Oakland Homes for Sale

Welcome to Oakland, Wisconsin – a charming community nestled in the heart of Jefferson County. Known for its picturesque landscapes and friendly atmosphere, Oakland offers a unique blend of rural tranquility and convenient access to modern amenities. This quaint village is surrounded by lush greenery and serene lakes, making it an ideal location for those who appreciate nature and outdoor activities.

In Oakland, you can enjoy a slower pace of life while still being just a short drive away from larger cities like Jefferson and Fort Atkinson. The area boasts excellent schools, local parks, and a close-knit community that fosters a sense of belonging. Whether you’re looking for a peaceful retreat or a place to raise a family, Oakland has something for everyone.

For those interested in making Oakland their home, a variety of homes for sale are available to suit diverse tastes and budgets. From charming single-family residences to spacious properties with sprawling yards, the real estate options here cater to both first-time buyers and seasoned homeowners. Many of these homes feature modern amenities while maintaining the character and charm that define this lovely community.

As you explore the real estate market in Oakland, you’ll discover not just houses, but homes filled with potential and warmth. Experience the beauty of Wisconsin living in a place where community spirit thrives. Whether you’re drawn by the scenic views, the friendly neighbors, or the promise of a peaceful lifestyle, Oakland is waiting to welcome you home. Don’t miss your chance to find the perfect property in this delightful village!

Newest Oakland Homes for Sale

$389,900

1 Baths

Welcome home to this fabulous bungalow with 60ft of frontage on beautiful Lake Ripley! Whether you're looking for the perfect weekend getaway or an extended summer retreat, this FULLY FURNISHED home is ready to enjoy. Thoughtfully designed, the seller has created distinct living spaces, including a kitchen, dining area, cozy sitting area, two sleeping areas, and a full bath. Relax on the maintenance-free composite deck, with composite walkways adding to the home's easy-care appeal. A storage shed provides extra space, and the private shared driveway offers convenient access. Just minutes from downtown Cambridge with an easy commute to Madison and Milwaukee. There's still time to enjoy the rest of summer and beautiful fall days at the lake!

N4228 Sleepy Hollow Rd, Oakland

Listing courtesy of Realty Executives Integrity-East Troy.

$249,000

2 Beds ⋅ 1 Baths

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 for everyday living, summer getaways, or weekend retreats. Enjoy the sun-filled living/dining room combo with vaulted ceilings & expansive windows, and galley style kitchen that's well equipped with a functional layout. The large primary bedroom features walk-in closet, convenient laundry area, & direct bathroom access, while the second bedroom offers built in drawers & additional good closet space. This home also offers a bonus cozy loft space perfect for the little ones to sleep or a dedicated fun play space. Behind the home, you'll find a storage shed & well manicured yard/garden.

N4550 E Shore Place Rd, Oakland

Listing courtesy of Century 21 Circle-Westchester.

$575,000

5 Beds ⋅ 3 Baths

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

Listing courtesy of First Weber, Inc.-Cambridge.

$599,900

2 Beds ⋅ 2 Baths

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. Bathed in sunlight from morning to evening, the home's coveted western exposure delivers sunset views that paint the sky each night. Inside, the thoughtfully updated kitchen blends style & function w/warm maple cabinetry, gleaming granite countertops & a full suite of stainless steel appliances, ideal for both everyday living & entertaining. This home is truly turnkey, simply arrive & start enjoying lake life from day one. A private pier with space for two boats makes getting out on the water effortless, while the oversized 2.5-car garage offers ample room for vehicles & all your lake gear.

N4175 Island Ln, Oakland

Listing courtesy of Lake Country Flat Fee.

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