Oregon Real Estate

Oregon Real Estate

Welcome to Oregon, Wisconsin, a charming village nestled in the heart of Dane County. Known for its friendly atmosphere and picturesque landscapes, Oregon offers a delightful blend of small-town charm and modern conveniences, making it an ideal place to call home.

With a population of around 10,000 residents, Oregon boasts a tight-knit community where neighbors become friends. The village is renowned for its excellent school system, which is consistently recognized for its commitment to academic excellence and student development. Families are drawn to Oregon not only for its educational opportunities but also for its abundant recreational activities. The area is dotted with parks, scenic trails, and sports facilities, providing ample opportunities for outdoor enthusiasts to explore nature and enjoy the fresh Wisconsin air.

The downtown area is brimming with local shops, cozy cafes, and eateries that reflect the village's vibrant culture. Whether you're in the mood for a leisurely stroll or a delightful meal, Oregon's welcoming ambiance invites you to experience its unique charm.

Oregon is also conveniently located just a short drive from Madison, the state capital, allowing residents to enjoy the best of both worlds—peaceful suburban living with easy access to the bustling city life. From cultural events and farmer's markets to festivals that celebrate the changing seasons, Oregon fosters a sense of community that is hard to find elsewhere.

If you’re seeking a place where community spirit thrives amidst stunning natural beauty, Oregon, Wisconsin, is the perfect destination to plant your roots. Come discover the warmth and charm of this delightful village—your new home awaits!

Newest Listings in Oregon

$850,000
4 Beds ⋅ 3 Baths ⋅ 2026945 MLS ⋅ ACTIVE Status
Showings start Friday on this exceptional custom home in Ravenoaks offering privacy, character & craftsmanship on a beautifully landscaped 1.28-acre lot near Paoli, the Badger State Trail & Oregon schools. This 4-bedroom, 2.5-bath home with a 3-car garage has been thoughtfully updated within the last six years, including hardwood floors, seamless steel siding with lifetime warranty, garage doors, front deck, remodeled bath & new furnace/A/C. Rich architectural details shine throughout with Craftsman-style staircase & fireplace & solid wood 5-panel doors, trim & baseboards. Floor-to-ceiling windows & skylights flood the home with natural light while showcasing stunning views, also enjoyed from the remodeled three-season sunroom. Designed for entertaining, the kitchen offers abundant cabinetry, storage & a convenient butler’s pantry. The private primary suite holds a surprise—secret doors leading to an incredible walk-in closet complete with its own dedicated laundry area.

6239 Trail Ridge Ct, Oregon
$1,195,000
6 Beds ⋅ 4 Baths ⋅ 2028669 MLS ⋅ ACTIVE Status
Showing Start Sat 7/25 at noon - This stunning ranch home delivers spacious, high-quality living with an excellent open floor plan. The home features 6 bedrooms and 4 full bathrooms. A highlight is the massive six plus car heated garage measuring over 1,500 square feet, providing exceptional space for vehicles, storage, and hobbies while remaining comfortable in all seasons. The main level includes a private suite in its own separate wing, along with a dedicated home office and workout room. The lower level boasts a large, sunny walkout basement complete with a custom home theater—ideal for entertaining and enjoyment. This property offers the privacy and presence of a gated-style home without the added taxes or ongoing fees. It is also barrier-free design directly from the garage. Set on beautifully landscaped grounds, the home is move-in ready and includes a 2-year UHP home warranty for added peace of mind. Combining thoughtful design, generous living space, and practical luxury.

980 Brynhill Dr, Oregon
$589,900
3 Beds ⋅ 3 Baths ⋅ 2028336 MLS ⋅ ACTIVE Status
This inviting two-story home offers over 2,000 square feet of above-grade living space, blending timeless character with functional design. The spacious sunroom showcases exposed ceilings and walls, a beautifully painted brick fireplace, and direct access to the private, fenced backyard surrounded by mature trees. The kitchen features warm wood cabinetry, granite countertops, a peninsula for additional seating, a new sink, and abundant storage. Upstairs, the primary suite includes a walk-in closet and ensuite bath with a double vanity and granite countertops, while two additional bedrooms provide comfortable living space, with one featuring vaulted ceilings and an arched window. A partially finished lower level offers flexible living space and generous storage, complemented by an attached two-car garage and thoughtful details like a convenient laundry chute from the primary suite.

873 Peregrine Cir, Oregon
$300,000
2 Beds ⋅ 3 Baths ⋅ 2028288 MLS ⋅ ACTIVE Status
Looking for a low-maintenance lifestyle, but also craving something special that feels like home? This beautiful 2-bed, 2.5 bath townhouse, meticulously cared for by its original owner, delivers the quality touches that set it apart. Colorful perennials & an airy skylit foyer greet & invite you in. Its open floor plan is bathed in natural light & adorned w/elegant crown molding. Quartz countertops, high quality cabinets, & stainless appliances grace the kitchen. The dining area’s glass doors open to a private patio where sunrises & morning coffee are on the menu. Relax among lilies, irises, & hydragenas. Upstairs, the huge primary suite features a soaring cathedral ceiling, sitting area, walk-in closet, & bath. A generously sized 2nd bedroom sits next to its own full bath, w/convenient laundry nearby. Spotless LL offers storage or extra living space. Bath rough-in & egress window make future finishing easy. Close to charming downtown Oregon & walking paths. Short drive to Madison!

