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$574,900
3 Beds ⋅ 2.5 Baths
Tucked away on a cul-de-sac with a quiet neighborhood setting, this inviting two-story home offers nearly 2,500 square feet of above-grade living space, blending timeless character with functional design. Located just two blocks from Anderson Farm Park, outdoor recreation is close at hand, with expansive green space and a large dog exercise area providing convenient opportunities to walk, explore, and enjoy time outside. Inside, the spacious sunroom showcases exposed ceilings and walls, a beautiful 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 an ensuite bath with a double vanity and granite countertops. Two additional bedrooms provide comfortable living space, including one with vaulted ceilings and a distinctive arched window.

873 Peregrine Circle, Oregon

Listing courtesy of MHB Real Estate.

$300,000
2 Beds ⋅ 2.5 Baths
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 Circle, Oregon

Listing courtesy of Lindsay Gallagher & Associates.

$499,900
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 Road, Oregon

Listing courtesy of First Weber Inc.

$499,900
4 Beds ⋅ 2 Baths
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 Road, Oregon

Listing courtesy of First Weber Inc.

$799,900
4 Beds ⋅ 3.5 Baths
Completion date: September 30, 2026. Exceptional custom built 4-bedroom home offering the perfect blend of comfort and thoughtful design! 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 with access to the patio, making it ideal for everyday living and entertaining. 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. LVP flooring, 2nd floor laundry, 3 car garage and more!

480 Foxfield Court, Oregon

Listing courtesy of Pinnacle Real Estate Group LLC.

$799,900
4 Beds ⋅ 2.5 Baths
PRICED BELOW ASSESSED VALUE!!! This spacious ranch invites you to relax on 4.21 acres located on a peaceful cul de sac in a rural subdivision. A large open great room invites you to just come inside, sit by the fireplace, and look out the massive windows. Others might want to relax on the screened porch for a quick dip in the hot tub while overlooking the woods. The kitchen includes tons of cabinets surrounding the functional island, bright new tile, and updated fixtures. The primary suite feels like a relaxing spa with a large soaking tub, new tile shower, and stylish updates around the double vanity. The lower level makes entertaining easy around the large basement bar, relaxing by the pellet stove, or walk directly outside private deck. There?s room for a home office or workout area. The two legal bedrooms include large windows to bring in natural light. I could ramble on, but this rambling ranch speaks for itself. Schedule your showing today!

546 Echo Valley Road, Oregon

Listing courtesy of EXP Realty, LLC.

$429,900
3 Beds ⋅ 2.5 Baths
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 Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$1,250,000
Turnkey standalone restaurant and bar now available in Oregon, WI - fully equipped and ready to operate from day one. All furniture, fixtures, and equipment are included in the sale, and the property holds an active liquor license from the Village of Oregon. The main dining and bar space spans over 4,300 sq. ft. with an open floor plan, private party room, and patio seating, plus approximately 1,500 sq. ft. of basement storage. Ownership is motivated to sell but will consider leasing to experienced, qualified operators. A rare opportunity to step into a fully built-out, licensed hospitality concept without the typical startup burden. Serious inquiries only.

830 Oregon Center Drive, Oregon

Listing courtesy of Accord Realty.

$539,900
3 Beds ⋅ 2.5 Baths
Discover this stunning new home, designed with both comfort and style in mind. Boasting 1968 square feet of living space, this modern residence offers a spacious and open floor plan. The interior features three bedrooms, three bathrooms, and luxurious low-maintenance LVP flooring throughout. The brand new kitchen is a dream, complete with sleek stainless steel appliances, custom cabinetry with soft-close, with a large center island. Cozy up by the gas-burning fireplace on chilly evenings. Located on a peaceful street, this home is great for families with children, offering easy access to nearby schools. Don't miss this opportunity to make this beautiful new home your own!

1055 Autumn Blaze Court, Oregon

Listing courtesy of Alterra Real Estate Group LLC.

$394,900
3 Beds ⋅ 2.5 Baths
This Emerson 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.

1043 Merri-Hill Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$539,900
3 Beds ⋅ 2 Baths
Move-in ready 9/3/26. This Harlow 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.

