Middleton Homes under $400,000

Welcome to Middleton, Wisconsin – a charming city nestled in Dane County, known for its picturesque landscapes, vibrant community, and exceptional quality of life. Just a stone's throw from the bustling capital of Madison, Middleton offers the perfect blend of suburban serenity and urban convenience. With its lush parks, scenic trails, and a thriving downtown area filled with delightful shops and restaurants, Middleton is an ideal place for families, professionals, and retirees alike.

One of the standout features of this delightful city is its diverse real estate market, particularly for those seeking homes under $400,000. Middleton presents a variety of options, from cozy single-family homes to modern townhouses, each offering unique charm and character. Buyers can find well-maintained properties that boast spacious yards, updated interiors, and access to excellent schools, making it a fantastic choice for families looking to settle down.

In addition to its affordable housing options, Middleton is renowned for its strong sense of community. Residents enjoy a plethora of recreational activities, including the popular Pheasant Branch Conservancy, where outdoor enthusiasts can hike, bike, and explore nature. The city also hosts numerous events throughout the year, fostering connections among neighbors and creating lasting friendships.

With its affordable homes, welcoming atmosphere, and prime location, Middleton is not just a place to live; it’s a place to thrive. Explore the possibilities and discover why so many are choosing to call this lovely city home!

Newest Middleton Homes under $400,000

$345,000

2 Beds ⋅ 3 Baths ⋅ 2033782 MLS ⋅ ACTIVE UNDER CONTRACT Status

Beautiful private-entry townhouse condo offering stylish, low-maintenance living in the Middleton school district! The open, airy main level features maple hardwood floors, a gas fireplace, and a stunning kitchen with hickory cabinetry, stainless steel appliances, and granite island with seating. Upstairs, enjoy convenient in-unit laundry and a spacious primary suite with tray ceiling, en-suite bath, and walk-in closet. 2nd bedroom has walk in closet too! Two heated parking spaces and two storage units add exceptional convenience. Move-in ready and designed for easy living—this one is a must-see!

9344 Old Sauk Rd, Middleton

6230 Middleton Springs Dr Unit 6230, Middleton

$289,000

2 Beds ⋅ 2 Baths ⋅ 2033394 MLS ⋅ ACTIVE Status

Open floor plan lit by the sun at several angles. Upper level 2 bedroom, 2 bath with private deck. Great location with easy access to shopping. Private garage and laundry. Middleton schools.

6230 Middleton Springs Dr Unit 6230, Middleton

$254,900

2 Beds ⋅ 1 Baths ⋅ 2033126 MLS ⋅ ACTIVE Status

Great location in the Middleton-Cross Plains School District and just minutes from downtown Madison! This well-maintained, 2 bedroom, Condo features a gourmet kitchen with cherry cabinets, granite countertops, tile backsplash & stainless steel appliances. Convenient in-unit washer/dryer. Enjoy the spacious balcony with beautiful views of Lake Mendota and Marshall Park. Walk to Lakeview Park with splash pad, tennis courts, and baseball fields. A wonderful combination of location, convenience and views!

2051 Allen Blvd Unit 401, Middleton

$385,000

3 Beds ⋅ 2 Baths ⋅ 2032423 MLS ⋅ ACTIVE Status

Welcome to Orchid Heights Townhomes! Located close to beautiful Lake Mendota, walking trails and the scenic 682 acres of Pheasant Branch Conservancy. Enjoy low-maintenance living with lawn care and snow removal included, a community pool and picnic area. This beautifully updated townhome features a completely renovated kitchen, updated bathrooms, updated flooring and new carpet on the upper level. The spacious kitchen offers plentiful cabinetry, granite counters, formal dining area flows into the inviting living room. Step out to a private patio where you can relax and enjoy amazing views and breathtaking sunsets. Upstairs are three spacious bedrooms with ample closet space. The finished lower level includes, a large rec room, a freestanding shower, and plenty of storage. An oversized one-car garage, guest parking across from the unit, and an unbeatable location make this move-in-ready home one you won’t want to miss! *New Roof and Gutters being installed week of Sept. 23*

3550 Valley Ridge Rd, Middleton

2814 Pleasant View Rd Unit 202, Middleton

$250,000

2 Beds ⋅ 1 Baths ⋅ 2031873 MLS ⋅ ACTIVE UNDER CONTRACT Status

Enjoy easy condo living in a fantastic Middleton location! This bright and spacious 2nd-floor unit sits directly across from Firefighter’s Memorial Park and features abundant natural light and an open-concept layout perfect for everyday living and entertaining. Step outside to your private balcony for morning coffee or a relaxing evening outdoors. Both bedrooms offer generous space, including a walk-in closet in the primary. Additional conveniences include in-unit laundry, a private garage, and an extra-large storage unit. Located in the sought-after Middleton-Cross Plains School District with quick access to parks, shopping, schools, dining, and the Beltline. Professionally managed condo association with pets and rentals allowed. A great opportunity to enjoy space, convenience, and a prime Middleton location!

2814 Pleasant View Rd Unit 202, Middleton

$250,000

1 Beds ⋅ 2 Baths ⋅ 2031821 MLS ⋅ ACTIVE Status

Neat, clean, updated floors and windows, move-in ready, ranch-style condo. Floor-to-ceiling west-facing windows and doors bring in wonderful natural light and overlook the beautiful Harbor Village grounds and nearby Pheasant Branch Conservancy. In-unit washer and dryer, fireplace, and den or study off the living room. Underground parking, basement storage, basic cable, pool, tennis courts, and cabana add to the convenience. Pets permitted, subject to association rules.

