Four Winds Real Estate

Welcome to Four Winds, a charming subdivision nestled in the heart of Wisconsin. This picturesque community offers a perfect blend of tranquility and convenience, making it an ideal place to call home.

Four Winds is renowned for its lush greenery, well-maintained streets, and friendly atmosphere. The neighborhood features a variety of housing options, from cozy single-family homes to spacious townhouses, ensuring there is something for everyone.

Residents of Four Winds enjoy easy access to a range of amenities, including parks, shopping centers, restaurants, and top-rated schools. The community is also just a short drive away from major highways, making it simple to explore all that Wisconsin has to offer.

Nature enthusiasts will appreciate the abundance of outdoor recreational opportunities available near Four Winds. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the scenic beauty of the area is sure to captivate you.

With its peaceful surroundings and strong sense of community, Four Winds provides the perfect setting for those seeking a place to put down roots. Come discover all that this wonderful subdivision in Wisconsin has to offer – your dream home awaits in Four Winds.

Newest Listings in Four Winds

$130,999

ACTIVE Status

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 Court Unit Lt19, Ashippun

Listing courtesy of Westar Realty.

$875,000

4 Beds ⋅ 3.5 Baths ⋅ ACTIVE Status

The opportunity to own in Four Winds for under $1 million is becoming increasingly rare. Nestled among luxury homes in one of Hartland's finest neighborhoods and adjacent to Blue Ribbon Swallow School, this 4BR, 3.5BA ranch offers over 3,800 sq. ft. of thoughtfully designed living space and new roof. Situated on a quiet cul-de-sac with direct access to the neighborhood trail leading to school, the open-concept floor plan features a granite kitchen with maple cabinetry, a spacious great room with cathedral ceilings and gas fireplace, a private primary suite with sitting room or nursery, and LVP flooring throughout the main living areas. The finished lower level includes a rec room, bar area, full bath, and fourth bedroom. Exceptional location, award-winning schools, and outstanding value.

363 Sunshine Drive, Hartland

Listing courtesy of Wisconsin Realtor Group.

$122,500

ACTIVE Status

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

ACTIVE Status

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

ACTIVE Status

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 Court Unit Lt20, Ashippun

Listing courtesy of Westar Realty.

$134,999

ACTIVE Status

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

ACTIVE Status

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

ACTIVE Status

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 life--where refinement, location, & lifestyle converge.

W2427 Mariah Lane Unit Lt60, Ashippun

Listing courtesy of Westar Realty.

$89,000

ACTIVE Status

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

ACTIVE Status

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 charm--all 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 Oconomowoc--with shopping, restaurants, beaches, festivals, and parks--and only 15 minutes to the high school, this is a rare opportunity to enjoy both convenience and serenity. Low Dodge County taxes!

W2426 Mariah Lane, Ashippun

Listing courtesy of Real Broker Milwaukee.

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