Middleton Homes for Sale

Welcome to Middleton, a charming city nestled in the heart of Wisconsin, where small-town warmth meets modern convenience. Known for its picturesque landscapes and vibrant community spirit, Middleton offers residents a unique blend of suburban tranquility and urban accessibility. With its rich history, beautiful parks, and a bustling downtown area filled with eclectic shops and delicious dining options, Middleton is a place where everyone can feel at home.

One of the highlights of living in Middleton is its strong sense of community. The city hosts numerous events throughout the year, including farmers' markets, art fairs, and seasonal festivals that bring neighbors together and celebrate local culture. Families will appreciate the highly-rated schools and safe neighborhoods, making it an ideal place to raise children.

For those looking to make Middleton their home, there is an array of homes for sale that cater to various tastes and budgets. From charming historic houses with character to modern, energy-efficient builds, the real estate market here is diverse and inviting. Whether you’re seeking a cozy starter home, a spacious family residence, or a luxurious property with stunning views, Middleton has something for everyone.

With its friendly atmosphere, excellent amenities, and beautiful surroundings, Middleton is not just a place to live; it’s a community where you can thrive. Explore the homes for sale in this delightful city and discover the perfect spot to create lasting memories. Your dream home awaits in Middleton!

Newest Middleton Homes for Sale

$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. 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. This remarkable home offers privacy, luxury, and access to top-rated schools.

6 Zaloga Way, Middleton

$1,875,000

5 Beds ⋅ 4 Baths ⋅ 73574923 MLS

Tucked away at the end of a private cul-de-sac, this exceptional 6+ acre estate offers exceptional privacy, natural beauty, and waterfront living. Surrounded by mature trees, the property features a pond and approx. 1,000 feet of Ipswich River frontage, creating a secluded retreat with tranquil views, and abundant wildlife. A heated gunite pool enhances the setting. Inside, the home offers a grand foyer, sunken family room, wood-burning fireplace, bright kitchen with breakfast area, office, laundry, half bath, and formal living room with vaulted ceiling and French doors to the dining room. Upstairs features a spacious primary suite with skylights and custom closets, two large bedrooms, loft, bonus room, and full guest bath. Second-floor bedrooms overlook picturesque views of the pond and surrounding woodlands. The walk-out lower level includes a separate entrance, second kitchen, full bath, and office with in-law potential.

19 Devonshire Road, 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

$899,000

2 Beds ⋅ 2 Baths ⋅ 73572720 MLS

A pristine home awaiting new ownership! Tucked away on one of Middleton’s most sought-after streets, this beautifully maintained home offers the perfect blend of privacy, comfort, and convenience, with plenty of opportunity to make it your own. Set on a picturesque 1.1-acre lot, the home features a dramatic living room with soaring ceilings, a wood-burning fireplace, and abundant natural light. The updated kitchen is complete with an oversized center island, stainless steel appliances, and generous cabinetry, flowing seamlessly into the dining area for effortless entertaining. The first-floor primary suite offers the convenience of one-level living with a private ensuite bath. A generously sized guest bedroom and additional full bath complete this level. A two-car garage adds everyday convenience and additional storage. A full unfinished upper level and lower level provide exceptional storage and exciting future potential. Ideally located near Route 114, Richardson’s Ice Cream, and the Masconomet school system.

109 Flint Farm Rd, 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

$345,000

2 Beds ⋅ 1 Baths ⋅ 5101269 MLS

Enjoy year round living with deeded access to beautiful Sunrise Lake from this sun filled, 2-3 bedroom home! Whether you're searching for your primary residence, a weekend retreat, or a place to create lasting family memories, this property offers the perfect blend of comfort and relaxation. The open concept living area creates a warm and inviting space for everyday living, while the finished lower level family room provides plenty of additional space for movie nights, game days, a home office, fitness area, or overnight guests. A whole house generator offers added peace of mind and comfort throughout every season. Step outside and enjoy evenings around the fire pit, the perfect place to relax or entertain under the stars. A storage shed provides plenty of room for lawn equipment, outdoor gear, and all your lake toys. Just a short walk to one of the two community beaches, you'll enjoy swimming, boating, kayaking, fishing, or simply relaxing by the water all year long. Conveniently located with easy access to Route 16, this home offers an easy commute to the Seacoast, the Lakes Region, and surrounding communities while enjoying the lake lifestyle. Whether you're looking for your first home, your forever home, or a weekend getaway, this property offers the perfect balance of everyday comfort and year round recreation.

11 Dudley Dr, Middleton

$679,000

2 Beds ⋅ 2 Baths ⋅ 73552573 MLS

Situated at 15 Hilldale Ave in Middleton, MA, this single family residence, of appx 1408 square feet of living space, plus a screened room and large deck. This property represents a unique opportunity to acquire a residence in a desirable community. The residence encompasses two bedrooms, one on each floor each designed to provide comfort and privacy. Complementing these sleeping quarters are two full bathrooms, The property is further enhanced by a rear lot on Belleview Road for a total of 14444 square feet, providing a great location for an Accessory Dwelling Unit (ADU), or another house lot, subject to Middleton Rules and regulations.

15 Hilldale Ave, Middleton

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 73550711 MLS ⋅ ['The Village At Boston Brook'] BLDG.

Units 141&143 MODEL OPEN FOR SHOWINGS ~ 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.

141 Essex Street Unit 141, Middleton

$649,000

3 Beds ⋅ 4 Baths ⋅ 5098090 MLS

BIG PROGRESS update on this newly built, quality home with lake access. Construction is in its final phase and the home is on track for September delivery. Built with quality and perfect for spending time with friends & family, the main level centers on an open concept kitchen, dining, and living area built for flexible entertaining with a large bonus room just 4 steps up from the first level over the garage. The first-floor primary suite includes a large walk-in closet and ensuite. Two generous bedrooms on the second floor include a shared full-bath and a large landing that can be used for reading or a home office. This home home is built for entertaining with year-round comfort, ready for New England winters, not just summer weekends. You’ll find character at every turn with the ease of maintenance that most “comp” properties in this area simply cannot offer. Set in the Sunrise Lake district with water rights, the lot itself does a lot of the work: quiet, wooded, the kind of setting where you actually hear the difference. Low-maintenance, new construction means more time on the water and less time on upkeep, whether this is a seasonal escape or your everyday address. Move in by fall: with September 1 delivery locked in, there's still time to make this one yours before the season turns. If you're looking for new construction with real square footage, real materials, and real water access in the NH Lakes region, come see it before someone else does.

73 Spruce Rd, Middleton

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