Middleton Real Estate

**Discover Middleton: A Hidden Gem in the Heart of Wisconsin**

Nestled in the picturesque landscapes of Dane County, Middleton, Wisconsin, is a vibrant city that perfectly blends small-town charm with modern conveniences. Known as the "Good Neighbor City," Middleton boasts a rich community spirit, making it an ideal place for families, young professionals, and retirees alike. With its stunning parks, excellent schools, and a variety of local businesses, it’s no wonder that Middleton consistently ranks among the best places to live in the state.

The city is renowned for its natural beauty, featuring an abundance of green spaces such as the scenic Pheasant Branch Conservancy and the popular Middleton Beach. Residents and visitors can enjoy outdoor activities year-round, from hiking and biking in the summer to ice skating and sledding in the winter. The vibrant downtown area offers a delightful mix of boutique shops, cozy cafes, and acclaimed restaurants, ensuring there’s something for everyone to enjoy.

Culturally rich, Middleton is home to various events and festivals throughout the year, including the popular Middleton Farmers Market and the annual Taste of Middleton. These gatherings foster a strong sense of community and provide a platform for local artisans and farmers to showcase their talents.

With its proximity to Madison, residents can easily access the amenities of a larger city while enjoying the tranquility of suburban life. Whether you’re looking to settle down or invest in a thriving community, Middleton offers a welcoming atmosphere and a promising future. Come and discover why so many are proud to call Middleton home!

Newest Listings in 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. 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

$799,900

3 Beds ⋅ 3 Baths ⋅ 73573510 MLS ⋅ ['Ferncroft Tower'] BLDG.

Rarely available 3-bedroom residence at the desirable Ferncroft Tower, where sweeping views overlooking nearly the entire front nine of the Ferncroft Country Club golf course and the expansive horizon beyond create an extraordinary setting from virtually every room. Perched high above the fairways, the elevated vantage point offers a remarkable backdrop year-round. Bathed in natural light, this spacious residence features floor-to-ceiling windows and sliders that open to an expansive private balcony spanning nearly 44 feet and offering approximately 251 square feet of outdoor living space, seamlessly blending indoor and outdoor living. Hardwood floors, crown molding, and custom built-ins enhance the interior. The flexible floor plan includes 3 bedrooms, one currently configured as an office, ideal for remote work, guests, or additional living space. Additional highlights include an oversized walk-in closet, in-unit laundry with a second refrigerator, two garage parking spaces, and extra storage. Residents enjoy elevator access, a heated outdoor pool, health club w/sauna, on-site management, security, and guest parking. HOA fee includes ALL Utilities. Offers due 9/15 by 10:00am. See video, floor plans, and offer instructions.

40 Village Rd Unit 1608, 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

$1,200,000

3 Beds ⋅ 4 Baths ⋅ 73572300 MLS ⋅ ['Villas At Ironwood'] BLDG.

Rarely does an opportunity like this come to market! Located along the 5th fairway of Ferncroft Country Club, this exceptional townhome offers nearly 4,000 square feet of beautifully appointed living space, panoramic golf course views, and an exceptional lifestyle. Unit 6 was the model unit for the Phase 3 build-out, showcasing many of the thoughtful features and design elements of the development.The open floor plan features 3 bedrooms, 3 full baths, and 1 half bath, including a desirable first-floor bedroom suite. The eat-in kitchen offers quartz countertops, stainless steel appliances, a separate pantry, and a large peninsula with bar seating—perfect for casual dining and entertaining.The main living level is filled with natural light and opens to a large composite deck overlooking the 5th fairway, creating an ideal spot for morning coffee, al fresco dining, or relaxing while enjoying the ever-changing golf course views.The true showstopper is the approximately 1,200-square-foot lower level, completely remodeled in 2025. Designed for flexibility, this exceptional space includes a full bath, kitchenette with quartz countertops, exercise room, and spacious living area, all with a walk-out directly to the golf course. The possibilities are endless—create a private retreat for guests or extended family, an in-law, a home office, au pair suite, recreation space, or additional self-contained living. Combining sophisticated living, exceptional golf course views, and an incredibly versatile floor plan, 6 Country Club Lane is a truly special offering and a rare opportunity at Ferncroft Country Club.

