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2232 Tower Dr, Pleasant Springs
$439,900
3 Beds ⋅ 2 Baths ⋅ 2035104 MLS ⋅ ACTIVE UNDER CONTRACT Status
Paradise in the country! Once you pull into your driveway you'll feel as you are a world away from the hustle and bustle of the city. This home is situated on over an acre along a quiet country road offering commanding views of the countryside. Step inside and you'll find the kitchen and baths have been updated and you'll appreciate the wood floors throughout most of the main level. All appliances are included and a the main level laundry is just off the kitchen. The lower level offers a walk-out to the back yard and contains a Rec room along with a second kitchen - ideal if you are relaxing and watching a football game! An oversized garage w/steps directly into the basement. Don't worry about the commute you are minutes from Stoughton or the beltline!

2232 Tower Dr, Pleasant Springs

2681 Church St, Pleasant Springs
$1,230,000
4 Beds ⋅ 4 Baths ⋅ 2032542 MLS ⋅ ACTIVE Status
2-1 BUY-DOWN CREDIT IF CLOSED BEFORE 11/26! Turn into the driveway & feel the world slow down as this 4br/3.5ba retreat comes into view on nearly 6 wooded acres. Inside, stunning vaulted pine ceilings & hardwood floors create a warm, elevated feel. The beautifully updated kitchen flows into the living & dining spaces, perfect for entertaining. Retreat to the spacious primary ensuite w/ remodeled shower & abundant closet space, or unwind on the deck overlooking nature. The finished walkout LL offers a kitchenette, pool table, bedroom/office, workshop & storage galore! An oversized 3-car garage w/ basement access adds everyday convenience. Enjoy privacy, nature, hunting & foraging. Take peaceful walks past nearby churches & bike rides through beautiful surroundings. Updates include newer roof, mechanicals, outbuilding, industrial water filtration & freshly sealed driveway. Rural, private setting w/ low taxes & easy access to Madison, the airport, Milwaukee & Chicago. DON’T miss it!

2681 Church St, Pleasant Springs

2466 County Hwy N, Pleasant Springs
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 2031371 MLS ⋅ ACTIVE Status
Rare opportunity to own a versatile 44.25± acre rural property in the Town of Pleasant Springs, combining productive farmland, quality improvements, and country living. Frontage along County Highway N and Center Avenue provides excellent access and future flexibility. The well-maintained, move-in-ready 1,512 sq. ft. home features 4 bedrooms, 1.5 bathrooms, and numerous updates. A 30' x 50' shop includes an insulated concrete floor and a 14' x 10' sliding door, ideal for equipment, storage, or workshop use. A 30' x 60' partially finished outbuilding offers power, heat, and a maintained shop area, well suited for hobbies, contracting, business operations, or recreation. Established apple and pear trees enhance the homestead setting. The farm includes 40.07± FSA tillable acres. Minutes away from Lake Kegonsa State Park and only 20 minutes from downtown Madison.

2466 County Hwy N, Pleasant Springs

3129 Sunnyside St, Pleasant Springs
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 2029440 MLS ⋅ ACTIVE Status
NOW OFFERING SUBSTANTIAL CLOSING CREDIT IF CLOSE BY 11/26/27! From sunrise to sunset, experience the rare combination of level frontage, 4-bed, 3-bath home offers 50 feet of unforgettable waterfront views. Beautifully refinished hardwood floors and an open, inviting floor plan designed to maximize natural light and showcase the stunning lake scenery. The charming sunroom just off the dining area provides the perfect place to enjoy your morning coffee. Upstairs, retreat to your spacious primary suite, a true private oasis featuring a spa-inspired shower, convenient second-floor laundry, and a hot tub room where you can soak while taking in spectacular sunset views over the water. Enjoy sipping a glass of wine on your shaded patio, spend the day boating, swimming, or fishing. Take in the wildlife and serenity on the suspended boardwalk of the new Lower Yahara River Trail just steps away from your door. Every day feels like a vacation living the lake life.

