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181 Union St, Sun Prairie
$410,000
4 Beds ⋅ 3 Baths ⋅ 2031440 MLS ⋅ ACTIVE UNDER CONTRACT Status
AS SWEET AS THEY COME! This 4 bedroom two story offers it all. Located in the heart of Sun Prairie this home has the character and charm of yesteryears with all the conveniences that give you the perfect package! Enjoy the large living room, fabulous eat-in-kitchen, formal dining room, plus family room all on the main! You will be beyond delighted by the size of the bedrooms including the 24x13 primary suite with private full bath, 19x12 second bedroom and 3rd bedroom with its own outside porch. Newly finished L/L bedroom W/large egress window and walk-in closet. All this is nestled on a large lot, close to all the vibe of our downtown activities, from coffee shops, bookstore, farmers market, museum, restaurants and so much more. With updates galore, including a newly finished 4th bedroom in the lower level, appliances, new windows and doors, water heater and water softener. You have nothing to do but move in!

181 Union St, Sun Prairie

1065 Tara Dr, Sun Prairie
$399,900
3 Beds ⋅ 2 Baths ⋅ 2031590 MLS ⋅ ACTIVE Status
Ready for your new home? This well maintained 3 bedroom ranch home has the comforts and amenities you need. Some features include a new furnace (2026), New water heater and water softener (2026), 2 new sump pumps (2024), newer 15" of insulation in the attic, and a roof that is less than 10 years old. And, I have to tell you about the fantastic yard with beautiful perennials, not a weed to be found, 2 storage sheds, and a huge deck for entertaining, grilling, or sitting out and enjoying the quiet neighborhood. Just a stones throw to Madison and close to schools, parks, shopping, and more. There's even a limited 13 month UHP home warranty included. You can't pass this up. This is truly the cats meow! Schedule a private showing today! You'll be glad you did.

1065 Tara Dr, Sun Prairie

1042 Okeeffe Ave, Sun Prairie
$399,900
3 Beds ⋅ 3 Baths ⋅ 2031573 MLS ⋅ ACTIVE UNDER CONTRACT Status
Engineered for quiet and designed for comfort, this Veridian-built Emerson features a shared-wall system designed for privacy and quieter living. This 2019 Smith’s Crossing twin offers 3 bedrooms, 2.5 baths, 1,776 finished sq ft and three living levels. The bright main level has 9-foot ceilings, an open kitchen with oversized granite island, cabinetry and walk-in pantry, plus laundry and half bath. Updates include fresh paint, brand-new carpeting and a new upstairs bathroom vanity. The finished lower level offers flexible living space, plumbing for a future 4th bath and unfinished space for storage or expansion. Enjoy a covered front porch, fenced-in yard, oversized patio, no neighbors behind and stunning sunsets. The unusually large garage includes a 20x20 parking area plus extra space for storage, bikes, tools or hobbies. Walk to Creekside Elementary, parks and neighborhood paths.

1042 Okeeffe Ave, Sun Prairie

1357 Overlook Pass, Sun Prairie
$539,900
4 Beds ⋅ 3 Baths ⋅ 2031568 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home! This beautifully updated 4-bedroom, 3-full-bath home in Sun Prairie offers the space and comfort today's buyers want, all within walking distance to the local elementary school. The spacious open-concept kitchen boasts abundant counter space and a large pantry, flowing seamlessly into a vaulted living room filled with natural light. The finished basement adds valuable living space, ideal for a rec room, home gym, or a guest retreat, while storage space throughout keeps everything organized. Outside, enjoy a large backyard, a patio for relaxing evenings, and a hot tub perfect for unwinding after a long day. Major updates are already done, including a new roof, new furnace, and new AC system, offering true peace of mind from day one. With its unbeatable blend of comfort, function, and location, this Sun Prairie home won't last long. Schedule your showing today!