6 Country Club Lane Unit 6, 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

$1,495,000

73572364 MLS

Excellent opportunity to acquire Mike’s Discount Liquors, including the real property, established retail liquor business and applicable business licenses, offered at $1,495,000. Located at 21 South Main Street in Middleton, this offering provides an ideal opportunity for an owner-operator or investor seeking an established package store in a convenient location. The sale includes the real estate, business and licenses. Inventory is not included in the purchase price but may be purchased separately outside of the real estate transaction. Buyers and buyer representatives are responsible for performing their own due diligence and verifying all licensing, financial and property information.

21 South Main, Middleton

$449,000

1 Beds ⋅ 1 Baths ⋅ 73569642 MLS ⋅ ['Ironwood On The Green'] BLDG.

Come see this pristine Bedroom + Den unit (use the den "your way") ! This property is conveniently located at the junction of routes 1 and 95 abutting the famed and breathtakingly beautiful Ferncroft Golf Course. Enjoy resort style living which includes, an outdoor heated pool with expansive patio space and furnishings, a grand foyer, Celebration Room with kitchen (can be rented for personal occasions) a game / sharing library room, pick-up, drop-off dry cleaning service, package delivery room, pet relief park and SO MUCH MORE! Unit 614 has green space views from it's private balcony, and is in move-in condition! Deeded garage parking and an assigned space outdoors for your guests! This is an Estate Sale and will require Court approval which is not expected to be protracted. Seller is going to pre- pay the Assessment for Balcony Project be done 2027. BUYERS AGENT NOTE: please call with 24 hours of notice for showings.

38 Village Road Unit #614, Middleton

$499,900

1 Beds ⋅ 1 Baths ⋅ 73568213 MLS ⋅ ['Ferncroft Tower'] BLDG.

Rarely offered,1200 s.f. CORNER 1 bedroom, 1 bath condo with walls of windows which open to a 25 ft. private balcony overlooking the pool, lush grounds and offering a beautiful tranquil space. This lovely condo features a large primary bedroom offering a wall of closet plus a walk-in closet. The magnificent totally updated kitchen is a chef's dream featuring custom cabinets galore, wall oven, induction cook top, Marmoleum floor, granite counters, and best of all, enjoy your morning coffee looking out at the Ferncroft Golf course. The main bath has been totally updated and --surprise, this pristine unit comes with a great laundry room. Adjacent to the dining area is your private office with sliding glass doors for privacy. Other features include: an assigned garage parking space, extra storage space, fitness center, function room, heated outdoor pool, 24-hour security, on-site manager and resident building superintendent, easy access to highways are only some of the many amenities one enjoys at the prestigious Ferncroft Tower. BEST OF ALL--THE HOA FEE INCLUDES ALL UTILITIES. SINGLE-LEVEL LIVING AT ITS BEST!

40 Village Rd. Unit 308B, Middleton

$575,000

2 Beds ⋅ 2 Baths ⋅ 73567395 MLS ⋅ ['Village At Masi Meadow'] BLDG.

WELCOME TO THE VILLAGE AT MASI MEADOW! Units rarely become available at this coveted 55+ community and it's easy to see why! This second floor unit is absolutely pristine and has been impeccably updated, maintained and very lightly lived in during the sellers ownership. Loaded with natural light, the unit features an open concept living room/dining area, updated kitchen featuring newer stainless steel appliances, 2 spacious bedrooms, an office and 2 full baths. 3 car parking including 1 garaged spot, ample closet and storage space, central AC, in unit washer/dryer. Enjoy either the front porch or covered private screened back porch overlooking conservation area as the perfect spot for a morning cup of coffee or evening cocktail! Professionally managed and maintained, this property is not to be missed!

3C Masi Meadow Unit C, 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

$384,000

1 Beds ⋅ 2 Baths ⋅ 73565417 MLS ⋅ ['Ferncroft Tower'] BLDG.

Enjoy bucolic grounds & pool views from Walls of Windows opening to a 20 ft. private patio in this beautiful, pristine 1 bedroom, 1.5 bath 945 s.f. condo. Single-level living at its best in the desirable Ferncroft Tower! This lovely unit offers a fully applianced kitchen with plenty of custom cabinets and counter space. The prime bedroom features a large walk-in closet and ensuite bath. The half bath has been updated. New sliders and window were installed recently. Garage parking, extra storage, newly renovated fitness center with sauna, function room with full kitchen and capacity for 125 guests, on-site manager and maintenance superintendent, easy access to shopping and major highways, 24-hr. security are just a few of the many amenities this fine home offers. The condo fee INCLUDES ALL utilities. Move right in, put your feet up and savor the spectacular views!!! Sold in "AS IS" condition.

40 Village Rd Unit 108A, Middleton

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