Oakland Real Estate

Welcome to the charming city of Oakland, Wisconsin, nestled in the heart of Jefferson County. This picturesque community offers a unique blend of small-town charm and modern conveniences, making it an ideal place for families, retirees, and everyone in between. With a population that embraces the spirit of neighborliness, Oakland is a place where you can truly feel at home.

One of the standout features of Oakland is its stunning natural beauty. Surrounded by lush landscapes and serene lakes, residents enjoy an abundance of outdoor activities, from hiking and biking to fishing and kayaking. The nearby Kettle Moraine State Forest provides endless opportunities for exploration, while local parks offer perfect spots for picnics and community gatherings.

Culturally rich and vibrant, Oakland boasts a variety of local events and festivals that celebrate the community's heritage and bring residents together. The annual Oakland Community Days is a highlight, featuring fun activities for all ages, including live music, delicious food, and engaging games.

Education is a top priority in Oakland, with access to quality schools that focus on fostering a supportive and enriching environment for students. Families will appreciate the strong sense of community, as well as the commitment to providing a well-rounded education.

With its convenient location just a short drive from larger cities like Madison and Milwaukee, Oakland offers the perfect balance of rural tranquility and urban accessibility. Whether you’re looking to buy your first home, invest in a property, or simply explore, Oakland, Wisconsin, is a delightful place to discover your next chapter. Come and see what makes this community so special!

Newest Listings in Oakland

$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.

$275,000

Perched atop a scenic knoll, this beautiful 1.5-acre wooded homesite offers the ideal setting to build your dream home. Nestled among mature trees in a charming lakeside community, it combines peaceful privacy with the warmth and character of small-town Wisconsin living. Minutes from the property are Ripley Park on Lake Ripley, featuring a sandy beach, playgrounds, and tennis and pickleball courts; CamRock County Park, with scenic hiking and biking trails; and a charming downtown filled with boutiques, cafes, wineries, antique shops, and locally owned restaurants. With natural beauty, a vibrant community atmosphere, and convenient access to Madison just 30 minutes away, this property offers the perfect balance of relaxation and connection.

N4087 County Road A -, Oakland

Listing courtesy of RE/MAX Community Realty.

$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.

$94,900

Bring your house plans! 3 lots to choose from. Country like feel, yet close to the conveniences of the quaint little city of Cambridge. Easy access to HWY 12 and just 30 minutes from Madison. Opportunities like this don't present themselves very often in the Cambridge community. Co-listed with

Lt3 Woodcrest Ln, Oakland

Listing courtesy of Century 21 Integrity Group - Jefferson.

$89,900

Lt4 Woodcrest Ln, Oakland

Listing courtesy of Century 21 Integrity Group - Jefferson.

$114,900

Lt2 Woodcrest Ln, Oakland

Listing courtesy of Century 21 Integrity Group - Jefferson.

Start Your Search

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.