1357 Overlook Pass, Sun Prairie

893 Chalfont Dr, Sun Prairie
$524,900
5 Beds ⋅ 3 Baths ⋅ 2031240 MLS ⋅ ACTIVE Status
Immaculately maintained 5-bedroom ranch in desirable Westwynde! You’ll love the open floor plan with vaulted ceilings, gas fireplace & spacious kitchen with island & breakfast bar. The main level offers 3 bedrooms, 2 full baths & direct access to the deck & backyard. The expanded lower level adds a bedroom, office & rec room - ideal for guests, hobbies, working from home or multi-generational living - plus ample storage. Major updates include roof & furnace (2024), water heater & softener (2025) & upgraded windows with lifetime warranty. Additional improvements: flooring, lighting, countertops, paint, laundry room, stainless steel appliances, radon mitigation, dual sumps & alarm, landscaping & garage door/opener. Enjoy the beautiful yard, 3-car garage & spacious bedrooms. All on a quiet Westwynde street near parks & in the Sun Prairie school district. Don’t miss this opportunity!

893 Chalfont Dr, Sun Prairie

1182 Broadway Dr, Sun Prairie
$515,000
4 Beds ⋅ 3 Baths ⋅ 2031015 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this beautiful home with a new roof in 2022, new furnace, air conditioner and water softener in 2021, plus new carpet in 2026 and updated flooring. All adding value and peace of mind to this spacious 4-bedroom, 2.5-bath split-level home with 2,704 sq ft. Inside, the inviting kitchen features white cabinetry, a large wood-topped island and a solar tube bringing natural light to the heart of the home. Crown molding, built-in shelving, a laundry chute, generous closets and a spacious primary suite with ensuite bath add thoughtful touches throughout. The lower level offers a comfortable family room, laundry room with utility sink and abundant storage with shelving and a workbench. Enjoy an attached 2-car garage and wonderful outdoor living on the back deck with composite tile flooring and pergola.

1182 Broadway Dr, Sun Prairie

430 Woodview Dr, Sun Prairie
$374,900
3 Beds ⋅ 1 Baths ⋅ 2031395 MLS ⋅ ACTIVE Status
Completely renovated interior and exterior! Located in a quiet eastside neighborhood, walking distance to farmers market, coffee shop and resturants. Updates in 2026 include new roof, vinyl siding w/ LP smartside trim, windows, exterior/patio doors, soffit/fascia, gutters with oversized down spouts, blown in insulation in the attic, garage door and opener, Lennox furnace, Lennox air conditioner, water heater, water softener, bathtub w/ tile surround, bathroom vanity w/ quartz top, bathroom tile floor, laminate flooring, carpet, kitchen cabinets, stainless steel whirlpool appliances, kitchen countertops, tile backsplash, interior paint, interior doors, light fixtures, interior white craftsman style trim, professional duct cleaning, 6' privacy side yard fence, and landscaping. 12x10 shed with new overhead door located in the back yard. Garage is wired with 240V outlet.

430 Woodview Dr, Sun Prairie

500 E Main St Unit 6, Sun Prairie
$199,900
2 Beds ⋅ 1 Baths ⋅ 2031275 MLS ⋅ ACTIVE Status
Motivated sellers offering this great new price! Delightful 2 bedroom garden condo in the heart of Sun Prairie and steps from restauraunts, shops, and Sun Prairie's famous farmers market. Simi-private entry leads to the spacious living room w/patio door that leads to your private deck. Entertaining will be a snap with the fully appointed kitchen (new refrigerator) & breakfast bar all open to the large dining room featuring custom storage & display cabinets. There are 2 generous bedrooms, a nice bath and all freshly painted. Newer high effeciency windows and patio door is a plus. Common areas include a community room w/1/2 bath and shared onsite laundry. Extra bonus is a guest suite located next door which is available for nightly rent for those out of town guests. Utility Aveages: Nat Gas $38/month & Electric, water & sewer $105/month. A must see.

500 E Main St Unit 6, Sun Prairie

926 Frederick St, Sun Prairie
$385,000
4 Beds ⋅ 2 Baths ⋅ 2031011 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this beautiful 4-bedroom, 2-bath tri-level home with a private backyard, mature trees and great outdoor space! Recent updates include a new roof and gutters (2025), new garage floor, driveway, sidewalk and steps (2025), and air conditioner (2026). The bright main level features tile and wood flooring, a spacious dining area and comfortable living room. The exposed lower level offers a large rec room with wood-burning stove, bedroom and full bath. Upstairs, all 3 bedrooms feature wood floors, along with a full bath with jetted tub. Enjoy the large deck, fenced backyard, storage shed and playset. Attached 1-car garage and plenty of functional living space make this a wonderful Sun Prairie home!

