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 offers a perfect blend of scenic beauty and small-town charm, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle with easy access to modern amenities.

Pleasant Springs is renowned for its picturesque landscapes, featuring rolling hills, lush greenery, and serene lakes that provide endless opportunities for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply soaking in the beauty of nature, this community has it all. The nearby Lake Kegonsa State Park is a favorite among locals, offering trails and recreational activities that cater to every age group.

The town's rich history is reflected in its friendly neighborhoods and well-preserved architecture, creating a warm and inviting atmosphere. Residents take pride in their community spirit, with various local events and festivals throughout the year that foster connections among neighbors and celebrate the unique culture of Pleasant Springs.

Education is a priority here, with access to quality schools that emphasize academic excellence and personal growth. Families will appreciate the safe and nurturing environment, making it easier to raise children and build lifelong friendships.

Conveniently located just a short drive from Madison, Pleasant Springs offers the tranquility of rural living while keeping you close to the vibrant city life. With its welcoming community, stunning natural surroundings, and strong sense of belonging, Pleasant Springs is not just a place to live—it's a place to call home. Come discover the charm of Pleasant Springs, where every day feels like a breath of fresh air!

Newest Listings in 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
$599,900
4 Beds ⋅ 2 Baths ⋅ 2027765 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this warm and inviting Prairie/Craftsman-style home tucked into a beautiful wooded setting on nearly an acre in Pleasant Springs. Offering 4 bedrooms, 2 full baths, and over 2,500 finished sq ft, this home blends privacy, character, and functional living space. The main level features an open kitchen with island & granite countertops, spacious dining area, living room with energy efficient wood stove fireplace, 1st-floor bedroom, full bath, laundry, and a sun-filled 4-season room overlooking the peaceful yard. Upstairs you’ll find 2 generous bedrooms & a full bath, while the exposed walkout lower level adds a large rec room & 4th bedroom. Enjoy mature trees, a deck, detached 2.5-car garage, & a quiet rural subdivision setting just minutes from Stoughton & Lake Kegonsa area conveniences. Metal roof, newer water heater & pressure tank offer peace of mind for years to come. A rare mix of space, setting & charm. This one has the “I could live here” feeling!

2555 Brown Deer Rd, 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
$995,900
4 Beds ⋅ 4 Baths ⋅ 2027280 MLS ⋅ ACTIVE Status
It's all here! This country home with a brand new exterior is situated on 4+ acres of beauty in the much sought after Town of Pleasant Springs. This site offers peace and serenity and yet you are less than 15 minutes from Madison. Step inside and you're sure to appreciate all the extras in place as this home was built by a builder for his own home. You'll find plenty of bedrooms, baths and rooms to gather with your friends and family. Outside you'll find an in-ground pool, hot tub, green house and a 30' X 50' additional garage building with shop that is heated and even has a car hoist for the hobbyist. If you are looking for a hone in the country this is the one!

2082 Tower Dr, Pleasant Springs
$1,174,900
5 Beds ⋅ 5 Baths ⋅ 2027003 MLS ⋅ ACTIVE Status
A once-in-a-generation custom estate overlooking Stoughton Country Club and Lake Kegonsa. Perfectly positioned on nearly an acre along the 16th fairway with beautiful water views, this 5,446 sq. ft. home features 5 bedrooms and 5 bathrooms. Commuting is effortless at a mere 12 minutes to the Beltline, with drive times getting even shorter once the upcoming Highway 51 improvements are complete. Built with steel-reinforced ICF construction for unmatched strength and efficiency, the home boasts radiant in-floor heating, an ERV, Marvin windows, and custom built-ins. Highlights include a private office off the primary suite, four en-suite bedrooms, two Rumford fireplaces, a steam shower, and a Jacuzzi. Relax in the screened three-season lounge with hardwood floors and a gas grill hookup. Additional features include a concrete theater/storm shelter, Cat5 wiring, underground irrigation, a brand-new roof (Fall 2025), a new water softener, and a heated 3-car garage with an EV charger.

3002 Linnerud Dr, Pleasant Springs
$749,900
4 Beds ⋅ 4 Baths ⋅ 2026516 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings start July 3. Beautiful one owner home nestled into the middle of this quiet country subdivision just north of Stoughton. Open concept with split bedrooms and a bonus space off the entrance for an office. Well laid out kitchen overlooking the living room and dining area. Walk right out the door to your screened-in porch with one door leading to a fenced area for your pets or out the other door leading to your spacious yard for quiet days/nights around your fire pit. Do you enjoy entertaining, well then let's take a walk down the stairs to your newly finnished basement with 1 additional bedroom, a workout room and a huge family room area to game or movie night with friends. There is even a storage area that many homes don't have the space for.

1789 Lunde Cir, Pleasant Springs
$550,000
3 Beds ⋅ 2 Baths ⋅ 2026061 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to your own private retreat! Tucked away on just under 8 beautiful wooded acres, this property offers the peace privacy, & natural beauty of country living while still being conveniently located. Enjoy the charm of a secluded setting w/ the added benefit of Pleasant Springs’ favorable property taxes. This spacious ranch-style home offers the ease & convenience of having everything you need on one floor. The full walkout lower level creates endless possibilities with a second kitchen, additional living space, & the option to add a third bathroom. This flexible space is perfect for guests, extended family, or a future in-law suite. The attached garage provides direct access to the lower level, where you’ll find a workshop sure to impress any hobbyist, woodworker, or outdoor enthusiast. With mature trees, room to explore, & a setting that feels miles away from it all. This is the opportunity to finally enjoy the country lifestyle you’ve been dreaming of.

2232 Tower Dr, Pleasant Springs
$519,900
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
$459,000
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
$2,050,000
4 Beds ⋅ 4 Baths ⋅ 2022262 MLS ⋅ ACTIVE Status
THIS is the lake house you have been looking for! Panoramic views of beautiful Lake Kegonsa on THE desired side, water depth at the dock, sunrise/sunset views, and right by the Stoughton Country Club. You could be on the course, or on the water within minutes. With an elevated view of the lake overlooking the modern styled and usable boat house that has a storage loft and included dock, the layout is perfect for entertaining. The beautiful, open kitchen even has a Butler's Pantry! Interior is tastefully done with nicely designed rooms. The full walkout in the finished lower level makes 3 floors of well thought out space. A large 4 car garage allows for plenty of toys.

3066 Shadyside Dr, Pleasant Springs
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