Ashippun Real Estate

Welcome to Ashippun, Wisconsin—a hidden gem nestled in the heart of Dodge County. This charming village, with its serene landscapes and close-knit community, offers a perfect blend of rural tranquility and modern convenience. Ashippun is ideally situated just a stone’s throw away from larger cities like Oconomowoc and Watertown, making it an ideal spot for those seeking a peaceful retreat without sacrificing access to urban amenities.

With a population that prides itself on community spirit, Ashippun is known for its friendly atmosphere and welcoming residents. The village features a variety of parks and recreational areas, providing ample opportunities for outdoor enthusiasts to explore nature. Whether you’re hiking the scenic trails, fishing in nearby lakes, or simply enjoying a picnic with family, Ashippun’s natural beauty is sure to captivate.

The local economy is robust, with a mix of small businesses and larger employers contributing to the area’s growth. Families will appreciate the quality education provided by the nearby schools, which emphasize both academic achievement and character development.

Ashippun is also rich in history, with charming architecture that tells the story of its past. From quaint homes to well-preserved buildings, the village offers a picturesque backdrop for anyone looking to settle down.

If you’re searching for a place that combines the best of small-town living with easy access to metropolitan conveniences, Ashippun is the perfect choice. Come explore this delightful village and discover all that it has to offer!

Newest Listings in Ashippun

$363,900

3 Beds ⋅ 1 Baths

Escape the hustle in this lovingly maintained one-owner home, ideally located just minutes from Oconomowoc. Nestled in a peaceful setting with low taxes, this 1 story ranch offers quiet country living with everything you need. The spacious kitchen is equipped with all appliances & opens to huge living room w/ vaulted ceilings. Recent updates include a Furnace, AC, Water Heater, Water Softener, and Iron Curtain, all installed 2021. Roof was done 2010. Step outside to your private backyard oasis featuring mature trees, beautiful flower gardens & spacious deck. The oversized tandem garage accommodates three vehicles. Enjoy your morning coffee or unwind on warm summer evenings from the charming covered front porch. Pride of ownership is evident throughout this one-you won't want to miss it!

W2392 Julianne St, Ashippun

Listing courtesy of Lake Country Flat Fee.

$130,999

This exceptional lot offers stunning views and a peaceful country setting, all just minutes from the shopping, dining, beaches, and year-round attractions of downtown Oconomowoc. Surrounded by beautifully crafted custom homes, Four Winds is an architecturally controlled community with thoughtful deed restrictions designed to preserve the neighborhood's beauty and value. Located within the Oconomowoc School District with an Oconomowoc mailing address, this is the perfect place to build the home you've always envisioned. Residents enjoy a shared 2-acre private pond featuring a fountain, fishing, & a scenic walking path, creating a tranquil gathering place to relax and enjoy the outdoors. Opportunities like this are becoming increasingly rare, don't miss your chance to call Four Winds h

W2371 Gabriel Ct Unit Lt19, Ashippun

Listing courtesy of Westar Realty.

$699,000

4 Beds ⋅ 3 Baths

Carefully placed at the edge of a picturesque 8.66 acre lot, this updated ranch offers a haven surrounded by nature. Thoughtfully renovated with open concept layout, gorgeous kitchen and baths. Primary suite has full bath w/dual sinks, 2 closets, & flex room- use as an office, gym, or nursery. Additional 3 beds/2 baths allow privacy for everyone. Potential for multi-generational living in walkout lower with full bath & kitchenette. Enjoy spectacular sunsets and the sights and sounds of the natural world from lg screen porch. Rural setting's surprisingly convenient-just 11 min. to groceries in Hartford OR Oconomowoc. Lot has pond, apple/pear orchard & newer heated 30x40 outbuilding for toys! New roof & fence '25. Oconomowoc Schools. Much of interior painted Apr. '26. Home Warranty included!

N1259 County Road P -, Ashippun

Listing courtesy of Shorewest Realtors, Inc..

$122,500

Beautiful corner lot in the sought-after Four Winds Subdivision, just a short drive north of Oconomowoc. An ideal setting to build your dream home, offering access to a private 2-acre pond and scenic common area. The community features tasteful architectural guidelines, sewer access, and private well. A rare opportunity to secure one of Lake Country's most attractive values.

