Pleasant Springs Real Estate

Pleasant Springs Real Estate

Welcome to Pleasant Springs, Wisconsin—a hidden gem nestled in the heart of Dane County. This charming town is renowned for its picturesque landscapes, friendly neighborhoods, and a vibrant sense of community that makes it an ideal place to call home.

Pleasant Springs boasts a rich history and a serene environment, making it perfect for families, retirees, and anyone in between. With its lush parks and scenic trails, outdoor enthusiasts will find plenty of opportunities for hiking, biking, and enjoying nature. The nearby lakes offer a variety of recreational activities, including fishing and boating, ensuring that every weekend can be filled with adventure.

The town is conveniently located just a short drive from Madison, the state capital, providing residents with easy access to a wealth of cultural attractions, dining options, and shopping experiences. Whether you're interested in exploring local farmers' markets, attending community events, or indulging in the culinary delights of nearby restaurants, Pleasant Springs has something for everyone.

Education is a top priority in the area, with highly-rated schools that foster a nurturing environment for children. The community is dedicated to providing quality education, ensuring that the next generation is well-prepared for the future.

Pleasant Springs is more than just a place to live; it’s a community where neighbors become friends and memories are made. With its blend of natural beauty, friendly faces, and convenient amenities, it’s no wonder that so many people are choosing to make Pleasant Springs their forever home. Come visit and discover the charm of this delightful town for yourself!

Newest Listings in Pleasant Springs

$1,195,000
3 Beds ⋅ 3 Baths ⋅ 2029440 MLS ⋅ ACTIVE Status
Welcome to Sunnyside on beautiful Lake Kegonsa, where lakefront living meets everyday luxury. This custom-built, 3-bed, 3-bath home offers 50 feet of level shoreline and unforgettable waterfront views. Step inside to discover 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
$624,900
4 Beds ⋅ 2 Baths ⋅ 2029121 MLS ⋅ ACTIVE 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
$400,000
4 Beds ⋅ 2 Baths ⋅ 2026450 MLS ⋅ ACTIVE UNDER CONTRACT Status
Inviting home on a spacious cul de sac lot in Stoughton’s Oak Knoll neighborhood, just moments from beautiful parks and the scenic Yahara River. The open layout creates an inviting flow for entertaining and everyday living. Enjoy warm weather in the expansive fenced backyard, offering plenty of space for outdoor activities or summer gatherings. The finished lower level adds exceptional flexibility with a family room perfect for movie or game nights, plus a convenient kitchenette and walkout to the backyard. Stainless steel appliances, generous living space throughout, and a two car detached garage complete this comfortable home. A wonderful combination of space, location, and value.

1734 Oakview Dr, Pleasant Springs
$399,900
4 Beds ⋅ 2 Baths ⋅ 2027332 MLS ⋅ ACTIVE UNDER CONTRACT Status
Enjoy peaceful country living in this inviting 4-bedroom, 1.5-bath ranch situated on more than half an acre in a quiet neighborhood across from the Yahara River. The home features beautiful hardwood floors, an updated main bathroom and a basement bedroom with an egress window. Large rec room and bar space in lower level. Major improvements completed within the past six years include the roof, furnace, central air, pressure tank, water heater, water softener and water filtration system. 16x16 composite deck overlooks the deep lot. A spacious 40' x 25' outbuilding provides excellent storage, workshop space or room for recreational equipment. The large yard also includes a trampoline and playground equipment. A wonderful opportunity for anyone seeking comfortable one-level living, extra outdoor space and a peaceful country setting.