926 Frederick St, Sun Prairie

401 Woodview Dr, Sun Prairie
$454,900
4 Beds ⋅ 2 Baths ⋅ 2030968 MLS ⋅ ACTIVE Status
This beautifully maintained 5-bedroom, 2-bath raised ranch sits on a corner lot in a convenient Sun Prairie location near parks, schools, and a bike path. A spacious Trex deck overlooks the backyard, while the front entry is enhanced by seven app-controlled recessed exterior lights with customizable colors, dimming capabilities, and holiday-ready lighting scenes. Major updates include top of the line dishwasher and stove in 2025, the roof and gutters in 2022, windows in 2021, furnace and AC with Aprilaire air purification in 2022, and full duct cleaning in 2025 help make the home move-in ready. With flexible living spaces throughout and the big-ticket improvements already complete, this inviting home is ready for your personal touch. Showings begin with the open house on Saturday, August 29th.

401 Woodview Dr, Sun Prairie

1155 Twisted Branch Way, Sun Prairie
$489,900
3 Beds ⋅ 3 Baths ⋅ 2030926 MLS ⋅ ACTIVE Status
Welcome to a home where pristine condition meets everyday convenience! This beautifully maintained property offers 3 spacious bedrooms and 2.5 bathrooms, plus a bonus first-floor office and a large mudroom with plenty of storage. The kitchen shines with granite and quartz counters, a beautiful backsplash, & upgraded cabinetry featuring soft-close drawers & pull-out shelves. LVP Flooring on the main & solid Maple Doors throughout. Retreat to the primary suite’s beautiful tiled rainfall shower and huge walk-in closet. The unfinished lower level is plumbed for a third bath, offering endless potential. Enjoy the 2+ car garage, professionally landscaped yard, and a beautiful light-up patio perfect for relaxing evenings. Just 1 minute from Grand Avenue’s wonderful dining, shopping, and movie theatre, and 5 minutes to Hwy 151 and I-90/94 for an easy commute. Near parks with scenic walking & bike paths, too! Truly not a thing to do but move in — schedule your private showing today!

1155 Twisted Branch Way, Sun Prairie

1219 Crane Meadow Way, Sun Prairie
$520,000
4 Beds ⋅ 4 Baths ⋅ 2030903 MLS ⋅ ACTIVE Status
Welcome to this beautifully designed two-story home offering 4 bedrooms and 3.5 baths in Smith's Crossing! The gourmet kitchen features a center island with snack bar, granite countertops, subway tile backsplash and stainless steel appliances, flowing seamlessly into the spacious family room and dinette. Step outside to your private deck and enjoy peaceful views of the incredible green space beyond. The private primary suite offers a tray ceiling, walk-in closet and luxurious en suite bath. The exposed lower level adds even more living space with a fourth bedroom, full bathroom and generous rec room - perfect for guests or hobbies. Close to schools, parks, walking trails and shopping. Additional highlights include a convenient main-floor laundry, beautiful white trim and doors throughout, and a 2-car garage.

1219 Crane Meadow Way, Sun Prairie

858 Chalfont Dr, Sun Prairie
$549,500
5 Beds ⋅ 4 Baths ⋅ 2030873 MLS ⋅ ACTIVE UNDER CONTRACT Status
Appealing 5 bedroom 3.5 bath colonial w/peaceful backyard! Formal living + dining or office/den, ample kitchen, stainless steel appliances, fireplace, 3 car garage! Primary features walk-in closet + tub/shower, double sink vanities throughout! Enjoy year-round comfort in the 3 season porch, which offers a seamless transition between indoor & outdoor living! The finished basement adds versatility for leisure or additional storage. New roof within the last 5 yrs. Refinished deck. Sump pump & radon mitigation system! Located w/easy access to HWY-151 in the Sun Prairie School District & close to Westwynde Park, this property is well-situated for convenience and community engagement! This solid home is ready for you to bring your own ideas and custom updates!