148 Alpine Meadow Cir, Oregon
$499,900
2028273 MLS ⋅ ACTIVE Status
Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. Several outbuildings on the property including the original barn, 3 car detached garage and two pole sheds provide multiple possibilities for storage, hobbies or animals. Includes a Foursquare farm house. House and some outbuildings are in need of some TLC. Property is also listed as Single Family. Seller is selling AS-IS.

5 Acres Lincoln Rd, Oregon
$499,900
4 Beds ⋅ 2 Baths ⋅ 2028272 MLS ⋅ ACTIVE Status
Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. This classic foursquare farm house features spacious kitchen and dining room, four bedrooms and main level laundry. Several outbuildings on the property including the original barn, 3 car detached garage and two pole sheds provide multiple possibilities for storage, hobbies or animals. House and some outbuildings are in need of TLC. Property is also listed as vacant land. Seller is selling AS-IS.

5794 Lincoln Rd, Oregon
$465,000
4 Beds ⋅ 2 Baths ⋅ 2028121 MLS ⋅ ACTIVE UNDER CONTRACT Status
Discover the perfect blend of peace and tranquility in this meticulously updated ranch, ideally located just minutes from Oregon and Madison. Situated on an expansive lot with a newly installed metal fence, this home offers the desired amenities of modern living with none of the work. The interior boasts 4 spacious bedrooms and 2 well-appointed bathrooms. Significant mechanical updates provide peace of mind, featuring a brand-new roof (2025) and a high-efficiency furnace (2023). The heart of the home has been refreshed with classy kitchen updates. Step outside to your private oasis, complete with raised garden beds and a cozy fire pit perfect for entertaining. Don’t miss your chance to own this move-in-ready gem—schedule your private showing today!

1055 Glenway Rd, Oregon
$465,000
3 Beds ⋅ 3 Baths ⋅ 2028087 MLS ⋅ ACTIVE Status
Looking for a well-maintained ranch home in a great neighborhood? This 3 bed/3 bath home on 1/3 acre lot in the Oregon School District is it! The main level boasts an updated eat-in kitchen with granite counters and SS appliances, LVP flooring throughout much of the home, and newer carpet in the sizable living room and bedrooms. A substantial primary suite with a private full bath w/skylight, walk-in closet, walkout to deck, and a fireplace is an absolute highlight. The beautiful large 4-season sunroom w/fireplace and expansive deck are a must see! Two secondary bedrooms and full bath round out the main level. The lower level features a large rec room w/bar and wood burning stove, den/office, full bath, laundry room, and plenty of storage. The oversized 2-car garage is an added bonus! Updates include a new roof and furnace (22), newer appliances incl washer/dryer, and more! Located close to schools, parks, and an easy commute to Madison, Epic and everything the area has to offer!

855 Clover Ln, Oregon
$450,000
3 Beds ⋅ 3 Baths ⋅ 2028027 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home that's filled with natural light and inviting spaces from the moment you walk in. One of the standout features is the beautiful sun porch overlooking a private backyard with mature landscaping, the perfect place to enjoy your morning coffee or relax at the end of the day. The oversized primary bedroom offers plenty of room to unwind, while the finished lower level provides extra living space for entertaining, a playroom, home office, or whatever fits your lifestyle, plus excellent storage. The thoughtful layout makes this home feel comfortable, functional, and easy to enjoy.

489 Cherry Wood Dr, Oregon
$799,900
4 Beds ⋅ 4 Baths ⋅ 2027752 MLS ⋅ ACTIVE Status
Completion date: September 30, 2026. Exceptional custom built 4-bedroom home overlooking Foxboro Golf Club! This well appointed home offers an incredible gourmet kitchen with custom cabinets, quartz counters, stainless appliances, hidden walk-in pantry and center island with snack bar. Enjoy the sun filled great room with gas fireplace, large dinette leading to a patio and great view of the course. Master suite features large walk-in closet and private master bath with double vanity and tiled shower. The finished lower level expands your living space with a spacious rec room, 4th bedroom and full bathroom - perfect for guests or entertaining. LVP flooring, 2nd floor laundry, 3 car garage and more!

480 Foxfield Ct, Oregon
$435,000
4 Beds ⋅ 2 Baths ⋅ 2027678 MLS ⋅ ACTIVE Status
If you're looking for a beautiful blend of yesteryear charm & modern updates, don't miss this Oregon charmer! Gorgeous woodwork, stained glass, exposed brick and hardwood floors create a warm, memorable space. An updated kitchen is the true heart of the home and is as functional as it is inviting - with room to gather, tons of counter space & storage (don't miss the huge pantry!). Two large living spaces offer a flexible floor plan and room for everyone to find their favorite spot in the home. Upstairs, a truly spectacular primary bedroom addition shines with vaulted ceilings, incredible natural light & and a large walk-in closet. If you love outdoor spaces, there are so many great options - a welcoming, lemonade-sipping front porch; a large, sunny deck; and a beautifully landscaped, fully fenced yard. Numerous updates, including windows, HVAC, and a newer garage! Incredible location - walking distance to parks, schools, and downtown Oregon.

145 Dewey St, Oregon
$429,900
3 Beds ⋅ 3 Baths ⋅ 2027563 MLS ⋅ ACTIVE Status
Move-in ready 9/16/26. This Tribeca home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 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.

456 Savannah Dr, Oregon
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