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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

1053 Winged Foot Dr, Oregon
$1,275,000
5 Beds ⋅ 5 Baths ⋅ 2021000 MLS ⋅ ACTIVE UNDER CONTRACT Status
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 Dr, Oregon

1098 Brynhill Dr, Oregon
$999,900
5 Beds ⋅ 4 Baths ⋅ 2031393 MLS ⋅ ACTIVE UNDER CONTRACT Status
Experience refined luxury in The Legend at Bergamont with this impressive former parade home showcasing sophisticated finishes and breathtaking views! The front of the home overlooks hole #7, while the backyard offers peaceful pond views for a truly picturesque setting. Inside, the beautiful chef’s kitchen takes center stage opposite a striking floor-to-ceiling stacked-stone gas fireplace. 5 spacious bedrooms, an extended mudroom w/ laundry, and 2 flex/office spaces add exceptional everyday functionality. The finished walk-out LL is designed for entertaining with an impressive bar & 2nd gas fireplace. Outdoors, enjoy the views from the Trex deck or relax beneath the covered patio. A rare opportunity to own a truly stunning home in one of the area's most desirable communities!

1098 Brynhill Dr, 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

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

541 Union Rd, Oregon
$799,900
3 Beds ⋅ 2 Baths ⋅ 2030248 MLS ⋅ ACTIVE UNDER CONTRACT Status
A country property unlike the rest! Set on 22.08 acres, this unique 3-bedroom, 2-bath home offers an open multi-level design with vaulted ceilings, exposed wood accents and a distinctive sunken sound/living room. Relax in the spacious four-season room surrounded by windows and overlooking the beautiful backyard and countryside. Approximately 15 acres are tillable and currently rented for corn/soybeans. This awesome property has an attached 2-car garage, a 47x34 shop with concrete floor/insulated walls/heated/built in compressed air/ventilation system, with room for 2+ additional vehicles. Plus 2 additional equipment/storage buildings—ideal for hobbies, equipment, animals or projects. RM-16 Zoning offers agricultural and other rural uses, with additional possibilities subject to zoning/CUP approval. Horses allowed. Updates include furnace/AC 2024, windows 2025, water heater 2021. Mature trees even apple, plenty of room to make this property your own! Ultimate UHP Warranty Included

541 Union Rd, Oregon

480 Foxfield Ct, Oregon
$799,900
4 Beds ⋅ 4 Baths ⋅ 2027752 MLS ⋅ ACTIVE UNDER CONTRACT Status
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 Ct, Oregon

300 N Bergamont Blvd, Oregon
$715,000
4 Beds ⋅ 3 Baths ⋅ 2027731 MLS ⋅ PENDING Status
Welcome home to this stunning custom-built 4-bedroom, 2.5-bath residence, where quality craftsmanship and thoughtful design come together seamlessly. Featuring beautiful upgrades throughout, this home offers an open and functional layout that's perfect for both everyday living and entertaining. The thoughtfully designed floor plan features expansive living spaces, a beautifully upgraded kitchen with premium finishes, and a luxurious primary suite designed for comfort and relaxation. The finished basement features a welcoming recreation area, a convenient dry bar, and abundant storage, providing versatile space for entertaining and everyday enjoyment. Every detail has been carefully considered, creating a home that is as practical as it is beautiful.

300 N Bergamont Blvd, Oregon

2001 Timber Lake Rd, Oregon
$625,000
4 Beds ⋅ 3 Baths ⋅ 2033369 MLS ⋅ ACTIVE UNDER CONTRACT Status
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 Rd, Oregon

803 Liliana Ter, Oregon
$599,900
4 Beds ⋅ 3 Baths ⋅ 2032906 MLS ⋅ ACTIVE UNDER CONTRACT Status
Set in Autumn Ridge - Oregon Subdivision this newer two-story has the light and flow buyers keep asking for. The open main level moves from a STUNNING granite kitchen with work island, breakfast bar and large pantry into a dining room crowned by a three-tier French vintage chandelier enhance by cathedral-ceiling + wrapped with sun-filled five windows leading to the patio and private fenced backyard. Settle in by the stone gas fireplace, pour a nightcap in the cocktail lounge/flex room, and drop everything in the custom rear-foyer mudroom area. Crisp white cabinetry and trim plus east and west-facing windows keep the whole house bright from morning to evening. Upstairs holds four bedrooms, two granite-topped full bathrooms and second-floor laundry + the GORGEOUS primary suite offers two walk-in closets & a private full bath w/tile walk-in shower! The lower level is ready to finish with 8'+ ceilings, two egress windows, and a bathroom stub-in.