3120 Creek View Dr Unit 1, Middleton

$158,500

1 Beds ⋅ 1 Baths ⋅ 2031265 MLS ⋅ ACTIVE Status

Opportunity to own in Middleton at an approachable price point! This updated 1-bedroom, 1-bath lower-level condo offers a spacious, open layout with plenty of room to relax, dine and entertain. The refreshed kitchen features white cabinetry, generous counter space, stainless steel appliances and a large peninsula overlooking the dining and living areas. Updated flooring and crisp neutral finishes carry throughout the unit for a clean, move-in-ready feel. The generously sized bedroom provides great closet space, while the full bath offers plenty of room and functionality. Whether you're looking for your first home, downsizing, or stop paying rent, this condo delivers an affordable opportunity to own in Middleton!

7401 Century Pl Unit 9, Middleton

$190,000

2 Beds ⋅ 1 Baths ⋅ 2030919 MLS ⋅ ACTIVE Status

Currently leased through May 2027 at $1,520/month — this is a rare opportunity: a rentable condo in desirable Middleton, ideal for investors or an owner occupant. This tastefully updated, well-maintained first-floor 2-bedroom, 1-bath condo offers comfortable living with a practical, easy-to-maintain layout. The location is a standout, with convenient access to Hilldale shopping, scenic trails, conservancies, parks, and Lake Mendota, plus everyday amenities close by. Outdoor lovers will appreciate having the water and green space close by, year-round. A straight shot to downtown Madison means commuting is simple. This property offers an attractive, turnkey opportunity for investors seeking an established rental in a sought-after area, combining location, condition, and long-term rental potential.

7106 Fortune Dr Unit 3, Middleton

$299,900

3 Beds ⋅ 2 Baths ⋅ 2030645 MLS ⋅ ACTIVE Status

Adjacent to Pheasant Branch Conservancy, this large Middleton 3-bedroom, 2 full baths, updated condo could be all yours! Surrounded by Cedar Trees, with a ground-level patio offering lush greenery & privacy. Great common space w/ a Gazebo, Warm underground parking, private storage unit, & large storage locker. Water Softener and Filters maintained by Maintenance; this unit has extra storage, including its own washer & dryer. Full Kitchen Remodel, floor plan has been opened up, newly remodeled & designed for efficiency, easy living, & lots of natural light throughout! See list of improvements in Associated Docs. This building is well cared for by its association; owners have gratitude for the beautiful community found here. Easy Access to Downtown Middleton/Madison. Bus Stops at Driveway. Easy access to hiking and biking in Pheasant Branch. Short walk to Lake Mendota & Mendota County Park. Located a few blocks from Dane Co. best restaurants & Shops. Dues include high-speed internet

3412 Valley Ridge Rd Unit 4, Middleton

2805 Century Harbor Rd Unit 4, Middleton

$307,500

2 Beds ⋅ 2 Baths ⋅ 2030222 MLS ⋅ ACTIVE Status

Lake living meets modern convenience at Century Harbor Condominiums! Ideally situated just steps from beautiful Lake Mendota, this bright and inviting 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, updates, and an unbeatable location. The spacious primary suite features a walk-in closet and private half bath, while abundant windows and vaulted ceilings fill the home with natural light. Enjoy a thoughtfully updated interior with a total kitchen remodel and LVP flooring in kitchen , dining, living and full bath '18. 2022 remodeled half bath & 2025 new LVP flooring in beds. Spacious balcony with storage on both sides, plus enjoy the convenience of an in-unit washer/dryer & underground heated parking. Step outside and take advantage of Lake Mendota access, piers/boat slips upon availability. Walk to Harbor Athletic Club, coffee shops & local favorites incl. Midtown Pub, and C's Breakfast & Bakery. Come experience the easy, vibrant lifestyle of Century Harbor!

2805 Century Harbor Rd Unit 4, Middleton

$324,500

3 Beds ⋅ 2 Baths ⋅ 2030173 MLS ⋅ ACTIVE UNDER CONTRACT Status

Invest in your future and build equity with this 3-bedroom, 2-bath half-duplex in the heart of highly desirable Middleton! This inviting home features an updated & stylish kitchen, two separate living areas affording plenty of room to spread out, split bedrooms for home office or guest space, and an attached garage. Take advantage of yard space and an outstanding location within walking distance off Pheasant Branch Conservancy, schools, parks, Lake Mendota, restaurants, and more! This home combines space, convenience, opportunity, and an exceptional location - welcome home!

6404 Maywood Ave, Middleton

$269,900

1 Beds ⋅ 1 Baths ⋅ 2029617 MLS ⋅ ACTIVE Status

Your rent era is OVER! This 1-bedroom, 1-bath Middleton condo is a fresh way to make the move into homeownership without taking on the maintenance of a house. The open layout keeps life easy, with a breakfast bar ready for morning coffee, a gas fireplace for laid-back nights, and a sunroom that can flex from home office to chill space. Two spots in the heated underground garage mean no scraping windshields all winter, and an included storage unit gives your extras a home too. The community clubhouse adds an exercise room and extra kitchen, while the Greenway Blvd location keeps shopping, dining, recreation and daily essentials close. Less upkeep, more freedom, and a place where your monthly payment can start working toward something of your own.

8510 Greenway Blvd Unit 104, Middleton

Start Your Search

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.