3129 Sunnyside St, Pleasant Springs

2991 County Hwy Mn, Pleasant Springs
$624,900
4 Beds ⋅ 2 Baths ⋅ 2029121 MLS ⋅ ACTIVE UNDER CONTRACT Status
Escape to the peace of country living without giving up the convenience of the city! Nestled on 8.95 scenic acres in the Town of Pleasant Springs. This tri-level home is full of opportunity to make it your own. Built in 1987, it offers fresh paint, new carpet, a spacious living room, dining area off the kitchen, and enjoy morning coffee on your cozy 3-season porch. The primary features a walk-in closet, double vanity, and walk-in shower, while the finished lower level offers a rec room, 4th bedroom, and walk-out to the patio! A charming front porch, 2-car garage, new septic and A/C (2023), and nearly 9 acres provide the perfect backdrop for your next chapter. Enjoy the privacy of country life with quick interstate access and just minutes to McFarland, Madison, Lake Waubesa, parks, trails, shopping, and dining. Welcome home!

2991 County Hwy Mn, Pleasant Springs

2542 Brown Deer Rd, Pleasant Springs
$459,900
3 Beds ⋅ 2 Baths ⋅ 2025454 MLS ⋅ ACTIVE UNDER CONTRACT Status
Nestled on a beautiful 1.1-acre lot in a peaceful country subdivision, this stunning home has been completely transformed, a rare find in the Stoughton market, offering the space of a country acreage with the peace of mind that comes only with a total, high-end renovation. Step inside to well planned living space with brand-new flooring throughout. The fully remodeled kitchen and island serves as the heart of the home, beautifully complemented by stylishly updated bathrooms. Beyond the aesthetics, enjoy major capital upgrades including a durable new metal roof and a brand-new septic system. Experience the perfect blend of rural serenity, wide-open outdoor space, and neighborhood community—all just minutes from downtown Stoughton and the Madison area. There is absolutely nothing left to do but move right in and enjoy!

2542 Brown Deer Rd, Pleasant Springs

Skyline Drive Dr, Pleasant Springs
$495,000
2023298 MLS ⋅ ACTIVE Status
Build your dream home on this rare 3.4-acre buildable lot located on Skyline Drive in the Town of Pleasant Springs. This unique property offers the perfect blend of peaceful rural living and convenient access to nearby city amenities. Enjoy the beauty of a lovely pond on the property and proximity to beautiful Lake Kegonsa for year-round outdoor recreation. The property has already perked for a mound system, or buyers may explore the option of bringing in municipal services. Zoned RR-2, this versatile parcel provides endless possibilities for your custom home, hobby farm, or private retreat. A truly special opportunity to own a scenic piece of countryside while staying close to Madison, shopping, dining, and major highways. Bring your vision and make this one-of-a-kind property your own!

Skyline Drive Dr, Pleasant Springs

1854 Sheryl Ln, Pleasant Springs
$830,000
4 Beds ⋅ 3 Baths ⋅ 2020518 MLS ⋅ ACTIVE Status
BRAND NEW ROOF! Welcome to this beautifully maintained 4-bedroom, brick-built ranch nestled in Stoughton's highly desirable golf course neighborhood. The open floor plan creates an easy flow for everyday living and entertaining. Enjoy fresh updates throughout, including new carpet, fresh paint, rebuilt water filtration system to include new high efficient iron filter, water heater, and A/C for added comfort and peace of mind. Enter the Primary Bathroom and you'll discover a new shower with Kohler finishes throughout, new floor tiles, paint, and fixtures. Downstairs, you’ll find a spacious family and rec room featuring a bar area and movie projector—perfect for hosting and entertaining. Set on a half-acre lot with no neighbors to the rear, this property offers rare privacy and peaceful surroundings while still being part of a vibrant community. A wonderful blend of space, updates, and location—this is one you won’t want to miss.

1854 Sheryl Ln, Pleasant Springs

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.

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