Jackson Homes under $400,000

Welcome to Jackson, Wisconsin – a hidden gem nestled in the heart of Washington County! Known for its quaint charm and vibrant community, Jackson offers residents a perfect blend of small-town tranquility and easy access to urban amenities. With its picturesque landscapes, lush parks, and friendly neighborhoods, it’s no wonder that families and individuals alike are choosing to call this delightful town home.

Jackson boasts a rich history and a strong sense of community, making it an ideal place for those looking to settle down. The town is dotted with local shops, cozy cafes, and recreational facilities that foster a welcoming atmosphere. With its close proximity to larger cities like West Bend and Milwaukee, residents enjoy the best of both worlds – the peace of suburban life with the excitement of city living just a short drive away.

For homebuyers on a budget, Jackson is a fantastic choice. The real estate market offers a variety of charming homes under $400,000, providing options for first-time buyers, growing families, and retirees alike. Whether you’re seeking a cozy single-family home or a modern townhouse, you’ll find properties that suit your lifestyle and budget.

With its affordable housing, excellent schools, and a strong sense of community, Jackson, WI is the perfect place to plant your roots. Explore the possibilities of homeownership in this enchanting town and discover why so many are choosing to make Jackson their forever home!

Newest Jackson Homes under $400,000

$288,000

2 Beds ⋅ 2 Baths

With stylish updates, thoughtful features & valuable mechanical improvements already done, this Jackson condo is turnkey ready! LR features a cozy gas fireplace. Open concept main living space starring the kitchen with sprawling countertops made of durable quartz (2023), $10k+ KitchenAid appliance updates & dense hardwood floors added in 2024. Two large BR boasting newer Pella windows. Ample closets throughout! Guest bath offers accessible walk-in jetted tub; en-suite has walk-in shower. 2 car attached garage with sealed flooring and extra cabinet storage. Driveway fits up to 4 cars (one of the few oversized driveways available)! Condo fees include recreation facility, sewer!, water!, snow removal & lawn maintenance. Furnace & AC (2019), water heater & softener (2024). ZERO ENTRY condo!

N161W18927 Heather Lynn Cir, Jackson

Listing courtesy of Greystone Asset, LLC.

$299,900

2 Beds ⋅ 2 Baths

Great opportunity for condo living without sacrificing space. This home features a spacious open concept kitching/living room with soaring ceilings opening to a family room loft! In addition to the main space living area is a lovely den. Plenty of room to spread out or in home office, exercise room, or more. With updated LVP flooring, and breakfast bar you'll feel right at home when you move in! This home features 2 bedrooms and 2 full baths plus FULL SIZE washer dryer. Your balcony overlooks open fields offering privacy and rural feeling. Attached two car garage has extra space for hobbies storage with bult in cabinets. These spacious condo homes don't become available often, so this is a great time for you to buy! PLUS NEW ROOF AND NEW WATER HEATER! WOW!

N161W19088 Oakland Dr, Jackson

Listing courtesy of Century 21 Benefit Realty.

$399,900

3 Beds ⋅ 3 Baths

Welcome home to this inviting 3-bedroom, 3-bath ranch in Jackson! Beautiful wood floors add warmth and character, while the natural fireplace creates a cozy gathering space. Enjoy the ease of ranch-style living with plenty of room to spread out. The finished lower level offers fantastic additional living space, complete with a spacious family room, bar area and full bathroom--perfect for entertaining or relaxing. Step outside to enjoy the deck, ideal for grilling or unwinding, while the backyard shed provides convenient extra storage. With comfortable living spaces inside and out, this home offers a wonderful combination of charm, functionality and room to entertain. Come see all it has to offer! Room dimensions are not verified by seller or listing broker.

N171W19840 Cherry Hill Ct, Jackson

Listing courtesy of The Wisconsin Real Estate Group.

$383,793

3 Beds ⋅ 2 Baths

Welcome home to The BIRCH by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 Beds, 2 Baths and a 1 Car garage. The kitchen comes w/ quartz countertops, island, and large pantry. LVP flooring in kitchen, dinette, and great room. You will find quality craftsmanship throughout such as 2x6 construction exterior walls, 8' first floor ceilings, and active radon system. Basement includes lookout windows. Deck included. Great room bump out. We offer a total Kohler/Sterling home experience. The Focus on Energy program provides each home with a Certified Energy-Efficient Certificate stating that our homes are more energy efficient than current WI code. Photos include AI and digitally enhanced images.

N162W21867 Poppy Rd, Jackson

Listing courtesy of Grapevine Realty.

$295,000

3 Beds ⋅ 2 Baths

Welcome home to this light-filled 2nd floor condo with vaulted ceilings and an open concept layout. The kitchen offers stainless steel appliances, generous counter space, a pantry & breakfast bar. Relax in the sunny living room by the gas fireplace, then step out to the spacious balcony. A cozy den/office opens to a 2nd balcony, perfect for morning coffee. The primary suite features double closets, its own balcony access & a spacious bath w/double sinks, soaking tub & shower. Two more bedrooms each have walk-in closets. A dining room, full bath, laundry & attached 2-car garage complete the home. Near Hickory Lane Park, featuring a free splash pad, new inclusive playground, ballfields, basketball & sand volleyball courts, a paved walking path & rentable pavilion!