858 Chalfont Dr, Sun Prairie

1214 Chicory Way, Sun Prairie
$292,500
3 Beds ⋅ 1 Baths ⋅ 2030743 MLS ⋅ ACTIVE UNDER CONTRACT Status
Charming ranch in a convenient Sun Prairie location with NO HOA! Welcome to 1214 Chicory Way, where comfortable one-level living meets inviting indoor-outdoor spaces. The main living areas feature beautiful hardwood floors throughout and a cozy fireplace featuring a striking floor-to-ceiling stone surround. The kitchen is open to the dining and living areas, creating a connected layout for everyday living and entertaining. French doors open directly to the large patio with privacy fence and fully fenced backyard, complete with an in-ground fire pit, creating an easy flow for entertaining, relaxing, and enjoying the outdoors. The yard also features a spacious garden area, perfect for those who love to garden or simply want room to create their own outdoor retreat. A detached 1-car garage provides convenient parking and storage, along with an extra-large concrete driveway. Ideally located near Sun Prairie's everyday everyday amenities, this charming home offers character and function!

1214 Chicory Way, Sun Prairie

1331 Pinnacle Cir, Sun Prairie
$579,900
4 Beds ⋅ 3 Baths ⋅ 2030649 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this beautifully maintained, move-in-ready ranch tucked away at the end of a peaceful cul-de-sac! Step inside to a bright, welcoming layout featuring vaulted ceilings, skylights, a private primary suite with walk-in closet, first-floor laundry, and thoughtful touches throughout. The exposed lower level expands your living space with a comfortable family room, cozy gas fireplace, and 4th bedroom - perfect for guests or a home office. Step outside and enjoy your morning coffee or evening gatherings on the screened porch overlooking the spacious backyard. The oversized 3-car garage offers plenty of room for vehicles, toys, a boat, or utility equipment. A central vacuum system adds convenience, while the large yard and two nearby parks provide plenty of opportunities to enjoy the outdoors. Located on the largest lot in Ridgecrest Subdivision, this is the kind of home that is truly ready for you to move in and enjoy!

1331 Pinnacle Cir, Sun Prairie

1786 Waverly Way, Sun Prairie
$694,900
4 Beds ⋅ 3 Baths ⋅ 2030423 MLS ⋅ ACTIVE Status
Move-in ready 10/29/26. This Bryant home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 4 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

1786 Waverly Way, Sun Prairie

2103 Winding Stream Way, Sun Prairie
$699,900
3 Beds ⋅ 2 Baths ⋅ 2030419 MLS ⋅ ACTIVE Status
Move-in ready 11/3/26. This Conrad home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler® and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

2103 Winding Stream Way, Sun Prairie

258 262 N Bristol St, Sun Prairie
$375,000
2030363 MLS ⋅ ACTIVE Status
Excellent investment opportunity with owner-occupancy potential in the heart of Sun Prairie! This well-maintained duplex features two spacious 3-bedroom units with separate entrances, utilities, and in-unit laundry. The main level unit (258) is vacant and move-in ready, offering beautifully refinished living spaces with hardwood floors, original woodwork, fresh paint throughout, updated flooring, remodeled bathroom, newer appliances, updated lighting, and a screened porch. The upper unit (262) features newer LVP flooring, a finished attic space, private deck, and is occupied by a long-term month-to-month tenant of over 8 years, providing immediate rental income with future flexibility. Major recent improvements include two new furnaces (2024), both water heaters (2025), roof updates including new decking and shingles on the addition and garage (2025), resealed roofing, new garage doors and openers, updated second-floor plumbing, and extensive exterior maintenance.

258 262 N Bristol St, Sun Prairie

829 Edgemore Dr, Sun Prairie
$459,900
3 Beds ⋅ 2 Baths ⋅ 2030252 MLS ⋅ ACTIVE Status
Welcome to 829 Edgemore Drive! This beautifully maintained 3-bedroom home offers an inviting blend of comfort, style, and functionality. The spacious great room features vaulted ceilings, abundant natural light, and a seamless flow into the dining area and custom-designed kitchen with cabinetry, quartz countertops, tile flooring, and a premium stainless appliance package with a Wolf gas stove and Sub-Zero refrigerator. The finished lower level provides a cozy room with built-ins, wet bar, and gas fireplace, plus flexible space for an office, guest room, or hobbies. Outside, enjoy a private fenced backyard with professional landscaping, stamped-concrete patio, and upper deck, great for relaxing or entertaining. Attached 2-car garage with workbench and storage. Conveniently located near parks, shopping, dining, and more!

