Oakland Homes with Detached Garage description

Welcome to Oakland, Wisconsin—a charming village nestled in Jefferson County that perfectly blends small-town warmth with a vibrant community spirit. Known for its picturesque landscapes and friendly atmosphere, Oakland offers a serene lifestyle while being conveniently located near larger urban centers. With its rich history and a strong sense of community, this delightful village is an ideal place for families, retirees, and anyone seeking a peaceful retreat.

As you explore Oakland, you'll find a variety of homes that cater to diverse tastes and lifestyles. One standout feature of many properties in this area is the presence of detached garages. These versatile spaces not only provide ample storage for your vehicles but can also serve as workshops, hobby spaces, or even additional storage for outdoor gear. Imagine the convenience of having a dedicated space for your projects or a safe haven for your prized possessions, all just a stone's throw away from your front door.

The homes in Oakland are characterized by their charming architecture and well-maintained properties, offering a perfect backdrop for your next chapter. Whether you're looking for a cozy starter home or a spacious family residence, the options are plentiful. With the added benefit of detached garages, these homes provide both functionality and a touch of character, making them a perfect fit for those who appreciate both practicality and style.

Discover the allure of Oakland, Wisconsin, where community, comfort, and convenience come together to create a perfect place to call home. Come and experience the charm of this delightful village today!

Newest Oakland Homes with Detached Garage description

$575,000

5 Beds ⋅ 4 Baths ⋅ 2022659 MLS ⋅ ACTIVE Status

Tucked away down a scenic driveway on 1.76 acres along the Lake Ripley Channel, this secluded 5-bedroom, 3.5-bath home offers 3,332 sq ft of versatile living space in a serene, park-like setting with new AC. Enjoy Lake Ripley views from the expansive deck or relax in the 3-season room. The thoughtful layout features multiple living areas, a second kitchenette, split-bedroom design, and a cozy gas fireplace, creating an excellent opportunity for multi-generational living or guest accommodations. The spacious primary suite provides a private retreat, while the 3-car detached garage offers ample storage. Enjoy fishing, kayaking, canoeing, and the peaceful waterfront lifestyle. A rare opportunity to own a private slice of paradise with space, flexibility, and incredible natural surroundings.

W8919 Ripley Rd, Oakland

$374,900

4 Beds ⋅ 2 Baths ⋅ 2020920 MLS ⋅ ACTIVE UNDER CONTRACT Status

A stone’s throw and just a quick walk to Lake Ripley, this 4-bedroom, 2-bath home is a rare opportunity—finding something under $400K this close to the lake is almost unheard of. Even better? Located in the Town of Oakland, with lower property taxes compared to many nearby areas. The prior owner previously shared the home began as a cabin with additions over the years, then when he purchased, fully gutted and rebuilt prior to 2019. Also the prior owner was a professional contractor, with guidance from an engineer—so it was done right, not rushed. Inside, enjoy a large kitchen with abundant counter space and storage, plus a bright, spacious living area. With two bedrooms and a full bath on each level, the layout offers flexibility, and the lower level has been successfully used as a short-term rental/Airbnb. Optional HOA access includes use of the dock and beach making this an ideal primary home, getaway, or investment. Opportunity awaits!

W9354 Oakland Rd, Oakland

$797,000

3 Beds ⋅ 2 Baths ⋅ 2019467 MLS ⋅ ACTIVE Status

Lake Ripley frontage with 67 ft of shoreline and a true turn-key opportunity. Offered fully furnished this property is ready for immediate enjoyment or well-suited for short-term rental use, with over $12K in 2026 bookings already in place (option to honor or cancel). Take in the lake from the new concrete patio or through the wall of windows inside, with gradual, swimmable frontage. The main level features an open family room with fireplace flowing into the kitchen with countertop peninsula (plumbed for future sink), plus a full bath with laundry and a main-level bedroom. Upstairs offers a split bedroom layout with the primary suite set apart from two additional bedrooms, along with a living area and flex space for dining or office use. Heating includes hot water boiler plus a new furnace with central air and ductwork for the upper level. Backyard has been leveled, is partially fenced, and is just minutes from local parks and lake activities. Pier included for immediate lake access.

W9384 Ripley Rd, Oakland

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