Pleasant Springs Real Estate

Pleasant Springs Real Estate

Welcome to Pleasant Springs, Wisconsin – a hidden gem nestled in Dane County that perfectly embodies the charm of small-town living with the conveniences of modern life. Known for its picturesque landscapes and friendly community, Pleasant Springs offers a serene environment that feels like a retreat from the hustle and bustle of city life.

With its lush greenery, sparkling lakes, and rolling hills, Pleasant Springs is an outdoor enthusiast’s paradise. The area is dotted with beautiful parks and nature trails, making it ideal for hiking, biking, and leisurely strolls. Residents and visitors alike can enjoy the calming views of Lake Kegonsa, where fishing, boating, and picnicking create perfect weekend getaways.

Pleasant Springs is also strategically located just a short drive from Madison, the vibrant state capital. This proximity allows residents to enjoy the cultural and educational offerings of the city while returning home to the tranquility of their quaint community. The local schools are highly regarded, providing excellent education and fostering a strong sense of community among families.

The town itself boasts a warm, welcoming atmosphere, where neighbors become friends and local businesses thrive. With charming shops, delicious eateries, and community events throughout the year, there’s always something happening in Pleasant Springs.

Whether you’re looking to settle down, raise a family, or simply enjoy a peaceful lifestyle, Pleasant Springs, WI, offers the perfect blend of nature, community, and convenience. Discover your dream home in this idyllic setting and experience all that Pleasant Springs has to offer!

Newest Listings in 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
$579,900
3 Beds ⋅ 3 Baths ⋅ 2031368 MLS ⋅ ACTIVE UNDER CONTRACT Status
Privacy with neighbors on a dead end street across from the Yahara river with river access across the street. Large .89 acre lot surrounded by mature pines, trees and bushes. A 20x12 deck that overlooks the huge back yard which includes a 12x12 firepit area, apple trees, garden spaces, perennial spaces and room to roam. A house to make your home with space to grow under a newer roof. Sellers have added their touches - a partial wall removed to make it a even more open concept main area plus hardwood floors, corner gas fireplace, updated master bathroom. A kitchen with everything needed to serve meals on the deck or in the dinette area - granite counter tops, double oven, large refrigerator, microwave, dishwasher and reverse osmosis filtered water, with storage galore. Right now the current workshop can be direct accessed from the 3 garage or the lower level hallway. Add the ceiling to complete it and what will it be for you? The 3 car garage is for everything you have!

2071 Yahara Dr, Pleasant Springs
$1
2031213 MLS ⋅ ACTIVE Status
161.60± surveyed acres of quality farmland in the Town of Pleasant Springs, Dane County, Wisconsin, selling at public auction on October 14, 2026. Offered in three tracts, this property presents an outstanding opportunity for farmers, investors, and rural land buyers. Tract 1 consists of 61.70± acres with 44.13 FSA cropland acres and an NCCPI of 68.4. Tract 2 includes 55.48± acres with approximately 50.08 FSA cropland acres and an NCCPI of 77.6. Tract 3 contains 44.42± acres with approximately 37.18 FSA cropland acres and an NCCPI of 73.2. The property will be offered on a price-per-acre basis using the Buyer's Choice auction method, allowing the successful bidder to select any tract or combination of tracts. Productive soils, strong agricultural value, and a desirable location in Dane County make this a rare land acquisition opportunity. Online bidding available.

161.60 Acres Koshkonong Rd, Pleasant Springs
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 2029440 MLS ⋅ ACTIVE Status
PRE INSPECTED ! Welcome to 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
$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
$489,900
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
$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
$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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