Rutland Real Estate

Welcome to Rutland, Wisconsin, a charming town nestled in the heart of Dane County. Known for its picturesque landscapes and tight-knit community, Rutland offers a serene escape from the hustle and bustle of city life while still being conveniently located near Madison, the state capital.

Rutland boasts a rich history that dates back to the mid-1800s, and its quaint downtown area reflects the town's heritage with beautifully preserved architecture and friendly local shops. Residents enjoy a tranquil lifestyle surrounded by lush greenery, rolling hills, and stunning views that make every season a delight. Whether you’re taking a leisurely stroll through one of the town’s many parks or enjoying an afternoon of fishing at one of the nearby lakes, Rutland is a haven for outdoor enthusiasts.

The community is also known for its strong sense of belonging, with numerous events and activities throughout the year that bring residents together. From summer festivals to farmers' markets, there’s always something happening that fosters camaraderie and connection among neighbors.

Families will appreciate the quality of life in Rutland, with access to excellent schools and a safe environment for children to grow and thrive. The town's commitment to maintaining a welcoming atmosphere makes it an ideal place for both young families and retirees looking for a peaceful retreat.

With its blend of natural beauty, community spirit, and convenient location, Rutland, WI, is not just a place to live; it’s a place to call home. Come discover the charm of Rutland and see why so many are proud to be part of this delightful community!

Newest Listings in Rutland

$599,000

2027832 MLS ⋅ ACTIVE Status

Discover a rare opportunity to own 19.8± acres in the Town of Rutland, conveniently located along Biglow Road near the US Highway 14 and State Highway 92 roundabout. This highly visible Dane County property offers an attractive combination of open tillable ground, mature hardwoods, wetlands, and scenic pond habitat. Uniquley situated adjacent to Harveys marsh waterfowl production area. Comprising of over 600 acres of public lands.

19.79 M/L Acres Biglow Rd, Rutland

$679,900

3 Beds ⋅ 2 Baths ⋅ 2026843 MLS ⋅ ACTIVE UNDER CONTRACT Status

Fantastic rural location in desirable Rutland! This beautifully updated 3 bedroom, 2 bath home sits on 4.3 acres and is move-in ready. Inside, you'll find updated kitchen cabinets, an updated main level bathroom, hardwood floors in the bedrooms, and stylish flooring throughout the rest of the home. The walkout lower level is nicely finished with impressive 9' ceilings. The entire home has been freshly painted and features newer roof and windows. Outside you'll enjoy a large storage shed for lawn toys plus a incredible 40'x80' outbuilding complete with, hot water, floor drain, updated electrical, lighting and all new cement floors with in-floor heat! Oversized doors on each end perfect for big equipment. Property has been converted from LP to Natural gas This turn-key property offers the perfect blend of country living with modern updates. Don't miss out — schedule your showing today before this gem is gone!

3898 Old Stone Rd, Rutland

$900,000

3 Beds ⋅ 2 Baths ⋅ 2026294 MLS ⋅ ACTIVE UNDER CONTRACT Status

VRP $900,000 to $950,000. Escape to your own private retreat on approximately 32.40 gorgeous acres with a serene, wooded setting. This spacious ranch home features a vaulted great room with a stone fireplace and wood stove, plus formal living and dining areas with custom built-ins. The full lower level includes an additional kitchen, ready to finish for extra living space. A detached outbuilding offers ample room for a shop and storage of outdoor equipment and toys. Sale includes 3 separate parcels, with possible opportunity to re-survey and rezone for future building parcels post-closing. A fantastic investment opportunity with endless potential — don't miss this one! House being sold 'As is' with pre-inspection report available.

4011 County Road A, Rutland

$929,500

4 Beds ⋅ 4 Baths ⋅ 2025168 MLS ⋅ ACTIVE UNDER CONTRACT Status

This is the life you've been looking for...stunning home , beautiful pool/patio for relaxing and a great view out back of rural America. This home has plenty of well laid out space, 3+ acres (with a little piece of prairie), privacy, outbuildings and just a short drive to Madison. Be wowed by the soaring vaulted ceiling and wall of windows, cozy up in the movie/bar area or choose one of several bonus rooms for your office needs. Main floor Primary with a jetted tub AND walk in shower, dazingly cook's kitchen with loads of counter space, sky high vaulted ceiling in the LR with a wall of windows, smaller guest bed on main makes a perfect office. Lofted private bedroom area with 2 more beds and a full bath; perfect reading/homework nook overlooking the main floor. Lower level is made for play - loads of options- Media area with fireplace and bar, open rec area, two bonus den/offices. And outside provides a great yard, outbuildings and that spectacular pool!

782 Center Rd, Rutland

$3,588,000

2023172 MLS ⋅ ACTIVE Status

Rare +/- 156ac just minutes from Stoughton featuring 1,875 ft of Island Lake Frontage, high-ground tillable, and excellent homesite potential. Strong frontage on County Hwy 158 and Lake Kegonsa Rd in a rapidly growing Dane County corridor. Highly productive soil offer immediate farm income with long-term development upside. Historic farmhouse showcases tall ceilings and original woodwork - ideal for a remodel. Abundant wildlife and lake views from multiple vantage points. A standout opportunity with exceptional land quality and future potential.

