Ashippun Real Estate

Welcome to Ashippun, Wisconsin — a charming village nestled in the heart of Dodge County. With its picturesque landscapes and a close-knit community feel, Ashippun is the perfect blend of rural tranquility and modern convenience. This hidden gem offers a delightful escape from the hustle and bustle of city life while still being conveniently located near larger urban centers.

Ashippun boasts a rich history, with roots dating back to the mid-1800s. Today, it retains its small-town charm with tree-lined streets, cozy homes, and friendly neighbors. The village is surrounded by beautiful parks and scenic nature trails, making it an ideal location for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the natural beauty of Ashippun is sure to captivate you.

Residents appreciate the strong sense of community, with local events and gatherings fostering connections among neighbors. The village is served by the Oconomowoc Area School District, known for its commitment to excellence in education, making it a great place for families to settle down.

For those looking for recreational activities, the nearby lakes and rivers offer opportunities for fishing, boating, and swimming during the warmer months. In winter, residents can embrace the snowy landscape with ice skating and sledding.

With its blend of history, community spirit, and natural beauty, Ashippun, WI, is more than just a place to live; it’s a place to call home. Discover the charm of Ashippun and experience the warmth of this inviting village today!

Newest Listings in Ashippun

$144,999

Build your dream home with a beautiful pond view! Located in the peaceful and upscale Four Winds Subdivision, this finished lot offers an Oconomowoc address and schools, sewer, and quality deed restrictions. Enjoy a gorgeous neighborhood with easy access to year-round recreation, while downtown Oconomowoc's shopping, dining, beaches, festivals, golf, and more are just a short drive away. The tranquility of country living with city conveniences nearby. Lake Country living at its finest!

N971 Winds Way Unit Lt8, Ashippun

Listing courtesy of Westar Realty.

$489,000

3 Beds ⋅ 2 Baths

Small-town charm, spacious living and room to grow! This beautifully maintained, one-owner ranch sits on a .41-acre lot in a picture-perfect Ashippun neighborhood with an Oconomowoc address and schools. Step inside to an open, airy layout with tall ceilings, abundant natural light and comfortable main-floor living. The kitchen flows effortlessly into the dining and living spaces, while the primary suite offers a large walk-in closet and private bath. Downstairs, a huge unfinished lower level is a blank canvas ready for whatever comes next. Peaceful surroundings, a great yard and an easy-living ranch layout make this one feel like home the minute you walk in.

N645 North Ave, Ashippun

Listing courtesy of Heritage Realty.

$144,999

You'll be hard pressed to find a Lake Country lot of this caliber at this price point! Wake up each morning to breathtaking water views from Lot 1 in the exclusive Four Winds Subdivision. Perfectly suited for a partial exposure, this exceptional homesite offers the ideal blend of natural beauty and everyday convenience. Located just minutes from downtown Oconomowoc, you'll enjoy the best of Lake Country living with easy access to boutique shopping, outstanding restaurants, beautiful beaches, parks, and year-round community events. This architecturally controlled neighborhood features sewered lots, is served by the Oconomowoc Area School District, and offers a shared pond and green space perfect for leisurely walks, fishing, and simply enjoying the peaceful surroundings.

W2444 Mariah Ln Unit Lt1, Ashippun

Listing courtesy of Westar Realty.

$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.

$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.