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4246 Old Stage Rd, Rutland
$1,750,000
7 Beds ⋅ 6 Baths ⋅ 2023296 MLS ⋅ CLOSED Status
Truly one-of-a-kind hilltop country estate on 65.48 breathtaking acres with panoramic views stretching across multiple counties! Wall of windows overlooking panoramic countryside views. This remarkable steel-framed home with stucco exterior was built on an impressive 50x100 concrete slab and offers endless possibilities. Inside features an extraordinary racquetball court-sized recreation area perfect for basketball, volleyball, fitness, entertaining, hobbies, or future customization. Enjoy peace, privacy, and abundant wildlife including deer and turkey in this serene rural setting. Whether you’re seeking a recreational retreat, hobby property, unique homestead, or private getaway, this exceptional property delivers unmatched space, scenery, versatility, and country living at its finest.Approximately 25 minutes south of Madison.

4246 Old Stage Rd, Rutland
1089 Hwy 14, Rutland
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2005207 MLS ⋅ CLOSED Status
Stunning 16.15-Acre Estate only 10 min to Madison. Beautifully designed 4-bed, 3.5-bth residence offers 4,300+ sq ft of living space, a 3-car attached garage, & breathtaking views of the countryside. Open-concept has a spacious kitchen that flows seamlessly into the dining area, a dramatic 2-story great room, & a bright sunroom. Step outside to a massive deck & covered porch. Upstairs, the primary suite includes a large walk-in closet & a private bath w/ a jetted tub. Cat-walk leads to additional 2 beds w/full bath. Walkout LL, complete w/ a 2nd full kitchen, large living area, 4th bedroom, & full bath. Outside, a 60x40 metal outbuilding w/ concrete floors & an additional 700 sq ft finished living space that offers heat & AC—perfect for running your business, or adding a gym or game room.

1089 Hwy 14, Rutland
901 Gallagher Ln, Rutland
$1,049,000
4 Beds ⋅ 3 Baths ⋅ 2007642 MLS ⋅ CLOSED Status
Tucked way back on a Quiet Dead End Road! Sitting way off the road on 4 Acres on the Beautiful Tree Lined Driveway! This spacious Ranch style home is Absolutely Beautiful! 3800+Fin. Sq. Ft. New Kitchen (Wolf, Subzero, Cove) Granite, New Cabinets. Lighting throughout. New Master Bath! Cabinets, Counter, Airjet Tub, Steam shower. Walk in closets. Hard wd floors, Formal Dining, Gas FP, Sun Room overlooking yard. Deck. Low. Level Fam.rm, 4th Bed., Full Bath, Family room w/ 2nd kitchen and storage galore! Steps to Garage. 48x32 Heated Pole Building. Newer Roof on Home. Garden Shed. **This is one of those "Hard to find properties in the Country, Not in a Subdivision and convenient location to Stoughton, Oregon, Madison!

901 Gallagher Ln, Rutland
782 Center Rd, Rutland
$898,000
4 Beds ⋅ 4 Baths ⋅ 2025168 MLS ⋅ CLOSED 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
5 Shady Willow Rd, Rutland
$875,000
5 Beds ⋅ 4 Baths ⋅ 2022512 MLS ⋅ CLOSED Status
This countryside oasis awaits you! Step onto the maple floors into the spacious home featuring 5 beds and 3.5 baths. Kitchen features tons of counter space, custom hickory cabinets, and new appliances (fridge 2024, stove, dishwasher and microwave from 2020). Brand new water softener (2026). Ensuite bath with double vanity and walk-in closet. Owner's suite with serene views of the 4 acre property. Bring your living from inside to out with the 3 seasons porch and large deck that leads down to the shaded patio off of the LL. Detached heated workshop. Horses allowed. 3 car garage with large paved driveway. Schedule your showing today! Buyer to verify measurements.

5 Shady Willow Rd, Rutland
3230 Old Stone Rd, Rutland
$865,000
3 Beds ⋅ 4 Baths ⋅ 2008271 MLS ⋅ CLOSED Status
A rare find with 726' of frontage on a private lake shared w/only 10 homes, nearly 4 acre retreat offers perfect sunset views, a sandy bottom swim area & wooded trails just 25 minutes from the capitol. Outdoor living shines with a 44' deck, 3 season porch, manicured walking path, a matching 7x12 lakeside shed & an expansive Montana flagstone firepit. Inside, the open-concept main floor features vaulted ceilings, a gas FP, & seamless indoor-outdoor flow. The primary suite offers its own FP, steam shower, air (jet) tub, & walk-in closet. Upstairs, a loft connects to a versatile bedroom or office w/full bath & walk-in closet. The finished walk-out LL serves as an entertainment retreat w/a family room, additional bedroom, full bath, & a bar accented by handcrafted live-edge wood countertops.

