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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.

7 Beds ⋅ 6 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of Bunbury & Assoc, REALTORS. Selling Office: .

$898,000

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!

4 Beds ⋅ 3.5 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of Stark Company, REALTORS. Selling Office: .

$875,000

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 Beds ⋅ 3.5 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of EXIT Realty HGM. Selling Office: .

$850,000

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.

3 Beds ⋅ 2 Baths ⋅ 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

Listing courtesy of EXP Realty, LLC. Selling Office: .

$750,000

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.

3 Beds ⋅ 2 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of CMI Brokers, LLC. Selling Office: .

$688,500

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!

3 Beds ⋅ 2 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of Stark Company, REALTORS. Selling Office: .

$655,000

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!

4 Beds ⋅ 3 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of EXP Realty, LLC. Selling Office: .

$650,000

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

3 Beds ⋅ 3.5 Baths ⋅ 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 Road Road, Rutland

Listing courtesy of Keller Williams Realty. Selling Office: .

$595,000

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.

3 Beds ⋅ 2.5 Baths ⋅ 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 Trail Trail, Rutland

Listing courtesy of EXP Realty, LLC. Selling Office: .

$330,000

Lovingly maintained by the same owner for the past 41 years, this 4-bedroom, 1-bath home offers ample space and opportunity for updating. Recent improvements include a new electric stove, water heater, and jet pump for the well. Additional features include partial vinyl siding and completed foundation repairs. Whether you're seeking a primary residence, investment property, or renovation project, this property offers the opportunity to make it your own. Property is being sold as-is, where-is. More photos coming soon!

4 Beds ⋅ 1 Baths ⋅ CLOSED Status

Lovingly maintained by the same owner for the past 41 years, this 4-bedroom, 1-bath home offers ample space and opportunity for updating. Recent improvements include a new electric stove, water heater, and jet pump for the well. Additional features include partial vinyl siding and completed foundation repairs. Whether you're seeking a primary residence, investment property, or renovation project, this property offers the opportunity to make it your own. Property is being sold as-is, where-is. More photos coming soon!

467 Lake Kegonsa Road Road, Rutland

Listing courtesy of Boardwalk Realty LLC. Selling Office: .

$310,000

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

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

Listing courtesy of RE/MAX Preferred. Selling Office: .