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1206 Tivoli Cir, Oregon
$420,000
2 Beds ⋅ 2 Baths ⋅ 2035904 MLS ⋅ ACTIVE Status
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 Cir, Oregon
1206 Tivoli Cir, Oregon
$420,000
2 Beds ⋅ 2 Baths ⋅ 2035903 MLS ⋅ ACTIVE Status
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 Cir, Oregon
850 Tipperary Rd, Oregon
$515,000
3 Beds ⋅ 3 Baths ⋅ 2035615 MLS ⋅ ACTIVE UNDER CONTRACT Status
Room to roam, views to savor, and possibilities galore! Nestled on 2.76 picturesque acres in the Town of Oregon and surrounded by Hann's Christmas Farm, this unique property offers a peaceful country setting with stunning views in every direction. The home features 3–4 bedrooms, a dedicated office, 2.5 baths, and a walkout lower level. A covered partial wraparound deck provides the perfect spot to relax, entertain, and take in the beautiful surroundings. Two substantial outbuildings add incredible versatility, including a 62' x 40' pole barn and a second building featuring two separate rooms measuring 33' x 11' and 34' x 9'. Whether you're dreaming of a workshop, hobby space, storage for recreational toys, or room to pursue your passions, the possibilities are plentiful. A new roof installed in November 2024 adds peace of mind. A rare opportunity to enjoy country living with space, privacy, and flexibility!

850 Tipperary Rd, Oregon
750 Leeward Ln, Oregon
$499,900
4 Beds ⋅ 4 Baths ⋅ 2035500 MLS ⋅ ACTIVE Status
Beautifully updated 4-bedroom, 3.5-bath two-story home with an open-concept layout and gas fireplace! The stunning kitchen features Starmark Quarter-Sawn oak cabinetry w/recessed doors/dovetail drawers, quartz countertops, tile backsplash and under-cabinet lighting. Main-level office offers ideal work-from-home space! The beautifully remodeled primary bath features a new shower, stylish tile, updated vanity and countertop, creating a fresh, modern retreat. Finished lower level offers an en suite bedroom and a versatile space for a rec room, home gym or entertaining! Enjoy a 14' x 16' composite deck, fenced yard, extensive landscaping, raised garden bed and large shed. Extra-deep heated garage, expanded driveway, exterior 30-amp/220V RV hookup and RV cleanout are rare bonuses! Roof, windows, furnace, exterior doors and garage door replaced in 2019; A/C in 2018, water softener in 2025 and microwave 2026. Walk to schools and Bergamont Golf Course! Exceptional condition and move-in ready!

750 Leeward Ln, Oregon
712 Dunn Ave, Oregon
$269,900
2 Beds ⋅ 2 Baths ⋅ 2034587 MLS ⋅ ACTIVE Status
New Price of $269,900. Step into this bright and inviting condo where modern updates and comfort come together beautifully. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating a warm and welcoming space perfect for everyday living or entertaining guests. You’ll love the updated luxury plank flooring, newer carpet, and refreshed appliances that give the home a fresh, contemporary feel throughout. Stay comfortable year-round with a newer furnace, air conditioning, water heater, and roof—major systems already taken care of so you can enjoy peace of mind from day one. Step outside to the updated deck, a relaxing retreat with nice views where you can enjoy your morning coffee or unwind in the evening. This well-maintained condo offers the perfect blend of style, functionality, and easy living in a comfortable setting. Don’t miss the opportunity to make this charming home your own!

712 Dunn Ave, Oregon
1048 Brynhill Dr, Oregon
$924,900
5 Beds ⋅ 4 Baths ⋅ 2032196 MLS ⋅ ACTIVE UNDER CONTRACT Status
Legend at Bergamont! This Alterra parade home with high end finishes shows well. Home features custom Amish cabinets, Quartz counters, large open spaces, engineered hardwood floors, transom windows, shiplap accent walls, new carpet & fresh paint. Kitchen features a large breakfast bar island, custom tin inlaid ceiling, SS appliances & modern lighting. Nearby walk-in pantry has a beverage fridge & pass-through window to the Screen Porch! Screen Porch has slider weatherproof windows, gas fireplace & built-in bar top. Primary suite has reading nook, oversized WIC & en-suite w/ large custom tiled shower. Lower level has a sizable Rec room w/ 3rd gas FP, game area, full bath & 5th bedroom. Backyard patio overlooks the mature (professionally) landscaped backyard. 4-car garage (with tandem stall) can accommodate a boat or extra toys. Located across the street from the golf course and walking distance to the pool, tennis courts & clubhouse restaurant. A smart purchase!