3656 Hwy 138, Rutland

$2,200,000

2020133 MLS ⋅ ACTIVE UNDER CONTRACT Status

Experience an extraordinary ~200ac luxury investment offering in Dane County. This rare legacy property blends highly productive tillable acreage with premier lakefront development potential and unmatched recreational appeal. Enjoy two exceptional build opportunities and 2,100+ ft of pristine Bass Lake frontage. Currently generating ~$43k/yr from crop and home lease with significant upside. Abundant wildlife, private lake access, and direct views of the 1,400+ ac protected Bad Fish Creek Wildlife Area create a truly exclusive setting, just 20 minutes from Madison. A remarkable opportunity for the discerning investor.

+/- 200ac 200ac Old Stone Rd, Rutland

$1,500,000

2020128 MLS ⋅ ACTIVE Status

Discover an exceptional ~30ac luxury investment opportunity in Dane County. This rare offering blends productive acreage with premier lakefront development potential and refined recreational appeal. Offered with 2 density units (additional units available) and 880+ ft of pristine Bass Lake frontage, creating an ideal canvas for an estate-level or multi-residence vision. Abundant wildlife, private lake access, and direct views of the 1,400+ ac protected Bad Fish Creek Wildlife Area elevate the setting, just 20 minutes from Madison. A rare opportunity for the discerning buyer.

+/- 30ac 30ac Old Stone Rd, Rutland

$415,000

2016759 MLS ⋅ ACTIVE Status

Discover the perfect blend of privacy and convenience with this beautiful 5+ acre wooded parcel in Stoughton. Nestled in a peaceful rural setting, this spacious property offers a serene backdrop surrounded by mature trees and natural beauty, making it an ideal location for your dream home. Enjoy the quiet of country living while remaining just minutes from local amenities, shopping, dining, and everyday conveniences. With ample space, stunning wooded views, and endless possibilities, this property offers the privacy you’ve been searching for without sacrificing accessibility. Bring your builder and start creating your vision today.

L1 Flint, Rutland

$345,000

2015438 MLS ⋅ ACTIVE UNDER CONTRACT Status

Accepted Offer - Only 1 of 2 lots remains! Tucked just south of Oregon on Windmill Road, this exceptional parcel offers the perfect blend of space, privacy, and convenience. With this being the Souther of the 2 lots available and includes a little more wooded area. Easy access to Oregon, Stoughton, Fitchburg, and Madison, the location puts you minutes from Southern Dane County’s key hubs while still feeling wide open and peaceful. The land features multiple ideal build sites with plenty of room to create a generous buffer from neighbors, making it perfect for a private estate, hobby farm, or a variety of other future uses. Bring your own builder and design exactly what you want—opportunities like this, with this combination of location, flexibility, and elbow room, don’t come along very often. Other 10 acre parcel is lot 1-2 Windmill road offered at $320,000

LOT 3-4 Windmill Rd, Rutland

$299,900

2015437 MLS ⋅ ACTIVE Status

Lot 1-2 still Available, but neighboring Lot 3-4 is now under contract! Tucked just south of Oregon on Windmill Road, this exceptional parcel offers the perfect blend of space, privacy, and convenience. With this being the Northern of the 2 lots available. Easy access to Oregon, Stoughton, Fitchburg, and Madison, the location puts you minutes from Southern Dane County’s key hubs while still feeling wide open and peaceful. The land features multiple ideal build sites with plenty of room to create a generous buffer from neighbors, making it perfect for a private estate, hobby farm, or a variety of other future uses. Bring your own builder and design exactly what you want—opportunities like this, with this combination of location, flexibility, and elbow room, don’t come along very often. Other 10 acre parcel is lot 3-4 Windmill road offered at $350,000

LOT 1-2 Windmill Rd, Rutland

$375,000

2004719 MLS ⋅ ACTIVE Status

This is the acreage you've been waiting for! Beautiful 5 acre parcel in the town of Rutland on a quiet country road close to Oregon and Stoughton! This level, buildable lot backs up to woods and is ready for you to plan and build your dream country estate! Property is in process of being surveyed and re-parceled; seller is open to re-parceling differently at your request. All lot lines shown in the photo are approximate.

72 Franklin Rd, Rutland

$3,500,000

1993103 MLS ⋅ ACTIVE UNDER CONTRACT Status

Incredible investment opportunity in Dane County. This truly unique ~236ac property brings endless opportunities with a great mix of highly productive tillable land, lake front development opportunities and endless recreational fun! The property includes 7 build opportunities with ~3000ft of Bass Lake shoreline. Currently producing ~$45k in income between the crop and the home lease with opportunities to do soo much more. The lake and land provide abundant wildlife and are located directly across the street from over 1400 acres of forever protected green space, Bad Fish Creek Wildlife Area! All of this conveniently located just 20 mins from Madison in the sought after town of Rutland. This is one you don't want to miss! Schedule your private showing today.

230 Ac Old Stone Rd, Rutland

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