3230 Old Stone Rd, Rutland
4011 County Road A, Rutland
$850,000
3 Beds ⋅ 2 Baths ⋅ 2026294 MLS ⋅ CLOSED 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
538 Windmill Rd, Rutland
$750,000
3 Beds ⋅ 2 Baths ⋅ 2019586 MLS ⋅ CLOSED Status
Welcome to Windmill Farm! Originally built circa 1900 and thoughtfully expanded in 2016 with an updated kitchen, main bath, and living room, you'll see timeless charm blend naturally with modern convenience at this 40-acre farmhouse. Outside, you'll find the same; a mix of newer and more vintage outbuildings offering exceptional flexibility for hobbies, storage, or workspace. The largest shop includes a 2-post vehicle lift, ideal for car enthusiasts, mechanics, or anyone needing serious shop space. With room for equipment, recreational vehicles, and more, this property offers the privacy, versatility, and functionality that rural buyers crave. Farmhouse 0510-193-9500-4 currently sits on 7.243 acres, and is being sold together with Parcel 0510-194-9000-8 that has an additional 31.595 Acres of beautiful Farmland and Outbuildings.

538 Windmill Rd, Rutland
4415 Old Stone Rd, Rutland
$730,500
3 Beds ⋅ 3 Baths ⋅ 2014971 MLS ⋅ CLOSED Status
This beautiful 3 bedroom, 3 bath ranch home is set on 17.56 serene acres surrounded by mature trees and open sky. The property blends wooded privacy with wide-open farmland, offering a rare mix of seclusion and usable space. The home sits comfortably within the landscape, providing peaceful views in every direction. Along the wooded border, the sellers have installed 4 tree stands that are ready to use! The spacious three-car garage provides ample room for vehicles, equipment, or hobby projects. On the main level, you'll find an open, bright living and kitchen area, laundry, fireplace, spacious bedrooms, and more. The primary ensuite features double walk-in closets, a double sink, and a shower and shower/tub combo! The sellers have made numerous updates over the last few years including: 2023: furnace, water heater and flooring. All the kitchen appliances (2022) are included! Come see this quiet retreat, with large indoor spaces, plentiful natural light, and numerous beautiful views!

4415 Old Stone Rd, Rutland
99 N Union Rd, Rutland
$699,000
4 Beds ⋅ 3 Baths ⋅ 2001520 MLS ⋅ CLOSED Status
Don't miss your opportunity to own this stunning and rare property at 99 N Union Rd—Wisconsin Picture Perfect! This 4-bedroom, 2.5-bath home (with a main-floor bedroom) offers the ideal blend of comfort, space, and country charm on 3.14 acres. The property features a large fenced backyard, a beautifully divided outbuilding shop and 4-stall horse barn (with electric and water access), pasture, and paddock. Inside, enjoy an updated kitchen with newer flooring (2024), a cozy stone gas fireplace, central vac, and storm windows (2025). Roof replaced in 2024 and furnace in 2023. The lower level offers an additional family room and half bath. Enjoy peaceful views from the patio, plus an attached 2-car garage for convenience. Built in 1998, this home has been exceptionally maintained

99 N Union Rd, Rutland
3898 Old Stone Rd, Rutland
$688,500
3 Beds ⋅ 2 Baths ⋅ 2026843 MLS ⋅ CLOSED 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
4432 Old Stage Rd, Rutland
$655,000
4 Beds ⋅ 3 Baths ⋅ 2017371 MLS ⋅ CLOSED Status
Set on almost 14 scenic acres, this versatile property combines comfort, flexibility, and rural charm. The land is mostly tillable with wooded areas, pasture, and a small creek - ideal for gardening, animals, or recreation. Two impressive metal sheds offer exceptional storage and workspace. Inside, enjoy newer hickory floors in the main living areas, updated flooring and tiled shower in the primary bath, and other thoughtful updates! The walk-out lower level enhances livability with a second kitchen, rec room, full bath, and patio doors opening to the yard and deck, while the main-level family room also opens to its own private deck - perfect for relaxing or entertaining. A rare opportunity to enjoy country living with space, style, and endless potential!

