Oakland Real Estate

Welcome to Oakland, Wisconsin – a charming gem nestled in Jefferson County, where small-town warmth meets the beauty of nature. With its picturesque landscapes and a friendly community, Oakland offers a serene escape from the hustle and bustle of city life while still providing easy access to urban conveniences.

Oakland is known for its rich agricultural heritage and stunning rural vistas. The town is surrounded by lush fields and tranquil lakes, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply taking leisurely strolls, the natural beauty of Oakland invites you to explore its scenic parks and nature trails.

The community spirit here is palpable, with local events and gatherings that bring residents together throughout the year. From farmers’ markets showcasing fresh produce to seasonal festivals celebrating the town’s culture, there’s always something happening in Oakland. Families will appreciate the strong sense of community and the excellent educational opportunities available in the area.

Conveniently located near major highways, Oakland provides easy access to nearby cities like Jefferson and Fort Atkinson, where you can find shopping, dining, and entertainment options. Yet, despite its proximity to urban amenities, Oakland retains its peaceful charm, making it an ideal place for those seeking a balanced lifestyle.

If you’re looking for a place to call home that combines the tranquility of rural living with the vibrancy of community life, Oakland, Wisconsin, is the perfect choice. Discover the warmth and charm of this delightful town – your new home awaits!

Newest Listings in Oakland

$798,900

3 Beds ⋅ 2 Baths ⋅ 2028428 MLS ⋅ ACTIVE Status

Estimated completion late August 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 this special community grows around you. Expansive windows fill the great room with light around a striking 3-sided fireplace with custom cabinetry. Lit built-in niches welcome you at the foyer. The kitchen shines with quartz counters and high-end appliances, including induction cooking, perfect for entertaining. The primary suite offers a large walk-in closet and a spa-style tiled shower with glass door, and private toilet room. Tailored Living shelving outfits every closet — entry, rear foyer, and laundry included. The oversized 3 car garage is zero-barrier, drywalled, and gas-line ready, so you can move in and build a workshop anytime. Enjoy a covered deck ready for future screening, plus a lower-level finished family room with bar rough-in and two beds and a bath roughed for future equity.

W8794 Goldenrod Trl, Oakland

$962,000

5 Beds ⋅ 3 Baths ⋅ 2027943 MLS ⋅ ACTIVE Status

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 spacious kitchen with Amish-built cabinetry, a large island with breakfast bar, and seamless flow into the dining area and living room with a beautiful fireplace. The private primary suite includes a spa-like bath with dual sinks, a gorgeous tiled walk-in shower, heated tile floors, a large walk-in closet, and convenient access to the laundry room. Enjoy the peaceful, tree-lined backyard from the screened porch. The finished walkout lower level is perfect for entertaining with a spacious rec room, wet bar, two additional bedrooms, full bath, and walkout access to the patio. Decorative wall accents, ceiling beams, tile flooring, Andersen windows, LP siding, brick accents, and charming flower boxes complete this exceptional home that perfectly blends luxury, comfort, and timeless design.

W8778 Blue Violet Ct, Oakland

$125,000

2027544 MLS ⋅ ACTIVE Status

Rare opportunity to build your dream home on a buildable, partially wooded lot in the heart of the Lake Ripley area. Centrally located on Park Rd in between Hwy 12 & Hwy. 18 across the street from Lake Ripley's community public beach. This lot offers easy access to the lake, Lake Ripley Country Club, bike trails and scenic surroundings. Bring your own builder and create a home tailored to your lifestyle. Easy walk to downtown to enjoy dining, quaint downtown shops, and parks for local festivals and concerts. Lot will require a drilled well, while having the convenience of municipal sewer. A sewer hookup fee required. The perfect setting for your custom-built new home!

Lot 2 Park, Oakland

$685,000

3 Beds ⋅ 2 Baths ⋅ 2027189 MLS ⋅ ACTIVE Status

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. Featuring a barn and multiple outbuildings, there's plenty of space for hobbies, storage, animals, or recreational use. Updated kitchen ties in the country feel with modern living. Enjoy evenings and mornings in the 3 season room and also entertain all your guests in the basement rec room and bar area. Whether you're looking for a peaceful homestead, weekend getaway, or your own private oasis, this property delivers the perfect blend of nature, space, and rural charm.