1003 Merri-Hill Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$1,100
Well-maintained ground-level office suite overlooking the Foxboro Golf Course in a prime location with strong exposure and easy access. This professional space features multiple private offices, a shared kitchenette, common area bathrooms just steps from the entrance, abundant natural light, exterior monument signage, and ample parking for tenants and guests. Ideal opportunity for professional, medical, or service-based businesses seeking a functional space in an attractive setting.

602 Pleasant Oak Drive, Oregon

Listing courtesy of Collective Real Estate Group.

$90,132
Position your business in this well-maintained 6,438-square-foot office building conveniently located in Oregon's established business and industrial district, just minutes from Madison and easy access to major transportation routes. The property offers a professional corporate environment ideal for engineering, professional services, administrative headquarters, technology firms, medical office users, or other office-intensive operations. The flexible floor plan accommodates a variety of configurations, including private offices, conference rooms, collaborative work areas, and support spaces.

550 N Burr Oak Avenue, Oregon

Listing courtesy of RE/MAX Preferred Commercial.

$168,000
3 Beds ⋅ 1 Baths
Ideally located within walking distance of schools and downtown Oregon, this move-in ready 3-bedroom, 1-bath home blends affordability with thoughtful updates throughout. The main floor features a spacious primary bedroom, a warm and welcoming living room, and a convenient main-floor laundry room. The remodeled kitchen impresses with ample cabinetry, generous counter space, and an eat-in dining area. Brand-new luxury vinyl plank flooring and carpet flow seamlessly throughout. Step into the charming enclosed 3-season room at the front of the home; it's an ideal spot to unwind and enjoy the outdoors in comfort. Upstairs, two additional bedrooms. Outside, the fully fenced double lot provides exceptional privacy. Two garages offer abundant space for vehicles, a workshop, or extra storage; a rare find at this price point. A newer roof completes the package, giving buyers added confidence and peace of mind. Opportunities like this don't last long. Schedule your private showing today!

304 N 3rd Street, Oregon

Listing courtesy of DC Rise Real Estate.

$995,000
Schedule a showing to walk the property. 60+ acres in the beautiful Town of Oregon, offering a rare blend of partially wooded acreage, productive cropland, and potential home site opportunities. Peaceful and private, yet with easy access to Madison, this property invites endless possibilities?build your dream estate, enjoy recreation, or hold as a long-term land investment. A scenic setting with room to roam, all just a convenient drive from Madison and area amenities.

Lots Purcell, Oregon

Listing courtesy of Sprinkman Real Estate.

$625,000
4 Beds ⋅ 3 Baths
Tucked among the trees on over an acre, this private ranch-style retreat offers comfort and natural beauty. Inside, a striking stone fireplace sets the tone for gatherings, while the sun-filled sunroom invites quiet moments overlooking the woods, stunning sunsets, and state capital views. The primary ensuite feels like a personal sanctuary with its own fireplace and deck access. The deck extends the living space outdoors, perfect for entertaining or simply enjoying the peaceful wooded backdrop. Evenings are best spent gathered around the built-in firepit under the stars. The walk-out lower level adds versatility with a welcoming family room and wood pellet stove along with space for games, recreation, fitness, and generous home office. Room to relax, recharge, and entertain. Wood floors, 2 fireplaces + wood burning stove, vaulted ceilings, an abundance of windows and 3-car garage! SF/dim/lot approx. - Buyer?s responsibility to verify. All pertinent info/docs are in MLS docs

2001 Timber Lake Road, Oregon

Listing courtesy of Sprinkman Real Estate.

$384,000
4 Beds ⋅ 2.5 Baths
Must-see 3BR Ranch-style condo with updates and flexible living space! Main level features newer granite counters, appliances & flooring, gas fireplace, primary suite, laundry & 1/2 bath. Exposed lower level offers 2 bedrooms, full bath, spacious family room that could serve as a 4th bedroom, plus ample storage. New roof & siding in 2026. Newer deck off dining area. Ideally located close to parks, schools, shopping, restaurants, and everyday conveniences. This home offers a great combination of comfort, flexibility, and location. Condo is located adjacent to the Highway 14 corridor.

828 Dunn Avenue, Oregon

Listing courtesy of Century 21 Affiliated Roessler.

