Rutland Real Estate

Rutland Real Estate

Welcome to Rutland, Wisconsin – a charming gem nestled in the heart of Dane County. Known for its picturesque landscapes and a close-knit community, Rutland offers a serene escape from the hustle and bustle of city life while still providing easy access to urban amenities.

With a population that embraces a friendly, small-town atmosphere, Rutland is perfect for families, retirees, and anyone seeking a peaceful place to call home. The town is surrounded by lush greenery, scenic parks, and tranquil lakes, making it an outdoor lover’s paradise. Residents enjoy a variety of recreational activities, from hiking and biking on the beautiful trails to fishing and kayaking in the nearby waters.

Rutland is also conveniently located just a short drive from the vibrant city of Madison, allowing residents to enjoy the benefits of city life while returning to their quiet haven at the end of the day. The area boasts excellent schools, making it an ideal location for families looking to provide their children with a quality education in a safe environment.

In addition to its natural beauty and community spirit, Rutland hosts various local events and gatherings throughout the year, fostering a sense of belonging and camaraderie among its residents. Whether you're exploring the quaint shops or attending seasonal festivals, there's always something happening in this delightful town.

If you're considering a move to a place that embodies tranquility, community, and natural beauty, Rutland, WI, is waiting to welcome you home. Come discover the charm and warmth of this lovely town that truly has something for everyone!

Newest Listings in Rutland

$375,000
2032398 MLS ⋅ ACTIVE Status
A rare opportunity to secure 37.5 acres of productive tillable ground just outside Oregon, WI in the Town of Rutland. This high, rolling acreage offers excellent drainage, strong yield potential and easy access off County Rd A with quick connection to HWY 14. Its proximity to town makes it an exceptional piece of income-producing farmland. Ideal for operators looking to expand their tillable portfolio or investors seeking a stable, land-based asset. Quality acres this close to Oregon are increasingly hard to find, making this a standout addition to any operation or investment strategy.

Rutland
$335,000
2 Beds ⋅ 1 Baths ⋅ 2031048 MLS ⋅ ACTIVE Status
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
$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
$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
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This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.