Oakland, WI Homes for Sale (15 Real Estate Listings)

$1,695,380 Lake Ripley

W9225 Ripley Road, Oakland

A truly rare offering on Lake Ripley—where distinctive architecture, remarkable privacy, and extraordinary waterfront living come together. Designed by acclaimed architect Helmut Ajango, thi...

$1,200,000

N3810 Scheppert Road, Oakland

Escape to your own private retreat on 38 beautiful acres! This lovingly maintained full-log cabin offers 3 bedrooms, a finished lower level with bonus room, and versatile space ideal for gue...

$949,000

W8778 Blue Violet Court, Oakland

Completed and ready for its new owners, this stunning June 2026 Parade of Homes ranch offers quality craftsmanship and upscale finishes throughout. The open-concept floor plan features a spa...

$798,900

W8794 Goldenrod Trail, Oakland

Estimated completion late September 2026. Welcome to this brand new home in The Preserve at Oakland, a Parade of Homes neighborhood served by Cambridge schools. Be among the first owners as...

$797,000 Lake Ripley

W9384 Ripley Road, Oakland

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....

$669,000

N3301 Asje Road, Oakland

Here's your Private Country Retreat! Nestled on nearly 7 secluded acres surrounded by mature woods, this unique rural property offers the peace and privacy you've been searching for. Featuri...

$649,900 Lake Ripley

W9056 Ripley Road, Oakland

One-owner home meticulously maintained located on main lake road with seasonal views of Lake Ripley, and membership to Lake Association offering the convenience of shared frontage to picnic,...

$639,000

N3977 Meadow Drive, Oakland

Amazing ranch home set on a rare double lot in a quiet, private dead-end neighborhood! This 4-bedroom, 3-bath home has been beautifully updated with fresh paint, new luxury vinyl plank floor...

$599,900

W9236 Highway 18, Oakland

This storybook home is ready to come to life with a new owner's vision and industrious spirit. The 6+ acre lot is private with wooded surroundings and trails, just minutes from town. Inside,...

$550,000 Lake Ripley

W9295 Oakland Road, Oakland

Discover the peace & quiet of coveted lake living in the Shoreplace neighborhood! Beautifully remodeled & thoughtfully updated, offers quality finishes throughout, including custom kitchen c...

$549,900 Lake Ripley

W8919 Ripley Road, Oakland

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 set...

$549,900 Lake Ripley

N4175 Island Ln, Oakland

Welcome home to the perfect 2-bedroom, 2-bath home with bonus loft. This best lakefront retreat that Lake Ripley has to offer. Enjoy 50 feet of pristine sandy frontage all summer long. Bathe...

Lake Country Flat Fee

$269,900

N4524 Wolff Road, Oakland

Looking to downsize without giving up comfort? Or simply want a home that is just the right size? This move-in-ready 2-bedroom, 2-bath condo offers easy living with thoughtful updates throug...

$239,000 Lake Ripley

N4550 E Shore Place Rd, Oakland

Looking for that perfect, low maintenance cabin near the lake that's just steps from the private beach & parks, then here it is! The open layout creates a comfortable gathering space perfect...

Century 21 Circle-Westchester

$56,000

##2 - N3525 Trieloff Road, Oakland

Motivated Seller!! Wonderful double wide mobile home with updates in a clean, well-managed park close to Cambridge and Fort Atkinson. This home features 2 spacious bedrooms and 2 full baths....