N3301 Asje Rd, Oakland

$689,900

4 Beds ⋅ 3 Baths ⋅ 2021636 MLS ⋅ ACTIVE Status

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 flooring, and new carpet. The open floor plan features vaulted ceilings and abundant natural light. The spacious primary suite offers a walk-in tiled shower and heated floors for a spa-like retreat. Enjoy outdoor living with both an expansive deck and a private covered deck overlooking the mature landscaping, filled with vibrant annual and perennial flowers. The attached 3-car garage provides plenty of everyday storage, while the detached garage with an attached screened porch offers the perfect space for hobbies, entertaining, or relaxing. Ideally located just minutes from Lake Ripley and the Red Cedar Lake State Natural Area, this peaceful property offers the perfect blend of privacy, comfort, and convenience. Your private oasis is ready to welcome you home!

N3977 Meadow Dr, Oakland

$2,125,000

4 Beds ⋅ 4 Baths ⋅ 2024520 MLS ⋅ ACTIVE Status

Welcome to Deer Country! 35+ heavenly acres in a serene setting, curated for outdoor enthusiasts! Mother Nature provided the perfect portrait framed by trees & trails to enjoy meadows, deer, birds & wildlife. Custom-built, modern/rustic farmhouse with amazing amenities. (see list) The expansive greatroom w/full view windows allows enjoyment of all seasons. Entertaining is a breeze in the open floor plan w/ full-slab quartz island, spacious dining area, living room with FP & wetbar & conversation spaces. Main floor includes 2 en-suites, 3rd guest BR with bathroom. You’ll find an abundance of cabinetry, closets, walk-in service pantry w/butcher block countertops & spacious laundry/mud room. Start & end your days on the screen porch with calming breezes & FP. Partially finished bsmt has family/rec room, 4th BR & bath & office (non-egress 5th BR). Unfinished area has endless possibilities: golf simulator, theater, bar, gym space etc. Additional accessory garage for toys & yard equipment.

W9650 Rucks Rd, Oakland

$56,000

2 Beds ⋅ 2 Baths ⋅ 2022817 MLS ⋅ ACTIVE UNDER CONTRACT Status

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. The master bathroom has a corner tub with jets and a separate shower stall. Warm up by the gas fireplace during the cold Wisconsin winters. New kitchen appliances and counters in 2019. Kitchen Island adds to the ample cabinet storage. The home also includes a shed. Buyer encouraged to verify room sizes if important. Manufactured Mobile Home – sold as Personal Property. Mobile Home financing may be available through County City Credit Union in Jefferson, WI. Buyer must be approved by the park as a tenant. Seller currently pays $623 plus $12.34 municipal fee per month for lot rent. Sewer and water is additional (approx $25-$30/month). Includes trash pick up. List agent is related to the seller.

N3525 Trieloff Rd Unit #2, Oakland

$275,000

2022803 MLS ⋅ ACTIVE Status

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, cafés, 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 Rd A, Oakland

$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

$549,000

4 Beds ⋅ 2 Baths ⋅ 2021789 MLS ⋅ ACTIVE Status

Enjoy Lake Ripley views from this one family owned, custom-built home set on pilings anchored into bedrock for lasting stability and peace of mind. Lovingly maintained and used as a summer retreat, the 4 season home offers bright, inviting spaces designed for relaxation. A sunny screened-in front porch is perfect for morning coffee or unwinding in the evening breeze. The low maintenance yard gives you more time to enjoy the outdoors, and just steps away you’ll find a private beach and easy lake access for swimming, kayaking, fishing, and more. A rare opportunity to own a well-cared-for lakeside escape in a serene setting. For additional piece of mind, AC and Furnace, and water softener are all less than 5 years old. Almost all furniture is negotiable as well as the golf cart.

W9304 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

Start Your Search

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.