829 Edgemore Dr, Sun Prairie

1398 Overlook Pass, Sun Prairie
$520,000
4 Beds ⋅ 4 Baths ⋅ 2030058 MLS ⋅ ACTIVE Status
Welcome to Hickory Grove Estates, where everyday convenience meets the feeling of a private retreat! This spacious 4-bedroom, 3.5-bath home offers room to spread out, entertain and grow. The inviting main level features an open kitchen with island, comfortable living spaces and a dining area & addtl formal dining room ready for gatherings. Upstairs, unwind in the spacious primary suite featuring a luxurious tiled walk in shower, plus two additional bedrooms and a full bath. The finished lower level adds even more flexibility with a rec room, wet bar, full-size refrigerator, fourth bedroom and full bath. Outside, enjoy the oversized corner lot, beautiful fenced-in yard, large deck and established garden—perfect for relaxing or harvesting your own fresh produce. With restaurants, shopping and schools just minutes away, this is the best of both convenience and privacy!

1398 Overlook Pass, Sun Prairie

212 Major Way, Sun Prairie
$375,000
3 Beds ⋅ 2 Baths ⋅ 2029922 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this charming ranch in a convenient Sun Prairie location! Hardwood floors, a floor-to-ceiling stacked-stone gas fireplace, & an oversized front window create an inviting living room filled with natural light. The ML offers a functional layout, galley kitchen, and 3 comfortable bedrooms, all with hardwood floors. Downstairs, the finished LL expands your living space with a spacious fmly room complete with theater equipment & projector for the ultimate movie nights, a full bath, and a versatile den usable as a 4th bedroom, home office, or workout space. Step outside to enjoy the fenced backyard featuring a paver patio, storage shed, and plenty of room to relax & entertain. All this in a fantastic location close to Main St conveniences & Hwy 151 for an easy commute!

212 Major Way, Sun Prairie

133 W Kohler St, Sun Prairie
$449,000
4 Beds ⋅ 2 Baths ⋅ 2029461 MLS ⋅ ACTIVE Status
Charming and move-in ready, this 3-bedroom home offers plenty of comfort, character, and space inside and out! The sunken living room features a beautiful cozy gas fireplace, while the updated kitchen is ready for everyday living and entertaining. Kitchen updates include maple cabinetry, quartz countertops, tile backsplash and stainless steel appliances. Opens up to formal dining room & living room, perfect for hosing friends and family or sipping coffee in the mornings. The true showstopper is the sunroom with slider windows, filled with natural light and overlooking the beautiful backyard. Step outside to a spacious patio and massive yard featuring mature and native plantings—perfect for gardening, playing, entertaining, or simply enjoying your own private retreat. Main level bathroom remodel '22. Conveniently located in walking distance of Wetmore Park, Northside school and downtown Sun Prairie! UHP Ultimate Home Warranty Included.

133 W Kohler St, Sun Prairie

1030 Carriage Dr, Sun Prairie
$430,000
4 Beds ⋅ 3 Baths ⋅ 2029277 MLS ⋅ ACTIVE Status
Back on the market & ready for its next owner! Welcome to this beautifully maintained 4-bed, 3-full-bath ranch in a desirable Sun Prairie neighborhood. With approx. 1,950 sq. ft. of finished living space, this home offers an inviting open layout, vaulted ceilings, abundant natural light & flexible space for work, guests & entertaining. The main level features 3 bedrooms and 2 full baths, while the finished lower level adds a spacious family room, 4th bedroom, full bath and dedicated office. Enjoy an exceptional location directly across from a 21-acre neighborhood park with a playground, walking paths, sports courts, fields, pond and sledding hill. A spacious backyard & deck provide a wonderful outdoor setting, while downtown Sun Prairie is just a short walk or bike ride away. The neighborhood's location adjacent to Patrick Marsh is excellent for nature lovers. Previous offers were unable to proceed due to buyer financing, creating a new opportunity to make this wonderful home your own

1030 Carriage Dr, Sun Prairie

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.