1787 Oakview Dr, Pleasant Springs
$1,114,900
5 Beds ⋅ 5 Baths ⋅ 2027003 MLS ⋅ ACTIVE Status
One of the best built custom homes in all of Dane County, this 5,446-square-foot estate sits on nearly an acre overlooking the 16th fairway of Stoughton Country Club, with gorgeous Lake Kegonsa views and an available boat slip just five minutes away. Enjoy lake recreation without sacrificing the space and privacy of a luxury home. Located in the outstanding Stoughton Area School District, it is minutes from historic downtown Stoughton, the Opera House, restaurants, and boutique shops—only 12 minutes from the Beltline and offering favorable Pleasant Springs taxes. Highlights include steel-reinforced ICF construction through the second floor, radiant heat, Marvin windows, five bedrooms, five bathrooms, four en-suite bedrooms, two Rumford fireplaces, a private primary-suite office, steam shower, Jacuzzi tub, golf simulator space, and a movie theater that doubles as a certified concrete storm shelter. A new roof was installed in fall 2025

3002 Linnerud Dr, Pleasant Springs
$499,900
3 Beds ⋅ 2 Baths ⋅ 2025454 MLS ⋅ ACTIVE 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
$699,900
3 Beds ⋅ 2 Baths ⋅ 2023925 MLS ⋅ ACTIVE UNDER CONTRACT Status
Rare Yahara River frontage meets beautifully designed ranch living. Custom built in 2014 and set on a wooded, landscaped lot with 157 feet of shoreline, this home captures the perfect balance of privacy, comfort, and extraordinary water views from the main living spaces. Designed with efficiency and accessibility in mind, it offers thoughtful single-level living, handicap-accessible features, vibrant gardens, and workbench space in both the garage and basement. The partially exposed lower level brings in natural light and lovely views, offering a blank canvas for future living, hobbies, or guests. Enjoy kayaking, fishing, wildlife, smaller boating, and quiet moments by the water from your own backyard.

2090 Yahara Dr, Pleasant Springs
$550,000
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
$424,000
2 Beds ⋅ 1 Baths ⋅ 2020049 MLS ⋅ ACTIVE Status
Completely remodeled 2 bedroom, 1 bathroom home located just across the street from the lake with beautiful lake views. This move in ready property has been extensively updated and offers peace of mind with a new roof, siding, windows, furnace, hot water heater, driveway, and all new interior finishes. The updated kitchen features modern cabinetry and fixtures, while the spacious bathroom includes a waterfall showerhead and ample room. The open floor plan is complemented by an electric fireplace, creating a warm and inviting main living area filled with natural light. Enjoy low maintenance living in a desirable location with a deeded lake access, making this home amazing for year round living or a relaxing retreat.

3101 Shadyside Dr, Pleasant Springs
$999,900
10 Beds ⋅ 5 Baths ⋅ 2022025 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to your private sanctuary where the possibilities are endless. Whether you need a spacious personal property with lots to keep you busy, or you are looking to make money off of the property, this is it. Think hobby farm, vacation rental, animal rescue organization, summer camps, non profit organizations, wedding venue, or combine two generations of family! Sitting on 20 private and beautiful acres, this home is waiting for your cosmetic finishing touches to add even more value. Home includes up to 10 bedrooms, including a massive finished basement, and a mother in law suite built in 04. 2 master suites! Bathrooms include custom tile showers and soaking tubs. Multiple outbuildings include a pool house, bb court, offices, animal stalls, work space, garage space, private deck, and more. Home recently appraised for over 1.2 million. Refer to document section for all the perks, too many to list here!

2296 Tower Dr, 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
$985,000
2015273 MLS ⋅ ACTIVE UNDER CONTRACT Status
Bring your imagination and creativity to this exceptional 7.85-acre parcel located directly across the street from Lake Kegonsa, adjacent to Lake Kegonsa State Park, and on the lower Yahara Bike Trail. The property offers both near-term and long-term development potential, with initial conversations indicating the site may support approximately 15 lots, including elevated homesites with year-round Lake Kegonsa and sunset views. Several potential lots also overlook the sweeping Door Creek Wetlands and the nearby Lower Yahara Bike Trail, creating a rare combination of water, open space, and recreation. Soil tests have already been completed in preparation for future development and are available for review. Develop immediately, or build your own private residence and hold the remaining land as a long-term investment in the continued growth of Dane County.

Lot 3 Sunnyside, Pleasant Springs
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