803 Liliana Ter, Oregon

6214 Knollwood Dr, Oregon
$599,900
4 Beds ⋅ 3 Baths ⋅ 2032732 MLS ⋅ ACTIVE UNDER CONTRACT Status
Tucked into the wooded Ravenoaks neighborhood, this spacious 4-bedroom, 2.5-bath contemporary style home offers privacy, mature trees, and a generous floor plan on a stunning 0.74 acre lot. The home features tall vaulted ceilings, a dramatic great room with an eye-catching wood burning fireplace, large bedrooms, primary suite with walk-in closet, loft, den/office, and finished lower level rec space. Enjoy the peaceful outdoors from the deck surrounded by mature hardwood trees, Raspberry bushes, an herb garden, and tons of wildflowers. The hardwoods provide a natural source of firewood for cozy evenings by the fireplace. A 3-car attached garage adds plenty of room for vehicles, hobbies, and storage. This tranquil setting remains conveniently close to Oregon's everyday necessities, including shopping, dining, schools, and more, with easy access to Madison.

6214 Knollwood Dr, Oregon

1083 Merri-Hill Dr, Oregon
$579,900
4 Beds ⋅ 3 Baths ⋅ 2029261 MLS ⋅ PENDING Status
Move-in ready 10/21/26 This Everest 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.

1083 Merri-Hill Dr, Oregon

994 Tipperary Rd, Oregon
$575,000
3 Beds ⋅ 2 Baths ⋅ 2033292 MLS ⋅ ACTIVE UNDER CONTRACT Status
Perched atop a scenic hill on 8+ beautiful acres, this property offers a rare opportunity to embrace country living just 15 minutes outside of Madison! Bring your animals and embrace the hobby-farm lifestyle with fenced pastures and a 32' x 24' pole barn complete with horse stables. The 3 bed/2 bath ranch home features a functional layout with two inviting living spaces, a spacious primary bedroom with en suite bath, and an unfinished lower level offering exciting potential for future living space. Whether you're dreaming of a hobby farm or a peaceful rural retreat for your family, this property offers the space, setting, and potential to make it your own—all in the highly sought-after Oregon School District! Put down roots and enjoy the best of country living!

994 Tipperary Rd, Oregon

255-259 Park St, Oregon
$575,000
2032203 MLS ⋅ ACTIVE UNDER CONTRACT Status
Calling all investors and owner occupants! Great opportunity to own a ranch-style side-by-side duplex in the heart of downtown Oregon. The 259 side has been gutted and completely redone, featuring new flooring and carpet, fresh paint, new doors and trim, new appliances and more—move-in ready for a new tenant or the perfect opportunity to live in one side while renting out the other! Major update with a new roof in 2024, plus one unit features a private, fenced-in backyard. Fantastic location just steps from schools, parks, pickleball courts, coffee shops, restaurants and everything downtown Oregon has to offer. Whether you're looking to add to your investment portfolio or offset your mortgage with rental income, this one is ready to go!

255-259 Park St, Oregon

431 Thomas Ct, Oregon
$449,900
4 Beds ⋅ 3 Baths ⋅ 2033919 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this 4 bed/3 bath ranch home located on a quiet cul-de-sac just minutes to everything Oregon has to offer & only 15 minutes to Madison! The open-concept main level features updated flooring & seamless flow between the kitchen, dining & living rm w/easy access to the backyard through a patio door. Updated kitchen offers white cabinetry, granite counters, tile backsplash, stainless steel appliance & large island w/breakfast bar. Spacious primary bedroom includes a large walk-in closet & private bath w/new flooring & extended vanity. Two additional bedrooms & a full bath complete the main level. The expansive lower level offers a large rec room with projector, 4th bedroom, full bath & two generous storage areas. Outside, enjoy a spacious backyard with an included hot tub, two storage sheds & pergola—ideal for relaxing & entertaining. Two-car attached garage adds convenience & storage. Great location and move-in ready!