N903 Winds Way Unit Lt54, Ashippun

Listing courtesy of Westar Realty.

$130,999

Check out this stunning cul-de-sac gem in the posh Four Winds Subdivision! AMAZING views! Only a hop, skip, and a jump away from downtown Oconomowoc's vibrant scene. Imagine crafting your dream home in this peaceful countryside haven, surrounded by top-notch custom homes. Plus, enjoy access to a charming 2-acre pond (shared by 61 lucky lots) with a fountain and fishy friends. With city sewer and a private well, bring your dream home plans, luxury living awaits you!

N998 Winds Way Unit Lt13, Ashippun

Listing courtesy of Westar Realty.

$130,999

You can have it all! Exclusive Four Winds Subdivision located just ten minutes from downtown Oconomowoc shopping, beaches, festivals, and parks! Luxury living in a serene country setting. Subdivision has beautiful custom homes that are built with quality deed restrictions to protect your investment. Oconomowoc school district and postal address. Common areas include a 2 acre private pond (deeded to 61 lots) with fountain and fish as well as a beautiful walking path and mature trees.

W2377 Gabriel Ct Unit Lt20, Ashippun

Listing courtesy of Westar Realty.

$144,999

Breathtaking pond views highlight this exceptional lot in the upscale Four Winds Subdivision. Perfectly positioned, it lends itself beautifully to a walk-out design. Enjoy peaceful surroundings with wildlife, fresh air, and spacious homesites, all just minutes from downtown Oconomowoc's dining, shopping, festivals, parks, and lake access. Located in the Oconomowoc School District, this sewered lot includes access to a scenic common area with pond and fountain, perfect for walking, relaxing, or fishing. A rare opportunity to build your dream home in beautiful Lake Country. This lot is also suitable for a walk-out!

N999 Winds Way Unit Lt12, Ashippun

Listing courtesy of Westar Realty.

$127,500

Nearly half-acre lot in Four Winds Subdivision--where peaceful, country-style living meets everyday convenience. Just minutes from downtown Oconomowoc's restaurants, shopping, festivals, parks, and lake access. Enjoy a scenic neighborhood with pond, walking trails, mature trees, and abundant wildlife. One of the best values in Lake Country--bring your vision and build your dream home in a setting that truly stands out.

N920 Winds Way Unit Lt51, Ashippun

Listing courtesy of Westar Realty.

$127,500

Designed for a walk-out lower level, this exceptional homesite offers a serene backdrop for quiet mornings & relaxed evenings. Located in the prestigious Four Winds Subdivision, the property combines privacy & elegance just 10 minutes from downtown Oconomowoc's shopping, dining, beaches, parks, & festivals. Four Winds is an upscale yet attainable community featuring distinctive custom homes & protected by quality deed restrictions to ensure lasting value. The property is served by Oconomowoc schools & has a desirable Oconomowoc postal address. Residents also enjoy access to a private 2-acre neighborhood pond, with a fountain & walking paths, creating a tranquil shared amenity. An ideal setting to bring your custom home vision to lifewhere refinement, location, & lifestyle converge.

W2427 Mariah Ln Unit Lt60, Ashippun

Listing courtesy of Westar Realty.

$89,000

Great opportunity with this excellent lot in a great area. Lower taxes in Dodge co, great schools of Oconomowoc! Build your dream home today! Sewer connection already paid for.

N909 Winds Way, Ashippun

Listing courtesy of ERA MyPro Realty.

$79,900

Build Your Dream Home in the Coveted Four Winds Subdivision! This affordable .43-acre lot (Lot 4) offers the perfect blend of luxury living and peaceful country charmall within the highly rated Oconomowoc School District. Situated on a large, flat homesite, one of the last abutting frontage on the subdivision's private 2-acre pond, enjoy picturesque views, a tranquil fountain, and stocked fishing right out your back door. Located just 10 minutes from downtown Oconomowocwith shopping, restaurants, beaches, festivals, and parksand only 15 minutes to the high school, this is a rare opportunity to enjoy both convenience and serenity. Low Dodge County taxes!

W2426 Mariah Ln, Ashippun

Listing courtesy of Real Broker Milwaukee.

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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.