Jackson Homes under $300,000

Jackson Homes under $300,000

Welcome to Jackson, Wisconsin—a charming village nestled in Washington County that perfectly blends small-town warmth with modern convenience. With its picturesque landscapes and friendly community, Jackson is an ideal place for families, young professionals, and retirees alike. Just a short drive from the bustling city of Milwaukee, residents enjoy the tranquility of suburban living while having easy access to urban amenities.

Jackson is known for its rich history and vibrant community spirit, hosting various events throughout the year that bring neighbors together. The village features beautiful parks, scenic walking trails, and recreational facilities, making it a haven for outdoor enthusiasts. Whether you’re hiking the trails of the nearby Kettle Moraine State Forest or enjoying a picnic at one of the local parks, there’s no shortage of ways to embrace the natural beauty that surrounds you.

For those looking to make Jackson their home, you'll be delighted to discover a variety of charming residences available for under $300,000. This affordable housing market offers a range of options, from cozy single-family homes to welcoming townhouses, ensuring there's something for everyone. With a commitment to community and a focus on quality living, Jackson provides an excellent opportunity for first-time homebuyers and those seeking to downsize.

Embrace the opportunity to settle in Jackson, where you can enjoy a peaceful lifestyle without sacrificing the conveniences of city living. Explore the homes available today, and find your perfect slice of Wisconsin paradise!

Newest Jackson Homes under $300,000

N161W18927 Heather Lynn Cir, Jackson
$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.

N161W19088 Oakland Dr, Jackson
$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.

W197N16873 Stonewall Dr, Jackson
$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.

W197N17002 Stonewall Dr, Jackson
$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.

W197N17128 Stonewall Dr, Jackson
$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.

W206N16729 Blackberry Cir Unit 1523, Jackson
$237,400
2 Beds ⋅ 2 Baths
Pets Allowed! Welcome to effortless condo living where comfort, style, and convenience come together beautifully. This impeccably maintained home features an inviting open floor plan, beautiful wood-look laminate flooring, vaulted ceilings, and a warm gas fireplace - perfect for relaxing or entertaining. The spacious primary suite offers a generous walk-in closet, while new bedroom carpeting (2025) adds a fresh, cozy feel. New HVAC (2022) provides added peace of mind. Enjoy in-unit laundry, 2 underground parking spaces, separate storage, and a private balcony. Community amenities include a clubhouse, fitness center, billiards, bar, and outdoor pool. Beautifully cared for and truly ready to welcome you home! ***Seller is offering Buyer incentive. Please contact for details.

W206N16729 Blackberry Cir Unit 1523, Jackson

Listing courtesy of Keene Realty Group.

W197N16879 Stonewall Dr, Jackson
$295,000
3 Beds ⋅ 2 Baths
This rare THREE BEDROOM upper condo will provide all the space you need at 1848 sq ft! Inviting open concept living has new LVP, cathedral ceiling, and gas fireplace. Patio doors provide cheery southern exposure and access to spacious deck. The chef will appreciate the stainless appliance package, all the counter space and loads of seating at the wraparound breakfast counter. Primary suite is bright and airy with cathedral ceiling, dual closets, patio door to private balcony, and an updated ensuite with soaking tub, shower stall and tile floor. In unit washer/dryer make laundry day a breeze. 2 car attached and 2 driveway spaces. Bring Fido or Felix as pets are allowed. Located just off Hwy 60 and Hwy 45 with many conveniences in walking distance. Water/Sewer included in condo fees.

W197N16879 Stonewall Dr, Jackson

Listing courtesy of RE/MAX United - 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.

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