$1,275,000
5 Beds ⋅ 4.5 Baths
Perfectly positioned on the Bergamont Golf Course, this stunning home offers some of the most breathtaking views in the community?overlooking the 10th & 18th fairways as well as the spectacular clubhouse. The gourmet kitchen is a true showstopper, complete with a large center island, high-end appliances including Sub-Zero, Viking and Thermador-perfect for the culinary enthusiast. The main living area is warm & inviting with gorgeous wood flooring, soaring vaulted ceilings, & a striking tiled fireplace that anchors the space. The walkout lower level is built for entertaining & enjoyment, offering a spacious family room, wet bar, wine room, dedicated entertainment space, & an exercise room. Stone fire pit area-perfect for outdoor gatherings.

1053 Winged Foot Drive, Oregon

Listing courtesy of First Weber Inc.

$559,900
4 Beds ⋅ 3.5 Baths
Move-in ready and waiting for you! This beautifully maintained 4-bedroom, 3.5-bath home has been freshly painted and is ready to enjoy from day one. The bright, inviting main level offers comfortable living spaces and easy access to the deck?perfect for grilling, entertaining, or relaxing outdoors. Upstairs, you?ll find four spacious bedrooms, including a private primary suite with its own bath and generous closet space. The finished walkout lower level adds even more living space with a large family room, full bath, and backyard access?ideal for guests, movie nights, hobbies, or a game room. Outside, enjoy the versatile sport court/patio for basketball, pickleball, entertaining, and more. Conveniently located in the desirable Oregon community near parks, trails, shopping, dining, and Madison. Fresh, well cared for, and truly move-in ready?come take a look!

422 Oakwood Drive, Oregon

Listing courtesy of First Weber Inc.

$420,000
2 Beds ⋅ 2 Baths
Thoughtfully updated condo that truly lives like a single-family home in a welcoming Oregon community! Condo Fees are $200/month. Enjoy a private entry and convenient 2-car attached garage, along with vaulted ceilings and abundant natural light throughout the inviting main living space. Upgraded lighting, new flooring, and an enhanced kitchen with added pantry cabinetry and butcher block counter add both style and function. The main level offers easy everyday living, while the unfinished lower level is already prepped for future expansion with plumbing and framing in place. Major exterior improvements include professional drainage, French drains, and striking rock retaining walls. Conveniently located near parks, dining, local amenities, and with quick access to Madison.

1206 Tivoli Circle, Oregon

Listing courtesy of Realty Executives Cooper Spransy.

$949,000
4 Beds ⋅ 3 Baths
No showings until 5/13. Nestled in a serene, park-like setting, this 4,000+ sf rustic European-inspired cottage offers exceptional privacy surrounded by mature hardwood forest, perennial gardens, and spring wildflowers. Beautiful nature views of the landscaped terminal moraine can be enjoyed from nearly every window. The home showcases outstanding craftsmanship with custom cabinetry and millwork crafted from wood milled directly from the property, including red oak laundry cabinetry, a cherry primary bath vanity, quarter-sawn oak office shelving, oak kitchen bow window trim, a cherry built-in bookcase, and a walnut window seat. Modern conveniences include high-speed internet, a dedicated home office, and an easy commute?just 10 minutes to Oregon, 25 minutes to Madison. Additional 24?x40? shop - basement features 220 volt outlets, equipped with 4" fine dust collection exhaust system for the artisan. The flagship property of this cul-de-sac. This is not just a home, this is a lifestyle.

4802 Country Meadows Road, Oregon

Listing courtesy of First Weber Hedeman Group.

$440,000
2 Beds ⋅ 3 Baths
Amazing Oregon condo propertunity with park-like setting and all the kitchen updates you are looking for. Enjoy meals outside watching nature on the deck or the bump-out dining area. This 2-bed has exposed lower windows if you need to add more. The open floor plan makes it easy to entertain from the updated kitchen with maple cabinets and quartz counters breakfast bar to dining and into the vaulted ceiling living room. The main level has two full bathrooms with the 3rd full bathroom in the lower level which also boasts a large family room. The unfinished area is perfect for a shop or other hobby. The level backyard and association area is perfect for cross-country skiing or playing yard games. Minutes from Madison and easy connections to the interstate.