W197N16873 Stonewall Dr, Jackson

Listing courtesy of RE/MAX Forward.

$384,900

3 Beds ⋅ 3 Baths

Welcome to this inviting 3-bedroom, 3-full-bath condo nestled in a peaceful, country-like setting! The spacious living room features vaulted ceilings and a cozy gas fireplace, creating the perfect space to relax or entertain. The kitchen offers plenty of storage and includes all appliances. Step out onto the deck and take in the beautiful view of the pond and its charming fountain. The primary suite features a walk-in shower, and convenient main-floor laundry adds to the ease of everyday living. A ramped garage entrance provides added accessibility. The finished lower level includes a bedroom, full bath, and additional living space with an egress window, making it ideal for holiday gatherings, entertaining, or hosting overnight guests.

N161W18939 Oakland Dr, Jackson

Listing courtesy of Real Broker Milwaukee.

$379,500

2 Beds ⋅ 2 Baths

Offering for sale, this 2 bedroom, 2 bath, 2.5 car ranch-style condo that has 1610 sq ft of living space above ground. In addition to 2 BR, there's a large living room w/vaulted ceiling, eat-in kitchen, and a sunroom / office that leads to private deck. Exposed lower level is partially finished and includes a rec room, an area walled off and plumbed for a bathroom, and a bedroom. and offers a great deal of additional potential living space that can be finished your way. Updated mehcanicals include: Roof (2023), Siding (2023), Furnace and A/C (2024), Fridge (2023), Washer,(2024), Set in a quiet area with mature trees, views of small pond in backyard, this condo is meticulously maintained with low condo fees. Enjoy condominium living in a sought-after area of Jackson.

W206N16187 Stonebrook Dr, Jackson

Listing courtesy of Realty Executives Integrity~Brookfield.

$269,000

2 Beds ⋅ 2 Baths

Welcome home to this inviting 2-bedroom, 2-bath upper condo offering a bright, open layout and comfortable living. Private entry welcomes you inside to vaulted ceilings and a cozy gas fireplace. The kitchen opens to the living room and features a breakfast bar, stainless steel appliances and pantry. Generously sized bedrooms and full baths, each with a bathtub, provide plenty of space. Enjoy the convenience of a private in-unit washer/dryer, owned water softener and private balcony. Recent updates include newer carpet and a furnace just one year old. A great opportunity for easy, low-maintenance condo living!

W197N17002 Stonewall Dr, Jackson

Listing courtesy of Redefined Realty Advisors LLC.

$372,900

3 Beds ⋅ 2 Baths

Welcome home to The BIRCH by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 Beds, 2 Baths and a 1 Car garage. This lot is a flat exposure. The kitchen comes w/ quartz countertops, island, pantry, and LG appliance package. LVP flooring in kitchen, dinette, and great room. You will find quality craftsmanship throughout such as 2x6 construction exterior walls, 8' first floor ceilings, and passive radon system. Basement includes daylight windows. We offer a total Kohler/Sterling home experience. The Focus on Energy program provides each home with a Certified Energy-Efficient Certificate stating that our homes are more energy efficient than current WI code.

N162W21919 Poppy Rd, Jackson

Listing courtesy of First Weber Inc- West Bend.

$374,900

3 Beds ⋅ 2 Baths

N162W21939 Poppy Rd, Jackson

Listing courtesy of First Weber Inc- West Bend.

$275,900

2 Beds ⋅ 2 Baths

Welcome to this beautifully maintained 2-bedroom, 2-bath condo on desirable Stonewall Drive in Jackson! The spacious open-concept kitchen features a breakfast bar, newer appliances, abundant cabinetry, and generous counter space. The dining area opens to a nice-sized patio through a sliding door, while the inviting living room offers a cozy corner gas fireplace and access to additional outdoor space. Enjoy the convenience of a private laundry room, a primary suite with walk-in closet and private bath, and a second bedroom with a large closet. Thoughtful touches include wood blinds, tile kickboard, updated bathrooms, and 2.5-car attached garage.

W197N17128 Stonewall Dr, Jackson

Listing courtesy of Homestead Advisors.

$389,900

2 Beds ⋅ 2 Baths

Welcome home to the LINDEN by Stepping Stone Homes. Homesite offers a lookout exposure. This efficiently designed home offers modern functionality, open-concept living, and quality craftsmanship throughout. Home features 2 bedrooms, 2 bathrooms, and 2-car garage. Interior finishes and selections include quartz countertops, durable flooring, energy-efficient features, and thoughtfully designed living spaces per specifications. Features, finishes, dimensions, and specifications subject to change without notice.

N162W21883 Poppy Rd, Jackson

Listing courtesy of First Weber Inc- West Bend.

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Source of listing data: Metro MLS. Copyright 2026 Multiple Listing Service, Inc. - All Rights Reserved. Information is supplied by seller and other third parties and has not been verified. IDX information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Jackson Homes under $400,000

Newest Jackson Homes under $400,000

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