431 Thomas Ct, Oregon

622 N Woods Edge Dr, Oregon
$424,900
3 Beds ⋅ 2 Baths ⋅ 2032391 MLS ⋅ PENDING Status
Seller accepted a sight unseen offer. Welcome to this charming home in a well-established, beautiful neighborhood! You will love being within walking distance to local parks, walking paths, and everything downtown Oregon offers.The main level features big, bright windows that flood the space with natural light, along with newer paint and updated light fixtures throughout the living and kitchen areas. The primary bedroom offers an en suite bathroom and dual closets for extra storage. Additional highlights include a partially finished basement featuring a large family room with convenient walk-out access directly to the fenced backyard. The basement also has rough-in plumbing already in place for a future basement bathroom.

622 N Woods Edge Dr, Oregon

1035 Merri-Hill Dr, Oregon
$424,900
3 Beds ⋅ 2 Baths ⋅ 2020446 MLS ⋅ PENDING Status
The Pilot Home (504 Greenview Preserve) 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.

1035 Merri-Hill Dr, Oregon

187 Sterling Dr, Oregon
$414,900
3 Beds ⋅ 2 Baths ⋅ 2030702 MLS ⋅ ACTIVE UNDER CONTRACT Status
Beautiful ranch home offering the perfect blend of comfort, convenience, and outdoor enjoyment. Stunning hardwood floors welcome you inside, while the remodeled kitchen is ready for everyday living and entertaining alike. Unwind in the spa-like bathroom, designed to feel like your own private retreat. Outside, enjoy a generous lot featuring cherry trees, apple trees, plum tree, raspberry bush, and plenty of room to garden, play, or relax. The new maintenance-free deck is perfect for summer gatherings and quiet mornings alike. A dedicated theater room, complete with all equipment included, provides the ultimate movie-night experience. The oversized 3-car garage offers ample storage and workspace. Conveniently located near shopping, restaurants, parks, and everyday amenities, this home combines thoughtful updates, beautiful outdoor spaces, and exceptional value. Roof '20/'21, Water Heater '21, Kitchen Appliances '22, Furnace & A/C '23!

187 Sterling Dr, Oregon

136 Alpine, Oregon
$368,000
3 Beds ⋅ 3 Baths ⋅ 2030034 MLS ⋅ PENDING Status
Spacious 3BD/3BA step-free condo in Oregon! Main-floor living with bonus lower level. Welcome home to this beautifully maintained condo on a quiet cul-de-sac in Oregon's Alpine Meadows community. Move-in ready with quality finishes and low-maintenance living. The main floor features LVP flooring throughout an open-concept living, dining, and kitchen area. The kitchen boasts granite countertops, stainless steel appliances, tile backsplash, and a peninsula island with seating for four. Two bedrooms, two full bathrooms, and main-floor laundry complete the level. The lower level offers a third bedroom with egress window, full bathroom, and flexible rec room space ideal as a home office or guest suite. Attached 2-car garage with ground-level entry. New roof 2025. New furnace/AC & water softener 2020. Private patio. One block to walking trail. Two blocks to library. Minutes to Madison. HOA $394.99/mo covers all exterior maintenance. No open house. Schedule your private showing today!

136 Alpine, Oregon

358 Alpine Meadow Cir, Oregon
$300,000
2 Beds ⋅ 2 Baths ⋅ 2029954 MLS ⋅ ACTIVE UNDER CONTRACT Status
Rare find! This 2-bedroom, 2-bath ranch condo offers easy one level living with vaulted ceilings, beautiful lvp floors, and a comfortable open feel with lots of natural light. The kitchen features brand-new appliances in 2026, along with an impressive list of recent updates including a new washer an dryer in 2025, furnace, A/C and water heater in 2024, and new roof in 2022. The spacious unfinished lower level offers plenty of potential for additional living space, with exposed windows and plumbing already in place for an additional bathroom. Enjoy the ease of low-maintenance condo living with the space, updates, and potential you've been looking for. Ranch condos like this don't come along often-don't miss this one!

358 Alpine Meadow Cir, Oregon

148 Alpine Meadow Cir, Oregon
$300,000
2 Beds ⋅ 3 Baths ⋅ 2028288 MLS ⋅ ACTIVE UNDER CONTRACT 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

304 N 3rd St, Oregon
$168,000
3 Beds ⋅ 1 Baths ⋅ 2025028 MLS ⋅ PENDING Status
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 St, 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.