1048 Brynhill Dr, Oregon
883 Park St Unit 102, Oregon
$250,000
2 Beds ⋅ 2 Baths ⋅ 2033130 MLS ⋅ ACTIVE Status
This 2-bed/2-bath condo is the best deal on the market in the Village of Oregon! 1st floor, zero-step entry from the garage and main entrance makes this condo accessibility-friendly. Laminate floors throughout most of the condo. New flooring in the bathrooms. Spacious primary bedroom features a walk-in closet and a walk-in shower in the attached bathroom. Huge pantry off the kitchen. Patio that backs up to a lovely, private green space. Move-in ready, yet room for your touches, if you're looking to put your personal stamp on your new home. 1-car attached garage. Hot water and water/sewer is included in the condo fee! Great location right off Highway 14 makes access to Madison so easy. Important amenities like schools, the senior center, a dog park, and Kwik Trip and Culver's are within walking distance. Homeownership is in reach with this great condo!

883 Park St Unit 102, Oregon
607 Hillcrest Dr, Oregon
$385,000
3 Beds ⋅ 2 Baths ⋅ 2033085 MLS ⋅ ACTIVE Status
Well-maintained multi-story home in the Village of Oregon offering 3 bedrooms, 1.5 baths, and plenty of flexible living space. The inviting sunroom is a great place to relax, enjoy your morning coffee, or take in the changing seasons. A finished basement provides additional room for a rec area, home office, workout space, or hobbies. Numerous updates throughout the home add comfort and convenience while still leaving room to make it your own. Conveniently located near Oregon schools, parks, and community amenities, with easy access to downtown Oregon and the surrounding Madison area. A comfortable and functional home in a great village location.

607 Hillcrest Dr, Oregon
381 Cherry Wood Dr, Oregon
$449,900
3 Beds ⋅ 2 Baths ⋅ 2033003 MLS ⋅ ACTIVE Status
Now Available to See. Welcome home to this beautiful 3-bedroom, 2-bath property in the desirable Hickory Estates Neighborhood. The spacious kitchen and dinette area offer plenty of room for everyday living and features a walkout to a deck, perfect for outdoor dining. Enjoy the large fenced backyard with ample space for recreation and gardening. The living room provides plenty of natural light and a second walkout to a smaller deck overlooking the back yard. There is a family room with a wood-burning fireplace, creating the perfect gathering space. The spacious primary bedroom offers double closets. There is a bonus room in the lower level perfect for a home office, workout room or additional living space. Ideally located across from a park and just minutes from downtown Oregon. Combining comfort, space, and a fantastic location, this home is ready for its next owner to enjoy. New Roof & Siding 2025, A/C 2026, Washer, Freshly Painted and New Carpet. Move-in Ready.

381 Cherry Wood Dr, Oregon
1232 Tivoli Cir, Oregon
$434,900
2 Beds ⋅ 2 Baths ⋅ 2032927 MLS ⋅ ACTIVE Status
The Villas are the ultimate in peace of mind living. Located within the Highlands of Netherwood, this unique neighborhood of Single Family homes brings all the conveniences of condo living (Fee: $200/mo) right to your door. Never mow your lawn or shovel your driveway again. Ideal for people that frequently travel or are in the area for part of the year. Walking path connects the neighborhood to a large park. Open-concept, ranch style homes have spacious living rms w/ direct deck access. Basements can be finished for extra living space & 3rd bed & bath. The majority of lots have half or full exposure in the basement. Multiple finish options & upgrades available. Builder is offering lots 1-30, see association docs.

1232 Tivoli Cir, Oregon
749 County Road Mm, Oregon
$450,000
3 Beds ⋅ 1 Baths ⋅ 2032332 MLS ⋅ ACTIVE UNDER CONTRACT Status
Inviting home on just under 4 acres within the top-rated Oregon School District, just 20 minutes from downtown Madison. The fantastic open layout creates an easy flow for entertaining, gathering with friends, and everyday living. You’ll love the character throughout, with original accents, exposed brick, gorgeous hardwood floors, and stylish finishes. Spend warm weather days on the patio taking in peaceful views of the surrounding landscape, then make the most of your 3.92 acres with a vegetable garden, apple orchard, chickens, or even your own hobby farm. The possibilities are wide open, whether you want room to roam, space for outdoor projects, or a place to create something all your own. The spacious 30x40’ heated 4+ car garage offers plenty of room for vehicles, equipment, a boat, or your own workshop. A rare opportunity to enjoy country living with Madison just minutes away.

749 County Road Mm, Oregon
899 County Rd, Oregon
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2032803 MLS ⋅ ACTIVE UNDER CONTRACT Status
A rare opportunity to own a luxury retreat on +/-13ac just outside Oregon, WI. This secluded estate is surrounded by mature forest and abundant wildlife, offering a peaceful country feel minutes from town. The home features a chef's kitchen with Wolf and Sub-Zero appliances, a grand entry, and refined living spaces with uninterrupted views of nature. The finished lower level includes its own kitchen, full bath, and walkout to a paver patio. This property is perfect for entertaining or escaping the hustle of daily life. Two impressive outbuildings, a 56x40 and a 30x24, provide exceptional versatility, including a batting cage and indoor basketball court. A one-of-a-kind property blending privacy, recreation and luxury. Schedule your private showing today. Open House - Sat and Sun!