357 Concord Drive, Oregon

Listing courtesy of KJK & Associates, LLC.

$420,000
2 Beds ⋅ 2 Baths
Thoughtfully updated condo that truly lives like a single-family home in a welcoming Oregon community! Condo Fees are $200/month. Enjoy a private entry and convenient 2-car attached garage, along with vaulted ceilings and abundant natural light throughout the inviting main living space. Upgraded lighting, new flooring, and an enhanced kitchen with added pantry cabinetry and butcher block counter add both style and function. The main level offers easy everyday living, while the unfinished lower level is already prepped for future expansion with plumbing and framing in place. Major exterior improvements include professional drainage, French drains, and striking rock retaining walls. Conveniently located near parks, dining, local amenities, and with quick access to Madison.

1206 Tivoli Circle, Oregon

Listing courtesy of Realty Executives Cooper Spransy.

$464,900
3 Beds ⋅ 2.5 Baths
This Gramercy 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 New Hampton Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$749,900
4 Beds ⋅ 3.5 Baths
Under Construction. Get ready to fall in love with your brand-new home on Autumn Blaze Court. Arriving in December 2026 is a stunning new construction by Alterra Design Homes. It offers the perfect balance of peace and proximity. Nestled on a scenic hill overlooking the Village of Oregon, you're just 15 minutes from the heart of Madison but worlds away from the noise.

1044 Autumn Blaze Court, Oregon

Listing courtesy of Alterra Real Estate Group LLC.

$2,999,999
Rare development opportunity in Oregon, Wisconsin, minutes from Madison and across from holes 13 and 14 of The Legend at Bergamont Golf Course. Located near established neighborhoods, Oregon?s new library, post office, schools, parks and downtown amenities. The approximately 621x1,298 foot property features substantial road frontage and rolling topography. Potential uses include a residential subdivision, luxury estate lots, single-family homes, twin homes, duplexes, townhomes, condominiums or small multifamily development. The property?s size, visibility, golf-course proximity and location in Dane County create an attractive opportunity for builders, developers, investors and land-banking buyers. Conceptual development renderings are available. Development is subject to rezoning, engineering, utility availability and municipal approval. Buyer to verify all development feasibility. Conceptual development renderings are in the photos.

5431 Lincoln Road, Oregon

Listing courtesy of Berkshire Hathaway HomeServices True Realty.

$799,000
Exceptional owner-occupy opportunity with serious income potential! This well maintained 3 unit property (with potential to convert to 5 units, buyer to verify) offers the perfect blend of personal residence and investment. Live comfortably in one unit while the other units help cover your mortgage - or maximize cash flow with additional rental configuration options. The property features spacious layouts, strong natural light and a solid rental appeal, making it attractive for long term tenants or short term rental possibilities (subject to local regulations). Outside enjoy a standout amenity rarely found in multifamily homes - a private pool, creating added lifestyle value for an owner occupant and premium rental appeal. Ample parking, Flexible use potential and a layout that supports both privacy and income make this a smart buy for investors and house hackers alike. This one checks all the boxes!

270 Brook Street, Oregon

Listing courtesy of Preferred Realty Group.

$795,000
Prime 3.2-acre development opportunity in the Village of Oregon, WI! This PD (Planned Development) zoned parcel offers flexibility with approved site plans that have included multifamily, duplex condos and a wide range of permitted uses. Ideal for developers and investors seeking a ready-to-advance project in a growing community. Utilities are available at the lot lines, providing a strong head start for development. The PD zoning allows for creative site planning and mixed-use possibilities, making this an outstanding opportunity for multifamily, build-to-rent, townhome, senior housing, or mixed-use developers looking for a near-term project in a high-demand submarket. Excellent location with convenient access to local amenities, schools, and major commuter routes. Bring your vision and capitalize on this versatile development site.

500 Bergamont Boulevard, Oregon

Listing courtesy of Real Broker LLC.

$399,900
3 Beds ⋅ 2.5 Baths
This Davis 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.

1087 Tundra Avenue, Oregon

Listing courtesy of Stark Company, REALTORS.

$429,900
3 Beds ⋅ 2.5 Baths
This Chelsea 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.

457 Savannah Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

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