering 3,388 square feet of thoughtfully designed living space in the Masconomet School District. Cared for by its original owners, this inviting home offers comfortable living spaces, quality features, and room to grow. The main level features an open-concept kitchen and living area with hardwood floors, recessed lighting, natural stone countertops, a peninsula with built-in desk space, and a cozy gas fireplace. A formal dining room provides plenty of space for entertaining. The spacious primary suite includes a walk-in closet and soaking tub. Fresh paint, new mirrors, and updated lighting in both bathrooms, along with a refreshed bedroom, add to the home's welcoming feel. The walk-out lower level offers exceptional flexibility and potential, with 9-foot ceilings, four full-size windows, and room to expand the finished space. Use it as a home gym, media room, playroom, office, or additional living area. Outside, enjoy a composite deck and direct backyard access to Middleton's Rail Trail. The trail provides a convenient route to Howe-Manning Elementary School, the adjacent park and baseball field, all less than a quarter-mile from home. The school bus also picks up directly at the driveway. With generous living space, flexible lower-level potential, and an exceptionally convenient location, 25 Essex Street offers a wonderful opportunity to make yourself at home in Middleton.

25 Essex St, Middleton

$2,160,000

4 Beds ⋅ 5 Baths ⋅ 73537542 MLS

Welcome to 4 Shipley Court, where nearly 5,000 sq ft of living space is paired with a backyard built for entertaining. The centerpiece of the property is a resort-like outdoor retreat featuring a Heated Saltwater Pool with custom water features, Jacuzzi, Outdoor Bar, Built-In Stone Fireplace, expansive stone patios, Bose Speaker System, and mature landscaping that creates exceptional privacy. Inside, the home offers 4 bedrooms, 5 bathrooms, a dramatic two-story family room with a floor-to-ceiling stone fireplace, hardwood flooring, and a custom kitchen featuring Russo cabinetry, granite countertops, pot filler, Viking range, and Thermador double wall ovens. The spacious primary suite includes a custom walk-in closet and oversized bath. A stone front exterior, 3-car garage, and thoughtfully designed spaces throughout make this a home equally suited for everyday living and unforgettable gatherings.

4 Shipley Ct, Middleton

$1,475,000

4 Beds ⋅ 4 Baths ⋅ 73533705 MLS

Tucked away at the end of a cul-de-sac in one of Middletons most desirable neighborhoods, and bordering over 750 acres of conservation land, this 4,139 sq. ft. home offers a rare combination of privacy, space, and neighborhood living. Featuring 4+ bedrooms and 3.5 baths, the home is designed for both everyday living and entertaining. The spacious kitchen with center island opens to a sun-filled dining area surrounded by windows overlooking the wooded setting. The primary suite includes a private bath and impressive walk-in closet with custom built-ins. Professionally landscaped grounds with a six-zone irrigation system enhance the home's curb appeal. Additional highlights include public water, natural gas heat, central air, a two-car garage, exterior painted in 2025, and a full walkout basement offering excellent storage and future expansion potential. A unique opportunity to own a well-maintained home that combines size, setting, and long-term value. Schedule a private showing today!

15 Erin Way, Middleton

$1,795,000

4 Beds ⋅ 4 Baths ⋅ 73515209 MLS

Welcome to 16 Couture Way in the highly desirable Northeast River Estates! This beautifully designed home offers an open floor plan perfect for everyday living and entertaining. The spacious kitchen features high-end appliances, a second prep sink, oversized walk-in pantry, and abundant cabinetry, flowing seamlessly into the great room with a gas fireplace. A separate bonus room off the main living area offers flexible space for a playroom, office, or media room. Elegant arched entryways lead into the formal dining room, adding timeless character throughout. The expansive primary suite features cathedral ceilings, a sitting area, two oversized walk-in closets, and a luxurious primary bath with heated floors. Convenient second-floor laundry and a walk-up attic provide excellent storage and functionality. Enjoy the spacious backyard complete with a patio and large side yard, perfect for entertaining and outdoor activities.

16 Couture Way, Middleton

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