899 County Rd, Oregon
377 Concord Dr, Oregon
$365,000
2 Beds ⋅ 2 Baths ⋅ 2030772 MLS ⋅ ACTIVE Status
Well maintained sun-lit 2-bed/2-bath condo in the highly-rated Oregon School District featuring great space, wonderful views, and offers the perfect balance of comfort and convenience. The main living area boasts vaulted ceilings, oversized windows, a cozy gas fireplace, and walkout to the balcony deck overlooking the property. The kitchen has abundant cabinetry, a spacious island, and an adjoining dining area surrounded by a bay of windows. The generous primary suite features a large walk-in closet and private bath. A sizeable 2nd bedroom, full bath, six-panel doors, office nook & convenient main-floor laundry round out the main level. The unit offers private entry and large 2-car attached garage! Close to restaurants, coffee shops, shopping, schools, & multiple nearby parks. Easy commute to Madison, Epic, and everything the area has to offer.

377 Concord Dr, Oregon
435 Peterson Trl, Oregon
$834,900
4 Beds ⋅ 3 Baths ⋅ 2030196 MLS ⋅ ACTIVE Status
Better than new, this 2023 Oregon ranch has been thoughtfully finished and upgraded since the day it was built. Step inside to an open, airy main level with wood floors that flow throughout and a great room made for gathering. The kitchen is a standout, featuring a large island, pantry, and quartz countertops, all opening naturally into the living and dining spaces. The primary suite is a true retreat with a walk-in closet and spa-like bathroom with walk-in shower. The main level laundry brings everyday convenience, and two additional bedrooms and a second full bath round out the level. Downstairs, the newly finished lower level adds serious value! The entire space is flooded with natural light, and features a rec room w/ wet bar, a fourth bedroom, a full bath, and an office. Out back, the patio with remote-control screened enclosure makes outdoor entertaining effortless, with easy access to patio and fenced yard. All this, with walking distance to library, parks and more!

435 Peterson Trl, Oregon
546 Echo Valley Rd, Oregon
$789,900
4 Beds ⋅ 3 Baths ⋅ 2027077 MLS ⋅ ACTIVE Status
PEACEFUL LIVING BY THE WOODS!!! 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. Bargain priced below assessed value. Schedule your showing today!

546 Echo Valley Rd, Oregon
422 Oakwood Dr, Oregon
$559,900
4 Beds ⋅ 4 Baths ⋅ 2020302 MLS ⋅ ACTIVE Status
Four bedrooms upstairs, a finished walkout lower level, and a backyard designed for fun! Discover the space and flexibility of this freshly painted, move-in-ready home in Oregon's Stoneridge neighborhood. The bright main level offers comfortable living and dining spaces with easy access to the deck for grilling and relaxing. Upstairs, all four bedrooms are conveniently located together, including a primary suite with a private bath. The finished walkout lower level adds a spacious family room, full bathroom, and direct backyard access—ideal for entertaining, movie nights, or hobbies. Outside, the versatile sport court doubles as a generous patio space, offering possibilities for basketball, outdoor gatherings, and recreation. With 2,558 square feet of finished living space, 3.5 bathrooms, and convenient access to Madison, this home offers room to spread out and make it your own. Schedule your showing and see the possibilities!

422 Oakwood Dr, Oregon
1044 Autumn Blaze Ct, Oregon
$749,900
4 Beds ⋅ 4 Baths ⋅ 2019010 MLS ⋅ ACTIVE Status
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 Ct, Oregon
655 Cypress Way, Oregon
$829,900
4 Beds ⋅ 4 Baths ⋅ 2012675 MLS ⋅ ACTIVE UNDER CONTRACT Status
Proposed Construction: The Stonehaven by Eldon Homes, an exceptional 4-bed, 4 bath Customizable Craftsman two-story in one of areas premier golf-course communities. Featuring a 3-car garage and striking open-to-below great room, this home blends luxury with comfort. The gourmet kitchen offers solid-surface counters and a large island that anchors the main living area. A main-level office/flex room and mudroom add daily convenience. The primary suite offers a customizable bath and walk-in closet. Upper-level bedrooms are well sized with a full bath. Finished lower-level options allow for a gym, theater, wet bar, add Bedroom (640 sqft rec room included). Located in The Legend at Bergamot with top-tier golf, clubhouse, pools, courts, and a vibrant community lifestyle.

655 Cypress Way, Oregon

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.

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