4432 Old Stage Rd, Rutland
498 Meander Wood Rd, Rutland
$650,000
3 Beds ⋅ 4 Baths ⋅ 2020577 MLS ⋅ CLOSED Status
Built in 1991, 2nd owner since '98. This well maintained home is move in ready, updated, freshly painted, smoke/ pet-free and will pass any pro home inspection, on DOUBLE LOT. The 1-of-a-kind hardwood floor outlasted this family and compliments the wooded double lot. Formal dining, granite counters, under mount sink, ice disp, coffee alcove, wood burning FP, ceiling rosette, solid wood doors & windows, fresh carpeting, rural forest views w/wildlife enjoying the lush lawn. An XL mud/laundry rm has plenty of closet space & adjoins TWO 2-car garages w/room for full sized pick-ups & pontoon w/a new 8x18 insulated gar door, heated workshop & well lit attic. SW facing ENSUITE is open and airy w/a vltd ceiling over both your bed/ full spa-bath w/X-wide+deep soaker tub, shower, vintage faux fireplace, corner windows & a big organized walk-in closet. Bedrms 2&3 easily fit Queen bed sets. LG deck & covered patio. Country living 10 min to Oregon, Stoughton,Evansville & 20-25 to all points Mad, UW

498 Meander Wood Rd, Rutland
422 Game Ridge Trl, Rutland
$595,000
3 Beds ⋅ 3 Baths ⋅ 2021418 MLS ⋅ CLOSED Status
This is the kind of home that feels right the moment you walk in. Set on a private 0.60-acre wooded lot, this 3-bedroom, 2.5-bath home offers a great mix of space, comfort, and style. Vaulted ceilings and skylights bring in natural light and create an open feel. The kitchen features granite countertops, stainless steel appliances, and opens to a small deck, perfect for stepping out with your morning coffee. A screened porch and sunroom (originally an office) provide flexible space for relaxing or working from home. Updated LVP flooring on the main level and new carpet upstairs give the home a fresh feel. The spacious primary bedroom includes a large walk-in closet. The lower level is ready for your ideas, plumbed for a bath with large windows and an exposed half wall. Private, wooded, and move-in ready.

422 Game Ridge Trl, Rutland
513 Meander Wood Rd, Rutland
$590,000
3 Beds ⋅ 3 Baths ⋅ 2016876 MLS ⋅ CLOSED Status
Set on a wooded corner lot in a peaceful country setting, this home blends privacy with timeless design. A welcoming wraparound porch overlooks perennial gardens and creates a picturesque outdoor escape. Inside, natural light streams through French doors and expansive windows, highlighting hardwood floors throughout the main level. The sunroom offers year-round enjoyment, while the kitchen is thoughtfully appointed with stainless steel appliances, solid surface countertops, a peninsula for gathering, and generous storage. Upstairs, the expansive bonus room above the garage provides flexible living space (home theatre or bdrm) and includes a conveniently located laundry room near the bedrooms. The primary suite features a tray ceiling, window seat, walk-in closets, and a private bath with a whirlpool tub. The full basement offers approximately 1,200 sqft ready for future expansion, complete with full-size windows, 8.5-foot ceilings, and stubbed for a bathroom. Pictures coming!

513 Meander Wood Rd, Rutland
3430 Old Stage Rd, Rutland
$576,750
4 Beds ⋅ 2 Baths ⋅ 2007281 MLS ⋅ CLOSED Status
Storybook 1860s farmhouse located on a treed 5-acre lot, surrounded by peaceful views & timeless charm. The heart of the home is a warm, inviting eat-in kitchen with a built-in banquette & easy access to a welcoming front porch. A formal dining room w/a wood stove sets the stage for cozy gatherings, while the spacious LR offers a fireplace, a wall of bookshelves, & a door to a 2nd porch—perfect for summer evenings. Upstairs you’ll find 3 bedrooms & a beautifully updated bath w/a tub & shower, while the main floor offers a 4th bedroom (currently set up as a home office) along w/another full bath. Lovely 3-season porch w/its own wood stove overlooks the sweeping backyard, where perennial gardens & winding paths invite quiet strolls. Quaint pergola & 2-car detached garage w/attic storage.

3430 Old Stage Rd, Rutland
308 County Road Mm Rd, Rutland
$435,000
4 Beds ⋅ 2 Baths ⋅ 2015375 MLS ⋅ CLOSED Status
5.5 acre propertunity in the Oregon School District ready for your dream home. This gem is nestled between Oregon and Brooklyn in the Town of Rutland. This 4-bedroom, 1.5 bath is NOT your dream house. The 5+ acre backyard is perfect to renovate this house or BUILD YOUR DREAM HOUSE while you live in the existing house. The land is level with trails for you to explore on your showing. Property is ideal for horse (s) or a startup hobby farm.

308 County Road Mm Rd, Rutland
308 County Road Mm, Rutland
$435,000
2009751 MLS ⋅ CLOSED Status
5.5 acre propertunity in the Oregon School District ready for your dream home. This gem is nestled between Oregon and Brooklyn in the Town of Rutland. The 5.5 acres already has a well and septic which are used by the existing house. The 4-bedroom, 1.5 bath home is fully functional ready to keep you warm as you build your new home. The land is level with trails for you to explore on your showing. Property is ideal for horse (s) or a startup hobby farm.

308 County Road Mm, Rutland
LOT 3-4 Windmill Rd, Rutland
$310,000
2015438 MLS ⋅ CLOSED 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

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.