Rutland Real Estate

Rutland Real Estate

Welcome to Rutland, Wisconsin – a charming small town nestled in the heart of Dane County. With its picturesque landscapes and friendly community atmosphere, Rutland embodies the quintessential Midwestern experience. This quaint village is known for its serene surroundings, making it an ideal retreat for those seeking a peaceful lifestyle while still being conveniently close to urban amenities.

Rutland is surrounded by rolling hills, lush farmland, and scenic trails, perfect for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking leisurely strolls, the natural beauty of this area will captivate you. In addition to its stunning scenery, Rutland is rich in history and community spirit. The town hosts various events throughout the year, fostering a close-knit environment that welcomes new residents with open arms.

Families will appreciate the excellent school system and the emphasis on community engagement, making Rutland a great place to raise children. Local parks provide ample space for recreation and social gatherings, while nearby attractions in Dane County offer a wealth of cultural and entertainment options. From farmers' markets to seasonal festivals, there’s always something happening in and around Rutland.

With easy access to larger cities like Madison, Rutland combines the tranquility of rural living with the conveniences of urban life. Whether you're looking for a cozy home or a spacious property to grow into, Rutland offers a variety of real estate options that cater to every lifestyle. Discover the charm of Rutland, WI, and experience the warmth of a community that feels like home.

Newest Listings in Rutland

$335,000
2 Beds ⋅ 1 Baths ⋅ 2031048 MLS ⋅ ACTIVE Status
Showings start Monday, August 24th. Beautifully updated ranch on nearly half an acre just minutes south of Oregon! Enjoy the feel of country living while still being close to everything Oregon has to offer. This 2-bedroom, 1-bath home has seen extensive recent updates, including a brand-new kitchen and bathroom, new siding (2026), and a new roof (2025). Inside, you'll find two nicely sized bedrooms and a comfortable, functional layout that's truly move-in ready. Outside, the .449-acre lot offers plenty of space to relax, entertain, garden, or simply enjoy the scenic farm field views in both the front and back. A rare opportunity to enjoy an updated home, extra space, and a peaceful country setting - all just minutes from Oregon and an easy drive to Madison!

991 Hwy 14, Rutland
$499,900
3 Beds ⋅ 2 Baths ⋅ 2031026 MLS ⋅ ACTIVE Status
Country beauty on a on 2.26 acres with a hidden pond! Well maintained home with hardwood flooring, newer kitchen appliances, new carpet in LL, updated Anderson windows, New Roof -2026 & newer mechanicals. The large windows in the living room give the house a mid century vibe with volumes of natural light. The light woodwork and custom features add to the modern feel. 3 good-sized bedrooms & full bath on the main level. In the LL you will find a large exposed family room with a wood burning fireplace, full bath and a large screen porch opening to the back yard with a trail to a secluded pond and plenty of room for gardens, chickens, perennials! Large walk in laundry mud room/storage room. If you are looking for privacy and a country setting close to Madison, do not miss this move-in-ready home!

158 King Lake Rd, Rutland
$1
2029756 MLS ⋅ ACTIVE Status
Exceptional opportunity to acquire premium Dane County, Wisconsin farmland near Stoughton. This offering includes 606.31± total acres with 527.44± high-quality tillable acres in one of South-Central Wisconsin's most desirable agricultural regions. The property will be offered in 11 tracts ranging from 33.47± to 109.16± acres, providing flexibility for farmers, investors, and rural lifestyle buyers. Tracts feature productive silt loam soils, strong crop-producing capabilities, excellent access to local grain markets, and long-term agricultural investment potential. Select tracts may also offer attractive rural homesite opportunities. Large-scale farmland offerings of this size and quality are rarely available in Wisconsin, making this a unique chance to own productive farmland in a highly sought-after farming community.

606.31 Acres 11 Tracts, Rutland
$799,000
3 Beds ⋅ 2 Baths ⋅ 2029201 MLS ⋅ ACTIVE Status
Rare opportunity with approximately 12 acres in Dane County! 2 tax parcels for sale 0510-191-9500-6 - 9.736 acres and 0510-202-9230-9 - 2.10 acres - both parcels to be sold together. The property includes eligibility for one potential land division/development right, which may be used on the property or transferred to another qualifying property, subject to all town and Dane County requirements and approvals. Opportunities galore with RR-8 Zoning - hobby farm, home base for your business, private county retreat - Bring your ideas! Property includes a 3 bedroom 2 bath house, 2 car garage and an outbuilding. Fenced in yard for peace of mind. Amazing country views surround you. Great location. Don't miss out on this one!

690 Hwy 14, 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
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